Organic light emitting device and apparatus including the same
By using a combination of three compounds in an organic light emitting device, an emission layer with a smooth energy level is formed, which solves the problem of insufficient emission efficiency and life in the prior art, realizes the preparation of high-performance organic light emitting devices, and simplifies manufacturing Craft.
Patent Information
- Application Number
- CN201911426185.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-09-04
- Filing Date
- 2019-12-30
- Publication Date
- 2025-01-17
- Estimated Expiration
- 2039-12-30
AI Technical Summary
Existing organic light emitting devices have challenges in improving emission efficiency and lifetime, especially in charge mobility and energy level smoothness, and traditional processes are difficult to achieve high-performance emission layer preparation.
The emission layer is formed by a solution coating process using an emission layer containing three different compounds, wherein the combination of the first compound, the second compound and the third compound has excellent solubility and compatibility, and regulates the mixing of the charged host compound. The ratio is to control the charge mobility to form an emission layer with smooth HOMO and LUMO energy levels.
High-performance organic light-emitting devices are realized, which significantly improves emission efficiency and emission life, and simplifies the manufacturing process through the solution coating process and is suitable for large-scale production.
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Figure CN111384300B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefits of Japanese Patent Application No. 2018-248433 filed in the Japan Patent Office on December 28, 2018, and Korean Patent Application No. 10-2019-0109515 filed in the Korean Intellectual Property Office on September 4, 2019, and all rights and interests arising therefrom, the contents of which are incorporated herein in their entirety by reference. Technical Field
[0003] One or more embodiments relate to an organic light emitting device and an apparatus (device) including the same. Background Art
[0004] Compared with other types of devices, organic light emitting devices are self-emissive devices that produce full-color images and have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] Aspects of the present disclosure provide an organic light emitting device including an emission layer including three compounds different from each other and an apparatus including the organic light emitting device.
[0007] 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.
[0008] One aspect of the present disclosure provides an organic light emitting device comprising:
[0009] a first electrode;
[0010] a second electrode; and
[0011] an emitting layer between the first electrode and the second electrode,
[0012] wherein the emission layer comprises a first compound, a second compound and a third compound,
[0013] The first compound includes at least one compound represented by one of Formulae 1-1 to 1-4,
[0014] The second compound includes at least one compound represented by one of Formulae 2-1 to 2-4, and
[0015] The third compound includes at least one of the following: a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, a bicarbazole group, or any combination thereof, wherein a band gap between a highest occupied molecular orbital (HOMO) energy level and a lowest unoccupied molecular orbital (LUMO) energy level of the third compound is 3.3 eV or greater:
[0016]
[0017]
[0018] In formulas 1-1 to 1-4,
[0019] X 11 -X 16 and X 21 -X 28 can be independently C or N,
[0020] X 11 -X 16 At least one of may be N,
[0021] X 21 -X 28 At least one of may be N,
[0022] L 1 -L 6 may be independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 1 -C 30 a heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group,
[0023] c3-c5 can be independently selected from integers of 1-3,
[0024] Ar 1 -Ar 6 may be independently selected from substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
[0025] In Ar 3 -Ar 5 Any two adjacent groups in which may be optionally linked to each other via a single bond to form a condensed ring,
[0026] a1-a3 can be independently selected from integers of 1-3,
[0027] R 1 -R 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy,
[0028] b1 can be selected from integers between 0 and 4.
[0029] b2 can be selected from integers between 0 and 6.
[0030] b3 can be selected from integers between 7 and 11, and
[0031] k can be 2 or 3.
[0032] In formulas 2-1 to 2-4,
[0033] A 1 -A 6 Can be independently selected from C 5 -C 30 Carbocyclic groups and C 1 -C 30 Heterocyclic groups,
[0034] L 11 -L 19 may be independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 1 -C 30 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0035] c11-c19 can be independently selected from integers of 1-3,
[0036] Ar 11 ,Ar 12 and Ar 14 -Ar 17may be independently selected from substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein Ar 14 and Ar 15 Both may not be indole and carbazole groups, and Ar 16 and Ar 17 Each may not be naphthyl at the same time,
[0037] Ar 13 Can be selected from substituted or unsubstituted C 6 -C 30 aryl and substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups,
[0038] R 11 -R 24 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
[0039] b11, b14, b15, b16 and b18-b24 can be independently selected from integers of 0-4,
[0040] b12, b13 and b17 can be independently selected from integers of 0-3,
[0041] Substituted C 6 -C 30 Arylene, substituted C 1 -C 30 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 6 -C 30 Aryl, substituted C 1 -C 30 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:
[0042] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy;
[0043] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 ) at least one substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy;
[0044] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0045] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 ) at least one substituted C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and
[0046] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), and -P(=O)(Q 38 )(Q 39 ),and
[0047] Q 11 -Q 19 , Q 21 -Q 29 and Q 31 -Q 39can 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, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, with at least one C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or a combination thereof substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group.
[0048] Another aspect of the present disclosure provides an apparatus including the organic light emitting device. For example, the apparatus may include a light emitting device and an electronic device, wherein the light emitting device may include a lighting device, and the electronic device may include a computer, a mobile phone, an electronic dictionary, a medical device, and a projector. BRIEF DESCRIPTION OF THE DRAWINGS
[0049] By combining Figure 1 These and / or other aspects will become clear and more readily understood from the following description of the embodiments contemplated herein. Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION
[0050] Hereinafter, the present disclosure will be described in detail by explaining the embodiments with reference to the accompanying drawings.In addition, the same reference numerals in the present specification and the accompanying drawings represent the same elements having substantially the same functions and / or features, and thus their description will be omitted.
[0051] It will be understood that when an element is referred to as being “on” another element, it can be directly on 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.
[0052] It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or 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 herein, the first element, component, region, layer or part discussed below may be referred to as a second element, component, region, layer or part.
[0053] The terms used herein are for the purpose of describing specific embodiments only and are not intended to be limiting. As used herein, "a", "an", "the", and "at least one" do not represent a limitation of quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "element" has the same meaning as "at least one element", unless the context clearly indicates otherwise.
[0054] "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items. It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of the stated features, regions, integers, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components and / or their collections.
[0055] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship between an element and another element as shown in the figure. It will be understood that, in addition to the orientations depicted in the figure, relative terms are also intended to include different orientations of the device (equipment). For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" may include both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, the element described as "below" or "below" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below..." or "below..." may include both "above..." and "below..." orientations.
[0056] As used herein, "about" or "approximately" includes 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 measurement 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 a range of ±10% or 5%.
[0057] Unless otherwise defined, all terms (including technical and scientific terms) used in this article have the same meaning as commonly understood by ordinary technicians in the field to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as their meanings consistent with their meanings in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly defined in this article.
[0058] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as shown herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. In addition, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions, and are not intended to limit the scope of the claims.
[0059] One aspect of the present disclosure provides an organic light-emitting device, comprising: a first electrode; a second electrode; and an emission layer between the first electrode and the second electrode, wherein the emission layer comprises a first compound, a second compound, and a third compound, the first compound comprising at least one compound represented by one of Formulas 1-1 to 1-4, the second compound comprising at least one compound represented by one of Formulas 2-1 to 2-4, and the third compound comprising at least one of the following: a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, a bicarbazole group, or any combination thereof, wherein a band gap between a highest occupied molecular orbital (HOMO) energy level and a lowest unoccupied molecular orbital (LUMO) energy level of the third compound is 3.3 eV or greater:
[0060]
[0061] Formulae 1-1 to 1-4 will be described in detail below.
[0062] X 11 -X 16and X 21 -X 28 They may each independently be C or N.
[0063] In one or more embodiments, X 11 -X 16 At least one of may be N, and X 21 -X 28 At least one of can be N.
[0064] For example, (i)X 11 Can be N, and X 12 -X 16 Each of them can be C, (ii) X 11 and X 12 can be N, and X 13 -X 16 Each of them can be C, (iii) X 11 and X 13 can be N, and X 12 and X 14 -X 16 Each of them can be C, (iv) X 11 and X 14 can be N, and X 12 , X 13 , X 15 and X 16 Each of them can be C, (v)X 11 -X 13 can be N, and X 14 -X 16 Each of them can be C, (vi) X 11 , X 12 and X 14 can be N, and X 13 , X 15 and X 16 Each of them may be C, or (vii) X 11 , X 13 and X 15 can be N, and X 12 , X 14 and X 16 Can each be C.
[0065] For example, (i)X 21 Can be N, and X 22 -X 28 Each of them can be C, (ii) X 22 Can be N, and X 21 and X 23 -X 28 Each of them can be C, (iii) X 21 and X 22 can be N, and X23 -X 28 Each of them can be C, (iv) X 21 and X 23 can be N, and X 22 and X 24 -X 28 Each may be C, or (v) X 21 and X 24 can be N, and X 22 , X 23 and X 25 -X 28 Can each be C.
[0066] L 1 -L 6 may be independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 1 -C 30 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0067] In one or more embodiments, L 1 -L 6 and L 11 -L 19 Can be independently selected from
[0068] single bond, phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronaphenylene, ovaphenylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, pyrazolylene Azolyl, Isopropylidene oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, benzofuranyl ... Azolyl, isobenzoyl Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, or dibenzocarbazolylene; and
[0069] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, at least one substituted phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanth ... phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronaphenylene, ovaphenylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, pyrazolylene Azolyl, Isopropylidene oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, benzofuranyl ... Azolyl, isobenzoyl Azolyl, triazolyl, tetrazolyl, A dioxadiazole group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylene group, and a dibenzocarbazolylene group, but embodiments of the present disclosure are not limited thereto.
[0070] c3-c5 may each independently be an integer of 1-3.
[0071] Ar 1 -Ar 6 may be independently selected from substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein Ar 3 -Ar 5 Any two adjacent groups therein may be optionally linked to each other via a single bond to form a condensed ring.
[0072] In one or more embodiments, Ar 1 -Ar 6 Can be independently selected from
[0073] Phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indolodibenzofuranyl, indolodibenzothiophenyl, indolofluorenyl, indolospiro-bifluorenyl, indolophenanthrenyl, indolobenzo[9,10]phenanthrenyl, indoloazadibenzofuranyl, and indoloazadibenzothiophenyl; or
[0074] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, at least one substituted phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, The invention also includes oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indolodibenzofuranyl, indolodibenzothiophenyl, indolofluorenyl, indolospiro-difluorenyl, indolophenanthrenyl, indolobenzo[9,10]phenanthrenyl, indoloazadibenzofuranyl, and indoloazadibenzothiophenyl, but the embodiments of the present disclosure are not limited thereto.
[0075] a1-a3 may each independently be an integer of 1-3.
[0076] In one or more embodiments, when a1 is an integer of 2 or greater, two or more -L 1 -Ar 1 The groups may be the same or different from each other. For example, when a1 is 3, three -L 1 -Ar 1 The groups may be different from each other. When having such a structure, the compound may have low crystallinity, thereby improving the solubility of the compound.
[0077] In one or more embodiments, when a2 is an integer of 2 or greater, two or more -L 2 -Ar 2 The groups may be the same or different from each other. For example, when a2 is 2, two -L 2 -Ar 2 The groups may be different from each other. When having such a structure, the compound may have low crystallinity, thereby improving the solubility of the compound.
[0078] In one or more embodiments, when a3 is an integer of 2 or greater, two or more -L 6 -Ar 6 The groups may be the same or different from each other. For example, when a3 is 2, two -L 6 -Ar 6The groups may be different from each other. When having such a structure, the compound may have low crystallinity, thereby improving the solubility of the compound.
[0079] R 1 -R 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy.
[0080] In one or more embodiments, R 1 -R 3 Can be independently selected from
[0081] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, or C 1 -C 20 alkoxy; or
[0082] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, and C 1 -C 20 At least one substituted C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy group, but the embodiments of the present disclosure are not limited thereto.
[0083] For example, R 1 -R 3 Can be independently
[0084] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, methoxy, ethoxy, propoxy, or butoxy; or
[0085] methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, methoxy, ethoxy, propoxy, or butoxy, each substituted by at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, methoxy, ethoxy, propoxy, and butoxy.
[0086] b1 may be an integer from 0 to 4, b2 may be an integer from 0 to 6, and b3 may be an integer from 7 to 11.
[0087] k can be 2 or 3.
[0088] In one or more embodiments, when k is 3, a compound having a structure in which three benzene rings are fused, such as an anthracene group or a phenanthrene group, may be included. When k is 4, a compound having a structure in which four benzene rings are fused, such as A compound containing a tetracene group, a benzanthracene group, or a benzanthracene group.
[0089] Hereinafter, Formulae 2-1 to 2-4 will be described in detail.
[0090] A 1 -A 6 Can be independently selected from C 5 -C 30 Carbocyclic groups and C 1 -C 30 Heterocyclic group.
[0091] In one or more embodiments, A 1 , A 2 , A 3 , A 4 , A 5 and A 6 Can be independently selected from
[0092] benzene group, naphthyl group, anthracene group, thiophene group, furan group, pyrrole group, indole group, indene group, benzothiorrole group, benzothiophene group, benzofuran group, carbazole group, fluorene group, dibenzothiorrole group, dibenzothiophene group, dibenzofuran group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo A oxadiazole group, and a benzothiadiazole group, but the embodiments of the present disclosure are not limited thereto.
[0093] For example, A 2 and A 5 may be independently selected from a phenyl group or a naphthalene group, and A 1 , A 3 , A 4 and A 6The benzothiophene group, the benzofuran group, the ... Azole group, benzothiazole group, benzo oxadiazole group, and benzothiadiazole group.
[0094] For example, A 1 -A 6 All of them may be phenyl groups.
[0095] L 11 -L 19 may be independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 1 -C 30 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
[0096] L 11 -L 19 Each can be understood by reference to the description provided herein.
[0097] c11-c19 may each independently be an integer of 1-3.
[0098] Ar 11 ,Ar 12 and Ar 14 -Ar 17 may be independently selected from substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Ar 14 and Ar 15 Both may not be indole and carbazole groups, and Ar 16 and Ar 17 Each may not be a naphthyl group at the same time.
[0099] In one or more embodiments, Ar 11 ,Ar 12 and Ar 14 -Ar 17 Can be independently selected from
[0100] Phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, or a group represented by the following formula a; or
[0101] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, and -N(Q 11 )(Q 12 ) is at least one substituted phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, and a group represented by the following formula a,
[0102] Ar 14 and Ar 15 Both may not be indole and carbazole groups, and Ar 16 and Ar 17 Each may not be a naphthyl group at the same time, and
[0103] Q 11 and Q 12 Each may independently be a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
[0104] Formula a
[0105]
[0106] In formula a,
[0107] R 4 -R 6 Can be independently
[0108] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy; or
[0109] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, and C 1 -C 20 At least one substituted C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy,
[0110] "*" indicates the binding site with the adjacent group, and
[0111] b4 and b5 are independently integers from 0 to 4, and
[0112] b6 is an integer from 0 to 2.
[0113] Ar 13 Can be selected from substituted or unsubstituted C 6 -C 30 Aryl and substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups.
[0114] In one or more embodiments, Ar 13 Can be selected from
[0115] Phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, perylenyl, pentaphenyl, hexaphenyl, pentacene, rubidinyl, coronenyl, and ovalenyl;
[0116] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, at least one substituted phenyl group selected from the group consisting of phenyl, tetraphenyl, phenanthrenyl, peryl, pentaphenyl, hexaphenyl, pentacene, rubenyl, coronenyl, and ovalenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The invention also includes a phenyl group, a tetracenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacene group, a rubenyl group, a coronenyl group, and an ovalenyl group, but the embodiments of the present disclosure are not limited thereto.
[0117] R 11 -R 24 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryl, and substituted or unsubstituted C 1 -C 30 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0118] In one or more embodiments, R 11 -R 24 Can be independently selected from
[0119] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, and C 1 -C 20 Alkoxy;
[0120] Each of the C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0121] phenyl, biphenyl, terphenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl; or
[0122] phenyl, biphenyl, terphenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl and dibenzocarbazolyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I and cyano; 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, and dibenzocarbazolyl, but embodiments of the present disclosure are not limited thereto.
[0123] b11, b14, b15, b16 and b18-b24 may each independently be an integer of 0-4.
[0124] b12, b13 and b17 may each independently be an integer of 0-3.
[0125] The third compound may include at least one compound represented by Formulae 3-1 to 3-4:
[0126]
[0127] In formulas 3-1 to 3-4,
[0128] X 21 Can be O or S,
[0129] L 21 -L 29 may be independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 1 -C 30 a heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group,
[0130] c21-c29 can each independently be an integer of 1-3,
[0131] Ar 21 -Ar 28 may be independently selected from hydrogen, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 1 -C 30heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
[0132] Ar 21 and Ar 22 Each may not be hydrogen at the same time,
[0133] Ar 26 and Ar 27 may be optionally linked via a single bond to form a fused ring,
[0134] R 31 -R 41 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy,
[0135] b31, b32, b34, b35, b36 and b40 may each independently be an integer from 0 to 3, and
[0136] b33, b37, b38, b39 and b41 may each independently be an integer of 0-4.
[0137] In one or more embodiments, Ar in Formula 3-2 23 and Ar 24 may be different from each other, and when having such a structure, the compound may have low crystallinity, thereby improving the solubility of the compound.
[0138] In one or more embodiments, L 21 -L 29 Can be independently selected from
[0139] single bond, phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronaphenylene, ovaphenylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, pyrazolylene Azolyl, Isopropylidene oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, benzofuranyl ... Azolyl, isobenzoyl Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, and dibenzocarbazolylene; or
[0140] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, at least one substituted phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanth ... phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronaphenylene, ovaphenylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, pyrazolylene Azolyl, Isopropylidene oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, benzofuranyl ... Azolyl, isobenzoyl Azolyl, triazolyl, tetrazolyl, A dioxadiazole group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylene group, and a dibenzocarbazolylene group, but the embodiments of the present disclosure are not limited thereto.
[0141] In one or more embodiments, Ar 21 -Ar 28 Can be independently selected from
[0142] hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, phenyl, tetraphenyl, perylenyl, pentaphenyl, hexaphenyl, pentacene, rubidinyl, coronenyl, and ovalenyl;
[0143] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, at least one substituted phenyl group selected from the group consisting of phenyl, tetraphenyl, phenanthrenyl, peryl, pentaphenyl, hexaphenyl, pentacene, rubenyl, coronenyl, and ovalenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, The following are examples of the present invention: 1. the phenyl group, ...
[0144] In one or more embodiments, Formula 1-1 can be represented by Formula 1-1(1),
[0145] Formula 1-2 can be expressed by Formula 1-2(1), and
[0146] Formula 1-4 can be represented by one of Formulas 1-4(1), 1-4(2) and 1-4(3):
[0147]
[0148] In formula 1-1(1), L 1a , L 1b and L 1c can be independently determined by reference to L 1 The description provided is understood and Ar 1a ,Ar 1b and Ar 1c can be independently determined by reference to Ar 1 description provided.
[0149] In formula 1-2(1), L 2a and L 2b can be independently determined by reference to L 2 The description provided is understood, Ar 2a and Ar 2b can be independently determined by reference to Ar 2 The description provided is understood, and R 2a , R 2b , R 2c and R 2d can be independently determined by reference to R 2 description provided.
[0150] In formulas 1-4(1) to 1-4(3), L 6a and L 6b can be independently determined by reference to L 6 The description provided is understood, Ar 6a and Ar 6b can be independently determined by reference to Ar6 The description provided is understood, and R 3a -R 3j can be independently determined by reference to R 3 description provided.
[0151] In formula 1-1(1), Ar 1a ,Ar 1b and Ar 1c may be different from each other, and a compound having such a structure may have low crystallinity, thereby improving the solubility of the compound.
[0152] The first compound may include at least one of the following compounds:
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178] The first compound may be an electron transport host compound having electron transport capability, and may include a single first compound or a combination of two or more first compounds.
[0179] The amount of the first compound may be about 10 wt % or more and 80 wt % or less, for example, about 25 wt % or more and about 60 wt % or less, based on 100 wt % of the total mass of the first, second and third compounds.
[0180] In particular, in terms of further improving current efficiency, the amount of the first compound may be about 30 wt % or more and 50 wt % or less, based on 100 wt % of the total mass of the first compound, the second compound, and the third compound. In addition, in terms of further improving durability, the amount of the first compound may be about 35 wt % or more and 55 wt % or less, based on 100 wt % of the total mass of the first compound, the second compound, and the third compound.
[0181] In one or more embodiments, Formula 2-1 can be represented by Formula 2-1(1),
[0182] Formula 2-2 can be expressed by Formula 2-2(1),
[0183] Formula 2-3 can be represented by one of Formulas 2-3(1) to 2-3(3), and
[0184] Formula 2-4 can be expressed by one of Formulas 2-4(1) to 2-4(3):
[0185]
[0186]
[0187] R in Formulas 2-3(1) to 2-3(3) 20a and R 20b can be independently determined by reference to R 20 description provided.
[0188] R in Formulas 2-4(1) to 2-4(3) 23a and R 23b can be independently determined by reference to R 23 description provided.
[0189] The second compound may include at least one of the following compounds:
[0190]
[0191]
[0192]
[0193] The second compound may be a hole transport host compound having hole transport capability. A single second compound or a combination of two or more second compounds may be included.
[0194] The amount of the second compound may be about 10 wt % or more and 80 wt % or less, for example, about 25 wt % or more and about 60 wt % or less, based on 100 wt % of the total mass of the first, second and third compounds.
[0195] The third compound may include at least one of the following compounds:
[0196]
[0197]
[0198]
[0199]
[0200] A single third compound or a combination of two or more third compounds may be included.
[0201] The third compound is a compound having a HOMO-LUMO energy gap (Eg) of 3.3 eV or more, and is also referred to as a wide band gap compound. When the HOMO-LUMO energy gap (Eg) is less than 3.3 eV, the long life effect obtained by applying the wide band gap compound as the host material may be degraded. In addition, the upper limit of the HOMO-LUMO energy gap (Eg) is not limited, but may be 4 eV or less.
[0202] In an example, among such wide bandgap compounds, characteristics are considered in terms of solubility in a coating solvent to be used, emission color, and compatibility with the first compound (i.e., electron transport host), the second compound (i.e., hole transport host), and dopant materials used together.
[0203] The amount of the third compound may be about 15 wt % or more and 40 wt % or less, for example, about 16 wt % or more and 35 wt % or less, based on 100 wt % of the total mass of the first, second and third compounds.
[0204] When the host compounds having three different characteristics are mixed in a state where phase separation does not occur to form an emission layer according to a solution process, the electron injection barrier is reduced because the HOMO and LUMO energy levels become smooth. In addition, at the same time, the charge mobility can be controlled by adjusting the mixing ratio of the charge host compounds, thereby realizing a high-performance device.
[0205] In addition, since the first compound, the second compound and the third compound show high solubility in a solvent, film-forming (film formation) capability by wet coating such as solution coating is significantly applicable. In addition, when manufactured by solution coating, an organic light-emitting device including the first compound, the second compound and the third compound can have improved emission efficiency and emission lifetime.
[0206] In one or more embodiments, the first compound may include at least one compound represented by the above formula 1-1 or 1-4, the second compound may include at least one compound represented by the above formula 2-1 or 2-4, and the third compound may include at least one compound represented by the following formula 3-2:
[0207]
[0208] In formula 3-2,
[0209] X 21 Can be O or S,
[0210] L 23 -L 24 may be independently substituted or unsubstituted C 6 -C 30 Arylene,
[0211] c23 and c24 can each independently be 1, 2 or 3,
[0212] Ar 23 and Ar 24 may be independently selected from hydrogen and substituted or unsubstituted C 6 -C30 Aryl,
[0213] R 34 and R 35 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy, and
[0214] b34 and b35 may each independently be an integer of 0-3.
[0215] In one or more embodiments, the first compound may include at least one compound represented by the above formula 1-1, the second compound may include at least one compound represented by the above formula 2-1, and the third compound may include at least one compound represented by the following formula 3-1:
[0216]
[0217] In formula 3-1,
[0218] L 21 -L 22 may be independently selected from substituted or unsubstituted C 6 -C 30 Arylene,
[0219] c21 and c22 can each independently be 1, 2 or 3,
[0220] Ar 21 and Ar 22 may be independently selected from hydrogen and substituted or unsubstituted C 6 -C 30 Aryl, where Ar 21 and Ar 22 Each may not be hydrogen at the same time,
[0221] R 31 -R 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy,
[0222] b31 and b32 may each independently be an integer from 0 to 3, and
[0223] b33 can be an integer from 0 to 4.
[0224] In one or more embodiments, the first compound may include at least one compound represented by the above formula 1-1, the second compound may include at least one compound represented by the above formula 2-1, and the third compound may include at least one compound represented by the following formula 3-4:
[0225]
[0226] In formula 3-4,
[0227] L 28 -L 29 may be each independently a single bond or a substituted or unsubstituted C 6 -C 30 Arylene,
[0228] c28 and c29 can each independently be an integer of 1, 2 or 3,
[0229] Ar 28 may be selected from hydrogen and substituted or unsubstituted C 6 -C 30 Aryl,
[0230] R 38 -R 41 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, and substituted or unsubstituted C 1 -C 60 Alkoxy,
[0231] b38, b39 and b41 may each independently be an integer from 0 to 4, and
[0232] b40 can be an integer from 0 to 2.
[0233] By combining the first compound, the second compound, and the third compound as described above, an emission layer having excellent emission efficiency and excellent lifespan characteristics can be easily prepared due to excellent solubility in a solvent.
[0234] In one or more embodiments, the emission layer may further include a fluorescent dopant, a phosphorescent dopant, or a combination thereof.
[0235] For example, for the fluorescent dopant and the phosphorescent dopant, the following materials may be used. For example, the fluorescent dopant may include perylene or a derivative thereof, rubrene or a derivative thereof, coumarin or a derivative thereof, 4-(dicyanomethylene)-2-(p-dimethylaminophenylvinyl)-6-methyl-4H-pyran (DCM) or a derivative thereof, pyrene or a derivative thereof, and the phosphorescent dopant may include an iridium complex such as bis[2-(4,6-difluorophenyl)pyridine]picolinate iridium(III) (Firpic), bis(1-phenylisoquinoline)(acetylacetonate)iridium(III) (Ir(piq)) 2 (acac)), tris(2-phenylpyridine)iridium(III) (Ir(ppy) 3 ), tris(2-(3-p-xylyl)phenylpyridine)iridium(III) (dopant), etc., osmium complex, platinum complex, etc., but the embodiments of the present disclosure are not limited thereto.
[0236] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0237] The emission layer may be formed to a thickness of about 10 nm to about 60 nm.
[0238] When the organic light emitting device is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer. In one or more embodiments, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer may emit white light.
[0239] Organic light-emitting devices
[0240] In the following, we will discuss Figure 1 An organic light emitting device according to an embodiment is described. Figure 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.
[0241] According to an embodiment, the organic light-emitting device 100 includes a substrate 110, a first electrode 120 disposed on the substrate 110, a hole injection layer 130 disposed on the first electrode 120, a hole transport layer 140 disposed on the hole injection layer 130, an emission layer 150 disposed on the hole transport layer 140, an electron transport layer 160 disposed on the emission layer 150, an electron injection layer 170 disposed on the electron transport layer 160, and a second electrode 180 disposed on the electron injection layer 170.
[0242] The substrate 110 may be any substrate used in an organic light-emitting device according to the related art. For example, the substrate 110 may be a glass substrate, a silicon substrate, or a transparent plastic substrate, each of which has excellent mechanical strength, thermal stability, surface smoothness, ease of handling, and water resistance, but the embodiments of the present disclosure are not limited thereto.
[0243] The first electrode 120 may be formed on the substrate 110. The first electrode 120 may be, for example, an anode, and may be formed of a material having a high work function to facilitate hole injection, such as an alloy or a conductive compound. The first electrode 120 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The first electrode 120 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 120 may be made of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO). On the transparent first electrode 120, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be disposed to form a reflective electrode. In one or more embodiments, the first electrode 120 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto.
[0244] The hole transport region may be disposed on the first electrode 120 .
[0245] The hole transport region may include at least one of a hole injection layer 130 , a hole transport layer 140 , an electron blocking layer (not shown), and a buffer layer (not shown).
[0246] The hole transport region may include only the hole injection layer 130 or the hole transport layer 140. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the constituent layers are sequentially stacked in the stated order starting from the first electrode 120.
[0247] The hole injection layer 130 may include, for example, at least one of triphenylamine containing poly(ether ketone) (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper phthalocyanine, 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N '-diphenylbenzidine (NPB), 4,4',4"-tris(diphenylamino)triphenylamine (TDATA), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / 10-camphorsulfonic acid (PANI / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).
[0248] The hole injection layer 130 may be formed to a thickness of about 10 nm to about 1,000 nm, for example, about 10 nm to about 100 nm.
[0249] The hole injection layer 130 may include, for example, at least one of: a carbazole derivative such as 1,1-bis[(di-4-methylphenylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole, and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), and poly(9,9-dioctyl-fluorene-co-N-(4-butylphenyl)-diphenylamine (TFB).
[0250] The hole transport layer 140 may be formed to a thickness of about 10 nm to about 1,000 nm, for example, about 10 nm to about 150 nm.
[0251] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.
[0252] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are 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 compounds containing a cyano group such as the following compound HT-D1 or compound HT-D2, but are not limited thereto:
[0253]
[0254] Meanwhile, when the hole transport region includes a buffer layer, the material for forming the buffer layer may be the material for the hole transport region described above or the material for the host to be described later. However, the material for the buffer layer is not limited thereto.
[0255] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be the material for the hole transport region described above or the material for the host described later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP.
[0256] The emission layer 150 may be formed on the hole transport region. The emission layer 150 is a layer that emits light according to a fluorescence or phosphorescence mechanism. The emission layer 150 may include a host and / or a dopant, and the host may include the first compound, the second compound, and the third compound that are different from each other. The first compound, the second compound, and the third compound are the same as described above.
[0257] The electron transport region may be formed on the emission layer 150 .
[0258] The electron transport region may include at least one of a hole blocking layer (not shown), an electron transport layer 160 , and an electron injection layer 170 .
[0259] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.
[0260] For example, in order to prevent the diffusion of excitons or holes to the electron transport layer 160, the organic light emitting device 100 may include a hole blocking layer between the electron transport layer 160 and the emission layer 150. The hole blocking layer may include, for example, at least one of the following: Oxadiazole derivatives, triazole derivatives, BCP, Bphen, and BAlq, but materials therefor are not limited thereto:
[0261]
[0262] The thickness of the hole blocking layer may be For example When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a significant increase in driving voltage.
[0263] The electron transport layer 160 may include tris(8-hydroxyquinoline)aluminum (Alq 3 ), BAlq; compounds containing pyridine rings such as 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene); compounds containing triazine rings such as 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine; compounds containing imidazole rings such as 2-(4-(N-phenylbenzimidazol-1-yl-phenyl)-9,10-dinaphthylanthracene; compounds containing triazole rings such as TAZ and NTAZ; 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBi), BCP, Bphen, etc.:
[0264]
[0265] In one or more embodiments, the electron transport layer 160 may include commercially available KLET-01, KLET-02, KLET-03, KLET-10, KLET-M1 (available from Chemipro Kasei), and the like.
[0266] The electron transport layer 160 may further include a material containing a metal in addition to the materials described above.
[0267] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:
[0268]
[0269] The electron transport layer 160 may be formed, for example, to a thickness of about 15 nm to about 50 nm.
[0270] The electron injection layer 170 may be formed on the electron transport layer 160 .
[0271] The electron injection layer 170 may include, for example, a lithium compound such as 8-hydroxyquinoline lithium (Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li 2O), or barium oxide (BaO).
[0272] The electron injection layer 170 may be formed to a thickness of about 0.3 nm to about 9 nm.
[0273] The second electrode 180 may be formed on the electron injection layer 170. The second electrode 180 may be specifically a cathode, and may be formed of a material having a small work function among metals, alloys, conductive compounds, or combinations thereof. For example, a reflective electrode formed of a metal such as lithium (Li), magnesium (Mg), aluminum (Al), calcium (Ca), etc., or an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used as the second electrode 180. In one or more embodiments, the second electrode 180 having a thickness of about 20 nm or less may be formed of a metal or alloy thin film or a transparent conductive film such as indium tin oxide (In2O3). 2 O 3 -SnO 2 ) and indium zinc oxide (In 2 O 3 -ZnO) is formed.
[0274] In addition, the stacking structure of the organic light-emitting device 100 according to the embodiment is not limited to the above embodiment. The organic light-emitting device 100 according to the embodiment may be formed to have other known stacking structures. For example, in the organic light-emitting device 100, one or more layers among the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, and the electron injection layer 170 may be omitted, or another layer may be further included. In addition, each layer of the organic light-emitting device 100 may be a single layer or a multilayer.
[0275] The method of manufacturing each layer of the organic light emitting device 100 according to the embodiment is not particularly limited, and for example, various methods such as vacuum vapor deposition, solution coating, Langmuir-Blodgett (LB) deposition, etc. may be used.
[0276] The solution coating may include spin coating, casting, micro-gravure coating, gravure coating, rod coating, roller coating, wire rod coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, and the like.
[0277] The solvent used in solution coating may include toluene, xylene, diethyl ether, chloroform, ethyl acetate, dichloromethane, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, anisole, hexamethylphosphoric acid triamide, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, dioxane, cyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, methyl ethyl ketone, cyclohexanone, butyl acetate, 2-ethoxyethanol, ethyl acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, 1,2-hexanediol, methanol, ethanol, propanol, isopropanol, cyclohexanol, N-methyl-2-pyrrolidone, and the like. The solvent is not limited as long as it can dissolve the materials for forming each layer.
[0278] Considering coating properties and the like, the concentration of the composition used in solution coating may be, for example, about 0.1 wt % to about 10 wt %, and for example, about 0.5 wt % to about 5 wt %, but embodiments of the present disclosure are not limited thereto.
[0279] The conditions for vacuum deposition may vary depending on the material being used, the structure and thermal properties of the desired layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 - Approx. 10 -3 Torr vacuum pressure, and However, the conditions are not limited thereto.
[0280] In one or more embodiments, the first electrode 120 may be an anode, and the second electrode 180 may be a cathode.
[0281] For example, the first electrode 120 may be an anode, and the second electrode 180 may be a cathode. The organic light emitting device 100 may further include an organic layer including an emission layer 150 and disposed between the first electrode 120 and the second electrode 180, and the organic layer may further include a hole transport region between the first electrode 120 and the emission layer 150 and an electron transport region between the emission layer 150 and the second electrode 180, wherein the hole transport region may include at least one of the hole injection layer 130, the hole transport layer 140, the buffer layer, and the electron blocking layer, and the electron transport region may include at least one of the hole blocking layer, the electron transport layer 160, and the electron injection layer 170.
[0282] In one or more embodiments, the first electrode 120 may be a cathode, and the second electrode 180 may be an anode.
[0283] In the above, we have already discussed Figure 1An organic light emitting device according to an embodiment is described.
[0284] Description of Substituents
[0285] The expression “X and Y may each independently be” as used herein refers to a case where X and Y may be the same as each other, or a case where X and Y may be different from each other.
[0286] As used herein, the term "substituted" refers to a substituent such as R 11 The hydrogen atoms in the compounds may be further replaced by other substituents.
[0287] As used herein, the term "C 1 -C 60 The term “alkyl” refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 1,2-dimethylpropyl, n-hexyl, isohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl, 3-ethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3- Methylbutyl, n-octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropyl, 1-tert-butyl-2-methylpropyl, n-nonyl, 3,5,5-trimethyldecyl, n-decyl, isodecyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, etc.
[0288] As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.
[0289] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60The invention also includes a monovalent group represented by an alkyl group, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentyloxy group, an isopentyloxy group, a tert-pentyloxy group, a neopentyloxy group, an n-hexyloxy group, an isohexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group, an octadecyloxy group, a 2-ethylhexyloxy group, a 3-ethylpentyloxy group, and the like.
[0290] As used herein, the term "C 3 -C 30 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 30 carbon atoms participating in the ring, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C 3 -C 30 "Cycloalkylene" as used herein refers to a cycloalkylene group having a 3 -C 30 Cycloalkyl is a divalent group of the same structure.
[0291] As used herein, the term "C 1 -C 10 The "heterocycloalkyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl.
[0292] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one double bond in its ring and not having aromaticity, and detailed examples thereof are cyclopentenyl, cyclohexenyl and cycloheptenyl. The C used herein 3 -C 10 Cycloalkenylene refers to a group having a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.
[0293] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms, and at least one double bond in its ring. 1 -C 10 Detailed examples of the heterocycloalkenyl group are 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 1 -C 10Heterocycloalkenylene refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.
[0294] As used herein, the term "C 6 -C 30 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 30 carbon atoms participating in the ring (i.e., when substituted with a substituent, the atoms included in the substituent are not counted as carbon participating in the ring), and the term "C 6 -C 30 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 30 carbon atoms. 6 -C 30 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 30 Aryl and C 6 -C 30 When the arylene groups each include two or more rings, the rings may be fused to each other.
[0295] As used herein, the term "C 6 -C 30 "Aryloxy" refers to a 103 (A 103 C 6 -C 30 The invention also includes a group represented by an aryl group, and examples thereof include 1-naphthyloxy, 2-naphthyloxy, 2-azulyloxy and the like.
[0296] As used herein, the term "C 6 -C 30 "Arylthio" refers to -SA 104 (A 104 C 6 -C 30 A group represented by an aryl group.
[0297] As used herein, the term "C 1 -C 30 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom of N, O, Si, P, Se, Ge, B and S as a ring atom, and 1 to 30 carbon atoms. As used herein, the term "C 1 -C 30 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, Se, Ge, B and S as a ring atom, and 1 to 30 carbon atoms. 1 -C 30Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 5 -C 30 Heteroaryl and C 5 -C 30 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.
[0298] As used herein, the term "C 1 -C 30 "Heteroaryloxy" refers to a 105 (A 105 C 1 -C 30 Examples thereof include 2-furyloxy, 2-thienyloxy, 2-indolyloxy, 3-indolyloxy, 2-benzofuranyloxy, and 2-benzothienyloxy.
[0299] As used herein, the term "C 1 -C 30 "Heteroarylthio" refers to -SA 106 (A 106 C 1 -C 30 A group represented by a heteroaryl group.
[0300] As used herein, the term "C 7 -C 30 "Aralkyl" refers to an alkylene group attached to an aryl group, and is a 7 -C 30 The aralkyl group is a monovalent group in which the total carbon atoms of the alkylene group and the aryl group are 7 to 30. Examples thereof include benzyl, phenethyl, phenylpropyl, naphthylmethyl and the like.
[0301] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring atoms, and not having aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
[0302] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2-60 carbon atoms) having two or more rings fused to each other, having at least one heteroatom of N, O, P, Si, Se, Ge, B and S as a ring-forming atom in addition to carbon atoms, and not having aromaticity in terms of its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0303] As used herein, the term "C 5 -C 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. As used herein, the term "C 5 -C 30 The "carbocyclic group" refers to a monocyclic group or a polycyclic group, and refers to a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group according to its chemical structure.
[0304] As used herein, the term "C 1 -C 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from the group consisting of N, O, Si, P, Se, Ge, B and S as a ring atom in addition to 1 to 30 carbon atoms. As used herein, the term "C 1 -C 30 The "heterocyclic group" refers to a monocyclic group or a polycyclic group, and refers to a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group according to its chemical structure.
[0305] In this specification, substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be
[0306] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or any combination thereof;
[0307] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 ) at least one substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy;
[0308] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof;
[0309] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 ) at least one substituted C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof; or
[0310] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or any combination thereof, and
[0311] Q 11 -Q 19 , Q21 -Q 29 and Q 31 -Q 39 may be each independently 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, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, with at least one C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or a combination thereof substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group.
[0312] other
[0313] The expression "AB" refers to a range starting from A to B.
[0314] In the above, the embodiments of the present disclosure have been described with reference to the accompanying drawings, but the present disclosure is not limited to these embodiments. It will be clear to those skilled in the art that various modifications or changes can be made within the technical scope of the present disclosure. It will be understood that various modifications belong to the technical scope of the present disclosure.
[0315] Hereinafter, an organic light emitting device including an emission layer including three different compounds will be described in detail with reference to Examples and Comparative Examples. The following Examples are merely examples, and the organic light emitting device according to the embodiment is not limited to the following Examples.
[0316] Example
[0317] Synthesis Example
[0318] Synthesis of ET-Host-A to ET-Host-F, HT-Host-A to HT-Host-D, and WG-Host-A to WG-Host-F
[0319] ET-Host, HT-Host and WG-Host used in the examples can be prepared by coupling and substitution reactions known to those of ordinary skill in the art. Such reactions are known techniques and are described in detail in a variety of documents. For example, examples of the documents are Yamamoto, Progress in Polymer Science, Vol. 17, p 1153 (1992); Colon et al., Journal of Polymer Science, Part A, Polymer chemistry Edition, Vol. 28, P. 367 (1990); T. Ishiyama et al., J. Org. Chem. 1995 60, 7508-7510; M. Murata et al., J. Org. Chem. 1997 62, 6458-6459; M. Murata et al., J. Org. Chem. 2000 65, 164-168; L. Zhu et al., J. Org. Chem. 2003 68, 3729-3732; Stille, JK Angew. Chem. Int. Ed. Engl. 1986, 25, 508; Kumada, M. Pire. Appl. Chem. 1980, 52, 669; Negishi, E. Acc. Chem. Res. 1982, 15, 340; and US5,962,631, etc.
[0320] Synthesis of materials for forming hole transport layer (P-1 and FA-14)
[0321] Based on the method for preparing compound T disclosed in International Patent Application No. 2011 / 159872 (incorporated herein as a reference), a polymer P-1 represented by the following formula was synthesized. Here, the number average molecular weight (Mn) of the polymer P-1 measured by gel permeation chromatography (GPC) was 141,000 g / mol, and the weight average molecular weight (Mw) of the polymer P-1 was 511,000 g / mol:
[0322]
[0323] Additionally, FA-14 was synthesized according to US2016 / 0315259, which is incorporated herein by reference (see the formula below):
[0324]
[0325] Evaluation Example 1: Measurement of Energy Band Gap
[0326] The HOMO and LUMO energy levels of the WG-Host compound used in the examples were measured by a density functional theory (DFT) method of a Gaussian program (structural optimization performed at the level of B3LYP, 6-31G (d, p)), and the results thereof are shown in Table 1.
[0327] Table 1
[0328] Compound HOMO(eV) LUMO(eV) Bandgap energy (eV) WG-Host-A 6.25 2.86 3.39 WG-Host-B 6.61 2.73 3.88 WG-Host-C 6.22 2.86 3.36 WG-Host-D 6.24 2.80 3.44 WG-Host-E 6.25 2.71 3.54 WG-Host-F 6.19 2.76 3.36
[0329]
[0330] Example 1
[0331] Form it with A glass substrate having an indium tin oxide (ITO) electrode (also referred to as a first electrode or anode) with a thickness of 1000 Å was ultrasonically treated with distilled water. Once the washing with distilled water was completed, the glass substrate was ultrasonically treated with isopropyl alcohol, acetone, and methanol in the order stated, dried, and provided to a plasma cleaning machine. Next, the glass substrate was cleaned using oxygen plasma for 5 minutes and provided to a vacuum evaporator.
[0332] The compound PEDOT-PSS (available from Sigma-Aldrich) was coated on the ITO electrode of the glass substrate by spin coating and dried to form a A solution obtained by dissolving P-1 and FA-14 in an anisole solvent (P-1:FA-14=80:20 wt %) was applied on the hole injection layer by spin coating and dried to form a hole injection layer having a thickness of The hole transport layer has a thickness of .
[0333] Next, tris(2-(3-p-xylyl)phenylpyridine)iridium(III) (TEG, see the following formula) was dissolved in a methyl benzoate solvent to obtain a solution. The solution was mixed with the host compound materials listed in Table 2 below to obtain a composition for forming an emission layer including 4 wt % of solid matter (doping amount: 10 wt %). The composition was applied on the hole transport layer by spin coating and dried at a temperature of 240° C. for 30 minutes to form a The thickness of the emission layer.
[0334] On the emission layer, (8-hydroxyquinoline) lithium (Liq) and KLET-03 (available from ChemiPro Hwaseung Co., Ltd.) were co-deposited at a weight ratio of 1:1 by vacuum deposition to form a LiF is vacuum deposited on the electron transport layer to form an electron transport layer having a thickness of An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form A second electrode (also called a cathode) with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0335]
[0336] Examples 2-17 and Comparative Examples 1-10
[0337] An organic light emitting device was manufactured in the same manner as in Example 1, except that when preparing the composition for forming an emission layer, the host compounds listed in Table 2 were used at corresponding ratios.
[0338] Evaluation Example 2: Evaluation of Characteristics of Organic Light-Emitting Device (1)
[0339] The current efficiency and lifespan characteristics of the organic light emitting devices manufactured according to Examples 1 to 17 and Comparative Examples 1 to 10 were evaluated. The specific measurement method is as follows, and the results are shown in Table 2.
[0340] (1) Measurement of current efficiency
[0341] After applying voltage to the fabricated organic light-emitting device, the current was increased until the brightness reached 6,000 nits (cd / m 2 ) and keep it constant. Here, the current density (i.e., the current per unit area, A / m 2 ), and the brightness (cd / m 2 ) divided by the current density (A / m 2 ), and the current efficiency (cd / A) was calculated from this.
[0342] (2) Lifespan measurement
[0343] For each organic light-emitting device, the time (T 95 ).
[0344] Table 2
[0345]
[0346]
[0347]
[0348]
[0349] Examples 18-24
[0350] An organic light emitting device was manufactured in the same manner as in Example 1, except that when preparing a composition for forming an emission layer, the host compounds listed in Table 3 were used at corresponding ratios, and a platinum complex represented by the following formula was used as a dopant:
[0351]
[0352] Evaluation Example 3: Evaluation of Characteristics of Organic Light-Emitting Device (2)
[0353] The current efficiency and lifespan characteristics of the organic light emitting devices manufactured according to Examples 18 to 24 were evaluated. The specific measurement method was the same as described above, and the results are shown in Table 3.
[0354] Table 3
[0355]
[0356] Example 25 and Comparative Examples 11-12
[0357] An organic light-emitting device was manufactured in the same manner as in Example 1, except that when preparing a composition for forming an emission layer, the host compounds listed in Table 4 were used at corresponding ratios, and an iridium complex represented by the following formula was used as a dopant:
[0358]
[0359] Evaluation Example 4: Evaluation of Characteristics of Organic Light-Emitting Device (3)
[0360] The current efficiency and lifespan characteristics of the organic light emitting devices manufactured according to Example 25 and Comparative Examples 11-12 were evaluated. The specific measurement method was the same as described above, and the results are shown in Table 4.
[0361] Table 4
[0362]
[0363] Example 26 and Comparative Example 13
[0364] An organic light emitting device was manufactured in the same manner as in Example 1, except that when preparing a composition for forming an emission layer, the host compounds listed in Table 5 were used at corresponding ratios, and FIrPic represented by the following formula was used as a dopant:
[0365]
[0366] Evaluation Example 5: Evaluation of Characteristics of Organic Light-Emitting Device (4)
[0367] The current efficiency and lifespan characteristics of the organic light emitting devices manufactured according to Example 26 and Comparative Example 13 were evaluated. The specific measurement method was the same as described above, and the results are shown in Table 5.
[0368] Table 5
[0369]
[0370] Example 27 and Comparative Examples 14 and 15
[0371] An organic light-emitting device was manufactured in the same manner as in Example 1, except that when preparing a composition for forming an emission layer, the host compounds listed in Table 6 were used at corresponding ratios, and BlueDopant-A represented by the following formula was used as a dopant:
[0372]
[0373] Evaluation Example 6: Evaluation of Characteristics of Organic Light-Emitting Device (5)
[0374] The current efficiency and lifespan characteristics of the organic light emitting devices manufactured according to Example 27 and Comparative Examples 14 and 15 were evaluated. The specific measurement method was the same as described above, and the results are shown in Table 6.
[0375] Table 6
[0376]
[0377] With reference to Tables 2-6, it is confirmed that the organic light-emitting device manufactured according to the embodiment using the three main compounds disclosed herein shows a current efficiency (i.e., luminous efficiency) that is almost equivalent to or higher than the organic light-emitting device manufactured according to the comparative example, and also shows significantly improved life characteristics. In addition, the organic light-emitting device manufactured according to the embodiment shows good film-forming ability. Therefore, it is confirmed that the main compound disclosed herein is useful as a material for forming an organic light-emitting device by solution coating.
[0378] In addition, since the host compound used in the embodiment can form an emission layer of an organic light-emitting device by a coating method, the host compound is preferable in consideration of mass production.
[0379] According to one or more embodiments, since three different compounds are included in an emission layer of an organic light emitting device, the organic light emitting device exhibits improved efficiency and lifespan characteristics.
[0380] 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.
[0381] 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 as defined by the following claims.
Claims
1. Organic light-emitting device, comprising: a first electrode; a second electrode; as well as an emitting layer between the first electrode and the second electrode, wherein the emission layer comprises a first compound, a second compound and a third compound, The first compound is an electron transport host compound, The second compound is a hole transport host compound, The first compound is a compound represented by Formula 1-1, The second compound is a compound represented by one of Formulae 2-1 and 2-4, and The third compound includes at least one of the following: a dibenzofuran group, a dibenzothiophene group, a fluorene group, a bicarbazole group, or any combination thereof, wherein the band gap between the highest occupied molecular orbital energy level and the lowest unoccupied molecular orbital energy level of the third compound is 3.3 eV or greater: Among them, in formula 1-1, X 11 -X 16 are each independently C or N, X 11 -X 16 At least one of them is N, L1 is independently selected from a single bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted C1-C 30 a heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, Ar1 is independently selected from substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C1-C 30 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, a1 is an integer from 1 to 3, R1 is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, and substituted or unsubstituted C1-C 60 Alkoxy, b1 is an integer from 0 to 4, and In formulas 2-1 and 2-4, A4-A6 are each independently selected from C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic groups, L 11 , L 12 , and L 16 -L 18 are each independently selected from a single bond, a substituted or unsubstituted C6-C 30 an arylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, c11, c12, and c16-c18 are each independently an integer of 1-3, Ar 11 ,Ar 12 ,Ar 16 and Ar 17 are each independently selected from substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein Ar 16 and Ar 17 Each is not simultaneously naphthyl, R 11 -R 14 and R 22 -R 24 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, 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 C6-C 30 aryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, b11, b14, and b22-b24 are each independently an integer of 0-4, b12 and b13 are each independently an integer from 0 to 3, The third compound is a compound represented by one of the following formulae 3-2 to 3-4: Among them, in formulas 3-2 to 3-4, X 21 is O or S, L 23 -L 29 are each independently selected from a single bond, a substituted or unsubstituted C6-C 30 an arylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, c23-c29 are each independently an integer of 1-3, Ar 23 and Ar 24 are each independently selected from substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Ar 25 -Ar 28 are each independently selected from hydrogen, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Ar 26 and Ar 27 are optionally linked to each other via a single bond to form a fused ring, R 34 -R 41 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, and substituted or unsubstituted C1-C 60 Alkoxy, b34, b35, b36 and b40 are each independently an integer from 0 to 3, and b37, b38, b39 and b41 are each independently an integer of 0-4, In the definition of formula 1-1, the substituted C6-C 30 Arylene, substituted C1-C 30 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-C 60 Alkoxy, substituted C6-C 30 Aryl, substituted C1-C 30 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: 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 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, and C1-C 60 Alkoxy; Each is selected from 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, 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, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 ) at least one substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, and 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, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Each is selected from 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 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, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 ) at least one substituted 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, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group; or -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、and -P(=O)(Q 38 )(Q 39 ), and In the definitions of Formulae 2-1, 2-4, and 3-2 to 3-4, the substituted C6-C 30 Arylene, 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-C 60 Alkoxy, substituted C6-C 30 At least one substituent of the aryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: 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 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, and C1-C 60 Alkoxy; Each is selected from 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, 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 group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 ) at least one substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, and 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 an arylthio group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group; Each is selected from 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 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 group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 ) at least one substituted 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 an arylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; or -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、and -P(=O)(Q 38 )(Q 39 ), Where Q 11 -Q 19 , Q 21 -Q 29 and Q 31 -Q 39 are each independently hydrogen, 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, 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, C1-C 60 Alkyl and C6-C 60 At least one substituted C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 an arylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
2. The organic light emitting device according to claim 1, wherein L1 is each independently selected from a single bond, phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, py ... phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronaphenylene, ovaphenylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, pyrazolylene Azolyl, Isopropylidene oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, benzofuranyl ... Azolyl, isobenzoyl Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, and dibenzocarbazolylene; or Each is selected from 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, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, at least one substituted phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanth ... phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronaphenylene, ovaphenylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, Isothiazolylidene, Azolyl, Isopropylidene oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzofuranyl, benzothiophenyl, benzofuranyl ... Azolyl, isobenzoyl Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenylene, benzocarbazolylene, and dibenzocarbazolylene, and L 11 , L 12 , and L 16 -L 18 Each of the following is independently selected from a single bond, phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, py ... phenylene, tetraphenylene, perylenene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinyl, coronenylenyl, ovaphenylene, benzocarbazolylene, and dibenzocarbazolylene; or Each is selected from 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, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, at least one substituted phenylene group selected from the group consisting of phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, phenanth ... The invention also includes phenylene, tetraphenylene, perylenene, pentaphenylene, hexaphenylene, pentaphenylene, rubidinylene, coronenylene, ovophenylene, benzocarbazolylene, and dibenzocarbazolylene.
3. The organic light emitting device according to claim 1, wherein Ar1 is each independently selected from: Phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indolodibenzofuranyl, indolodibenzothiophenyl, indolofluorenyl, indolospiro-bifluorenyl, indolophenanthrenyl, indolobenzo[9,10]phenanthrenyl, indoloazadibenzofuranyl, and indoloazadibenzothiophenyl; or Each is selected from 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, at least one substituted phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indolodibenzofuranyl, indolodibenzothienyl, indolofluorenyl, indolospiro-bifluorenyl, indolophenanthrenyl, indolobenzo[9,10]phenanthrenyl, indoloazadibenzofuranyl, and indoloazadibenzothienyl.
4. The organic light emitting device according to claim 1, wherein R1 is each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, and C1-C 20 Alkoxy; and Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, and C1-C 20 At least one substituted C1-C 20 Alkyl and C1-C 20 Alkoxy.
5. The organic light emitting device according to claim 1, wherein A4, A5 and A6 are each independently selected from a benzene group, a naphthyl group, an anthracene group, a thiophene group, a furan group, a pyrrole group, an indole group, an indene group, a benzothiorrole group, a benzothiophene group, a benzofuran group, a carbazole group, a fluorene group, a dibenzothiorrole group, a dibenzothiophene group, a dibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo oxadiazole group, and benzothiadiazole group.
6. The organic light emitting device according to claim 1, wherein Ar 11 ,Ar 12 ,Ar 16 , and Ar 17 Each independently selected from: Phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, A group represented by formula a is selected from the group consisting of: a naphthacene, a tetraphenylene, a perylenene, a pentaphenylene, a hexaphenylene, a pentacene, a rubinyl, a coronene, an ovophenyl, a benzocarbazolyl, a dibenzocarbazolyl, and a group represented by formula a; or Each is selected from 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronene, ovalenyl, benzocarbazolyl, dibenzocarbazolyl, and -N(Q 11 )(Q 12 ) is at least one substituted phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a group represented by the formula a, Ar 16 and Ar 17 are not each a naphthyl group at the same time, and Q 11 and Q 12 Each is independently phenyl, biphenyl, terphenyl, or naphthyl: Formula a in, In formula a, R4-R6 are each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, and C1-C 20 Alkoxy; and Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, and C1-C 20 At least one substituted C1-C 20 Alkyl and C1-C 20 Alkoxy, "*" indicates the binding site with the adjacent atom, b4 and b5 are independently integers from 0 to 4, and b6 is an integer from 0 to 2.
7. The organic light emitting device according to claim 1, wherein R 11 -R 14 and R 22 -R 24 Each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, and C1-C 20 Alkoxy; C1-C ... 20 Alkyl and C1-C 20 Alkoxy; phenyl, biphenyl, terphenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, benzocarbazolyl, and dibenzocarbazolyl; and phenyl, biphenyl, terphenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, benzocarbazolyl, and dibenzocarbazolyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, and cyano; 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, benzocarbazolyl, and dibenzocarbazolyl.
8. The organic light emitting device according to claim 1, wherein Ar 23 and Ar 24 Each independently selected from: Phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, phenyl, tetraphenyl, perylenyl, pentaphenyl, hexaphenyl, pentacene, rubenyl, coronenyl, and ovalenyl; and Each is selected from 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, anthracenyl, fluoranthenyl, pyrenyl, at least one substituted phenyl group selected from the group consisting of phenyl, tetraphenyl, phenanthrenyl, peryl, pentaphenyl, hexaphenyl, pentacene, rubenyl, coronenyl, and ovalenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, phenyl, tetraphenyl, perylenyl, pentaphenyl, hexaphenyl, pentacene, rubidinyl, coronenyl, and ovalenyl, and Ar 25 -Ar 28 Each independently selected from: hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, phenyl, tetraphenyl, perylenyl, pentaphenyl, hexaphenyl, pentacene, rubenyl, coronenyl, and ovalenyl; and Each is selected from 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, phenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, anthracenyl, fluoranthenyl, pyrenyl, at least one substituted phenyl group selected from the group consisting of phenyl, tetraphenyl, phenanthrenyl, peryl, pentaphenyl, hexaphenyl, pentacene, rubenyl, coronenyl, and ovalenyl, biphenyl, terphenyl, quaterphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, The following are examples of the present invention:
1. the phenyl group, ...
9. The organic light emitting device according to claim 1, wherein Formula 1-1 is represented by Formula 1-1(1), in, In formula 1-1(1), L 1a , L 1b and L 1c It is understood by reference to the description provided with respect to L1 of claim 1, and Ar 1a ,Ar 1b and Ar 1c This is understood by referring to the description provided with respect to Ar1 of claim 1.
10. The organic light emitting device according to claim 1, wherein The first compound includes at least one of the following compounds:
11. The organic light emitting device according to claim 1, wherein Formula 2-1 is represented by Formula 2-1(1), and Formula 2-4 is represented by one of Formulas 2-4(1) to 2-4(3): in, In formulas 2-4(1) to 2-4(3), R 23a and R 23b By reference to R of claim 1 23 description provided.
12. The organic light emitting device according to claim 1, wherein The second compound includes at least one of the following compounds:
13. The organic light emitting device according to claim 1, wherein The third compound includes at least one of the following compounds:
14. The organic light emitting device according to claim 1, wherein The first compound includes at least one compound represented by Formula 1-1, The second compound includes at least one compound represented by Formula 2-1 or 2-4, and The third compound includes at least one compound represented by Formula 3-2: in, In formula 3-2, X 21 is O or S, L 23 -L 24 are each independently selected from substituted or unsubstituted C6-C 30 Arylene, c23 and c24 are each independently 1, 2 or 3, Ar 23 and Ar 24 are each independently substituted or unsubstituted C6-C 30 Aryl, R 34 and R 35 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, and substituted or unsubstituted C1-C 60 Alkoxy, and b34 and b35 are each independently an integer of 0-3.
15. The organic light emitting device according to claim 1, wherein The first compound includes at least one compound represented by Formula 1-1, and The second compound includes at least one compound represented by Formula 2-1.
16. The organic light emitting device according to claim 1, wherein The first compound includes at least one compound represented by Formula 1-1, The second compound includes at least one compound represented by Formula 2-1, and The third compound includes at least one compound represented by Formula 3-4: in, In formula 3-4, L 28 and L 29 are each independently selected from a single bond and a substituted or unsubstituted C6-C 30 Arylene, c28 and c29 are each independently 1, 2 or 3, Ar 28 is selected from hydrogen and substituted or unsubstituted C6-C 30 Aryl, R 38 -R 41 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, and substituted or unsubstituted C1-C 60 Alkoxy, b38, b39 and b41 are each independently an integer from 0 to 4, and b40 is an integer from 0 to 2.
17. The organic light emitting device according to claim 1, wherein The emission layer further includes a fluorescent dopant, a phosphorescent dopant, or a combination thereof.
18. A light emitting device comprising the organic light emitting device according to any one of claims 1 to 17.
19. An electronic device comprising the organic light emitting device according to any one of claims 1 to 17.
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