Light-emitting device, electronic apparatus, electronic equipment, and heterocyclic compound
By using specific heterocyclic compounds in the light emitting device, the color purity and driving voltage of the light emitting device are improved, and the shortcomings of the light emitting device in the prior art are solved in these aspects, and better luminous performance and lifetime are achieved.
Patent Information
- Application Number
- CN202411549988.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-11-09
- Filing Date
- 2024-11-01
- Publication Date
- 2025-05-09
AI Technical Summary
The existing light emitting devices have room for optimization in terms of viewing angle width, contrast, response time and brightness driving voltage, especially in terms of the improvement of color purity and driving voltage.
A heterocyclic compound represented by formula 1, the specific structure includes a variety of substituents and cyclic groups, is used to construct an intermediate layer and an emitting layer of the light emitting device, thereby improving energy transfer and luminous emitting properties.
By using heterocyclic compounds, the color purity and driving voltage of the light emitting device are improved while extending the life characteristics of the device.
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Figure CN119954851A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0154571 filed in the Korean Intellectual Property Office on November 9, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The embodiments relate to a light emitting device including a heterocyclic compound, an electronic device including the light emitting device, an electronic equipment including the light emitting device, and the heterocyclic compound. Background Art
[0004] The light emitting device is a self-emitting device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] In the light-emitting device, the first electrode may be located on the substrate, and the hole transport region, the emission layer, the electron transport region, and the second electrode may be sequentially arranged on the first electrode. The holes provided from the first electrode move toward the emission layer through the hole transport region, and the electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers such as 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.
[0006] It should be understood that this background section is intended, in part, to provide a useful background for understanding the present technology. However, this background section may also include ideas, concepts, or realizations that were not part of what was known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention
[0007] Embodiments include a light emitting device including a heterocyclic compound, an electronic device including the light emitting device, electronic equipment including the light emitting device, and the heterocyclic compound.
[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of embodiments of the disclosure.
[0009] According to an embodiment, a light emitting device may include a first electrode, a second electrode facing the first electrode, an intermediate layer between the first electrode and the second electrode and including an emission layer, and a heterocyclic compound represented by Formula 1:
[0010]
[0011] In equation 1 and equation 2,
[0012] X1 It can be C(R 7 ) or N,
[0013] X 2 It can be C(R 8 ) or N,
[0014] X 3 It can be C(R 9 ) or N,
[0015] X 1 To X 3 At least one of can be N,
[0016] Ar 1 and Ar 2 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 A heterocyclic group or a group represented by Formula 2,
[0017] CY 1 and CY 2 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0018] T can be a single bond, a double bond, N(R 10 )、C(R 10 )(R 11 )、Si(R 10 )(R 11 ), S or O,
[0019] a1 can be an integer from 1 to 4,
[0020] a2 to a4 can each independently be an integer from 1 to 5,
[0021] a5 and a6 can each independently be an integer from 1 to 10,
[0022] When a1 is 2 or greater, a1 R 1 can be the same or different from each other,
[0023] When a2 is 2 or greater, a2 R 2 can be the same or different from each other,
[0024] When a3 is 2 or greater, a3 R 3 can be the same or different from each other,
[0025] When a4 is 2 or greater, a4 R 4 can be the same or different from each other,
[0026] When a5 is 2 or greater, a5 R 5 can be the same or different from each other,
[0027] When a6 is 2 or greater, a6 R 6 can be the same or different from each other,
[0028] R 1 To R 11 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3)、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0029] a2R 2 、a3R 3 and a4 R 4 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl,
[0030] R 10a Can be:
[0031] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0032] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11)、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0033] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0034] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31)(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0035] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Can be independently:
[0036] Hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0037] In an embodiment, the first electrode may be an anode, the second electrode may be a cathode, the intermediate layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer or any combination thereof.
[0038] In an embodiment, the intermediate layer may include the heterocyclic compound.
[0039] In an embodiment, the emission layer may include the heterocyclic compound.
[0040] In an embodiment, the emission layer may include a host and a dopant, and the host may include the heterocyclic compound.
[0041] The embodiment provides an electronic device which may include the light emitting device.
[0042] In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
[0043] An embodiment provides electronic equipment which may include the light emitting device.
[0044] In an embodiment, the electronic equipment can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a mobile phone or a tablet phone), a tablet personal computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays spliced together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0045] The examples provided herein illustrate heterocyclic compounds that may be represented by Formula 1.
[0046] In an embodiment, the heterocyclic compound may include at least one deuterium atom.
[0047] In an embodiment, X 1 To X 3 They can each be N.
[0048] In the embodiment, Ar 1 and Ar 2 At least one of them may each independently be a group represented by Formula 2.
[0049] In the embodiment, CY 1 and CY 2 can be each independently unsubstituted or substituted with at least one R 10aSubstituted phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolyl benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl
[0050] In an embodiment, in Formula 1, Can be different from each other.
[0051] In an embodiment, the heterocyclic compound may be represented by one of Formula 1-1 to Formula 1-3 described below.
[0052] In an embodiment, R 1 To R 11 Can be independently:
[0053] Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano;
[0054] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0055] Morpholinyl, phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, phenyl, pyridyl or any combination thereof.
[0056] In the embodiment, a2 R 2 、a3R 3 and a4 R 4 At least one of them can be independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each of which is unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro.
[0057] In an embodiment, the heterocyclic compound may satisfy at least one of Conditions I to III described below.
[0058] In an embodiment, the heterocyclic compound represented by Formula 1 may be one of Compounds 1 to 35 described below.
[0059] It should be understood that the above embodiments are described in a general and illustrative sense only and not for limiting purposes, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0060] The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and its principles. The above and other aspects and features of the present disclosure will become more apparent by describing the embodiments of the present disclosure in detail with reference to the accompanying drawings, in which:
[0061] Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;
[0062] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0063] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0064] Figure 4 is a schematic perspective view of an electronic device according to an embodiment;
[0065] Figure 5 is a schematic perspective view of the exterior of a vehicle as an electronic equipment including a light emitting device according to an embodiment; and
[0066] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0067] The present disclosure will now be described more fully below with reference to the accompanying drawings showing embodiments. However, the present disclosure may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. On the contrary, these embodiments are provided so that the present disclosure will be thorough and complete, and will fully convey the scope of the present disclosure to those skilled in the art.
[0068] In the drawings, the size, thickness, ratio and dimensions of elements may be exaggerated for convenience of description and clarity. The same reference numerals and / or the same reference symbols refer to the same elements throughout.
[0069] In the description, it will be understood that when an element (or region, layer, component, etc.) is referred to as being "on" another element, "connected to" or "coupled to" another element, the element may be directly on, directly connected to or directly coupled to the other element, or one or more intervening elements may be present between the element and the other element. In a similar sense, when an element (or region, layer, component, etc.) is described as "covering" another element, it may directly cover the other element, or one or more intervening elements may be present between the element and the other element.
[0070] In the description, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without an additional element, such as an adhesive element, between the two layers or two elements.
[0071] As used herein, expressions used in the singular such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0072] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a conjunctive or disjunctive sense and may be understood to be equivalent to "and / or".
[0073] In the specification and claims, for the purpose of its meaning and interpretation, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of..." For example, "at least one of A, B, and C" can be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, AC, BC, or AB. When the term "at least one of" precedes or follows a list of elements, it modifies the entire list of elements, rather than the individual elements in the list.
[0074] It will be understood that, although the terms first, second, etc. can be used in this article to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teaching of the present disclosure, the first element can be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element can be referred to as the first element.
[0075] For ease of description, spatially relative terms such as "below", "below", "below", "above", or "on" may be used herein to describe the relationship between one element or component and another element or component as shown in the figures. It will be understood that, in addition to the orientations depicted in the drawings, spatially relative terms are intended to cover different orientations of the device in use or operation. For example, in the case of a device shown in a flipped drawing, a device positioned "below" or "below" another device may be positioned "above" another device. Thus, the exemplary term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and thus the spatially relative terms may be interpreted differently depending on the orientation.
[0076] The terms "about" or "approximately" as used herein include the stated value and mean within an acceptable range of deviation from the stated value determined by one of ordinary skill in the art, taking into account the measurements in question and errors associated with the measurement of the stated quantity (e.g., limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.
[0077] It should be understood that the terms “comprises / comprising,” “includes / including,” “have / having,” and “contains / containing” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
[0078] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as those commonly understood by those skilled in the art to which the present disclosure belongs. It will be further understood that, unless explicitly defined in the specification, terms (such as those defined in commonly used dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and should not be interpreted in an ideal or overly formal sense.
[0079] According to an embodiment, the light emitting device may include: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1:
[0080]
[0081]
[0082] In equation 1 and equation 2,
[0083] X 1 It can be C(R 7 ) or N,
[0084] X 2 It can be C(R 8 ) or N,
[0085] X 3 It can be C(R 9 ) or N,
[0086] X 1 To X 3 At least one of them can each be N,
[0087] Ar 1 and Ar 2 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1-C 60 A heterocyclic group or a group represented by Formula 2,
[0088] CY 1 and CY 2 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0089] T can be a single bond, a double bond, N(R 10 )、C(R 10 )(R 11 )、Si(R 10 )(R 11 ), S or O,
[0090] a1 can be an integer from 1 to 4,
[0091] a2 to a4 can each independently be an integer from 1 to 5,
[0092] a5 and a6 can each independently be an integer from 1 to 10,
[0093] When a1 is 2 or greater, a1 R 1 can be the same or different from each other,
[0094] When a2 is 2 or greater, a2 R 2 can be the same or different from each other,
[0095] When a3 is 2 or greater, a3 R 3 can be the same or different from each other,
[0096] When a4 is 2 or greater, a4 R 4 can be the same or different from each other,
[0097] When a5 is 2 or greater, a5 R 5 can be the same or different from each other,
[0098] When a6 is 2 or greater, a6 R 6 can be the same or different from each other,
[0099] R 1 To R 11 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0100] a2R 2 、a3R 3 and a4 R 4 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl,
[0101] R 10a Can be:
[0102] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0103] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0104] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0105] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0106] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; Br; -I; hydroxyl; cyano; nitro; or C 1 -C 60 Alkyl, C 2 -C 60Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0107] In an embodiment, the heterocyclic compound may include at least one deuterium atom.
[0108] In the embodiment, a1 R 1 、a2R 2 、a3R 3 、a4R 4 、a5R 5 and a6 R 6 At least one of each may be deuterium.
[0109] In an embodiment, X 1 To X 3 Two of them can be N.
[0110] In an embodiment, X 1 To X 3 They can each be N.
[0111] In the embodiment, Ar 1 and Ar 2 Can be identical to each other.
[0112] In the embodiment, Ar 1 and Ar 2 Can be different from each other.
[0113] In the embodiment, Ar 1 and Ar 2 At least one of them may each independently be a group represented by Formula 2.
[0114] In the embodiment, Ar 1 and Ar 2 They may each independently be a group represented by Formula 2.
[0115] In the embodiment, CY 1 and CY 2 can be each independently unsubstituted or substituted with at least one R 10aSubstituted cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, 1-Hexyl, yl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolecarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthothiophenyl, benzonaphthothiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzofuranyl, dibenzothiophenyl, benzothiophene and dibenzothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, indazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl 1-4-nitro-2-oxo-1-yl, ...
[0116] In the embodiment, CY 1 and CY 2 can be each independently unsubstituted or substituted with at least one R 10aSubstituted phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolyl benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl
[0117] In an embodiment, T may be a single bond.
[0118] In the embodiment, a2 R 2 At least one of a3 R 3 At least one and a4 R 4 At least one of may be independently different.
[0119] In an embodiment, in Formula 1, Can be different from each other.
[0120] In an embodiment, R 2 To R 4 Can be different from each other.
[0121] In an embodiment, the heterocyclic compound may be represented by one of Formula 1-1 to Formula 1-3:
[0122]
[0123] In Formula 1-1 to Formula 1-3,
[0124] X 1 To X 3 ,Ar 1 ,Ar 2 , a1 to a4 and R 1 To R 4 may each be the same as described in Formula 1.
[0125] In an embodiment, R 1 To R 11 Can be independently:
[0126] Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano;
[0127] C unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, cyano or any combination thereof 1 -C 20 Alkyl; or
[0128] C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 alkyl or any combination thereof.
[0129] In an embodiment, R 1 To R 11 Can be independently:
[0130] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 alkyl;
[0131] Deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, nitro, C 1 -C 10 C substituted with at least one of alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl and pyrimidyl. 1 -C 20 alkyl;
[0132] Phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, C 1 -C 20Alkyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) and -B(Q 31 )(Q 32 ) is replaced by at least one of; or
[0133] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 ) or -B(Q 1 )(Q 2 ),and
[0134] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0135] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0136] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each of which is unsubstituted or substituted with deuterium, C 1 -C 10 The present invention is substituted with at least one of an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group and a triazinyl group.
[0137] In an embodiment, R 1 To R 11 Can be independently:
[0138] Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano;
[0139] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0140] Morpholinyl, phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, phenyl, pyridyl or any combination thereof.
[0141] In the embodiment, a2 R 2 、a3R 3 and a4 R 4 At least one of them may be independently unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, cyano, nitro and C 1 -C 10 At least one substituted C 1 -C 20 alkyl.
[0142] In the embodiment, a2 R 2 、a3R 3 and a4 R4 At least one of them can be independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, which are each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro.
[0143] In the embodiment, a2 R 2 、a3R 3 and a4 R 4 At least one of them can be independently: morpholinyl, phenyl, biphenyl or terphenyl, each of which is unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, phenyl, pyridyl or a combination thereof.
[0144] In an embodiment, the heterocyclic compound may satisfy at least one of conditions I to III:
[0145] [Condition I]
[0146] When a2 R 2 One of them is unsubstituted or replaced by at least one R 10a When the phenyl group is substituted, a3 R 3 and a4 R 4 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl;
[0147] [Condition II]
[0148] When a3 R 3 One of them is unsubstituted or replaced by at least one R 10a In the case of substituted phenyl, a2 R 2 and a4 R 4 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl; and
[0149] [Condition III]
[0150] When a4R 4 One of them is unsubstituted or replaced by at least one R 10aIn the case of substituted phenyl, a2 R 2 and a3 R 3 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl.
[0151] In an embodiment, the heterocyclic compound may satisfy at least one of conditions A to F:
[0152] [Condition A]
[0153] a2R 2 One of them may be unsubstituted or substituted with at least one R 10a substituted phenyl, and a3 R 3 At least one of may be unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, where R 3 may not be phenyl, and R 4 It may not be phenyl or C 1 -C 60 alkyl;
[0154] [Condition B]
[0155] a2R 2 One of them may be unsubstituted or substituted with at least one R 10a substituted phenyl, and a4 R 4 At least one of may be unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, where R 4 may not be phenyl, and R 3 It may not be phenyl or C 1 -C 60 alkyl;
[0156] [Condition C]
[0157] a3R 3 One of them may be unsubstituted or substituted with at least one R 10a substituted phenyl, and a2 R 2 At least one of may be unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, where R 2 may not be phenyl, and R 4 It may not be phenyl or C 1 -C60 alkyl;
[0158] [Condition D]
[0159] a3R 3 One of them may be unsubstituted or substituted with at least one R 10a substituted phenyl, and a4 R 4 At least one of may be unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, where R 4 may not be phenyl, and R 2 It may not be phenyl or C 1 -C 60 alkyl;
[0160] [Condition E]
[0161] a4R 4 One of them may be unsubstituted or substituted with at least one R 10a substituted phenyl, and a2 R 2 At least one of may be unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, where R 2 may not be phenyl, and R 3 It may not be phenyl or C 1 -C 60 Alkyl; and
[0162] [Condition F]
[0163] a4R 4 One of them may be unsubstituted or substituted with at least one R 10a substituted phenyl, and a3 R 3 At least one of may be unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, where R 3 may not be phenyl, and R 2 It may not be phenyl or C 1 -C 60 alkyl.
[0164] In an embodiment, the heterocyclic compound represented by Formula 1 may be one of Compound 1 to Compound 35:
[0165]
[0166]
[0167] The heterocyclic compound may be a compound having a structure represented by Formula 1, wherein in Formula 1, a2 R 2 、a3R 3 and a4 R 4 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl.
[0168] According to the heterocyclic compound according to the embodiment, unlike the compound satisfying a two-dimensional (2D) planar structure in the related art, since the heterocyclic compound is bonded to -Si(Ph) 3 The substituent of the phenyl group satisfies the three-dimensional (3D) structure and the asymmetric structure, so when the material is deposited, the accumulation of the material in the deposition source can be prevented. Therefore, the process stability can be improved by the heterocyclic compound.
[0169] The heterocyclic compound can improve the color purity and driving voltage of a light-emitting device, and in a light-emitting device including the heterocyclic compound, energy transfer in the device can be promoted, thereby obtaining improved lifespan characteristics.
[0170] A person of ordinary skill in the art may recognize a method for synthesizing the heterocyclic compound represented by Formula 1 by referring to the following Synthesis Examples and / or Examples.
[0171] At least one heterocyclic compound represented by Formula 1 may be used in a light emitting device (e.g., an organic light emitting device). Therefore, according to an embodiment, the light emitting device may include: a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer may include the heterocyclic compound represented by Formula 1.
[0172] In an embodiment, the first electrode of the light emitting device may be an anode,
[0173] The second electrode of the light emitting device may be a cathode,
[0174] The intermediate layer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode.
[0175] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0176] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0177] In an embodiment, the intermediate layer may include a heterocyclic compound.
[0178] In an embodiment, the emission layer may include a heterocyclic compound.
[0179] In an embodiment, the light emitting device may further include a capping layer outside the second electrode, and the capping layer may include a heterocyclic compound.
[0180] In an embodiment, the light emitting device may further include:
[0181] a first covering layer outside the first electrode; and
[0182] a second covering layer outside the second electrode,
[0183] Herein, a heterocyclic compound may be included in the first covering layer or the second covering layer.
[0184] In an embodiment, the emission layer may include a host and a dopant, and the host may include a heterocyclic compound.
[0185] In an embodiment, the dopant may be a phosphorescent dopant or a delayed fluorescent dopant.
[0186] In an embodiment, the host may include a first host including at least one electron donating group and a second host including at least one electron withdrawing group.
[0187] In an embodiment, the emissive layer may further include a sensitizer.
[0188] In an embodiment, the emitting layer may include a delayed fluorescent material.
[0189] In an embodiment, the emissive layer may emit blue light.
[0190] In an embodiment, the emission layer may further include a first host and a second host, wherein the first host may be a hole transport compound including at least one electron donating group, and the second host may be an electron transport host including at least one electron withdrawing group.
[0191] In an embodiment, the emission layer may further include a third compound, and the third compound may be a metal-containing compound.
[0192] In an embodiment, the third compound may function as a sensitizer, such as a phosphorescent sensitizer.
[0193] In an embodiment, the third compound may not emit light.
[0194] In an embodiment, the emission layer may further include at least one of an auxiliary dopant and a sensitizer.
[0195] In an embodiment, the auxiliary dopant and the sensitizer may each independently be an organometallic compound including Pt and a tetradentate ligand bonded to Pt, wherein the tetradentate ligand may include a carbene portion chemically bonded to Pt. In an embodiment, the auxiliary dopant and / or the sensitizer may include a third compound.
[0196] In an embodiment, the first host and the second host may serve as exciplex hosts.
[0197] In the specification, the term "electron donating group" may refer to any moiety having electron donating ability, and may be, for example, a π-electron-rich C 3 -C 60 The electron donating group may refer to a nitrogen-containing C 1 -C 60 Cyclic groups other than cyclic groups.
[0198] In the specification, the term "electron withdrawing group" may refer to any part having electron withdrawing ability, and may be, for example, -F, -CFH 2 , -CF 2 H, -CF 3 、-CN、-NO 2 , π-electron-deficient nitrogen-containing C 1 -C 60 A cyclic group or any combination thereof. However, the embodiment is not limited thereto.
[0199] Regarding the light emission path in the light emitting device according to the embodiment, the first host and the second host can form an exciplex (first step), energy can be transferred from the exciplex to the third compound (second step), and energy can be transferred from the third compound to the organic metal compound (third step).
[0200] In an embodiment, an amount of the third compound in the emission layer may be greater than 0 parts by weight and less than 50 parts by weight based on a total of 100 parts by weight of the emission layer.
[0201] In an embodiment, the first host may include at least one carbazole moiety, and the second host may include at least one azine moiety.
[0202] In an embodiment, the first body may be represented by Formula 301-1A or Formula 301-2A:
[0203]
[0204] In Formula 301-1A and Formula 301-2A,
[0205] Ring A 301 To Ring A 304may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0206] X 301 Can be O, S, N[(L 304 ) xb4 -R 304a ]、C(R 304a )(R 304b ) or Si(R 304a )(R 304b ),
[0207] X 302 Can be single bond, O, S, N[(L 305 ) xb5 -R 305a ]、C(R 305a )(R 305b ) or Si(R 305a )(R 305b ),
[0208] X 303 Can be single bond, O, S, N[(L 306 ) xb6 -R 306a ]、C(R 306a )(R 306b ) or Si(R 306a )(R 306b ),
[0209] xb22 and xb23 may each independently be an integer from 0 to 10,
[0210] L 301 To L 307 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0211] xb1 to xb7 may each independently be an integer from 0 to 5,
[0212] R 301 To R 303 , R 304a To R 306a , R304b To R 306b and R 311 To R 314 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),and
[0213] Q 301 To Q 303 can be independently related to Q 1 Same as described.
[0214] In an embodiment, the first host may be one of compounds HTH1 to HTH56, but the embodiment is not limited thereto:
[0215]
[0216]
[0217]
[0218] In an embodiment, the second body may be represented by equation 302:
[0219] In formula 302,
[0220] X 321 It can be C(R 321 ) or N,
[0221] X 322 It can be C(R 322 ) or N,
[0222] X 323 It can be C(R 323 ) or N,
[0223] X 321 To X 323 At least one of can be N,
[0224] L 324 To L 326 may be independently a single bond, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, *-C(Q 321 )(Q 322 )-*'、*-Si(Q 321 )(Q 322 )-*'、*-B(Q 321 )-*' or *-N(Q 321 )-*',
[0225] n324 to n326 may each independently be an integer from 1 to 5,
[0226] R 321 To R 326 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 323 )(Q 324 )(Q 325 )、-N(Q 323 )(Q 324 )、-B(Q 323 )(Q 324 )、-C(=O)(Q 323 )、-S(=O) 2 (Q 323 ) or -P(=O)(Q 323 )(Q 324 ),
[0227] Q 321 To Q 325 and R 321 To R 326 Two or more adjacent groups may be optionally bonded to each other to form a group that is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 30 Heterocyclic group,
[0228] * and *' each indicate a binding site with an adjacent atom,
[0229] R 10a may be the same as described herein, and
[0230] Q 321 To Q 325 can be independently compared with 1 Same as described.
[0231] In an embodiment, the second host may be one of compounds ETH1 to ETH86, but the embodiment is not limited thereto:
[0232]
[0233]
[0234]
[0235] In an embodiment, the third compound can be represented by Formula 401A: [Formula 401A]
[0236] M 401 (L 401 ) xc1 (L 402 ) xc2
[0237]
[0238]
[0239] In Formula 401A and Formulas 402A to 402D,
[0240] M 401 It may be a first-row transition metal of the periodic table, a second-row transition metal of the periodic table, or a third-row transition metal of the periodic table,
[0241] L 401 may be a ligand represented by one of Formulae 402A to 402D,
[0242] L 402 It can be a monodentate ligand, a bidentate ligand or a tridentate ligand,
[0243] xc1 can be 1 or 2,
[0244] xc2 can be an integer from 0 to 4,
[0245] A 401 To A 404 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0246] T 401 To T 404 can each independently be a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 405 )(R 406 )-*'、*-C(R 405 )=C(R 406 )-*'、*-C(R 405 )=*'、*-Si(R 405 )(R 406 )-*'、*-B(R 405 )-*'、*-N(R 405 )-*' or *-P(R 405 )-*',
[0247] k401 to k404 can each independently be 1, 2 or 3,
[0248] Y 401 To Y 404 can each independently be a single bond (eg, a covalent bond or a coordination bond), *-O-*', *-S-*', *-C(R 407 )(R 408 )-*'、*-Si(R 407 )(R 408 )-*'、*-B(R 407 )-*'、*-N(R 407 )-*' or *-P(R 407 )-*',
[0249] * in Formula 402A to Formula 402D 1 ,* 2 ,* 3 and* 4 Each indicates the same as M in formula 401A 401 The binding site
[0250] R 401 To R 408 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -Si(Q 1 )(Q2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0251] R 401 To R 408 may be optionally bonded to each other to form an unsubstituted or substituted group with at least one R 10a Substituted C 5 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0252] b401 to b404 may each independently be an integer from 0 to 10,
[0253] * and *' each indicate a binding site with an adjacent atom, and
[0254] Q 1 To Q 3 and R 10a Each may be the same as described herein.
[0255] In an embodiment, the compound represented by Formula 401A may be a carbene complex.
[0256] The term "carbene complex" as used herein may be a complex including a metal and a ligand bonded to the metal, wherein at least one bond between the metal and the ligand is a bond between the metal and a carbon atom of the carbene moiety.
[0257] In an embodiment, the sensitizer may include a compound represented by Formula 401A.
[0258] In an embodiment, the third compound may include one of compound PD1 to compound PD41, but the embodiment is not limited thereto:
[0259]
[0260]
[0261]
[0262] In the embodiment, R in Formula 301-1A and Formula 301-2A 301 To R 303 , R 304a To R 306a , R 304b To R 306b and R 311 To R 314 , R in Formula 302 321 To R 326 and R in Formula 401A and Formula 402A to Formula 402D 401 To R 408 Can be independently:
[0263] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0264] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof;
[0265] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnozinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl , benzothiophenyl, benzisothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 10 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnozinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl , benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, thiadiazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiophenyl, -Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32)、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0266] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0267] Q 1 To Q 3 and Q 31 To Q 33 Each may be the same as described herein.
[0268] In the embodiment, R in Formula 301-1A and Formula 301-2A 301 To R 303 , R 304a To R 306a , R 304b To R 306b and R 311 To R 314 , R in Formula 302 321 To R 326 and R in Formula 401A and Formula 402A to Formula 402D 401 To R 408 Can be independently:
[0269] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, nitro, C 1 -C 60 Alkyl, C2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;
[0270] A group represented by one of Formula 9-1 to Formula 9-61 or a group represented by one of Formula 10-1 to Formula 10-348; or
[0271] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ):
[0272]
[0273]
[0274]
[0275]
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282] In Formulae 9-1 to 9-61 and 10-1 to 10-348, * indicates a bonding site with an adjacent atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group, D represents a deuterium atom, and
[0283] Q 1 To Q3 Each may be the same as described herein.
[0284] In an embodiment, the electron transport region of the light emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In an embodiment, the hole blocking layer may contact (eg, directly contact) the emission layer.
[0285] In an embodiment, the light emitting device may include a cover layer outside the first electrode or outside the second electrode.
[0286] In an embodiment, the light emitting device may further include at least one of a first covering layer outside the first electrode and a second covering layer outside the second electrode, and at least one of the first covering layer and the second covering layer may include a heterocyclic compound represented by Formula 1. The first covering layer and / or the second covering layer may each be the same as described herein.
[0287] In an embodiment, the light emitting device may further include:
[0288] a first covering layer, outside the first electrode and including a heterocyclic compound represented by Formula 1;
[0289] a second covering layer, which is outside the second electrode and includes a heterocyclic compound represented by Formula 1; or
[0290] A first covering layer and a second covering layer.
[0291] In the specification, the expression "(the intermediate layer and / or the covering layer) includes at least one compound" may include an embodiment of "(the intermediate layer and / or the covering layer) includes the same heterocyclic compound represented by Formula 1" and an embodiment of "(the intermediate layer and / or the covering layer) includes two or more different heterocyclic compounds each independently represented by Formula 1".
[0292] In an embodiment, the intermediate layer and / or the covering layer may include only compound 1 as a heterocyclic compound. For example, compound 1 may be present in the emission layer of the light-emitting device. As another example, the intermediate layer may include compound 1 and compound 2 as heterocyclic compounds. As another example, compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the emission layer), or may be present in different layers (for example, compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport region).
[0293] In the specification, the term "intermediate layer" may be a single layer and / or a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0294] An embodiment provides an electronic device that may include a light emitting device. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor, the thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. Further details about the electronic device may be the same as described herein.
[0295] According to an embodiment, the electronic equipment may include an electronic device, and the electronic equipment may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a mobile phone or a tablet phone), a tablet personal computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0296] [ Figure 1 Description]
[0297] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .
[0298] In the following, reference will be made to Figure 1 A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment are described.
[0299] [First electrode 110]
[0300] exist Figure 1 In the embodiment, a substrate may be further included under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0301] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that easily injects holes.
[0302] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0303] The first electrode 110 may have a structure consisting of a single layer or a structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0304] [Middle layer 130]
[0305] The intermediate layer 130 may be located on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0306] The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0307] The intermediate layer 130 may further include a metal-containing compound such as an organic metal compound or an inorganic material such as a quantum dot, etc., in addition to various organic materials.
[0308] In an embodiment, the intermediate layer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer may be between adjacent units among the two or more emission units. When the intermediate layer 130 includes two or more emission units and at least one charge generation layer as described above, the light emitting device 10 may be a tandem light emitting device.
[0309] [Hole Transport Region in Intermediate Layer 130]
[0310] The hole transport region may have a structure composed of a layer including a single material, a structure composed of layers including different materials, or a structure including a plurality of layers including different materials.
[0311] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0312] In an embodiment, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in the order in which they are respectively stated, but the structure of the hole transport region is not limited thereto.
[0313] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0314]
[0315] In equation 201 and equation 202,
[0316] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0317] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0318] xa1 to xa4 can each independently be an integer from 0 to 5,
[0319] xa5 can be an integer from 1 to 10,
[0320] R201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0321] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (eg, compound HT16) (eg, carbazole groups),
[0322] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups, and
[0323] na1 can be an integer from 1 to 4.
[0324] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY217:
[0325]
[0326] In formula CY201 to formula CY217, R 10b and R 10c can be independently compared with R 10a Same as described, CY 201 To Ring CY204 Can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R as described above 10a replace.
[0327] In the embodiment, in Formula CY201 to Formula CY217, ring CY 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.
[0328] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY203.
[0329] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217.
[0330] In the embodiment, in formula 201, xa1 may be 1, R 201 may be one of the groups represented by formulae CY201 to CY203, xa2 may be 0, and R 202 It may be one of the groups represented by Formula CY204 to Formula CY207.
[0331] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include one of the groups represented by Formulas CY201 to CY203.
[0332] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include one of the groups represented by Formula CY201 to Formula CY203, and may each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0333] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include one of the groups represented by Formulas CY201 to CY217.
[0334] In an embodiment, the hole transport region may include one of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:
[0335]
[0336]
[0337]
[0338]
[0339]
[0340] The thickness of the hole transport region can be approximately To about For example, the thickness of the hole transport region can be about To about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about To about and the thickness of the hole transport layer can be in the range of about To about For example, the thickness of the hole injection layer can be about To about For example, the thickness of the hole transport layer can be about To about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0341] The emission auxiliary layer can improve the luminous efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0342] [p-dopant]
[0343] 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 dispersed in the hole transport region uniformly or non-uniformly (eg, in the form of a monolayer composed of the charge generating material).
[0344] The charge generating material may be, for example, a p-dopant.
[0345] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be less than or equal to approximately -3.5 eV.
[0346] In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0347] Examples of quinone derivatives may include TCNQ, F4-TCNQ, etc.:
[0348]
[0349] Examples of the cyano group-containing compound may include HATCN and a compound represented by Formula 221:
[0350]
[0351] In formula 221,
[0352] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and
[0353] R 221 To R 223 At least one of them can be independently: C 3 -C 60 Carbocyclic or C 1 -C 60 heterocyclic group, each substituted by: cyano; -F; -Cl; Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0354] In a compound including an element EL1 and an element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0355] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc. (e.g., tantalum (Tb), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
[0356] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0357] Examples of non-metals may include oxygen (O) and halogens (eg, F, Cl, Br, I, etc.).
[0358] Examples of compounds containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, or metal iodides), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, or metalloid iodides), metal tellurides, or any combination thereof.
[0359] Examples of metal oxides may include tungsten oxide (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxide (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO2 、MoO 3 、Mo 2 O 5 etc.) and rhenium oxide (e.g., ReO 3 wait).
[0360] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0361] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.
[0362] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and BaI 2 wait.
[0363] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3, VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), iron halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2, RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 , PtCl 2 , PtBr 2 , PtI 2 etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).
[0364] Examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and tin halides (e.g., SnI 2 wait).
[0365] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and SmI 3 wait.
[0366] Examples of metalloid halides may include antimony halides (eg, SbCl 5 etc.
[0367] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te and Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, and BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe and Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, and LuTe, etc.), etc.
[0368] [Emitting Layer in Intermediate Layer 130]
[0369] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to the sub-pixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
[0370] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0371] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0372] In an embodiment, the emissive layer may include quantum dots.
[0373] The emission layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emission layer.
[0374] The thickness of the emitter layer can be approximately To about For example, the thickness of the emission layer can be about To about When the thickness of the emission layer is within any of these ranges, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0375] [main body]
[0376] In an embodiment, the host may further include a compound represented by Formula 301:
[0377] [Formula 301]
[0378] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0379] In formula 301,
[0380] Ar 301 and L 301 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0381] xb11 can be 1, 2 or 3,
[0382] xb1 can be an integer from 0 to 5.
[0383] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0384] xb21 can be an integer from 1 to 5, and
[0385] Q 301 To Q 303 can be independently compared with 1 Same as described.
[0386] For example, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0387] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0388]
[0389] In Formula 301-1 and Formula 301-2,
[0390] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R10a Substituted C 1 -C 60 Heterocyclic group,
[0391] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0392] xb22 and xb23 can each independently be 0, 1 or 2,
[0393] L 301 , xb1 and R 301 may each independently be the same as described herein,
[0394] L 302 To L 304 can be independently related to L 301 Same as described,
[0395] xb2 to xb4 may each independently be the same as described herein with respect to xb1, and
[0396] R 302 To R 305 and R 311 To R 314 can be independently compared with the R 301 Same as described.
[0397] In an embodiment, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In an embodiment, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0398] In an embodiment, the host may include: one of Compound H1 to Compound H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-di(9-carbazolyl)benzene (mCP); 1,3,5-tri(9-carbazolyl)benzene (TCP); or any combination thereof:
[0399]
[0400]
[0401]
[0402]
[0403]
[0404]
[0405]
[0406] [Phosphorescent dopant]
[0407] In an embodiment, the phosphorescent dopant may include at least one transition metal as a central metal.
[0408] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0409] The phosphorescent dopant may be electrically neutral.
[0410] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0411] [Formula 401]
[0412] M(L 401 ) xc1 (L 402 ) xc2
[0413]
[0414] In equations 401 and 402,
[0415] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0416] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 can be the same or different from each other,
[0417] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, and when xc2 is 2 or greater, two or more L 402 can be the same or different from each other,
[0418] X 401 and X 402 may each independently be nitrogen or carbon,
[0419] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0420] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',
[0421] X 403 and X 404 can be independently a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0422] Q 411 To Q 414 can be independently compared with the Q 1 Same as described,
[0423] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),
[0424] Q 401 To Q 403 can be independently compared with the Q 1 Same as described,
[0425] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0426] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0427] For example, in equation 402, X 401 may be nitrogen, and X 402 Can be carbon, or X 401 and X 402 Each may be nitrogen.
[0428] In the embodiment, in Formula 401, when xc1 is 2 or greater, two or more L 401 The two rings A 401 It can be optionally connected via T as a linker 402 Connected to each other, or two rings A 402 It can be optionally connected via T as a linker 403 are connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 can be independently compared with the T 401 Same as described.
[0429] L in Formula 401 402 It can be an organic ligand. For example, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, -CN, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0430] The phosphorescent dopant may include, for example, one of Compound PD1 to Compound PD39 or any combination thereof:
[0431]
[0432]
[0433]
[0434] [Fluorescent dopant]
[0435] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0436] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0437]
[0438] In formula 501,
[0439] Ar 501 , L 501 To L 503 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0440] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0441] xd4 can be 1, 2, 3, 4, 5 or 6.
[0442] In the embodiment, in Formula 501, Ar 501 It may be a fused cyclic group in which three or more monocyclic groups are fused together (e.g., anthracenyl, yl or pyrene).
[0443] In an embodiment, in formula 501, xd4 may be 2.
[0444] In an embodiment, the fluorescent dopant may include: one of compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:
[0445]
[0446]
[0447]
[0448]
[0449] [Delayed fluorescence material]
[0450] The emitting layer may include a delayed fluorescent material.
[0451] In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0452] The delayed fluorescent material included in the emission layer may serve as a host or as a dopant according to the types of other materials included in the emission layer.
[0453] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be in the range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, up-conversion from the triplet state of the delayed fluorescent material to the singlet state may effectively occur, and therefore, the luminous efficiency of the light emitting device 10 may be improved.
[0454] In an embodiment, the delayed fluorescent material may include: at least one electron donor (eg, a π-electron-rich C 3 -C 60 A cyclic group, such as a carbazolyl group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, or a π-electron-deficient nitrogen-containing C 1 -C 60 or including C 8 -C 60 Polycyclic materials, the C 8 -C 60 The polycyclic group includes two or more cyclic groups fused to each other while sharing boron (B).
[0455] In an embodiment, the delayed fluorescent material may include at least one of Compound DF1 to Compound DF14:
[0456]
[0457]
[0458] [Quantum dot]
[0459] In an embodiment, the emissive layer may include quantum dots.
[0460] In the specification, the term "quantum dot" may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
[0461] The diameter of a quantum dot may be, for example, in the range of about 1 nm to about 10 nm.
[0462] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar to these.
[0463] The wet chemical process is a method that includes mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal, so that the growth of the quantum dot particles can be controlled by a lower cost process and can be carried out more easily than vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0464] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.
[0465] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS; a quaternary compound such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe or HgZnSTe; or any combination thereof.
[0466] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In an embodiment, the III-V semiconductor compound may also include a Group II element. Examples of the Group III-V semiconductor compound also including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
[0467] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 or InTe; ternary compounds such as InGaS 3 or InGaSe 3 ; or any combination thereof.
[0468] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 or AgAlO 2 ; or any combination thereof.
[0469] Examples of IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
[0470] Examples of Group IV elements or compounds may include: single element materials, such as Si or Ge; binary compounds, such as SiC or SiGe; or any combination thereof.
[0471] Each element included in a multi-element compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particle at a uniform concentration or a non-uniform concentration.
[0472] The quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell structure. For example, the material included in the core and the material included in the shell may be different from each other.
[0473] The shell of the quantum dot can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can be used as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the material present in the shell decreases toward the core.
[0474] Examples of materials forming the shell of quantum dots may include metal oxides, metalloid oxides or non-metal oxides, semiconductor compounds, and any combination thereof. Examples of metal oxides, metalloid oxides, or non-metal oxides may include binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 or NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 or CoMn 2 O 4; and any combination thereof. Examples of semiconductor compounds may include: II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; and any combination thereof. Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0475] The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dot may have a FWHM of an emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dot may have a FWHM of an emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of the quantum dot is within any of these ranges, color purity or color reproducibility may be improved. Light emitted by the quantum dot may be emitted in all directions, thereby improving a wide viewing angle.
[0476] Quantum dots can be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0477] Because the band gap can be adjusted by controlling the size of the quantum dots, light with various wavelength bands can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths can be realized. In an embodiment, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In an embodiment, the size of the quantum dots can be configured to emit white light through a combination of various colors of light.
[0478] [Electron Transport Region in Intermediate Layer 130]
[0479] The electron transport region may have a structure composed of a layer including a single material, a structure composed of layers including different materials, or a structure having a plurality of layers including different materials.
[0480] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0481] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked from the emission layer in their corresponding order of presentation, but the structure of the electron transport region is not limited thereto.
[0482] In an embodiment, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic base.
[0483] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[0484] [Formula 601]
[0485] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0486] In formula 601,
[0487] Ar 601 and L 601 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0488] xe11 can be 1, 2 or 3,
[0489] xe1 can be 0, 1, 2, 3, 4, or 5,
[0490] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0491] Q 601 To Q 603 can be independently compared with the Q 1 Same as described,
[0492] xe21 can be 1, 2, 3, 4, or 5, and
[0493] Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic base.
[0494] For example, in the embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.
[0495] In the embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0496] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0497]
[0498] In formula 601-1,
[0499] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and X 614 To X 616 At least one of them can each be N,
[0500] L 611 To L 613 can be independently compared with the L 601 Same as described,
[0501] xe611 to xe613 can each independently be the same as described herein with respect to xe1,
[0502] R 611 To R 613 can be independently compared with the R 601 Same as described, and
[0503] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0504] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0505] The electron transport region may include one of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, TAZ, NTAZ or any combination thereof:
[0506]
[0507]
[0508]
[0509]
[0510] The thickness of the electron transport region can be approximately To about For example, the thickness of the electron transport region can be in the range of about To about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about To about and the thickness of the electron transport layer can be in the range of about To about (For example, at about To about ). For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about To about For example, the thickness of the electron transport layer can be about To about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0511] In addition to the above materials, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material.
[0512] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion; and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may each independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0513] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0514]
[0515] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may contact (eg, directly contact) the second electrode 150.
[0516] The electron injection layer may have a structure composed of a layer including a single material, a structure composed of layers including different materials, or a structure having a plurality of layers including different materials.
[0517] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0518] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0519] The compound containing an alkali metal, the compound containing an alkaline earth metal, and the compound containing a rare earth metal may include oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, alkaline earth metal, and rare earth metal, or any combination thereof.
[0520] The compound containing an alkali metal may include: alkali metal oxides such as Li 2 O, Cs 2 O, or K 2 O; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The compound containing an alkaline earth metal may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying the condition 0 < x < 1), or Ba x Ca 1- x O (where x is a real number satisfying the condition 0 < x < 1), etc. The compound containing a rare earth metal may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 or any combination thereof. In an embodiment, the compound containing a rare earth metal may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 、Ce 2 Te3 , Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 He Lu 2 Te 3 .
[0521] The alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes may include: alkali metal ions, alkaline earth metal ions or rare earth metal ions; and a ligand bonded to the metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0522] The electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).
[0523] In an embodiment, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, or a LiF:Yb co-deposition layer, etc.
[0524] When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof can be uniformly or unevenly dispersed in a matrix including the organic material.
[0525] The thickness of the electron injection layer can be about To about For example, the thickness of the electron injection layer can be about To about When the thickness of the electron injection layer is within any of the ranges described above, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0526] [Second electrode 150]
[0527] The second electrode 150 may be located on the intermediate layer 130 having the above structure. The second electrode 150 may be a cathode as an electron injection electrode. When the second electrode 150 is a cathode, the material used to form the second electrode 150 may include a material having a low work function, such as a metal, an alloy, a conductive compound, or any combination thereof.
[0528] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0529] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0530] [Overlay]
[0531] The light emitting device 10 may include a first covering layer outside the first electrode 110 and / or a second covering layer outside the second electrode 150. In an embodiment, the light emitting device 10 may have a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in the stated order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in the stated order, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in the stated order.
[0532] Light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be emitted to the outside through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and through the first cover layer. Light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be emitted to the outside through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and through the second cover layer.
[0533] The first cover layer and the second cover layer can each increase the external emission efficiency according to the principle of constructive interference. Therefore, the light emission efficiency of the light emitting device 10 is improved, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0534] The first cover layer and the second cover layer may each include a material having a refractive index greater than or equal to about 1.6 (with respect to a wavelength of about 589 nm).
[0535] The first cover layer and the second cover layer may each independently be an organic cover layer including an organic material, an inorganic cover layer including an inorganic material, or an organic-inorganic composite cover layer including an organic material and an inorganic material.
[0536] At least one of the first covering layer and the second covering layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first covering layer and the second covering layer may each independently include an amine-containing compound.
[0537] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0538] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0539]
[0540] [membrane]
[0541] The fused ring compound represented by Formula 1 may be included in various films. Embodiments provide films that may include the fused ring compound represented by Formula 1. The film may be, for example, an optical member (or light control device) (e.g., a color filter, a color conversion member, a cover layer, a light emission efficiency improvement layer, a selective light absorption layer, a polarization layer, or a layer containing quantum dots, etc.), a light blocking member (e.g., a light reflecting layer or a light absorbing layer, etc.), or a protective member (e.g., an insulating layer or a dielectric layer, etc.).
[0542] [Electronic equipment]
[0543] A light emitting device may be included in various electronic devices (e.g., Figure 1 For example, the electronic device including the light emitting device may be a light emitting device or an authentication device.
[0544] In addition to the light emitting device, the electronic device (e.g., the light emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be located in at least one direction in which the light emitted from the light emitting device travels. For example, the light emitted from the light emitting device may be blue light or white light. The light emitting device may be a light emitting device as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.
[0545] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixels, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.
[0546] A pixel defining layer may be located between the plurality of sub-pixels to define each sub-pixel.
[0547] The color filter may further include a plurality of color filter areas and a light shielding pattern between the plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and a light shielding pattern between the plurality of color conversion areas.
[0548] The plurality of color filter regions (or the plurality of color conversion regions) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. For example, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be quantum dots as described herein. The first region, the second region, and / or the third region may each include a scatterer.
[0549] In an embodiment, the light emitting device may emit a first light, the first area may absorb the first light to emit a first-first color light, the second area may absorb the first light to emit a second-first color light, and the third area may absorb the first light to emit a third-first color light. In an embodiment, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0550] In addition to the light emitting device described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light emitting device.
[0551] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0552] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0553] The electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be located between the color filter and / or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be emitted to the outside, and may prevent ambient air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the encapsulation portion is a thin film encapsulation layer, the electronic device may be flexible.
[0554] Depending on the purpose of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may be included on the sealing portion. Examples of the functional layer may include a touch screen layer and a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living organism (e.g., a fingertip, a pupil, etc.).
[0555] In addition to the light emitting device as described above, the authentication device may also include a biometric information collector.
[0556] The electronic device can be applied to various displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices or endoscope displays), fish finders, various measuring instruments, meters (e.g., meters for vehicles, aircraft and ships) and projectors, etc.
[0557] [Electronic equipment]
[0558] The light emitting device may be included in various electronic equipment (e.g., Figure 1 The light emitting device 10).
[0559] For example, the electronic equipment including the light emitting device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a mobile phone or a tablet phone), a tablet personal computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall including multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0560] The light emitting device may have excellent effects in terms of light emitting efficiency, long life, and thus, electronic equipment including the light emitting device may have characteristics such as high brightness, high resolution, and low power consumption.
[0561] [ Figure 2 and Figure 3 Description]
[0562] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0563] Figure 2 The electronic device includes a substrate 100, a thin film transistor (TFT), a light emitting device (eg, Figure 1 The light emitting device 10) and the packaging part 300 that seals the light emitting device.
[0564] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent impurities from penetrating the substrate 100 and may provide a flat surface on the substrate 100.
[0565] The TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0566] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0567] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be located on the active layer 220 , and the gate electrode 240 may be located on the gate insulating film 230 .
[0568] Interlayer insulating film 250 may be located on gate electrode 240 . Interlayer insulating film 250 may be located between gate electrode 240 and source electrode 260 to insulate gate electrode 240 from source electrode 260 , and between gate electrode 240 and drain electrode 270 to insulate gate electrode 240 from drain electrode 270 .
[0569] The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may contact the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0570] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating layer, an organic insulating layer, or any combination thereof. The light emitting device may be disposed on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0571] The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270, and may expose a portion of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0572] A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and the intermediate layer 130 may be formed on the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Figure 2 Although not shown in the figure, at least some layers of the intermediate layer 130 may extend over the top of the pixel defining layer 290 to be provided in the form of a common layer.
[0573] The second electrode 150 may be located on the intermediate layer 130, and may further include a capping layer 170 on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0574] The encapsulation part 300 may be located on the cover layer 170. The encapsulation part 300 may be located on the light emitting device to protect the light emitting device from moisture or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic films and organic films.
[0575] Figure 3 is a schematic cross-sectional view of an electronic device according to an embodiment of the present disclosure.
[0576] Figure 3 An electronic device (eg, a light emitting device) and Figure 2 The difference of the electronic device may be at least that a light shielding pattern 500 and a functional area 400 are further included on the packaging portion 300. The functional area 400 may be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. Figure 3 The light-emitting device in the electronic device may be a series light-emitting device.
[0577] [ Figure 4 Description]
[0578] Figure 4 is a schematic perspective view of an electronic equipment 1 including a light emitting device according to an embodiment.
[0579] The electronic equipment 1 that can be a device for displaying moving images or still images can be not only portable electronic equipment such as mobile phones, smart phones, tablet personal computers (PCs), mobile communication terminals, electronic notebooks, electronic books, portable multimedia players (PMPs), navigation devices, or ultra-mobile PCs (UMPCs), but can also be various products such as televisions, laptop computers, monitors, billboards, or Internet of Things (IoT) equipment. The electronic equipment 1 can be any product or a part thereof as described above. In an embodiment, the electronic equipment 1 can be a wearable device such as a smart watch, a watch phone, a glasses-type display, or a head-mounted display (HMD) or a part of a wearable device. However, the embodiment is not limited thereto.
[0580] Examples of the electronic equipment 1 may include a central information display (CID) on a vehicle's dashboard, an instrument panel on a vehicle's dashboard, a center console or instrument panel of a vehicle, an interior mirror display replacing a vehicle's side mirror, an entertainment display for a rear seat of a car or a display located on the back of a front seat, a head-up display (HUD) mounted on the front of the vehicle or projected on the front windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 An embodiment in which the electronic equipment 1 is a smartphone is shown.
[0581] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through a two-dimensional array of pixels arranged in the display area DA.
[0582] The non-display area NDA may be an area where an image is not displayed, and may surround (e.g., completely surround) the display area DA. A driver for providing an electrical signal or power to pixels arranged in the display area DA may be arranged in the non-display area NDA. A pad as an area to which an electronic component or a printed circuit board may be electrically connected may be arranged in the non-display area NDA.
[0583] In the electronic equipment 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0584] [ Figure 5 and FIG. 6A to FIG. 6C Description]
[0585] Figure 5 According to the embodiment, the light emitting device 10 (see Figure 1 ) is a schematic perspective view of the exterior of a vehicle 1000 equipped with electronic equipment. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to an embodiment.
[0586] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C, embodiments of the vehicle 1000 may include various devices for moving a transported object such as a person, an object, or an animal from a starting point to a destination. Examples of the vehicle 1000 may include vehicles traveling on roads or tracks, ships moving on oceans or rivers, and airplanes flying in the sky using the action of air.
[0587] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a direction (e.g., a predetermined or selectable direction) according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled vehicle or a four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0588] The vehicle 1000 may include a body having an interior and an exterior and a chassis, which is a part other than the body in which mechanical equipment for driving is installed. The exterior of the vehicle body may include a front panel, a hood, a top panel, a rear panel, a trunk, and a column disposed at a boundary between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear wheels, and left and right wheels, etc.
[0589] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , an instrument cluster 1400 , a central control instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0590] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0591] The side window glass 1100 may be installed on a side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided, and the plurality of side window glasses 1100 may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the instrument cluster 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0592] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction. In an embodiment, the first side window glass 1110 and the second side window glass 1120 may be spaced apart in the x-axis direction or the -x-axis direction. For example, the virtual straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. For example, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or the -x-axis direction.
[0593] The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0594] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the outside of the vehicle body. In an embodiment, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be arranged on the outside of the first side window glass 1110, and another side view mirror 1300 may be arranged on the outside of the second side window glass 1120.
[0595] Instrument cluster 1400 may be arranged in front of the steering wheel. Instrument cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a driving recorder, an automatic shift selector indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0596] The central instrument panel 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are provided. The central instrument panel 1500 may be disposed at one side of the instrument cluster 1400 .
[0597] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, and the center console instrument panel 1500 is disposed between the passenger seat instrument panel 1600 and the instrument cluster 1400. In an embodiment, the instrument cluster 1400 may be disposed to correspond to a driver's seat (not shown), and the passenger seat instrument panel 1600 may be disposed to correspond to a passenger seat (not shown). In an embodiment, the instrument cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0598] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the instrument cluster 1400, the central control instrument panel 1500, and the passenger seat instrument panel 1600.
[0599] The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, a quantum dot display device, etc. Hereinafter, as the display device 2 according to an embodiment of the present disclosure, an organic light-emitting display device including a light-emitting device according to the present disclosure will be described as an example. However, various types of display devices as described above may be used in the embodiments.
[0600] refer to Fig. 6A , the display device 2 may be arranged on the central control instrument panel 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information about audio settings, video settings, or vehicle settings.
[0601] refer to Figure 6B , the display device 2 may be arranged on the instrument cluster 1400. When the display device 2 is arranged on the instrument cluster 1400, the instrument cluster 1400 may display driving information and the like through the display device 2. For example, the instrument cluster 1400 may digitally implement driving information. The digital instrument cluster 1400 may display vehicle information and driving information as images. In an embodiment, the pointer and instrument of the tachometer and various warning light icons may be displayed through digital signals.
[0602] refer to Figure 6C , the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument cluster 1400 and / or the information displayed on the central control instrument panel 1500. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the central control instrument panel 1500.
[0603] [Manufacturing method]
[0604] The corresponding layer included in the hole transport region, the emission layer, and the corresponding layer included in the electron transport region can be formed in the selected region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
[0605] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C. ... -8 Up to about 10 -3 Torr vacuum and at about / second to approximately The deposition was performed at a deposition rate of 2000 Å / s.
[0606] [Definition of terms]
[0607] As used herein, the term "C 3 -C 60 The term "carbocyclic group" may be a cyclic group consisting of a carbon atom as the only ring-forming atom and having 3 to 60 carbon atoms, and as used herein, 1 -C 60 The "heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and including heteroatoms as ring-constituting atoms in addition to carbon atoms. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The heterocyclic group can have 3 to 61 ring-forming atoms.
[0608] As used herein, the term "cyclic group" may be a C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0609] As used herein, the term "π-electron-rich C 3 -C 60 The "cyclic group" may be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60The "cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming part.
[0610] In an embodiment,
[0611] C 3 -C 60 The carbocyclic group may be a T1 group or a group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthrenyl or indenoanthryl),
[0612] C 1 -C 60 The heterocyclic group may be a T2 group, a group in which two or more T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiorolocarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiorolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl ... phenyl, benzothiophene and dibenzothiophene, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl quinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0613] Pi-electron-rich C 3 -C 60The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C 3 -C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothiophenyldibenzothiophenyl, etc.),
[0614] π-electron-deficient nitrogen-containing C 1 -C 60 The cyclic group may be a T4 group, a group in which two or more T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, yl, benzoisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0615] wherein the T1 group can be a cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl group,
[0616] The T2 group can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,
[0617] The T3 group may be a furyl group, a thienyl group, a 1H-pyrrolyl group, a thiol group or a borocyclopentadienyl group, and
[0618] The T4 group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0619] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The "cyclic group" may each be a group fused to any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula in which the corresponding term is used. In an embodiment, the "phenyl group" may be a benzo group, a phenyl group or a phenylene group, etc., which may be easily understood by a person of ordinary skill in the art based on the structure of the formula including the "phenyl group".
[0620] One Price C 3 -C 60 Carbocyclic or monovalent C 1 -C 60 Examples of heterocyclic groups may include 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 1 -C60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 3 -C 60 Carbocyclic or divalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0621] As used herein, the term "C 1 -C 60 The "alkyl" may be a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the "C 1 -C 60 Examples of the “alkyl” group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. As used herein, the term “alkyl” may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. 1 -C 60 The "alkylene" may be 1 -C 60 An alkyl group is a divalent group having the same structure.
[0622] As used herein, the term "C 2 -C 60 The "alkenyl" may be in C 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end thereof, and “C 2 -C 60 Examples of "alkenyl" may include ethenyl, propenyl, and butenyl. As used herein, the term "C 2 -C 60 The "alkenylene" may be a 2 -C 60 Alkenyl is a divalent group of the same structure.
[0623] As used herein, the term "C 2 -C 60 The "alkynyl" may be in C 2 -C 60 The alkyl group has at least one monovalent hydrocarbon group with a carbon-carbon triple bond in the middle or at the end thereof, and C 2 -C 60 Examples of alkynyl groups may include ethynyl and propynyl, etc. As used herein, the term “C 2 -C 60 The "alkynylene" group may be 2 -C 60 Alkynyl groups are divalent groups with the same structure.
[0624] As used herein, the term "C 1 -C 60 The "alkoxy" may be -O(A 101 ) represented by a monovalent group (wherein A 101 Can be C 1 -C 60 alkyl), and "C 1 -C 60 Examples of the "alkoxy group" may include methoxy, ethoxy and isopropoxy.
[0625] As used herein, the term "C 3 -C 10 The "cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and the "C 3 -C 10 Examples of "cycloalkyl" may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, and bicyclo[2.2.2]octanyl. As used herein, the term "C 3 -C 10 The "cycloalkylene" may be 3 -C 10 The cycloalkyl group has a divalent group of the same structure.
[0626] As used herein, the term "C 1 -C 10 The "heterocycloalkyl group" may be a monovalent cyclic group of 1 to 10 carbon atoms including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and the "C 1 -C 10 Examples of "heterocycloalkyl" may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10The "heterocycloalkylene" may be 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.
[0627] As used herein, the term "C 3 -C 10 The "cycloalkenyl group" may be a monovalent cyclic group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in its ring and having no aromaticity, and the "C 3 -C 10 Examples of "cycloalkenyl" may include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "cycloalkenyl" may include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 The cycloalkenylene group may be 3 -C 10 The cycloalkenyl group has a divalent group of the same structure.
[0628] As used herein, the term "C 1 -C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms and has at least one double bond in its cyclic structure. 1 -C 10 Examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 The "heterocycloalkenylene" may be 1 -C 10 The heterocycloalkenyl group has a divalent group of the same structure.
[0629] As used herein, the term "C 6 -C 60 The term "aryl" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 The "arylene group" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of the aryl group may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, corynyl and ovalenyl. 6 -C 60 Aryl and C 6 -C 60When the arylene groups each include two or more rings, the two or more corresponding rings may be fused to each other.
[0630] As used herein, the term "C 1 -C 60 The term "heteroaryl" as used herein may be a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 The "heteroarylene group" may be a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more corresponding rings may be fused to each other.
[0631] The term "monovalent non-aromatic fused polycyclic radical" as used in this article can be a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, only carbon atoms as ring atoms, and no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic radicals can include indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthryl. The term "divalent non-aromatic fused polycyclic radical" as used in this article can be a divalent group of the same structure as the monovalent non-aromatic fused polycyclic radical described above.
[0632] The term “monovalent non-aromatic fused heteropolycyclic group” as used herein may be a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings fused to each other, including at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothioyl group, a benzofuranyl group, a carbazolyl group, a dibenzothioyl group, a dibenzothioyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothioyl group, an azadibenzothioyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may be a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
[0633] As used herein, the term "C 6 -C 60 The "aryloxy" may be -O(A 102 ) represented by a group (wherein A 102 Can be C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 The "arylthio" group can be -S(A 103 ) represented by a group (wherein A 103 Can be C 6 -C 60 aryl).
[0634] As used herein, the term "C 7 -C 60 The "aralkyl" may be -(A 104 )(A 105 ) represented by a group (wherein A 104 Can be C 1 -C 54 Alkylene, and A 105 Can be C6 -C 59 aryl), and as used herein, the term "C 2 -C 60 The heteroarylalkyl group may be -(A 106 )(A 107 ) represented by a group (wherein A 106 Can be C 1 -C 59 Alkylene, and A 107 Can be C 1 -C 59 heteroaryl).
[0635] In the specification, the group term "R 10a " can be:
[0636] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0637] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0638] C 3 -C60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0639] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31)(Q 32 ).
[0640] In the specification, the group Q as used herein 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0641] The term "heteroatom" as used herein may be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0642] The term “third row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
[0643] In the specification, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, the term "ter-Bu" or "Bu t ” each refers to a tert-butyl group, and the term “OMe” refers to a methoxy group.
[0644] The term "biphenyl" as used herein may be a "phenyl group substituted with a phenyl group". For example, a "biphenyl group" may be a group having C 6 -C 60 A substituted phenyl group having an aryl group as a substituent.
[0645] The term "terphenyl" as used herein may be a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl substituted C 6 -C 60 A substituted phenyl group having an aryl group as a substituent.
[0646] Unless otherwise defined, the symbols * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0647] In the specification, the terms "x-axis (x-axis direction)", "y-axis (y-axis direction)", and "z-axis (z-axis direction)" are not limited to three axes (directions) in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and can be interpreted in a broader sense than the aforementioned three axes (directions). For example, the x-axis (x-axis direction), the y-axis (y-axis direction), and the z-axis (z-axis direction) can describe axes (directions) that are orthogonal to each other, or can describe axes (directions) in different directions that are not orthogonal to each other.
[0648] Hereinafter, the compound according to the embodiment and the light emitting device according to the embodiment will be described in detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A with the same molar equivalent.
[0649] [Example]
[0650] Synthesis Example 1 (Compound 13)
[0651]
[0652] Synthesis of Intermediate 13-1
[0653] In reactor A, 20 g of 1-bromo-4-(methyl-D3)benzene-2,3,5,6-D4 (Chemical Abstracts Service (CAS) Registry Number (hereinafter referred to as CAS): 263398-16-9) was dissolved in 140 mL of diethyl ether and stirred at -78°C.
[0654] In reactor B, 19.08 g SiCl 4 Dissolve in 120 mL of ether and stir at 0°C for 30 minutes.
[0655] When both reactors A and B were ready, 44.92 mL of 2.5 M n-BuLi was added dropwise to reactor A and stirred for 1 hour at 0° C. While maintaining the temperature at 0° C., the solution of reactor A was quickly added dropwise to reactor B using a cannula.
[0656] In reactor C, 17.63 g of bromobenzene was dissolved in 140 mL of ether and stirred at -78°C. 44.92 mL of 2.5 M n-BuLi was added dropwise thereto and stirred at 0°C for 1 hour. While maintaining the temperature at 0°C, the solution in reactor C was quickly added dropwise to reactor B using a cannula. After the reaction was completed, the resulting product was dried, and the filtrate of the residue was distilled and purified to obtain 9.54 g of intermediate 13-1 (yield: 31%). Intermediate 13-1 was identified by liquid chromatography-mass spectrometry (LC-MS). (C 13 H 5 D 7 Cl 2 Si: M+1 274.27)
[0657] Synthesis of intermediate 13-2
[0658] 16.69 g of 1,3-dibromobenzene-2,4,5,6-D4 was dissolved in 120 mL of ether and stirred at -78 ° C. 27.83 mL of 2.5 M n-BuLi was slowly added dropwise and stirred for 2 hours. 9.54 g of intermediate 13-1 was quickly added dropwise and stirred for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 5.72 g of intermediate 13-2 (yield: 60%). Intermediate 13-2 was identified by LC-MS. (C 25 H 5 D 15 Br 2 Si: M+1523.42)
[0659] Synthesis of intermediate 13-3
[0660] 5.72 g of intermediate 13-2, 1.38 g of (phenyl-D5) boronic acid, 0.32 g of Pd(PPh 3 ) 4 and 10.5 mL 2 M K 2 CO 3 The aqueous solution was dissolved in 40 mL of THF and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 2.62 g of Intermediate 13-3 (yield: 46%). Intermediate 13-3 was identified by LC-MS. (C 31 H 5 D 20 BrSi: M+1525.65)
[0661] Synthesis of Intermediate 13-4
[0662] 2.62 g of intermediate 13-3, 1.28 g of bis(pinacol)diboron, 1.49 g of KOAc and 0.18 g of Pd(dppf)Cl 2 Dissolved in 25 mL of 1,4-dioxane and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 2.31 g of Intermediate 13-4 (yield: 80%). Intermediate 13-4 was identified by LC-MS. (C 37 H 17 D 20 BO 2 Si: M+1 572.72)
[0663] Synthesis of compound 13
[0664] 1.86 g 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-D8) (CAS: 1268244-56-9), 2.31 g intermediate 13-4, 5.04 mL 2M K 2 CO 3 aqueous solution and 0.23 g Pd(PPh 3 ) 4 Dissolved in a solvent of 20 mL toluene and 5.04 mL ethanol, and stirred at 80 ° C for 12 hours. After the reaction is completed, the reaction solution is extracted, and the obtained organic layer is dried. The residue is separated and purified by column chromatography, and then recrystallized and sublimed to obtain 1.76 g of high-purity compound 13 (yield: 50%). By LC-MS and nuclear magnetic resonance hydrogen spectrum ( 1 H-NMR) to identify compound 13.
[0665] Synthesis Example 2 (Compound 17)
[0666]
[0667] Compound 17 was synthesized in the same manner as in Synthesis Example 1, except that 1-bromo-3-methylbenzene was used instead of bromobenzene in the synthesis of Intermediate 13-1.
[0668] Synthesis Example 3 (Compound 24)
[0669]
[0670] Synthesis of Intermediate 24-1
[0671] In reactor A, 20 g of 1-bromo-4-methylbenzene (CAS: 263398-16-9) was dissolved in 140 mL of diethyl ether and stirred at -78 °C.
[0672] In reactor B, 19.86 g SiCl 4 Dissolve in 120 mL of ether and stir at 0°C for 30 minutes.
[0673] When both reactors A and B were ready, 46.77 mL of 2.5 M n-BuLi was added dropwise to reactor A and stirred for 1 hour at 0° C. While maintaining the temperature at 0° C., the solution of reactor A was quickly added dropwise to reactor B using a cannula.
[0674] In reactor C, 19.86 g of bromobenzene was dissolved in 140 mL of ether and stirred at -78°C. 46.77 mL of 2.5 M n-BuLi was added dropwise thereto and stirred at 0°C for 1 hour. While maintaining the temperature at 0°C, the solution of reactor C was quickly added dropwise to reactor B using a cannula. After the reaction was completed, the resulting product was dried, and the filtrate of the residue was distilled and purified to obtain 10.93 g of intermediate 24-1 (yield: 35%). Intermediate 24-1 was identified by LC-MS. (C 13 H 12 Cl 2 Si: M+1 267.22)
[0675] Synthesis of intermediate 24-2
[0676] In reactor D, 9.83 g of 1,3-dibromobenzene-2,4,5,6-D4 (CAS: 263398-16-9) was dissolved in 70 mL of diethyl ether and stirred at -78°C.
[0677] In reactor E, 10.93 g of Intermediate 24-1 was dissolved in 60 mL of diethyl ether and stirred at -78°C for 30 minutes.
[0678] When both reactors D and E were ready, 16.36 mL of 2.5M n-BuLi was slowly dripped into reactor D at -78°C and stirred for 2 hours. The solution of reactor D was quickly dripped into reactor E using a cannula.
[0679] In reactor F, 7.28 g of 1-bromo-2-(methyl-D3)benzene-3,4,5,6-D4 was dissolved in 70 mL of THF and stirred at -78 ° C. 16.36 mL of 2.5 M n-BuLi was slowly added thereto at -78 ° C and stirred for 1 hour. The solution of reactor F was quickly added dropwise to reactor E using a cannula. After the reaction was completed, the resulting product was dried, and the filtrate of the residue was distilled and purified to obtain 6.05 g of intermediate 24-2 (yield: 54%). Intermediate 24-2 was identified by LC-MS. (C 26 H 12 D 11 BrSi: M+1 454.53)
[0680] Synthesis of intermediate 24-3
[0681] 6.05 g of intermediate 24-2, 3.38 g of bis(pinacol)diboron, 3.92 g of KOAc and 0.46 g of Pd(dppf)Cl 2 Dissolved in 25 mL of 1,4-dioxane and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 5.79 g of Intermediate 24-3 (yield: 76%). Intermediate 24-3 was identified by LC-MS. (C 32 H 24 D 11 BO 2 Si: M+1 501.59)
[0682] Synthesis of compound 24
[0683] 1.84 g 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-D8) (CAS: 1268244-56-9), 2 g intermediate 24-3, 4.98 mL 2M K 2 CO 3 aqueous solution and 0.23 g Pd(PPh 3 ) 4 Dissolved in a solvent of 20 mL toluene and 4.98 mL ethanol, and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, and then recrystallized and sublimated to obtain 1.69 g of high-purity compound 24 (yield: 61%). By LC-MS and 1 Compound 24 was identified by H-NMR.
[0684] Synthesis Example 4 (Compound 26)
[0685]
[0686] Compound 26 was synthesized in the same manner as in Synthesis Example 3, except that 1-bromo-3-methylbenzene was used instead of 1-bromo-4-methylbenzene in the synthesis of Intermediate 24-1 and 1-bromo-3-(methyl-D3)benzene-2,4,5,6-D4 was used instead of 1-bromo-2-(methyl-D3)benzene-3,4,5,6-D4 in the synthesis of Intermediate 24-2.
[0687] Synthesis Example 5 (Compound 31)
[0688]
[0689] Compound 31 was synthesized in the same manner as in Synthesis Example 4, except that 1-bromo-4-(methyl-D3)benzene-2,3,5,6-D4 (CAS: 263398-16-9) was used instead of 1-bromo-3-methylbenzene.
[0690] Synthesis Example 6 (Compound 33)
[0691]
[0692] Synthesis of Intermediate 33-1
[0693] In reactor A, 20 g of 1-bromo-4-(methyl-D3)benzene-2,3,5,6-D4 (CAS: 263398-16-9) was dissolved in 140 mL of diethyl ether and stirred at -78°C.
[0694] In reactor B, 19.08 g SiCl 4 Dissolve in 120 mL of ether and stir at 0°C for 30 minutes.
[0695] When both reactors A and B were ready, 44.92 mL of 2.5 M n-BuLi was added dropwise to reactor A and stirred for 1 hour at 0° C. While maintaining the temperature at 0° C., the solution of reactor A was quickly added dropwise to reactor B using a cannula.
[0696] In reactor C, 20 g of bromobenzene was dissolved in 140 mL of ether and stirred at -78°C. 44.92 mL of 2.5 M n-BuLi was added dropwise thereto and stirred at 0°C for 1 hour. While maintaining the temperature at 0°C, the solution in reactor C was quickly added dropwise to reactor B using a cannula. After the reaction was completed, the resulting product was dried, and the filtrate of the residue was distilled and purified to obtain 9.6 g of intermediate 33-1 (yield: 32%). Intermediate 33-1 was identified by LC-MS. (C14 D 14 Cl 2 Si: M+1 295.34)
[0697] Synthesis of Intermediate 33-2
[0698] 15.59 g of 1,3-dibromobenzene-2,4,5,6-D4 was dissolved in 120 mL of ether and stirred at -78 ° C. 26 mL of 2.5 M n-BuLi was slowly added dropwise thereto and stirred for 2 hours. 9.6 g of intermediate 33-1 was quickly added dropwise thereto and stirred for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 4.81 g of intermediate 33-2 (yield: 54%). Intermediate 33-2 was identified by LC-MS. (C 26 D 22 Br 2 Si: M+1544.49)
[0699] Synthesis of intermediate 33-3
[0700] 4.81 g of intermediate 33-2, 0.93 g of (4-(methyl-D3)phenyl-2,3,5,6-D4)boric acid, 0.26 g of Pd(PPh 3 ) 4 and 8.46 mL 2M K 2 CO 3 The aqueous solution was dissolved in 40 mL of THF and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 2.32 g of Intermediate 33-3 (yield: 46%). Intermediate 33-3 was identified by LC-MS. (C 33 D 29 BrSi: M+1 562.76)
[0701] Synthesis of Intermediate 33-4
[0702] 2.32 g of intermediate 33-3, 1.05 g of bis(pinacol)diboron, 1.21 g of KOAc and 0.14 g of Pd(dppf)Cl 2 Dissolved in 25 mL of 1,4-dioxane and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was purified to obtain 1.84 g of Intermediate 33-4 (yield: 78%). Intermediate 33-4 was identified by LC-MS. (C 39 H 12 D 29 BO 2 Si: M+1 609.83)
[0703] Synthesis of compound 33
[0704] 1.39 g 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-D8) (CAS: 1268244-56-9), 1.84 g intermediate 33-4, 3.77 mL 2M K 2 CO 3 aqueous solution and 0.17 g Pd(PPh 3 ) 4 Dissolved in a solvent of 15 mL toluene and 3.77 mL ethanol, and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was extracted, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification, thereby obtaining 1.5 g of high-purity compound 33 (yield: 55%). By LC-MS and 1 Compound 33 was identified by H-NMR.
[0705] For the compounds synthesized in Synthesis Examples 1 to 6, high resolution mass spectra (HR-MS) were measured, and the results are shown in Table 1. Those skilled in the art can easily recognize the synthesis methods of compounds other than the compounds of Synthesis Examples 1 to 6 by referring to the synthesis routes and source materials.
[0706] [Table 1]
[0707]
[0708] Example 1
[0709] As the anode, Corning The ITO glass substrate was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was provided to a vacuum deposition apparatus.
[0710] HATCN was deposited on a glass substrate to form After forming a hole injection layer with a thickness of BCFN is vacuum deposited with a thickness of SiCzCz is vacuum deposited to a thickness of to form a hole transport layer.
[0711] SiCzCz and compound 13 as a host and PtON-TBBI as a dopant were co-deposited on the hole transport layer in a weight ratio of 60:27:13 to form a The thickness of the emission layer.
[0712] On the emission layer mSiTrz is deposited with a thickness of mSiTrz and Liq (weight ratio of 1:1) are deposited to form an electron transport layer. LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form a A LiF / Al electrode (cathode) having a thickness of , thereby manufacturing the organic light-emitting device of Example 1.
[0713]
[0714] [Example 2 to Example 6 and Comparative Example 1 to Comparative Example 4]
[0715] The organic light-emitting devices of Examples 2 to 6 and Comparative Examples 1 to 4 were manufactured in the same manner as in Example 1, except that Compound 17, Compound 24, Compound 26, Compound 31, Compound 33, and CE1 to CE4 were respectively used instead of Compound 13 in Example 1.
[0716] [Evaluation Example 1]
[0717] In order to evaluate the characteristics of the organic light-emitting devices manufactured according to Examples 1 to 6 and Comparative Examples 1 to 4, the current at 10 mA / cm 2 The driving voltage and the maximum quantum efficiency at the current density of , and the results are shown in Table 2. The driving voltage of each of the multiple organic light-emitting devices was measured by using a source meter (Keithley Instrument Inc., 2400 series), and the maximum quantum efficiency of each of the multiple organic electroluminescent devices was measured using an external quantum efficiency (EQE) measurement device C9920-2-12 of Hamamatsu Photonics Inc., Japan. When evaluating the maximum quantum efficiency, the brightness / current density is measured by using a brightness meter calibrated for wavelength sensitivity, and the maximum quantum efficiency is converted by assuming that the angular brightness distribution (Lambert) of a perfect reflection diffuser is introduced.
[0718] Accumulation of material during deposition of the emission layer was evaluated visually, and the probability of accumulation was provided when the parameter was 3 or more. To evaluate process stability related to residues in the crucible after deposition, the lifetime of the light emitting device was measured more than 2 times, and its deviation was measured.
[0719] [Table 2]
[0720]
[0721]
[0722] By using the heterocyclic compound, a light-emitting device having high efficiency and long lifetime and high-quality electronic devices including the light-emitting device can be manufactured.
[0723] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described in conjunction with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments, unless otherwise specifically stated. Therefore, one of ordinary skill in the art will appreciate that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.
Claims
1. A light emitting device, wherein: The light emitting device comprises: a first electrode; a second electrode, facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and A heterocyclic compound represented by Formula 1: Formula 1 Formula 2 Among them, in formula 1 and formula 2, X1 is C(R7) or N, X2 is C(R8) or N, X3 is C(R9) or N, At least one of X1 to X3 is N, Ar1 and Ar2 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 A heterocyclic group or a group represented by Formula 2, CY1 and CY2 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, T is a single bond, a double bond, N(R 10 )、C(R 10 )(R 11 )、Si(R 10 )(R 11 ), S or O, a1 is an integer from 1 to 4, a2 to a4 are each independently an integer from 1 to 5, a5 and a6 are each independently an integer from 1 to 10, When a1 is 2 or more, a1 R1 are the same as or different from each other. When a2 is 2 or more, a2 R2 are the same as or different from each other, When a3 is 2 or more, a3 R3 are the same as or different from each other, When a4 is 2 or more, a4 R4 are the same as or different from each other. When a5 is 2 or more, a5 R5 are the same as or different from each other. When a6 is 2 or more, a6 R6 are the same as or different from each other. R1 to R 11 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), At least one of a2 R2, a3 R3 and a4 R4 is independently unsubstituted or substituted with at least one R 10a Substituted C1-C 60 alkyl, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof; C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; Br; -I; hydroxyl; cyano; nitro; or C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or a combination thereof.
2. The light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, The intermediate layer also includes: a hole transport region between the first electrode and the emission layer; and an electron transport region, between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer or a combination thereof.
3. The light emitting device according to claim 1, wherein: The intermediate layer includes the heterocyclic compound.
4. The light emitting device according to claim 1, wherein: The emission layer includes the heterocyclic compound.
5. The light emitting device according to claim 1, wherein: The emission layer includes a host and a dopant, and The host includes the heterocyclic compound.
6. An electronic device, wherein: The electronic device includes the light emitting device according to any one of claims 1 to 5.
7. The electronic device according to claim 6, wherein: The electronic device further comprises: Color filters, color conversion layers, touch screen layers, polarizing layers, or a combination thereof.
8. An electronic device, wherein: The electronic equipment includes the light emitting device according to any one of claims 1 to 5.
9. The electronic equipment according to claim 8, wherein: The electronic equipment is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device or a sign.
10. A heterocyclic compound, wherein The heterocyclic compound is represented by Formula 1: Formula 1 Formula 2 Among them, in formula 1 and formula 2, X1 is C(R7) or N, X2 is C(R8) or N, X3 is C(R9) or N, At least one of X1 to X3 is N, Ar1 and Ar2 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 A heterocyclic group or a group represented by Formula 2, CY1 and CY2 are each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, T is a single bond, a double bond, N(R 10 )、C(R 10 )(R 11 )、Si(R 10 )(R 11 ), S or O, a1 is an integer from 1 to 4, a2 to a4 are each independently an integer from 1 to 5, a5 and a6 are each independently an integer from 1 to 10, When a1 is 2 or more, a1 R1 are the same as or different from each other. When a2 is 2 or more, a2 R2 are the same as or different from each other, When a3 is 2 or more, a3 R3 are the same as or different from each other, When a4 is 2 or more, a4 R4 are the same as or different from each other. When a5 is 2 or more, a5 R5 are the same as or different from each other. When a6 is 2 or more, a6 R6 are the same as or different from each other. R1 to R 11 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), At least one of a2 R2, a3 R3 and a4 R4 is independently unsubstituted or substituted with at least one R 10a Substituted C1-C 60 alkyl, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof; C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; Br; -I; hydroxyl; cyano; nitro; or C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or a combination thereof.
11. The heterocyclic compound according to claim 10, wherein The heterocyclic compound includes at least one deuterium atom.
12. The heterocyclic compound according to claim 10, wherein X1 to X3 are each N.
13. The heterocyclic compound according to claim 10, wherein At least one of Ar1 and Ar2 is each independently a group represented by Formula 2.
14. The heterocyclic compound according to claim 10, wherein CY1 and CY2 are each independently unsubstituted or substituted with at least one R 10a Substituted phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolyl benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl, benzo[pi]yl 15. The heterocyclic compound according to claim 10, wherein In formula 1, Different from each other.
16. The heterocyclic compound according to claim 10, wherein The heterocyclic compound is represented by one of Formula 1-1 to Formula 1-3: Among them, in Formula 1-1 to Formula 1-3, X1 to X3, Ar1, Ar2, a1 to a4 and R1 to R4 are each as defined in Formula 1.
17. The heterocyclic compound according to claim 10, wherein R1 to R 11 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or Morpholinyl, phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, phenyl, pyridyl or a combination thereof.
18. The heterocyclic compound according to claim 10, wherein At least one of a2 R2, a3 R3 and a4 R4 is each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, and each is unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro.
19. The heterocyclic compound according to claim 10, wherein The heterocyclic compound satisfies at least one of conditions I to III: Condition I When one of a2 R2 is unsubstituted or replaced by at least one R 10a When the phenyl group is substituted, at least one of a3 R3 and a4 R4 is independently unsubstituted or replaced by at least one R 10a Substituted C1-C 60 alkyl; Condition II When one of a3 R3 is unsubstituted or replaced by at least one R 10a When the phenyl group is substituted, at least one of a2 R2 and a4 R4 is independently unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl; and Condition III When one of the a4 R4 is unsubstituted or replaced by at least one R 10a When the phenyl group is substituted, at least one of a2 R2 and a3 R3 is independently unsubstituted or substituted by at least one R 10a Substituted C1-C 60 alkyl.
20. The heterocyclic compound according to claim 10, wherein The heterocyclic compound represented by Formula 1 is one of Compound 1 to Compound 35:
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