Composition, light-emitting device, electronic equipment and electronic device including the light-emitting device, and organic metal compound
By using the composition of the organometallic compound represented by Formula 1 and a specific heterocyclic compound in the light emitting device, the problem of insufficient color purity, luminous efficiency and lifetime characteristics of the light emitting device in the prior art is solved, and the luminous performance with more efficient, durable and color-pure is achieved.
Patent Information
- Application Number
- CN202411393328.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-05
- Filing Date
- 2024-10-08
- Publication Date
- 2025-04-08
AI Technical Summary
There is room for improvement in color purity, luminous efficiency and life characteristics of existing luminescent devices, and it is difficult to meet the requirements of high efficiency, durability and color purity at the same time.
A composition is used to construct an emission layer of a light emitting device using an organometallic compound represented by formula 1 and a second compound containing at least one π electron-deficient nitrogen-containing C1-C60 heterocyclyl group, a third compound of a group represented by formula 3, a fourth compound that emits a delayed fluorescence, or any combination thereof.
The color purity, luminous efficiency and life characteristics of the luminous emitting device are realized, and the overall performance of the luminous performance is improved.
Smart Images

Figure CN119775320A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0132834 filed in the Korean Intellectual Property Office on October 5, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more aspects of the embodiments of the present disclosure relate to a composition, a light-emitting device, electronic equipment and electronic devices including the light-emitting device, and an organic metal compound. Background Art
[0004] The light-emitting device is a so-called "self-emissive" device (e.g., an organic light-emitting device) that has a relatively wide viewing angle, a relatively high contrast ratio, a relatively short response time, and / or excellent or appropriate characteristics in terms of brightness, driving voltage and / or response speed compared to other display devices.
[0005] In the light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are arranged on the first electrode in sequence. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Then, the holes and electrons recombine in the emission layer to generate excitons, which can transition (ie, relax) from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] One or more aspects of embodiments of the present disclosure are directed to compositions that can provide improved color purity, improved luminous efficiency, and / or improved lifetime characteristics.
[0007] One or more aspects of the embodiments of the present disclosure are directed to a light emitting device having improved color purity, improved luminous efficiency, and / or improved lifespan characteristics, and electronic equipment and electronic devices including the light emitting device.
[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 the presented embodiments of the disclosure.
[0009] According to one or more embodiments, the composition comprises:
[0010] an organometallic compound represented by Formula 1, and
[0011] Includes at least one π-electron-deficient nitrogen-containing C 1 -C 60a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound emitting (emit, for example, emitting) delayed fluorescence, or any combination thereof,
[0012] The organometallic compound, the second compound, the third compound and the fourth compound are different from each other:
[0013] Formula 1
[0014]
[0015] Formula 1A
[0016]
[0017] In formula 1, Ar 1 and Ar 2 may each independently be a group represented by Formula 1A,
[0018] Wherein, in Formula 1 and Formula 1A,
[0019] M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag) or copper (Cu),
[0020] L 1 It can be a monodentate ligand,
[0021] X 1 To X 3 and Y 1 To Y 3 can be independently C or N,
[0022] Cyclo 1 To Ring CY 3 and Ring A 1 To Ring A 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0023] Selected from X 1 The bond between M and X 2 The bond between M and X 3 The bond between M and L 1 Two of the four bonds between X and M may each be coordinate bonds, and two of the four bonds may each be covalent bonds, (e.g., X 1 The bond between M and X 2 The bond between M and X 3 The bond between M and L 1 The bond between M includes two coordination bonds and two covalent bonds).
[0024] n1 and n2 can each independently be 0 or 1,
[0025] R 1 To R 3 and T 1 To T 4 can be 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)(Q1 )(Q 2 ),
[0026] a1 to a3 and b1 to b4 may each independently be an integer selected from 0 to 20,
[0027] Selected from Cyclo 1 CY 2 , Ring A 2 , Ring A 3 , R 1 To R 3 and T 1 To T 4 At least two of them may not be bonded to each other or may be bonded to each other to form an unsubstituted or substituted 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,
[0028] * indicates the binding site with adjacent atoms,
[0029] R 10a Can
[0030] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,
[0031] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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(Q11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof,
[0032] Each unsubstituted or substituted 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 Heteroaralkyl: 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, 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
[0033] -Si(Q 31 )(Q32 )(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
[0034] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 may be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 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 group,
[0035] Formula 3
[0036]
[0037] In formula 3,
[0038] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0039] X 71 may be a single bond, or a linking group comprising O, S, N, B, C, Si or any combination thereof, and
[0040] * indicates a binding site with (eg, any) atom in the third compound but not in Formula 3 (eg, included in the remaining part other than Formula 3 in the third compound).
[0041] According to one or more embodiments, the light emitting device comprises
[0042] The first electrode,
[0043] a second electrode facing the first electrode,
[0044] an interlayer disposed between the first electrode and the second electrode and including an emitting layer, and
[0045] An organometallic compound represented by Formula 1.
[0046] According to one or more embodiments, an electronic device includes a light emitting device.
[0047] According to one or more embodiments, an electronic device includes a light emitting device.
[0048] According to one or more embodiments, an organometallic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0049] The accompanying drawings are included to provide a further understanding of the foregoing and other aspects, features and advantages of certain embodiments of the present disclosure, and are incorporated in and constitute a part of this specification. The drawings, together with the following description made with reference to the accompanying drawings, illustrate example embodiments. In the drawings:
[0050] Figure 1 is a schematic diagram of a structure of a light emitting device according to one or more embodiments;
[0051] Figure 2 and Figure 3 Each is a schematic diagram of a structure of a light emitting device as one of electronic equipment according to one or more embodiments; and
[0052] Figure 4 , Figure 5 , Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of a structure of an electronic device according to one or more embodiments. DETAILED DESCRIPTION
[0053] The embodiments in the accompanying drawings will now be explained in more detail with reference to their examples, wherein the same reference numerals refer to the same elements throughout the specification, and their repeated description may not be provided. In this regard, the present embodiment may have different forms and should not be interpreted as being limited to the description stated herein. Accordingly, the embodiments are described only by reference to the accompanying drawings to explain the various aspects of this description. As used herein, the term "and / or" includes any and all combinations of one or more related enumerated items. Statements such as "at least one of ...", "one of ..." and "selected from ...", when before / after the list of elements, modify the entire list of elements without modifying the individual elements of the list. For example, throughout this disclosure, the statement "at least one of a, b and c" indicates only a, only b, only c, both a and b (e.g., a and b at the same time), both a and c (e.g., a and c at the same time), both b and c (e.g., b and c at the same time), all a, b and c, or variations thereof.
[0054] Unless otherwise limited, all chemical names, technical terms and scientific terms and the terms defined in common dictionaries should be interpreted as having a meaning consistent with the context of the relevant field, and should not be interpreted in an ideal or overly formal sense. It will be understood that although the terms first, second, etc. can be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish an 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, the second element can be referred to as the first element.
[0055] As used herein, the singular forms such as “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0056] It will be further understood that the terms “comprise,” “comprises,” “comprising,” “has,” “have,” “having,” “include,” “includes,” and / or “including,” when used in the present specification, indicate the presence of specified features, steps, operations, elements, components, and / or groups thereof, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and / or groups thereof.
[0057] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0058] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.
[0059] The term "may" will be understood to refer to "one or more embodiments of the present disclosure," some of which include the described elements, and some of which do not include the elements and / or include optional elements. Similarly, optional language such as "or" refers to "one or more embodiments of the present disclosure," each of which includes the corresponding enumerated items.
[0060] It will be understood that when an element is referred to as being "on," "connected to," or "coupled to" another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present. When an element is referred to as being "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements.
[0061] For ease of description, spatially relative terms such as "below," "beneath," "below," "above," "above," "bottom," and "top," etc., may be used herein to describe the relationship of one element or feature to another element or feature as illustrated in the accompanying drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the accompanying drawings. For example, if the device in the drawings is turned over, elements described as being "below" or "beneath" other elements or features will be oriented "above" or "on" the other elements or features. Thus, the term "below" may encompass both orientations of above and below. The device may be otherwise oriented (rotated 90 degrees or in other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
[0062] In this context, "consisting essentially of" means that any additional components will not materially affect the chemical, physical, optical, or electrical properties of the semiconductor film.
[0063] In the present disclosure, "not include (or not including) one or any 'component'", "exclude (or excluding) one or any 'component'" and / or "does not contain a 'component'" etc. means that the 'component' is not added, selected or used as a component in the element / composition, but due to other impurities and / or external factors, the 'component' may still be included in an appropriate amount.
[0064] Further, in this specification, the phrase "on a plane" or "plan view" means observing a target portion from the top, and the phrase "in cross section" means observing a cross section formed by vertically cutting the target portion from the side.
[0065] Composition
[0066] One aspect of the present disclosure provides a composition comprising:
[0067] an organometallic compound represented by Formula 1; and
[0068] Includes at least one π-electron-deficient nitrogen-containing C 1 -C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound emitting (emit, for example, emitting) delayed fluorescence, or any combination thereof,
[0069] the organometallic compound, the second compound, the third compound and the fourth compound are different from each other,
[0070] Formula 1
[0071]
[0072] Formula 3
[0073]
[0074] In formula 3,
[0075] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0076] X 71 may be a single bond, or a linking group comprising O, S, N, B, C, Si or any combination thereof, and
[0077] * indicates a binding site with (eg, any) atom in the third compound but not in Formula 3 (eg, included in the remaining part other than Formula 3 in the third compound).
[0078] In the present specification, the organometallic compound represented by Formula 1 may be referred to as a 'first compound'.
[0079] Details regarding each of Formula 1 and Formula 3 may be referred to as described in the description provided herein.
[0080] In one or more embodiments, the composition may be included in a layer including 1) an organic metal compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof. The layer including the composition may include a mixture including 1) an organic metal compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof. Therefore, the layer including the composition is clearly distinguished (e.g., different) from, for example, a double layer including 1) a first layer including an organic metal compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof.
[0081] In one or more embodiments, the composition can be prepared by using one or more appropriate methods (such as deposition process and / or wet process, etc.) to form the following layer, which includes 1) an organic metal compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof. In one or more embodiments, the composition can be a premixed mixture prepared for use in a deposition process (e.g., a vacuum deposition process). The premixed mixture can, for example, be filled into a deposition source in a vacuum chamber, and one or two or more compounds included in the premixed mixture can then be co-deposited.
[0082] In one or more embodiments, a weight ratio of the organometallic compound represented by Formula 1 to the second compound in the composition may be in a range of about 10:90 to about 90:10 or about 20:80 to about 80:20.
[0083] Another aspect of the present disclosure provides a light emitting device, comprising:
[0084] a first electrode;
[0085] a second electrode facing the first electrode;
[0086] an interlayer disposed between the first electrode and the second electrode and including an emission layer; and
[0087] An organometallic compound represented by Formula 1.
[0088] The detailed description of Formula 1 is as described elsewhere herein.
[0089] The light-emitting device includes the organometallic compound represented by Formula 1 and thus may have improved color purity, improved light-emitting efficiency, and / or improved lifespan characteristics.
[0090] In one or more embodiments, an interlayer in a light-emitting device may include an organic metal compound represented by Formula 1.
[0091] In one or more embodiments, an emission layer in a light emitting device may include the organometallic compound represented by Formula 1.
[0092] In one or more embodiments, the light emitting device may further include: a nitrogen-containing C 1 -C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof,
[0093] The organometallic compound represented by Formula 1, the second compound, the third compound, and the fourth compound in the light-emitting device may be different from each other:
[0094] The second to fourth compounds in the composition and the light emitting device can each be as described elsewhere herein.
[0095] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
[0096] In one or more embodiments, the second to fourth compounds may each include at least one deuterium.
[0097] In one or more embodiments, the second compound may include at least one silicon.
[0098] In one or more embodiments, the third compound may include at least one silicon.
[0099] In one or more embodiments, in addition to the organic metal compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound and a third compound, wherein at least one of the second compound and the third compound may include at least one deuterium, at least one silicon, or a combination thereof.
[0100] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may each further include a second compound. At least one of the organometallic compound represented by Formula 1 and the second compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound represented by Formula 1 and the second compound, the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may each further include a third compound, a fourth compound, or any combination thereof.
[0101] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may each further include a third compound. At least one of the organometallic compound represented by Formula 1 and the third compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound represented by Formula 1 and the third compound, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a fourth compound, or any combination thereof.
[0102] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a fourth compound. At least one of the organometallic compound represented by Formula 1 and the fourth compound may include at least one deuterium. The fourth compound may have a role in improving the color purity, luminous efficiency and / or life characteristics of the light-emitting device. In one or more embodiments, in addition to the organometallic compound represented by Formula 1 and the fourth compound, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a third compound, or any combination thereof.
[0103] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound and a third compound. The second compound and the third compound may form an excited complex. At least one of the organometallic compound represented by Formula 1, the second compound, and the third compound may include at least one deuterium.
[0104] In one or more embodiments, the highest occupied molecular orbital (HOMO) energy level of the organometallic compound represented by Formula 1 may be in a range of about -5.70 electron volts (eV) to about -5.15 eV or about -5.61 eV to about -5.20 eV.
[0105] In one or more embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound represented by Formula 1 may be in the range of about -2.30 eV to about -1.80 eV or about -2.21 eV to about -2.06 eV.
[0106] The HOMO energy level and the LUMO energy level can be evaluated by cyclic voltammetry analysis of the organometallic compound represented by Formula 1 (refer to Evaluation Example 1).
[0107] In one or more embodiments, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of the film including the organic metal compound represented by Formula 1 may be in the range of about 430 nanometers (nm) to about 490 nm, about 430 nm to about 485 nm, about 430 nm to about 480 nm, about 430 nm to about 477 nm, about 440 nm to about 490 nm, about 440 nm to about 485 nm, about 440 nm to about 480 nm, about 440 nm to about 477 nm, about 450 nm to about 490 nm, about 450 nm to about 485 nm, about 450 nm to about 480 nm, about 450 nm to about 477 nm, about 457 nm to about 490 nm, about 457 nm to about 485 nm, about 457 nm to about 480 nm, or about 457 nm to about 477 nm.
[0108] In one or more embodiments, the full width at half maximum (FWHM) of the emission spectrum of the film including the organic metal compound represented by Formula 1 may be 110 nm or less, for example, in the range of about 10 nm to about 110 nm, about 30 nm to about 110 nm, about 50 nm to about 110 nm, about 61 nm to about 110 nm, about 10 nm to about 90 nm, about 30 nm to about 90 nm, about 50 nm to about 90 nm, about 61 nm to about 90 nm, about 10 nm to about 72 nm, about 30 nm to about 72 nm, about 50 nm to about 72 nm, or about 61 nm to about 72 nm.
[0109] In one or more embodiments, the photoluminescence quantum yield (PLQY) of the film including the organometallic compound represented by Formula 1 may be in a range of about 40% to about 99%, about 49% to about 90%, about 49% to about 80%, or about 49% to about 70%.
[0110] In one or more embodiments, the decay time of the film including the organometallic compound represented by Formula 1 may be in a range of about 1.80 microseconds (μs) to about 3.00 μs, about 1.90 μs to about 2.70 μs, or about 1.90 μs to about 2.50 μs.
[0111] For the film including the organometallic compound represented by Formula 1, the maximum emission wavelength, FWHM, PLQY and decay time of the organometallic compound represented by Formula 1 were evaluated, and the evaluation methods thereof can be each independently as described with reference to, for example, Evaluation Examples 2 and 3.
[0112] In one or more embodiments, an emission layer in a light emitting device may include: i) an organometallic compound represented by Formula 1; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, wherein the emission layer may emit blue light.
[0113] In one or more embodiments, the maximum emission wavelength of blue light may be in the range of about 430 nm to about 490 nm, about 430 nm to about 485 nm, about 430 nm to about 480 nm, about 430 nm to about 477 nm, about 440 nm to about 490 nm, about 440 nm to about 485 nm, about 440 nm to about 480 nm, about 440 nm to about 477 nm, about 450 nm to about 490 nm, about 450 nm to about 485 nm, about 450 nm to about 480 nm, about 450 nm to about 477 nm, about 457 nm to about 490 nm, about 457 nm to about 485 nm, about 457 nm to about 480 nm, or about 457 nm to about 477 nm.
[0114] In one or more embodiments, the full width at half maximum of the blue light may be 110 nm or less, for example, in the range of about 10 nm to about 110 nm, about 30 nm to about 110 nm, about 50 nm to about 110 nm, about 61 nm to about 110 nm, about 10 nm to about 90 nm, about 30 nm to about 90 nm, about 50 nm to about 90 nm, about 61 nm to about 90 nm, about 10 nm to about 72 nm, about 30 nm to about 72 nm, about 50 nm to about 72 nm, or about 61 nm to about 72 nm.
[0115] In one or more embodiments, the blue light may be deep blue light.
[0116] In one or more embodiments, the CIEx coordinate of blue light (eg, the CIEx coordinate of bottom emission) may be in a range of about 0.125 to about 0.140 or about 0.130 to about 0.140.
[0117] In one or more embodiments, the CIEy coordinate of blue light (eg, the CIEy coordinate of bottom emission) may be in the range of about 0.100 to about 0.130.
[0118] In one or more embodiments, the second compound may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0119] In one or more embodiments, the third compound may not include (eg, may exclude) the following compounds:
[0120]
[0121] In one or more embodiments, the difference between the triplet energy level (unit: eV) and the singlet energy level (eV) of the fourth compound may be in the range of about 0 eV or more to about 0.5 eV or less (or about 0 eV or more to about 0.3 eV or less).
[0122] In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including each of boron (B) and nitrogen (N) as a ring-constituting atom.
[0123] In one or more embodiments, the fourth compound may be a compound containing C 8 -C 60 A polycyclic compound comprising two or more cyclic groups fused together while sharing B.
[0124] In one or more embodiments, the fourth compound may include a fused ring in which at least one third ring is fused to at least one fourth ring,
[0125] wherein the third ring can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and
[0126] The fourth ring can be 1,2-azaborinyl, 1,3-azaborinyl, 1,4-azaborinyl, 1,2-dihydro-1,2-azaborinyl, 1,4-oxaborinyl, 1,4-thiaborinyl or 1,4-dihydroborinyl.
[0127] In one or more embodiments, the third compound may not include (eg, may exclude) the compound represented by Formula 3-1 described herein.
[0128] In one or more embodiments, the second compound may include a compound represented by Formula 2:
[0129] Formula 2
[0130]
[0131] Among them, in formula 2,
[0132] L 51 To L 53 may be independently a single bond, unsubstituted or substituted by 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,
[0133] b51 to b53 may each independently be an integer selected from 1 to 5,
[0134] X 54 Can be N or C(R 54 ), X 55 Can be N or C(R 55 ), X 56 Can be N or C(R 56 ), and X 54 To X 56 At least one of may be N, and
[0135] R 51 To R 56 and R 10a Each may be as described elsewhere herein.
[0136] In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0137] Formula 3-1
[0138]
[0139] Formula 3-2
[0140]
[0141] Formula 3-3
[0142]
[0143] Formula 3-4
[0144]
[0145] Formula 3-5
[0146]
[0147] Among them, in Formula 3-1 to Formula 3-5,
[0148] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0149] X 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a)(R 82b ),
[0150] X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0151] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0152] X 85 Can be C or Si,
[0153] L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a Substituted pyridyl, wherein Q 4 and Q 5 Please refer to Q 1 Described,
[0154] b81 to b85 may each independently be an integer selected from 1 to 5,
[0155] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may each be as described elsewhere herein,
[0156] a71 to a74 may each independently be an integer selected from 0 to 20, and
[0157] R 10a As may be described elsewhere herein.
[0158] In one or more embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0159] Formula 502
[0160]
[0161] Formula 503
[0162]
[0163] Among them, in equation 502 and equation 503,
[0164] Ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0165] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0166] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0167] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0168] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R508a )(R 508b ),
[0169] Y 51 and Y 52 may be independently B or P(=O),
[0170] R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b may each be as described elsewhere herein, and
[0171] a501 to a504 may each independently be an integer selected from 0 to 20.
[0172] In one or more embodiments, the light emitting device may satisfy at least one of conditions 1 to 4:
[0173] Condition 1
[0174] The LUMO energy level (eV) of the third compound is greater than (>) the LUMO energy level (eV) of the organometallic compound represented by Formula 1;
[0175] Condition 2
[0176] The LUMO energy level (eV) of the organometallic compound represented by Formula 1 is greater than (>) the LUMO energy level (eV) of the second compound;
[0177] Condition 3
[0178] The HOMO energy level (eV) of the organometallic compound represented by Formula 1 is greater than (>) the HOMO energy level (eV) of the third compound; and
[0179] Condition 4
[0180] The HOMO energy level (eV) of the third compound is greater than (>) the HOMO energy level (eV) of the second compound.
[0181] Here, each of the HOMO level and the LUMO level of each of the organometallic compound represented by Formula 1, the second compound, and the third compound may be a negative value and may be measured according to an appropriate method, for example, the method described in Evaluation Example 1 in this specification.
[0182] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the organic metal compound represented by Formula 1 and the LUMO energy level of the second compound may be in the range of about 0.1 eV or greater to about 1.0 eV or less, the absolute value of the difference between the LUMO energy level of the organic metal compound represented by Formula 1 and the LUMO energy level of the third compound may be in the range of about 0.1 eV or greater to about 1.0 eV or less, the absolute value of the difference between the HOMO energy level of the organic metal compound represented by Formula 1 and the HOMO energy level of the second compound may be 1.25 eV or less (e.g., about 0.2 eV or greater to about 1.25 eV or less), and the absolute value of the difference between the HOMO energy level of the organic metal compound represented by Formula 1 and the HOMO energy level of the third compound may be about 1.25 eV or less (e.g., about 0.2 eV or greater to about 1.25 eV or less).
[0183] When the relationship between the LUMO energy level and the HOMO energy level satisfies the aforementioned conditions, an appropriate or excellent balance between holes and electrons each injected into the emission layer can be achieved.
[0184] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0185] First embodiment
[0186] According to the first embodiment, the emission layer of the interlayer in the light-emitting device may include an organic metal compound represented by Formula 1, and may further include a host, wherein the organic metal compound represented by Formula 1 and the host may be different from each other, and the emission layer may emit phosphorescence or fluorescence emitted from the organic metal compound represented by Formula 1. For example, according to the first embodiment, the organic metal compound represented by Formula 1 may be a dopant or an emitter. For example, the organic metal compound represented by Formula 1 may be a phosphorescent dopant or a phosphorescent emitter.
[0187] Phosphorescence or fluorescence emitted from the organometallic compound represented by Formula 1 may be blue light.
[0188] The emission layer may further include an auxiliary dopant. The auxiliary dopant may effectively transfer energy to the organic metal compound represented by Formula 1 used as a dopant or an emitter, and in this regard, the auxiliary dopant may be used to improve the light emission efficiency of the organic metal compound represented by Formula 1.
[0189] The auxiliary dopant may be different from each of the organometallic compound represented by Formula 1 and the host.
[0190] In one or more embodiments, the auxiliary dopant may be a compound emitting delayed fluorescence.
[0191] In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including each of B and N as a ring-forming atom.
[0192] Second embodiment
[0193] According to a second embodiment, the emission layer of the interlayer in the light-emitting device may include an organic metal compound represented by Formula 1, and may further include a host and a dopant, wherein the organic metal compound represented by Formula 1, the host and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
[0194] In one or more embodiments, the organometallic compound represented by Formula 1 in the second embodiment is not a dopant but may be used as an auxiliary dopant that transfers energy to a dopant (or an emitter).
[0195] In one or more embodiments, the organometallic compound represented by Formula 1 in the second embodiment may be used as an emitter, and may also be used as an auxiliary dopant that transfers energy to a dopant (or emitter).
[0196] For example, phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0197] The dopant (or emitter) in the second embodiment may be (e.g., any) phosphorescent dopant material (e.g., an organic metal compound represented by Formula 1, an organic metal compound represented by Formula 401, or any combination thereof) or (e.g., any) fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof).
[0198] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength in the range of about 430 nm to about 490 nm, about 430 nm to about 485 nm, about 430 nm to about 480 nm, about 430 nm to about 477 nm, about 440 nm to about 490 nm, about 440 nm to about 485 nm, about 440 nm to about 480 nm, about 440 nm to about 477 nm, about 450 nm to about 490 nm, about 450 nm to about 485 nm, about 450 nm to about 480 nm, about 450 nm to about 477 nm, about 457 nm to about 490 nm, about 457 nm to about 485 nm, about 457 nm to about 480 nm, or about 457 nm to about 477 nm.
[0199] The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503.
[0200] In one or more embodiments, the host in the first embodiment and the second embodiment may be (eg, any) host material (eg, a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof).
[0201] In one or more embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
[0202] In one or more embodiments, the light emitting device may further include a capping layer disposed outside the first electrode (eg, and on the first electrode) and / or outside the second electrode (eg, and on the second electrode).
[0203] In one or more embodiments, the light-emitting device may further include at least one of a first capping layer disposed outside the first electrode (e.g., and on the first electrode) and a second capping layer disposed outside the second electrode (e.g., and on the second electrode), wherein at least one of the first capping layer and the second capping layer may include an organic metal compound represented by Formula 1. For more details about the first capping layer and / or the second capping layer, reference may be made to the description provided herein.
[0204] In one or more embodiments, the light emitting device may include:
[0205] A first capping layer disposed outside the first electrode (eg, and on the first electrode) and including an organic metal compound represented by Formula 1;
[0206] A second capping layer disposed outside the second electrode (eg, and on the second electrode) and including an organic metal compound represented by Formula 1; or
[0207] Both (eg, simultaneously) a first capping layer and a second capping layer.
[0208] The phrase “(the interlayer and / or the capping layer) includes the organic metal compound represented by Formula 1” as used herein may be understood as “(the interlayer and / or the capping layer) may include one kind of the organic metal compound represented by Formula 1 or two or more different kinds of organic metal compounds each represented by Formula 1”.
[0209] In one or more embodiments, the interlayer and / or the capping layer may include only Compound 1, which is an organic metal compound represented by Formula 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include Compound 1 and Compound 2, which are organic metal compounds represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in substantially the same layer (e.g., Compound 1 and Compound 2 may both (e.g., simultaneously) be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0210] The term "interlayer" as used herein refers to a single layer and / or each (eg, all) of a plurality of layers disposed between a first electrode and a second electrode of a light emitting device.
[0211] Another aspect of the present disclosure provides an electronic device including 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 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 one or more embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. For more details about the electronic device, reference may be made to the description provided herein.
[0212] Another aspect provides an electronic device including a light emitting device.
[0213] For example, the electronic device may be at least one selected from 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 retractable display, a laser printer, a phone, a portable phone, a tablet personal computer, a tablet phone, 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 tiled together, a theater screen, a stadium screen, a light therapy device, and a sign.
[0214] Another aspect of the present disclosure provides an organometallic compound represented by Formula 1. Details regarding Formula 1 may refer to the description provided herein.
[0215] The synthesis method of the organometallic compound represented by Formula 1 can be recognized by one of ordinary skill in the art by referring to the Synthesis Examples and / or Examples provided herein.
[0216] Description of Formula 1 and Formula 1A
[0217] In formula 1, Ar 1 and Ar 2 Each of may be a group represented by Formula 1A:
[0218] Formula 1
[0219]
[0220] Formula 1A
[0221]
[0222] Wherein, regarding formula 1 (or Ar in formula 1 1 and Ar 2 For more details of each of the descriptions in the specification, reference may be made to the description provided herein.
[0223] In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu). For example, M may be Pt.
[0224] In formula 1, L 1 It can be a monodentate ligand. 1 Further details are provided elsewhere in this article.
[0225] In Formula 1 and Formula 1A, X 1 To X 3 and Y 1 To Y 3 can each independently be C or N. For example, X 1 To X 3 and Y 1 To Y 3 Each of can be C.
[0226] In Formula 1 and Formula 1A, ring CY 1 To Ring CY 3 and Ring A 1 To Ring A 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group.
[0227] For example, CY 1 To Ring CY 3 and Ring A 1 To Ring A 4 Can be independently:
[0228] phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, imidazolyl, oxazolyl, thiazolyl or triazolyl; or
[0229] Phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, cyclohexyl, adamantyl, norbornyl or any combination thereof, each fused to phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, imidazolyl, oxazolyl or thiazolyl. Phenyl fused to phenyl is naphthyl, and pyridyl fused to phenyl and phenyl fused to pyridyl are quinolyl or isoquinolyl.
[0230] In one or more embodiments, CY 1 Can be:
[0231] imidazolyl fused to phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or any combination thereof; or
[0232] imidazolyl or triazolyl.
[0233] In one or more embodiments, CY 1 It may be imidazolyl, benzimidazolyl or pyridoimidazolyl.
[0234] In one or more embodiments, CY 2 Can be:
[0235] imidazolyl, oxazolyl or thiazolyl, each fused to phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or any combination thereof; or
[0236] imidazolyl, oxazolyl, thiazolyl or triazolyl.
[0237] In one or more embodiments, CY 2 It may be imidazolyl, benzimidazolyl, pyridoimidazolyl, oxazolyl, benzoxazolyl, pyridooxazolyl, thiazolyl, benzothiazolyl or pyridothiazolyl.
[0238] In one or more embodiments, CY 3 It may be phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, naphthyl, quinolyl or isoquinolyl.
[0239] In one or more embodiments, Ring A 1 To Ring A 4 Can be independently:
[0240] phenyl, pyridyl, pyrimidinyl, pyridazinyl or pyrazinyl; or
[0241] Phenyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, each fused to a cyclohexyl, adamantyl or norbornyl group.
[0242] In one or more embodiments, Ring A 1 To Ring A 4Each independently may be phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or 1,2,3,4-tetrahydronaphthyl.
[0243] In Formula 1, selected from X 1 The bond between M and X 2 The bond between M and X 3 The bond between M and L 1 Two of the four bonds between X and M may each be a coordinate bond, and the unselected two bonds of the four bonds (eg, the other two bonds) may each be a covalent bond (eg, X 1 The bond between M and X 2 The bond between M and X 3 The bond between M and L 1 The bond between M and M includes two coordination bonds and two covalent bonds).
[0244] In one or more embodiments, in Formula 1, X 1 The key between M and X 2 The bonds between X and M may each be coordination bonds, and X 3 The bond between M and L 1 The bonds between M and M may each be covalent bonds.
[0245] In one or more embodiments, in Formula 1, X 1 The key between M and X 2 The bonds between X and M can each be coordination bonds, where X 1 and X 2 Each of may be C, and C may be a carbon of a carbene moiety.
[0246] In Formula 1 and Formula 1A, n1 and n2 may each independently be 0 or 1. When n1 in Formula 1 is 0, Ring A 3 Can be combined with Y in Formula 1A 3 Direct bonding. n2 can represent Ar in formula 1 2 The number of
[0247] In Formula 1 and Formula 1A, R 1 To R 3 and T 1 To T 4 can be 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 10aSubstituted 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 ). Q 1 To Q 3 Each may be as described elsewhere herein.
[0248] In one or more embodiments, R 1 To R 3 and T 1 To T 4 Can be independently:
[0249] Hydrogen, deuterium, -F or cyano;
[0250] Unsubstituted or substituted by C 1 -C 20 Alkyl: deuterium, -F, cyano, C3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C 10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl)biphenyl or any combination thereof; or
[0251] Each unsubstituted or substituted C 3 -C 10 Cycloalkyl, phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, carbazolyl, dibenzofuranyl or dibenzothienyl: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C 10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl) biphenyl, carbazolyl, deuterated carbazolyl, fluorinated carbazolyl, (C 1 -C 20 alkyl)carbazolyl or any combination thereof.
[0252] As used herein, the term "C 1 -C 60 "alkyl" and "unsubstituted or substituted with at least one deuterium C 1 -C 20The “alkyl” radicals may each be, for example, 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 or tert-decyl, each of which is unsubstituted or substituted by at least one deuterium.
[0253] In one or more embodiments, the term "unsubstituted or substituted with at least one deuterium" as used herein 1 -C 60 "alkyl" and "unsubstituted or substituted with at least one deuterium C 1 -C 20 "Alkyl" may each be -CH 3 、-CDH 2 、-CD 2 H.-CD 3 、-CH 2 CH 3 、-CDHCH 3 、-CD 2 CH 3 、-CH 2 CDH 2 、-CDHCDH 2 、-CD 2 CDH 2 、-CH 2 CD 2 H, -CDHCD 2 H.-CD 2 CD 2 H, -CH 2 CD 3 、-CDHCD 3 、-CD 2 CD 3 , or a group represented by one of Formula X-1 to Formula X-30:
[0254]
[0255] In Formulae X-1 to X-30, * indicates a bonding site with an adjacent atom.
[0256] As used herein, the term "deuterated C 1 -C 60 Alkyl", "C substituted by (at least one) deuterium 1 -C 60 Alkyl", "deuterated C 1 -C 20"alkyl" or "C 1 -C 20 "Alkyl" may refer to a linear or branched C 1 -C 60 Alkyl (either straight chain or branched chain C 1 -C 20 alkyl) in which at least one hydrogen atom is replaced by deuterium, and examples thereof may be 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 or tert-decyl, each of which is substituted by at least one deuterium (e.g., -CDH 2 、-CD 2 H.-CD 3 、-CDHCH 3 、-CD 2 CH 3 、-CH 2 CDH 2 、-CDHCDH 2 、-CD 2 CDH 2 、-CH 2 CD 2 H, -CDHCD 2 H.-CD 2 CD 2 H, -CH 2 CD 3 、-CDHCD 3 、-CD 2 CD 3 , or a group represented by one of Formula X-2 to Formula X-6, Formula X-8 to Formula X-10, Formula X-12 to Formula X-22, and Formula X-24 to Formula X-30).
[0257] In Formula 1 and Formula 1A, a1 to a3 and b1 to b4 may each independently be an integer selected from 0 to 20. a1 to a3 and b1 to b4 respectively indicate R 1 To R 3 The number and T 1 To T 4 When a1 is 2 or more, two or more R 1 may be the same as or different from each other. When a2 is 2 or greater, two or more R 2 may be the same as or different from each other. When a3 is 2 or greater, two or more R 3may be the same as or different from each other. When b1 is 2 or greater, two or more T 1 may be the same as or different from each other. When b2 is 2 or greater, two or more T 2 may be the same as or different from each other. When b3 is 2 or greater, two or more T 3 may be the same as or different from each other, and when b4 is 2 or greater, two or more T 4 Can be the same as or different from each other.
[0258] In Formula 1 and Formula 1A, a ring selected from CY 1 CY 2 , Ring A 2 , Ring A 3 , R 1 To R 3 and T 1 To T 4 At least two of the R may be optionally bonded to each other (eg, may not be bonded (eg, not bonded) or may be bonded (eg, bonded)) to form an unsubstituted or substituted 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.
[0259] For example, as described in Condition A1 and Condition A2 and Formulas 1-5 to 1-10, the ring CY in Formula 1 and Formula 1A 1 and Ring A 3 can be bonded to each other.
[0260] For example, as described in Condition B1 and Condition B2 and Formula 1-9 and Formula 1-10, the ring CY in Formula 1 and Formula 1A 2 and Ring A 3 can be bonded to each other.
[0261] Unless stated otherwise herein, * indicates a binding site to an adjacent atom.
[0262] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
[0263] In one or more embodiments, the formula 1 is The group represented may be a group represented by one of the formulas CY1-1 to CY1-9:
[0264]
[0265] Among them, in Formula CY1-1 to Formula CY1-9,
[0266] X 1 and Ar 1 may each be as described elsewhere herein,
[0267] R 11 To R 14 Each can be referred to as R 1 Described,
[0268] * indicates the binding site with M in Formula 1, and
[0269] *' indicates the ring CY in formula 1 3 binding site.
[0270] In one or more embodiments, the formula 1 is The group represented may be a group represented by one of Formula CY2-1 to Formula CY2-9:
[0271]
[0272] Among them, in Formula CY2-1 to Formula CY2-9,
[0273] X 20 Can be N(R 20 )、N(Ar 2 ), O or S,
[0274] X 2 and Ar 2 may each be as described elsewhere herein,
[0275] R 20 To R 24 Each can be referred to as R 2 Described,
[0276] * indicates the binding site with M in Formula 1, and
[0277] *" indicates the same ring as CY in Formula 1 3 binding site.
[0278] In one or more embodiments, the formula 1 is The group represented may be a group represented by one of the formulas CY3-1 to CY3-5:
[0279]
[0280] Among them, in Formula CY3-1 to Formula CY3-5,
[0281] X 3 As described elsewhere in this document,
[0282] R31 To R 33 Each can be referred to as R 3 Described,
[0283] * indicates the binding site with M in Formula 1,
[0284] *' indicates the ring CY in formula 1 1 binding site, and
[0285] *" indicates the same ring as CY in Formula 1 2 binding site.
[0286] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition A1 or Condition A2:
[0287] Condition A1
[0288] In formula 1A, n1 is 0.
[0289] Ring A in Formula 1A 3 and the ring CY in formula 1 1 can be linked together by a single bond, and
[0290] From the ring CY in Formula 1 and Formula 1A 1 The ring atoms in 1 , Y 3 and Ring A 3 The ring formed by the ring-forming atoms in may be a 7-membered ring; and
[0291] Condition A2
[0292] In formula 1A, n1 is 1.
[0293] Ring A in Formula 1A 3 and the ring CY in formula 1 1 can be linked together by a single bond, and
[0294] From the ring CY in Formula 1 and Formula 1A 1 The ring atoms in 1 , Y 3 , Ring A 4 The ring atoms and ring A 3 The ring formed by the ring-forming atoms in may be a 9-membered ring.
[0295] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition B1 or Condition B2:
[0296] Condition B1
[0297] In formula 1, n2 can be 1,
[0298] n1 in formula 1A can be 0,
[0299] Ring A in Formula 1A 3 and the ring CY in formula 1 2 can be linked together by a single bond, and
[0300] From the ring CY in Formula 1 and Formula 1A 2 The ring atoms in 1 , Y 3 and Ring A 3 The ring formed by the ring-forming atoms in may be a 7-membered ring; and
[0301] Condition B2
[0302] In formula 1, n2 can be 1,
[0303] n1 in Formula 1A may be 1,
[0304] Ring A in Formula 1A 3 and the ring CY in formula 1 2 can be linked together by a single bond, and
[0305] From the ring CY in Formula 1 and Formula 1A 2 The ring atoms in 1 , Y 3 , Ring A 4 The ring atoms and ring A 3 The ring formed by the ring-forming atoms in may be a 9-membered ring.
[0306] In one or more embodiments, L in Formula 1 1 Can be *-(L 11 ) c1 -R 4 Represents the group.
[0307] In *-(L 11 ) c1 -R 4 middle,
[0308] L 11 It can be a single bond, *-O-*', *-S-*', *-C(R 41 )(R 42 )-*'、*-C(R 41 )=*'、*=C(R 41 )-*',
[0309] *-C(R 41 )=C(R 42 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-N(R 41 )-*', unsubstituted or replaced by 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,
[0310] c1 can be 1, 2 or 3,
[0311] R 4 , R 41 and R 42 Each can be referred to as R 1 Described,
[0312] R 10a may be as described elsewhere herein, and
[0313] * indicates the binding site to M in Formula 1.
[0314] For example, L 11 It may be a single bond, *-C≡C-*', 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, wherein C 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups may each independently be:
[0315] phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or carbazolyl; or
[0316] Phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or carbazolyl, each fused with a cyclohexyl group, an adamantyl group or a norbornyl group.
[0317] In one or more embodiments, R 4 , R 41 and R 42 Can be independently:
[0318] Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano;
[0319] Unsubstituted or substituted by C 1 -C 20 Alkyl: deuterium, -F, -Cl, -Br, -I, cyano, C 3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl)biphenyl or any combination thereof; or
[0320] Each unsubstituted or substituted C 3 -C 10 Cycloalkyl, phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C 10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl) biphenyl, carbazolyl, deuterated carbazolyl, fluorinated carbazolyl, (C 1 -C 20 alkyl)carbazolyl or any combination thereof.
[0321] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition C1 or Condition C2:
[0322] Condition C1
[0323] L 1 Can be *-(L 11 ) c1 -R 4 The group represented by
[0324] Where L 11 can be a single bond, and
[0325] R 4 may be -F, -Cl, -Br, -I or cyano; and
[0326] Condition C2
[0327] L 1 Can be *-(L 11 ) c1 -R 4 The group represented by
[0328] Where L 11 It can be *-C≡C-*',
[0329] c1 can be 1, and
[0330] R 4 may be hydrogen, or each unsubstituted or substituted by C 3 -C 10 Cycloalkyl, phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C 10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl) biphenyl, carbazolyl, deuterated carbazolyl, fluorinated carbazolyl, (C 1 -C 20 alkyl)carbazolyl or any combination thereof.
[0331] In one or more embodiments, the organometallic compound represented by Formula 1 may have a symmetrical structure.
[0332] In one or more embodiments, the organometallic compound represented by Formula 1 may have an asymmetric structure.
[0333] In one or more embodiments, in Formula 1, ring CY 1 and CY 2 Can be different from each other.
[0334] In one or more embodiments, in Formula 1, ring CY 1 and CY 2 Can be the same as each other.
[0335] In one or more embodiments, in Formula 1, n2 may be 0.
[0336] In one or more embodiments, in Formula 1, n2 may be 1, and Ar 1 and Ar 2 Can be different from each other.
[0337] In one or more embodiments, in Formula 1, n2 may be 1, and Ar 1 and Ar 2 Can be the same as each other.
[0338] In one or more embodiments, the organometallic compound represented by Formula 1 may be represented by one of Formulas 1-1 to 1-10 (eg, one selected therefrom):
[0339]
[0340]
[0341]
[0342] Among them, in Formula 1-1 to Formula 1-10,
[0343] X 20 Can be N(R 20 )、N(Ar 2 ), O or S,
[0344] M.L 1 ,Ar 1 ,Ar 2 and X 1 To X 3 may each be as described elsewhere herein,
[0345] X 11 Can be C(R 11 ) or N, X 12 Can be C(R 12 ) or N, X 13 Can be C(R 13 ) or N, and X 14 Can be C(R 14 ) or N, where R11 To R 14 Each can be referred to as R 1 Described,
[0346] X 21 Can be C(R 21 ) or N, X 22 Can be C(R 22 ) or N, X 23 Can be C(R 23 ) or N, and X 24 Can be C(R 24 ) or N, where R 20 To R 24 Each can be referred to as R 2 Described,
[0347] X 31 Can be C(R 31 ) or N, X 32 Can be C(R 32 ) or N, and X 33 Can be C(R 33 ) or N, where R 31 To R 33 Each can be referred to as R 3 Described,
[0348] Y 11 Can be C(T 11 ) or N, Y 12 Can be C(T 12 ) or N, and Y 13 Can be C(T 13 ) or N, where T 11 To T 13 Each can be referred to as T 1 Described,
[0349] Y 21 Can be C(T 21 ) or N, Y 22 Can be C(T 22 ) or N, Y 23 Can be C(T 23 ) or N, Y 24 Can be C(T 24 ) or N, and Y 25 Can be C(T 25 ) or N, where T 21 To T 25 Each can be referred to as T 2 Described,
[0350] Y 31 Can be C(T 31 ) or N, Y 32Can be C(T 32 ) or N, Y 33 Can be C(T 33 ) or N, and Y 34 Can be C(T 34 ) or N, where T 31 To T 34 Each can be referred to as T 3 Described,
[0351] Y 41 Can be C(T 41 ) or N, Y 42 Can be C(T 42 ) or N, Y 43 Can be C(T 43 ) or N, and Y 44 Can be C(T 44 ) or N, where T 41 To T 44 Each can be referred to as T 4 Described,
[0352] Y 51 Can be C(T 51 ) or N, Y 52 Can be C(T 52 ) or N, and Y 53 Can be C(T 53 ) or N, where T 51 To T 53 Each can be referred to as T 1 Described,
[0353] Y 61 Can be C(T 61 ) or N, Y 62 Can be C(T 62 ) or N, Y 63 Can be C(T 63 ) or N, Y 64 Can be C(T 64 ) or N, and Y 65 Can be C(T 65 ) or N, where T 61 To T 65 Each can be referred to as T 2 Described,
[0354] Y 71 Can be C(T 71 ) or N, Y 72 Can be C(T 72 ) or N, Y 73 Can be C(T 73 ) or N, and Y 74 Can be C(T 74) or N, where T 71 To T 74 Each can be referred to as T 3 described, and
[0355] Y 81 Can be C(T 81 ) or N, Y 82 Can be C(T 82 ) or N, Y 83 Can be C(T 83 ) or N, and Y 84 Can be C(T 84 ) or N, where T 81 To T 84 Each can be referred to as T 4 Descriptive.
[0356] In this specification, Formula 1 and Formula 1A and Ar 1 and Ar 2 All descriptions of can be applied to Formula 1-1 to Formula 1-10.
[0357] The organometallic compound represented by Formula 1 may have a tridentate ligand and a monodentate ligand (ie, ligand L) as determined by Formula 1. 1 ), and Ar in Formula 1 1 It may be a group represented by Formula 1A. Here, Formula 1A may include Ring A 2 and Ring A 3 , and may (eg, optionally) further include ring A 4 In this regard, the intermolecular interaction of the organometallic compound represented by Formula 1 having a square planar structure and / or the aforementioned interaction between the organometallic compound represented by Formula 1 and other compounds can be suppressed, thereby preventing or reducing the formation of excited molecules or excited complexes caused by such interactions. In addition, as the rigidity of the organometallic compound molecule represented by Formula 1 increases, the PLQY of the organometallic compound represented by Formula 1 can be improved. Accordingly, the light-emitting device including the organometallic compound represented by Formula 1 can have excellent or appropriate luminous efficiency and life characteristics.
[0358] In Formula 2, b51 to b53 respectively indicate L 51 To L 53 and each may be an integer selected from 1 to 5. When b51 is 2 or greater, two or more L 51 may be the same or different from each other. When b52 is 2 or greater, two or more L 52 may be the same as or different from each other, and when b53 is 2 or greater, two or more L 53In one or more embodiments, b51 to b53 may be 1 or 2, respectively.
[0359] In formula 2, L 51 To L 53 Can be independently:
[0360] a single key; or
[0361] phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isoxazolyl thiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilyl, dibenzothiosilyl, dibenzodihydroazosilyl, dibenzodihydrodisilyl, dibenzodihydrosilyl, dibenzodioxanyl, dibenzothioxanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithioinyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -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 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, and
[0362] Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0363] In one or more embodiments, in Formula 2, L 51 and R 51 The key between 52 and R 52 The key between 53 and R 53 The bond between two or more L 51 The bond between two or more L 52 The bond between two or more L 53 The bond between 51 With X 54 and X 55 The bonds between the carbons, L in Formula 2 52 With X 54 and X 56 The bonds between the carbons and L in Formula 2 53 With X 55 and X 56 The bonds between the carbon atoms in between may each be a "carbon-carbon single bond".
[0364] In formula 2, X 54 Can be N or C(R 54 ), X 55 Can be N or C(R 55 ), and X 56 Can be N or C(R 56 ), where X 54 To X 56 At least one of may be N. 54 To R 56 Each may be as described elsewhere herein. In one or more embodiments, X 54 To X 56 Two or three of them can each be N.
[0365] In this manual, R 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a, R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b can be 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(Q1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each may be as described elsewhere herein.
[0366] For example, i) R in Formula 1 1 To R 3 and T 1 To T 4 , and ii) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b Can be independently:
[0367] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0368] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl or any combination thereof;
[0369] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, 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, phenyl a dibenzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzothiorol group, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, pyrene, 1,2-benzophenanthryl, 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, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0370] -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
[0371] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0372] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2CD 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
[0373] 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 unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof:
[0374] Formula 91
[0375]
[0376] Among them, in formula 91,
[0377] Cyclo 91 and CY 92 may be each independently 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 1 -C 30 Heterocyclic group,
[0378] X 91 Can be single bond, O, S, N(R 91 )、B(R 91 )、C(R 91a )(R 91b ) or Si(R 91a )(R 91b ),
[0379] R 91 , R 91a and R 91b Can refer to R 82 , R 82a and R 82bDescribed,
[0380] R 10a may be as described elsewhere herein, and
[0381] *Indicates the binding site with adjacent atoms.
[0382] For example, in Equation 91,
[0383] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a substituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, and
[0384] R 91 , R 91a and R 91b Can be independently:
[0385] Hydrogen or C 1 -C 10 Alkyl; or
[0386] phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0387] In one or more embodiments, i) R in Formula 1 1 To R 3 and T 1 To T 4 , and ii) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508aand R 508b can be independently hydrogen, deuterium, -F, cyano, nitro, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a group represented by one of Formulas 9-1 to 9-19, a group represented by one of Formulas 10-1 to 10-246, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -P(=O)(Q 1 )(Q 2 )(Among which Q 1 To Q 3 More details can be found in the description provided in this article):
[0388]
[0389]
[0390]
[0391]
[0392]
[0393]
[0394]
[0395] Wherein, in Formulae 9-1 to 9-19 and Formulae 10-1 to 10-246, * indicates a bonding site with an adjacent atom, "Ph" represents a phenyl group, "D" represents a deuterium atom, and "TMS" represents a trimethylsilyl group.
[0396] In Formulas 3-1 to 3-5, Formula 502, and Formula 503, a71 to a74 and a501 to a504 each indicate R 71 To R 74 The number and R 501 To R 504 and may each independently be an integer selected from 0 to 20. When a71 is 2 or greater, two or more R 71 may be the same as or different from each other. When a72 is 2 or greater, two or more R 72may be the same as or different from each other. When a73 is 2 or greater, two or more R 73 may be the same or different from each other. When a74 is 2 or greater, two or more R 74 may be the same as or different from each other. When a501 is 2 or greater, two or more R 501 may be the same or different from each other. When a502 is 2 or greater, two or more R 502 may be the same or different from each other. When a503 is 2 or greater, two or more R 503 may be the same as or different from each other, and when a504 is 2 or greater, two or more R 504 a71 to a74 and a501 to a504 may each independently be an integer selected from 0 to 8.
[0397] In formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented by may each (for example, simultaneously) not be phenyl, (ie, if *-(L 51 ) b51 -R 51 is phenyl, then *-(L 52 ) b52 -R 52 may not be phenyl, and if *-(L 52 ) b52 -R 52 is phenyl, then *-(L 51 ) b51 -R 51 (It may not be phenyl).
[0398] In one or more embodiments, the formula 2 is represented by *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented may be the same as each other.
[0399] In one or more embodiments, the formula 2 is represented by *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented may be different from each other.
[0400] In one or more embodiments, in Formula 2, b51 and b52 may each be 1, 2 or 3, and L 51 and L 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0401] In one or more embodiments, R in Formula 2 51 and R 52 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 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, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0402] Q 1 To Q 3 may be each independently unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0403] In one or more embodiments,
[0404] In formula 2, *-(L 51 ) b51 -R 51 The group represented by may be a group represented by one of the formulas CY51-1 to CY51-26, and / or
[0405] In formula 2, *-(L 52 )b52 -R 52 The group represented by may be a group represented by one of the formulas CY52-1 to CY52-26, and / or
[0406] In formula 2, *-(L 53 ) b53 -R 53 The group represented by may be a group represented by one of the formulas CY53-1 to CY53-27, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ):
[0407]
[0408]
[0409]
[0410] Among them, in Formula CY51-1 to Formula CY51-26, Formula CY52-1 to Formula CY52-26 and Formula CY53-1 to Formula CY53-27,
[0411] Y 63 Can be single bond, O, S, N(R 63 )、B(R 63 )、C(R 63a )(R 63b ) or Si(R 63a )(R 63b ),
[0412] Y 64 Can be single bond, O, S, N(R 64 )、B(R 64 )、C(R 64a )(R 64b ) or Si(R 64a )(R 64b ),
[0413] Y 67 Can be single bond, O, S, N(R 67 )、B(R 67 )、C(R 67a )(R 67b ) or Si(R 67a )(R 67b ),
[0414] Y 68 Can be single bond, O, S, N(R 68)、B(R 68 )、C(R 68a )(R 68b ) or Si(R 68a )(R 68b ),
[0415] Y in formula CY51-16 and formula CY51-17 63 and Y 64 Each of may not be a single bond at the same time (e.g., simultaneously),
[0416] Y in formula CY52-16 and formula CY52-17 67 and Y 68 Each of may not be a single bond at the same time (e.g., simultaneously),
[0417] R 51a To R 51e , R 61 To R 64 , R 63a , R 63b , R 64a and R 64b Each can be referred to as R 51 described, where R 51a To R 51e Each of them may not be hydrogen,
[0418] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b Each can be referred to as R 52 described, where R 52a To R 52e Each of them may not be hydrogen,
[0419] R 53a To R 53e , R 69a and R 69b Each can be referred to as R 53 described, where R 53a To R 53e each may not be hydrogen, and
[0420] *Indicates the binding site with adjacent atoms.
[0421] For example,
[0422] In Formula CY51-1 to Formula CY51-26 and Formula CY52-1 to Formula CY52-26, R 51a To R 51eand R 52a To R 52e Can be independently:
[0423] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, 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, phenyl a dibenzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzothiorol group, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, Quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl or any combination thereof; or
[0424] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0425] Q 1 To Q 3 may be each independently phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof,
[0426] In formula CY51-16 and formula CY51-17, i) Y 63 Can be O or S, and Y 64 Can be Si(R 64a )(R 64b ), or ii) Y 63 Can be Si(R 63a )(R 63b ), and Y 64 can be O or S, and
[0427] In formula CY52-16 and formula CY52-17, i) Y 67 Can be O or S, and Y 68 Can be Si(R 68a )(R 68b ), or ii) Y 67 Can be Si(R 67a )(R 67b ), and Y 68 Can be O or S.
[0428] In Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0429] a single key; or
[0430] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*';or
[0431] phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, pyridyl, pyrrolyl, benzoxadiazolyl or benzothiadiazolyl, each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -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 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, and
[0432] Q 4 , Q 5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0433] In one or more embodiments, the formula 3-1 and the formula 3-2 are represented by The group represented by may be a group represented by one of formula CY71-1(1) to formula CY71-1(8), and / or
[0434] In formula 3-1 and formula 3-3, The group represented by may be a group represented by one of formula CY71-2(1) to formula CY71-2(8), and / or
[0435] In formula 3-2 and formula 3-4, The group represented may be a group represented by one of formula CY71-3(1) to formula CY71-3(32),
[0436] In formula 3-3 to formula 3-5, The group represented by may be a group represented by one of formula CY71-4(1) to formula CY71-4(32), and / or
[0437] In formula 3-5, The group represented may be a group represented by one of the formulas CY71-5(1) to CY71-5(8):
[0438]
[0439]
[0440]
[0441]
[0442] Among them, in formula CY71-1(1) to formula CY71-1(8), formula CY71-2(1) to formula CY71-2(8), formula CY71-3(1) to formula CY71-3(32), formula CY71-4(1) to formula CY71-4(32) and formula CY71-5(1) to formula CY71-5(8),
[0443] X 82 To X 85 , L 81 ,b81,R 81 and R 85 may each be as described elsewhere herein,
[0444] X 86 Can be single bond, O, S, N(R 86 )、B(R 86 )、C(R 86a )(R 86b ) or Si(R 86a )(R 86b ),
[0445] X 87 Can be single bond, O, S, N(R 87 )、B(R 87 )、C(R 87a )(R 87b ) or Si(R 87a )(R 87b ),
[0446] X in Formula CY71-1(2) to Formula CY71-1(4), Formula CY71-4(2) to Formula CY71-4(4), Formula CY71-4(10) to Formula CY71-4(12), Formula CY71-4(18) to Formula CY71-4(20), and Formula CY71-4(26) to Formula CY71-4(28) 86 and X 87 Each of may not be a single bond at the same time (e.g., simultaneously),
[0447] X 88 Can be single bond, O, S, N(R 88 )、B(R 88 )、C(R 88a )(R 88b ) or Si(R 88a )(R 88b ),
[0448] X 89 Can be single bond, O, S, N(R 89 )、B(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0449] X in formula CY71-2(2) to formula CY71-2(4), formula CY71-3(2) to formula CY71-3(4), formula CY71-3(10) to formula CY71-3(12), formula CY71-3(18) to formula CY71-3(20), formula CY71-3(26) to formula CY71-3(28), and formula CY71-5(2) to formula CY71-5(4) 88 and X 89 Each of may not be a single bond at the same time (e.g., simultaneously), and
[0450] R 86 To R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b Each can be referred to as R 81 Descriptive.
[0451] Examples of Compounds
[0452] In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from Compound 1 to Compound 100:
[0453]
[0454]
[0455]
[0456]
[0457]
[0458]
[0459]
[0460] In compounds 1 to 100, Respectively
[0461] In one or more embodiments, the second compound may be one selected from compounds ETH1 to ETH100:
[0462]
[0463]
[0464]
[0465]
[0466] In one or more embodiments, the third compound may be one selected from compound HTH1 to compound HTH46:
[0467]
[0468]
[0469] In one or more embodiments, the fourth compound may be one selected from compound DFD1 to compound DFD29 and compound DFD051:
[0470]
[0471]
[0472] In the compounds herein, Ph represents phenyl, and D N Indicates substitution with an amount N of deuterium.
[0473] Figure 1 Description
[0474] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments. The light emitting device 10 includes a first electrode 110 , an interlayer 130 , and a second electrode 150 .
[0475] 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 one or more embodiments are described.
[0476] First electrode 110
[0477] exist Figure 1 In the embodiment, the substrate may be additionally arranged under the first electrode 110 or on the second electrode 150. In one or more embodiments, a glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include plastics having excellent or appropriate heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0478] The first electrode 110 may be formed, for example, by 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 facilitates injection of holes.
[0479] The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, the material used to form 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 one or more embodiments, when the first electrode 110 is a transflective 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.
[0480] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0481] Mezzanine 130
[0482] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0483] The interlayer 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 .
[0484] In addition to one or more suitable organic materials, the interlayer 130 may further include metal-containing compounds (such as organometallic compounds) and / or inorganic materials (such as quantum dots), etc.
[0485] In one or more embodiments, the interlayer 130 may include i) two or more light emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer disposed between two adjacent light emitting units. When the interlayer 130 includes two or more light emitting units and the charge generation layer, the light emitting device 10 may be a tandem light emitting device.
[0486] Hole transport region in interlayer 130
[0487] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other, or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.
[0488] 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.
[0489] For example, the hole transport region may have a multi-layer 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 in each structure are stacked sequentially from the first electrode 110.
[0490] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0491] Formula 201
[0492]
[0493] Formula 202
[0494]
[0495] Among them, in equation 201 and equation 202,
[0496] L 201 To L204 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,
[0497] 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,
[0498] xa1 to xa4 may each independently be an integer selected from 0 to 5,
[0499] xa5 may be an integer selected from 1 to 10,
[0500] R 201 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,
[0501] R 201 and R 202 may be optionally substituted by a single bond, unsubstituted or 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 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60Polycyclic groups (e.g., carbazole groups, etc.) (e.g., see compound HT16, etc.),
[0502] R 203 and R 204 may be optionally substituted by a single bond, unsubstituted or 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
[0503] na1 may be an integer selected from 1 to 4.
[0504] For example, each of Formula 201 and Formula 202 may include (eg, selected from) at least one of the groups represented by Formula CY201 to Formula CY217:
[0505]
[0506] Among them, in formula CY201 to formula CY217, R 10b and R 10c Each can be referred to as R 10a Described, Cyclic 201 To Ring CY 204 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 10a replace.
[0507] In one or more embodiments, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.
[0508] In one or more embodiments, each of Formula 201 and Formula 202 may include (eg, selected from) at least one of the groups represented by Formula CY201 to Formula CY203.
[0509] In one or more embodiments, Formula 201 may include (eg, selected from) at least one of the groups represented by Formulas CY201 to CY203 and (eg, selected from) at least one of the groups represented by Formulas CY204 to CY217.
[0510] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be (for example, selected from) one of the groups represented by Formula CY201 to Formula CY203, xa2 may be 0, and R 202 It may be (for example, selected from) one of the groups represented by Formula CY204 to Formula CY207.
[0511] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY203.
[0512] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY203, and may include (eg, be selected from) at least one of the groups represented by Formula CY204 to Formula CY217.
[0513] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY217.
[0514] For example, the hole transport region may include: at least one selected from the group consisting 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:
[0515]
[0516]
[0517]
[0518]
[0519]
[0520] The thickness of the hole transport region may be about to about For example, 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 For example, about to about and the thickness of the hole transport layer may be in the range of about to about For example, 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.
[0521] The emission auxiliary layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The materials that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0522] p-dopant
[0523] In addition to the aforementioned materials, the hole transport region may further include a charge generation material for improvement of conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (eg, in the form of a single layer including (eg, consisting of) the charge generation material).
[0524] The charge generating material may be, for example, a p-dopant.
[0525] For example, the p-dopant may have a LUMO level of -3.5 electron volts (eV) or less.
[0526] In one or more embodiments, 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.
[0527] Examples of the quinone derivative may include TCNQ and / or F4-TCNQ, and the like.
[0528] Examples of cyano-containing compounds may include HAT-CN and / or a compound represented by Formula 221, etc.:
[0529]
[0530] Formula 221
[0531]
[0532] Among them, in formula 221,
[0533] R221 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
[0534] R 221 To R 223 At least one of them may be independently C each substituted by 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0535] 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.
[0536] Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), and / or cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), and / or 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.); ), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.); and / or lanthanide metals (e.g., lanthanum (La), 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) and / or lutetium (Lu), etc.); etc.
[0537] Examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te), among others.
[0538] Examples of non-metal may include oxygen (O) and / or halogen (eg, F, Cl, Br, and / or I, etc.), and the like.
[0539] For example, the compound including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides and / or metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0540] Examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 and / or W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 and / or V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 and / or Mo 2 O 5 etc.) and / or rhenium oxide (e.g., ReO 3 etc.
[0541] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides, among others.
[0542] 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, and / or CsI, among others.
[0543] 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 , SrBr2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 wait.
[0544] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 and / or TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 and / or ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 and / or HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 and / or VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 and / or NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 and / or TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 and / or CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 and / or MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 and / or WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 and / or MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl2 , TcBr 2 and / or TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 and / or ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 and / or FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 and / or RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 and / or OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 and / or CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 and / or RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 and / or IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 and / or NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 and / or PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 and / or PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr and / or AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr and / or AuI, etc.), etc.
[0545] Examples of late transition metal halides may include zinc halides (eg, ZnF 2 、ZnCl 2 、ZnBr 2 and / or ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 etc.
[0546] 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 / or SmI 3 wait.
[0547] Examples of metalloid halides may include antimony halides (eg, SbCl 5 etc.
[0548] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te and / or Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or 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 2Te, CuTe, Ag 2 Te, AgTe and / or Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.), etc.
[0549] Emission layer in interlayer 130
[0550] 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 one or more embodiments, 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, wherein the two or more layers are in contact with each other or separated from each other to emit white light. In one or more embodiments, 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, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0551] In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In one or more embodiments, in addition to the host and the dopant (or emitter), the emission layer may further include an auxiliary dopant that promotes energy transfer to the dopant (or emitter). When the emission layer includes a dopant (or emitter) and an auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
[0552] The organometallic compound represented by Formula 1 in the present specification may be used as a dopant (or emitter), or may be used as an auxiliary dopant.
[0553] The amount (weight) of the dopant (or emitter) in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0554] In one or more embodiments, the emission layer may include an organic metal compound represented by Formula 1. The amount of the organic metal compound represented by Formula 1 in the emission layer may be in a range of about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight based on 100 parts by weight of the emission layer.
[0555] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within these ranges, excellent or appropriate light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0556] main body
[0557] In one or more embodiments, the host in the emission layer may include the second compound, the third compound, or any combination thereof.
[0558] In one or more embodiments, the host may include a compound represented by Formula 301:
[0559] Formula 301
[0560] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0561] Wherein, in Formula 301,
[0562] 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,
[0563] xb11 can be 1, 2 or 3,
[0564] xb1 may be an integer selected from 0 to 5,
[0565] R 301 It may be 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 -C60 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 ),
[0566] xb21 may be an integer selected from 1 to 5, and
[0567] Q 301 To Q 303 Please refer to Q 1 Descriptive.
[0568] For example, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 Can be connected to each other via a single bond.
[0569] In one or more embodiments, the host may include at least one selected from the group consisting of a compound represented by Formula 301-1, a compound represented by Formula 301-2, and any combination thereof:
[0570] Formula 301-1
[0571]
[0572] Formula 301-2
[0573]
[0574] Among them, in Formula 301-1 and Formula 301-2,
[0575] 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 R 10a Substituted C 1 -C 60 Heterocyclic group,
[0576] X 301 Can be O, S, N[(L304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0577] xb22 and xb23 can each independently be 0, 1 or 2,
[0578] L 301 , xb1 and R 301 may each be as described elsewhere herein,
[0579] L 302 To L 304 Can be independently as reference L 301 Described,
[0580] xb2 to xb4 may each independently be as described with reference to xb1, and
[0581] R 302 To R 305 and R 311 To R 314 Each can be referred to as R 301 Described elsewhere in this article.
[0582] In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0583] In one or more embodiments, the host may include at least one selected from Compound H1 to Compound H130, 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(carbazolyl-9-yl)benzene (TCP), or any combination thereof:
[0584]
[0585]
[0586]
[0587]
[0588]
[0589]
[0590] In one or more embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0591] The body may have one or more suitable variations. For example, the body may include only one type of compound, or may include two or more types of different compounds.
[0592] Phosphorescent dopants
[0593] The emission layer may include the organic metal compound represented by Formula 1 as a phosphorescent dopant.
[0594] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0595] The phosphorescent dopant may include at least one transition metal as a central metal.
[0596] 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.
[0597] The phosphorescent dopant may be electrically neutral.
[0598] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0599] Formula 401
[0600] M(L 401 ) xc1 (L 402 ) xc2
[0601] Formula 402
[0602]
[0603] Among them, in equation 401 and equation 402,
[0604] 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)),
[0605] L 401may 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 may be the same or different from each other,
[0606] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,
[0607] X 401 and X 402 can be independently N or C,
[0608] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0609] 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(Q 411 )-*',
[0610] 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 ),
[0611] Q 411 To Q 414 Please refer to Q 1 Described,
[0612] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1 -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 60 Heterocyclic 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 ),
[0613] Q 401 To Q 403 Please refer to Q 1 Described,
[0614] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0615] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0616] For example, in equation 402, i)X 401 may be nitrogen and X 402 Can be carbon, or ii) X 401 and X 402 Each of may be nitrogen.
[0617] In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two or more L 401 The two rings A 401 They may not be connected to each other or may be connected via T as a connecting group. 402 Connected to each other, or two rings A 402 They may not be connected to each other or may be connected via T as a connecting group. 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Each can be referred to as T 401 Descriptive.
[0618] In formula 401, L 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, a -CN group, a phosphorus-containing group (e.g., a phosphine group and / or a phosphite group, etc.), or any combination thereof.
[0619] The phosphorescent dopant may include, for example, at least one selected from Compound PD1 to Compound PD25 or any combination thereof:
[0620]
[0621]
[0622] Fluorescent dopants
[0623] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0624] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 is used as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0625] The fluorescent dopant and the auxiliary dopant may each independently include an aromatic amine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0626] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include at least one compound represented by Formula 501:
[0627] Formula 501
[0628]
[0629] Wherein, in Formula 501,
[0630] 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,
[0631] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0632] xd4 can be 1, 2, 3, 4, 5 or 6.
[0633] For example, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracenyl, 1,2-triphenylenyl and / or pyrene, etc.).
[0634] For example, xd4 in equation 501 may be 2.
[0635] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each include at least one of compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
[0636]
[0637]
[0638]
[0639] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a fourth compound represented by Formula 502 or Formula 503.
[0640] Electron transport region in interlayer 130
[0641] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other, or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.
[0642] 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.
[0643] 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 in each structure are stacked sequentially from the emission layer.
[0644] The electron transport region (eg, 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 Heterocyclic group.
[0645] For example, the electron transport region may include a compound represented by Formula 601:
[0646] Formula 601
[0647] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0648] Wherein, in Formula 601,
[0649] 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,
[0650] xe11 can be 1, 2 or 3,
[0651] xe1 can be 0, 1, 2, 3, 4 or 5,
[0652] 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)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0653] Q 601 To Q 603 Please refer to Q 1 Described,
[0654] xe21 can be 1, 2, 3, 4, or 5, and
[0655] 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 Heterocyclic group.
[0656] For example, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be connected to each other via a single bond.
[0657] In one or more embodiments, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0658] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
[0659] Formula 601-1
[0660]
[0661] Among them, in formula 601-1,
[0662] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), and X 616 Can be N or C(R 616 ), where X 614 To X 616 At least one of may be N,
[0663] L 611 To L 613 Each can be referred to as L 601 Described,
[0664] xe611 to xe613 may each be as described with reference to xe1,
[0665] R 611 To R 613 Each can be referred to as R 601 described, and
[0666] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1 -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.
[0667] For example, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each independently be 0, 1, or 2.
[0668] The electron transport region may include: at least one selected from the group consisting of Compound ET1 to Compound ET46; 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:
[0669]
[0670]
[0671]
[0672] The thickness of the electron transport region can be about to about For example, 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 in the range of about to about For example, about to about and the thickness of the electron transport layer can be in the range of about to about For example, 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.
[0673] In addition to the aforementioned materials, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.
[0674] 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 metal ion of the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0675] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) and / or compound ET-D2:
[0676]
[0677] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0678] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other, or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.
[0679] In one or more embodiments, the electron injection layer may include 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.
[0680] 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, and the rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd or any combination thereof.
[0681] The alkali metal-containing compound, the alkaline earth metal-containing compound and the rare earth metal-containing compound may be oxides, halides (eg, fluorides, chlorides, bromides or iodides) or tellurides of alkali metals, alkaline earth metals and rare earth metals or any combination thereof.
[0682] Alkali metal compounds may include: alkali metal oxides, such as Li 2 O、Cs2 O and / or K 2 O, etc.; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI, etc.; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal compound 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 one or more embodiments, the rare earth metal compound 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 Te 3 , 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 and / or Lu2 Te 3 wait.
[0683] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include i) one metal ion selected from alkali metals, alkaline earth metals and rare earth metals, and ii) as a ligand bonded to the metal ion (e.g., the selected metal ion), for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0684] In one or more embodiments, the electron injection layer may include (e.g., 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 herein. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0685] In one or more embodiments, the electron injection layer may include (e.g., consisting of) i) an alkali metal compound (e.g., an alkali metal halide), or ii) a) an alkali metal compound (e.g., an alkali metal halide), and b) 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, and / or a LiF:Yb co-deposition layer, etc.
[0686] When the electron injection layer further 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 may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0687] The thickness of the electron injection layer can be about to about And, for example, about to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0688] The second electrode 150
[0689] The second electrode 150 is disposed on the interlayer 130 having the aforementioned structure. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for forming the second electrode 150, metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used.
[0690] The second electrode 150 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, Yb, 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.
[0691] The second electrode 150 may have a single-layer structure, or a multi-layer structure including a plurality of layers.
[0692] Capping layer
[0693] The first capping layer may be disposed on the outer side of the first electrode 110 (and, for example, on the first electrode 110), and / or the second capping layer may be disposed on the outer side of the second electrode 150 (and, for example, on the second electrode 150). In detail, the light emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the order recited, a structure in which the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are sequentially stacked in the order recited, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are sequentially stacked in the order recited.
[0694] Light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first capping layer. Light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second capping layer.
[0695] The first capping layer and the second capping layer can increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 can be increased, and accordingly, the light emitting efficiency of the light emitting device 10 can be improved.
[0696] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or greater (at 589 nm).
[0697] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0698] At least one selected from the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin 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 be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include an amine-containing compound.
[0699] In one or more embodiments, at least one selected from 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.
[0700] In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include: at least one selected from compounds HT28 to HT33; at least one selected from compounds CP1 to CP6; β-NPB; or any combination thereof:
[0701]
[0702] Electronic equipment
[0703] The light emitting device may be included in one or more suitable electronic devices. For example, the electronic device including the light emitting device may be a light emitting device and / or an authentication device.
[0704] In addition to the light-emitting device, the electronic device (e.g., light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged 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, green light, or white light. For details about the light-emitting device, reference may be made to the description provided herein. In one or more embodiments, the color conversion layer may include quantum dots.
[0705] The electronic device may include a first substrate, the first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.
[0706] A pixel defining layer may be disposed between the plurality of sub-pixel regions to define each sub-pixel region.
[0707] The color filter may further include a plurality of color filter regions and a light shielding pattern therebetween, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern therebetween.
[0708] 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. For example, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. In particular, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include (e.g., may exclude) quantum dots. For details on quantum dots, reference may be made to the description provided herein. Each of the first region, the second region, and / or the third region may further include a scatterer.
[0709] For example, in a light emitting device that emits a first light, a first region may absorb the first light to emit 1-1 color light, a second region may absorb the first light to emit 2-1 color light, and a third region may absorb the first light to emit 3-1 color light. Here, the 1-1 color light, the 2-1 color light, and the 3-1 color light may have different maximum emission wavelengths from each other. In particular, the first light may be blue light, the 1-1 color light may be red light, the 2-1 color light may be green light, and the 3-1 color light may be blue light.
[0710] In addition to the aforementioned light emitting device, 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.
[0711] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.
[0712] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.
[0713] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged 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 extracted to the outside, and simultaneously (e.g., simultaneously) prevents 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 sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0714] In addition to the color filter and / or the color conversion layer, various functional layers may be additionally arranged on the sealing portion according to the purpose of the electronic device. Examples of the functional layer may include a touch screen layer and / or 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 body (e.g., a fingertip and / or a pupil, etc.).
[0715] In addition to the light emitting device as described herein, the authentication equipment may further include a biometric information collector.
[0716] The electronic equipment can be applied to one or more appropriate displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices or endoscope displays), fish finders, one or more appropriate measuring tools, instruments (e.g., instruments for vehicles, aircraft and ships) and / or projectors, etc.
[0717] Figure 2 and Figure 3 Description
[0718] Figure 2 is a cross-sectional view showing a light emitting device as an example of an electronic device according to one or more embodiments.
[0719] Figure 2 The light emitting apparatus includes a substrate 100, a thin film transistor (TFT), a light emitting device, and a packaging portion 300 that seals the light emitting device.
[0720] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and provide a flat surface on the substrate 100.
[0721] The TFT may be disposed 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.
[0722] 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.
[0723] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220 , and the gate electrode 240 may be disposed on the gate insulating film 230 .
[0724] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate these electrodes from each other.
[0725] The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source and drain regions of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed portions of the source and drain regions of the active layer 220.
[0726] 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 film, an organic insulating film, or any combination thereof. The light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0727] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be disposed to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed portion of the drain electrode 270.
[0728] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a specific region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond an upper portion of the pixel defining layer 290 to be disposed in the form of a common layer.
[0729] The second electrode 150 may be disposed on the interlayer 130, and the second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0730] The encapsulation part 300 may be disposed on the second capping layer 170. The encapsulation part 300 may be disposed on the light emitting device to protect the light emitting device from moisture and / 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; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0731] Figure 3 is a cross-sectional view of a light emitting device as an example of an electronic device according to another embodiment.
[0732] Figure 3 Lighting equipment and Figure 2 The light emitting device is substantially the same as that of the embodiment of the present invention, except that the light shielding pattern 500 and the functional area 400 are additionally arranged on the packaging portion 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, the light emitting device includes: Figure 3 The light-emitting device in the light-emitting apparatus may be a series-connected light-emitting device.
[0733] Figure 4 Description
[0734] Figure 4 1 is a schematic perspective view of an electronic device 1 including a light emitting device according to one or more embodiments. As a device for displaying a moving image or a still image, the electronic device 1 may be a portable electronic device, such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an electronic book, a portable multimedia player (PMP), a navigation and / or an ultra mobile PC (UMPC), etc., and one or more suitable products, such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device, or a part of such one or more suitable products. In some embodiments, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a display of a glasses type or type, or a head-mounted display (HMD), or a part of such a wearable device. However, the embodiments of the present disclosure are not limited thereto. For example, the electronic device 1 may include a dashboard of a vehicle, a center information display on a center console or dashboard of a vehicle, an interior rearview mirror display replacing a side mirror of a vehicle, an entertainment display arranged on a rear seat of a vehicle or arranged on a backrest of a front seat, a head-up display (HUD) mounted in front of the vehicle or projected on the front window glass, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For the convenience of explanation, Figure 4 Explained is a case in which the electronic device 1 is a smartphone.
[0735] The electronic device 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 an array of a plurality of pixels two-dimensionally arranged in the display area DA.
[0736] The non-display area NDA is an area where no image is displayed, and may surround (e.g., completely surround) the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to a display element arranged in the display area DA may be arranged. In the non-display area NDA, a pad may be arranged, which may be electrically connected to an electronic element or a printed circuit board.
[0737] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. In one or more embodiments, as Figure 4 As shown in FIG. 1 , the length in the x-axis direction may be shorter than the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be the same as the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0738] Figure 5 and FIG. 6A to FIG. 6C Description
[0739] Figure 5 is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to one or more embodiments. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.
[0740] See also Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable equipment for moving an object to be transported, such as a person, object, or animal, from a starting point to a destination point. The vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on an ocean or river, and / or an airplane flying in the air using the action of air.
[0741] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train traveling on a track.
[0742] The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical equipment required for driving is installed as other parts outside the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries 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 / or left and right wheels, etc.
[0743] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side mirrors 1300 , an instrument panel 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0744] The side window glass 1100 and the front window glass 1200 may be partitioned by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0745] The side window glass 1100 may be mounted on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the instrument panel 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0746] In one or more embodiments, the side window glass 1100 may be separated and / or spaced apart from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). For example, the first side window glass 1110 and the second side window glass 1120 may be separated and / or spaced apart from each other in the x-axis direction or the -x-axis direction. In other words, the imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. For example, the imaginary 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.
[0747] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0748] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In one or more embodiments, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be arranged outside the second side window glass 1120.
[0749] Instrument panel 1400 may be arranged in front of the steering wheel. Instrument panel 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 tachometer, an automatic shift lever indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0750] The center console 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a seat heater are provided. The center console 1500 may be disposed on one side of the instrument panel 1400 .
[0751] The passenger seat instrument panel 1600 may be separated and / or spaced apart from the instrument panel 1400, and the center console 1500 is disposed between the passenger seat instrument panel 1600 and the instrument panel 1400. In one or more embodiments, the instrument panel 1400 may be disposed to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be provided to correspond to the passenger seat. In one or more embodiments, the instrument panel 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.
[0752] In one or more embodiments, 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 one or more embodiments, 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 panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0753] The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, and / or a quantum dot display device, etc. Hereinafter, as a display device 2 according to one or more embodiments, an organic light-emitting display device including the aforementioned light-emitting device will be described as an example, but one or more appropriate types (kinds) of the aforementioned display devices may be used in the embodiments.
[0754] See also Fig. 6A , the display device 2 may be arranged on the center console 1500. In one or more embodiments, the display device 2 may display navigation information. In one or more embodiments, the display device 2 may display audio, video, or information related to vehicle settings.
[0755] See also Figure 6B, the display device 2 may be arranged on the instrument panel 1400. When the display device 2 is arranged on the instrument panel 1400, the instrument panel 1400 may display driving information and the like through the display device 2. For example, the instrument panel 1400 may be implemented digitally. The instrument panel 1400 may digitally display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and one or more appropriate warning light icons may be displayed through digital signals.
[0756] See also 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 one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500.
[0757] Manufacturing method
[0758] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a specific region by using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and / or laser induced thermal imaging.
[0759] 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 within a range of about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr range under vacuum and about 0.01 angstroms per second to about Deposition is carried out at a deposition rate within a range of .
[0760] Definition of terms
[0761] As used herein, the term "C 3 -C 60 "Carbocyclic group" refers to a cyclic group consisting only of carbon as a ring atom and having 3 to 60 carbon atoms, and the term "C 1 -C 60 The term "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further having a hetero atom as a ring-forming atom in addition to carbon. 3 -C60 Carbocyclic and C 1 -C 60 The heterocyclic group may each 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 number of ring-forming atoms of the heterocyclic group may be 3 to 61.
[0762] As used herein, the term "cyclic group" may include (for example, simultaneously) C 3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups.
[0763] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The term "heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.
[0764] For example,
[0765] C 3 -C 60 The carbocyclic group may be i) a group T1 or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylene group, a peryl group, a pentaphenanthrenyl group, a heptalenyl group, a tetracenyl group, a phenanthrenyl group, a hexacenyl group, a pentacene group, a rubinyl group, a coronet group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, or an indenoanthryl group),
[0766] C 1 -C 60The heterocyclic group may be i) a group T2, ii) a condensed ring group in which at least two groups T2 are condensed to each other, or iii) a condensed ring group in which at least one group T2 and at least one group T1 are condensed 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, benzofuranodibenzofuran ... dibenzothiophene, 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, benzo quinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazoline, benzoquinazoline, phenanthroline, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl and / or azadibenzofuranyl, etc.),
[0767] Pi-electron-rich C 3 -C 60 The cyclic group may be i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which at least one group T3 and at least one group T1 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, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl and / or benzothiophenylodibenzothiophenyl, etc.),
[0768] π-electron-deficient nitrogen-containing C 1-C 60 The heterocyclic group may be i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzoimidazolyl, benzoxazolyl, benzisoxazolyl, 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, azadibenzothiophenyl and / or azadibenzofuranyl, etc.),
[0769] The radical T1 can be 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,
[0770] The radical T2 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,
[0771] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiolyl or borocyclopentadienyl, and
[0772] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0773] 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 "heterocyclic group" may refer to a group fused with any cyclic group (which is fused with another cyclic group (e.g., phenyl and / or naphthyl, etc.)), a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, and / or a tetravalent group, etc.) according to the structure of the formula using the corresponding term. For example, "phenyl" may be benzo, phenyl, and / or phenylene, etc., and those of ordinary skill in the art can easily understand these groups based on the structure of the formula including "phenyl".
[0774] Depending on the context, a divalent group may refer to or may be a multivalent group (eg, trivalent, tetravalent, etc., rather than just divalent), depending on, for example, the structure of the formula associated with the term used.
[0775] Unit Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of the heterocyclic group 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 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 An example of a heterocyclic group is 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.
[0776] As used herein, the term "C 1 -C 60 The term “alkyl” refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof 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 “C 1 -C 60 "Alkylene" refers to C 1 -C 60 The alkyl group has a divalent group having substantially the same structure.
[0777] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 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 examples thereof may include vinyl, propenyl and / or butenyl, etc. As used herein, the term “C 2 -C 60 "Alkenylene" refers to C 2 -C 60 An alkenyl group has a divalent group having substantially the same structure.
[0778] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end thereof, and examples thereof may include ethynyl and / or propynyl, etc. As used herein, the term “C 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups have substantially the same structure as divalent groups.
[0779] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60The monovalent group represented by an alkyl group may include a methoxy group, an ethoxy group, an isopropoxy group, and the like.
[0780] As used herein, the term "C 3 -C 10 The term "cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.
[0781] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and specific examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl, etc. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.
[0782] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond in its ring and no aromaticity, and specific examples thereof may include cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group is a divalent group having substantially the same structure.
[0783] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms which further includes at least one heteroatom as a ring-forming atom and at least one double bond in addition to carbon atoms in its ring structure. 1 -C 10Examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to C 1 -C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.
[0784] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentenyl, rubenyl, coronenyl and / or ovalenyl, etc. When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, these rings may be fused to each other.
[0785] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms which further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms which further includes 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 / or naphthyridinyl, etc. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, these rings may be fused to each other.
[0786] The term "monovalent non-aromatic fused polycyclic group" as used in this article refers to 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 the entire molecule. Examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. The term "divalent non-aromatic fused polycyclic group" as used in this article refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group described in this article.
[0787] The term “monovalent non-aromatic heterocondensed polycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic heterocondensed polycyclic radical are pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0788] As used herein, the term "C 6 -C 60 Aryloxy" indicates -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 Arylthio" indicates -SA 103 (A 103 C 6 -C 60aryl).
[0789] As used herein, the term "C 7 -C 60 "Aralkyl" refers to -A 104 A 105 (A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59 aryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 106 A 107 (A 106 C 1 -C 59 Alkylene, and A 107 C 1 -C 59 heteroaryl).
[0790] As used herein, the term " 10a " can be:
[0791] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0792] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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;
[0793] Each unsubstituted or substituted 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 Heteroaralkyl: 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, 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
[0794] -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 ).
[0795] Q in this manual 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 each is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 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 group.
[0796] As used herein, the term "heteroatom" refers to any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0797] The term "transition metal" as used herein may include Hf, Ta, W, Re, Os, Ir, Pt and / or Au, among others.
[0798] As used herein, "Ph" refers to phenyl, as used herein, "Me" refers to methyl, as used herein, "Et" refers to ethyl, as used herein, "tert-Bu" or "Bu" refers to ethyl. t " refers to a tert-butyl group, and "OMe" as used herein refers to a methoxy group.
[0799] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In other words, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0800] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0801] Unless otherwise indicated, *, *' and *" each indicate a binding site to an adjacent atom in the corresponding formula or moiety.
[0802] Terms such as "substantially," "about," and "approximately" are used as relative terms and not as terms of degree, and are intended to take into account the inherent deviations in measurements or calculations that one of ordinary skill in the art will recognize. They may include deviations from the stated value and an acceptable range determined by one of ordinary skill in the art, taking into account the limitations and errors associated with the measurement of that quantity. For example, "about" may refer to one or more standard deviations of the stated value, or ±30%, ±20%, ±10%, or ±5% of the stated value.
[0803] Numerical ranges disclosed herein include and are intended to disclose all subranges of the same numerical precision. For example, a range of "1.0 to 10.0" includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Applicants therefore reserve the right to amend this specification (including the claims) to expressly set forth any subranges contained within the ranges expressly set forth herein.
[0804] The light-emitting device, light-emitting element and / or any other related device or component according to the embodiments of the present disclosure described herein may be implemented using any appropriate hardware, firmware (e.g., a dedicated integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the light-emitting device and / or the light-emitting element may be formed on an integrated circuit (IC) chip or on a separate IC chip. Further, the various components of the light-emitting device and / or the light-emitting element may be implemented on a flexible printed circuit film, a tape carrier package (TCP), or a printed circuit board (PCB), or formed on a substrate. Further, the various components of the device and / or element may be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functions described herein. The computer program instructions are stored in a memory, which may be implemented in a computing device using a standard storage device such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-temporary computer-readable media, such as, for example, a CD-ROM or a flash drive, etc. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a dedicated computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[0805] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in more 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 in the same molar equivalent.
[0806] Example
[0807] Synthesis Example 1: Synthesis of Compound 77
[0808]
[0809] Synthesis of Intermediate 77-A
[0810] 2.83 g (12.0 mmol) of 1,3-dibromobenzene, 10.09 g (30.0 mmol) of N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine, 1.10 g (1.2 mmol) of tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3), 0.99 g (2.4 mmol) of S-Phos and 5.77 g (60.0 mmol) of sodium tert-butoxide (NaOtBu) were added to a reaction vessel and suspended in 120 milliliters (mL) of toluene. The reaction temperature was raised to 110°C and the mixture was stirred for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and subjected to an extraction process using ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried over sodium sulfate. The residue obtained from the resulting dried product from which the solvent had been removed was separated using column chromatography to obtain 6.27 g (8.4 mmol) of intermediate 77-A.
[0811] Synthesis of Intermediate 77-B
[0812] 6.27 g (8.4 mmol) of intermediate 77-A and 75 mL (462.0 mmol) of triethyl orthoformate (CH(OEt) 3 ) and 1.8 mL (20.2 mmol) of HCl 35 wt% solution were added to the reaction vessel, and stirred for 12 hours after the reaction temperature was raised to 80° C. After the reaction was completed, the reaction product was cooled to room temperature, and the residue obtained by removing the solvent was recrystallized to obtain 4.62 g (5.5 mmol) of Intermediate 77-B.
[0813] Synthesis of Intermediate 77-C
[0814] 4.62 g (5.5 mmol) of Intermediate 77-B, 2.28 g (6.1 mmol) of dichloro(1,5-cyclooctadiene)platinum (Pt(COD)Cl 2 ) and 1.35g (16.5mmol) of sodium acetate (NaOAc) were suspended in 220mL of dioxane. After the reaction temperature was raised to 120°C, the reaction mixture was stirred for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature and subjected to an extraction process using ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried over sodium sulfate. The residue obtained from the resulting dried product from which the solvent had been removed was separated using column chromatography to obtain 1.37g (1.4mmol) of intermediate 77-C.
[0815] Synthesis of compound 77
[0816] The sodium hydroxide of 0.21g (2.1mmol) phenylacetylene and 0.50g (12.6mmol) was suspended in 20mL methanol and stirred at room temperature for 30 minutes. At room temperature, the intermediate 77-C containing 1.37g (1.4mmol) and 1.4mL of dichloromethane (DCM) were slowly added dropwise thereto, and then stirred at room temperature for 12 hours. After the reaction terminates, ethyl acetate is used to extract the reaction product. The organic layer thus obtained is then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. Column chromatography is used to separate the residue obtained from the obtained dry product having removed the solvent, to obtain 0.11g (0.1mmol) of compound 77.
[0817] Synthesis Example 2: Synthesis of Compound 96
[0818]
[0819] Synthesis of Intermediate 96-A
[0820] 2.59 g (11.0 mmol) of 1,3-dibromobenzene, 0.65 g (5.5 mmol) of benzimidazole, 0.10 g (0.6 mmol) of cuprous iodide, 60 mg (0.6 mmol) of L-proline and 2.33 g (11.0 mmol) of tripotassium phosphate (K 3 PO 4 ) was added to a reaction vessel and suspended in 55 mL of dimethylformamide (DMF). The reaction temperature was raised to 160° C. and the mixture was stirred for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature and subjected to an extraction process using ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried over sodium sulfate. The residue obtained from the resulting dried product from which the solvent had been removed was separated using column chromatography to obtain 1.07 g (3.9 mmol) of intermediate 96-A.
[0821] Synthesis of Intermediate 96-B
[0822] 1.07 g (3.9 mmol) of intermediate 96-A, 2.0 g (5.9 mmol) of N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine, 0.18 g (0.2 mmol) of tris(dibenzylideneacetone)dipalladium, 0.16 g (0.4 mmol) of S-Phos and 0.75 g (7.8 mmol) of sodium tert-butoxide were added to a reaction vessel and suspended in 40 mL of toluene. The reaction temperature was raised to 110°C, and the mixture was stirred for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and subjected to an extraction process using ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried over sodium sulfate. The residue obtained from the resulting dry product from which the solvent had been removed was separated using column chromatography to obtain 1.43 g (2.7 mmol) of intermediate 96-B.
[0823] Synthesis of Intermediate 96-C
[0824] 1.43 g (2.7 mmol) of intermediate 96-B and 24 mL (148.5 mmol) of CH(OEt) 3 and 0.28 mL (3.2 mmol) of HCl 35 wt% solution were added to the reaction vessel, and stirred for 12 hours after the reaction temperature was raised to 80° C. After the reaction was completed, the reaction product was cooled to room temperature, and the residue obtained by removing the solvent was recrystallized to obtain 1.15 g (2.0 mmol) of Intermediate 96-C.
[0825] Synthesis of Intermediate 96-D
[0826] 1.15g (2.0mmol) of intermediate 96-C and 0.57g (4.0mmol) of iodomethane (MeI) are added to a reaction vessel and suspended in 20mL of toluene. After the reaction temperature is raised to 80°C, the reaction mixture is stirred for 3 hours. After the reaction is completed, the reaction product is cooled to room temperature, the solvent is partially removed, and distilled water is added to the reaction product. The resulting solid is filtered and the filtrate is then purified using a recrystallization method to obtain 1.0g (1.4mmol) of intermediate 96-D.
[0827] Synthesis of compound 96
[0828] 1.0g (1.4mmol) of intermediate 96-D, 0.58g (1.54mmol) of dichloro (1,5-cyclooctadiene) platinum and 0.34g (4.2mmol) of sodium acetate were suspended in 55mL of dioxane. After the reaction temperature was raised to 120°C, the reaction mixture was stirred for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, 20mL of distilled water was added thereto, and an extraction process was performed using ethyl acetate. The organic layer thus obtained was then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. The residue obtained from the resulting dried product from which the solvent was removed was separated using column chromatography to obtain 160mg (0.20mmol) of compound 96.
[0829] Synthesis Example 3: Synthesis of Compound 93
[0830]
[0831] 0.21g (2.1mmol) of phenylacetylene and 0.50g (12.6mmol) of sodium hydroxide were suspended in 20mL of methanol and stirred at room temperature for 30 minutes. At room temperature, the compound 96 containing 1.10g (1.4mmol) and the solution of 1.4mL of DCM were slowly added dropwise thereto, and then stirred at room temperature for 12 hours. After the reaction terminates, ethyl acetate is used to extract the reaction product. The organic layer thus obtained is then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. Column chromatography is used to separate the residue obtained from the obtained dry product having removed the solvent, to obtain 0.12g (0.14mmol) of compound 93.
[0832] Synthesis Example 4: Synthesis of Compound 3
[0833]
[0834] 0.10g (2.1mmol) of sodium cyanide was suspended in 20mL of methanol and stirred at room temperature for 30 minutes. At room temperature, the compound 96 containing 1.10g (1.4mmol) and the solution of 1.4mL of DCM were slowly added dropwise thereto, and then stirred at room temperature for 12 hours. After the reaction terminates, ethyl acetate is used to extract the reaction product. The organic layer thus obtained is then washed with an aqueous solution of saturated sodium chloride and dried with sodium sulfate. Column chromatography is used to separate the residue obtained from the obtained dry product having removed the solvent, to obtain 0.10g (0.13mmol) of compound 3.
[0835] Synthesis Example 5: Synthesis of Compound 2
[0836]
[0837] Synthesis of intermediate 2-A
[0838] Intermediate 2-A was synthesized in substantially the same manner as the synthesis of Intermediate 96-A of Synthesis Example 2, except that imidazole was used instead of benzimidazole.
[0839] Synthesis of Intermediate 2-B, Intermediate 2-C, Intermediate 2-D and Intermediate 2-E
[0840] Intermediate 2-B, intermediate 2-C, intermediate 2-D and intermediate 2-E were synthesized sequentially in substantially the same manner as the synthesis of intermediate 96-B, intermediate 96-C, intermediate 96-D and compound 96 in Synthesis Example 2, except that intermediate 2-A, intermediate 2-B, intermediate 2-C and intermediate 2-D were used instead of intermediate 96-A, intermediate 96-B, intermediate 96-C and intermediate 96-D, respectively.
[0841] Synthesis of compound 2
[0842] 80 mg (0.11 mmol) of Compound 2 was obtained in substantially the same manner as in the synthesis of Compound 3 in Synthesis Example 4, except that Intermediate 2-E was used instead of Compound 96.
[0843] Synthesis Example 6: Synthesis of Compound 31
[0844]
[0845] 0.15 g (0.15 mmol) of Compound 31 was obtained in substantially the same manner as in the synthesis of Compound 3 in Synthesis Example 4, except that Intermediate 77-C was used instead of Compound 96.
[0846]
[0847] 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. The synthesis methods of compounds other than the compounds of Synthesis Examples 1 to 6 can be easily recognized by those skilled in the art by referring to the synthesis routes and raw materials.
[0848] Table 1
[0849]
[0850] Evaluation Example 1
[0851] The HOMO energy level and LUMO energy level of each of Compounds 77, 93, 96, 2, 3, 31, A, B, and C were evaluated according to the method described in Table 2, and the results are shown in Table 3.
[0852] Table 2
[0853]
[0854]
[0855] Table 3
[0856] Compound No. HOMO level (eV) LUMO level (eV) 77 -5.50 -2.06 93 -5.37 -2.10 96 -5.61 -2.21 2 -5.51 -2.15 3 -5.41 -2.14 31 -5.43 -2.11 A -5.40 -2.01 B -5.42 -2.07 C -5.43 -2.05
[0857]
[0858] Evaluation Example 2
[0859] Compound 77 (2 mg), compound ETH2 (10 mg), compound HTH29 (10 mg) and CH 2 Cl 2 The PMMA (wherein the weight of PMMA is 50mg) in the film was mixed together, and the resulting product was coated on a quartz substrate by using a spin coater. The quartz substrate was heat treated in an oven at 80°C, and then cooled to room temperature to prepare a film 77 with a thickness of 40nm. Next, 93, film 96, film 2, film 3, film 31, film A, film B and film C were prepared in substantially the same manner as film 77, except that compound 93, compound 96, compound 2, compound 3, compound 31, compound A, compound B and compound C were used instead of compound 77.
[0860] The emission spectrum of each of the films 77, 93, 96, 2, 3, 31, A, B and C was measured by using a Quantaurus-QY absolute PL quantum yield spectrometer manufactured by Hamamatsu Corporation (equipped with a xenon light source, a monochromator, a photon multichannel analyzer and an integrating sphere) and PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, the excitation wavelength was scanned from 320 nanometers (nm) to 380 nm at intervals of 10 nm, and the spectrum measured at an excitation wavelength of 340 nm was taken to obtain the maximum emission wavelength (emission peak wavelength) and the full width at half maximum (FWHM) of the film including the organometallic compound represented by Formula 1. The results are summarized in Table 4.
[0861] Next, the photoluminescence quantum yield (PLQY) of each of Film 77, Film 93, Film 96, Film 2, Film 3, Film 31, Film A, Film B, and Film C was measured by scanning the excitation wavelength from 320 nm to 380 nm at intervals of 10 nm with a Quantaurus-QY absolute PL quantum yield spectrometer manufactured by Hamamatsu Corporation, and the PLQY measured at an excitation wavelength of 330 nm was taken to obtain the PLQY of the film including the organometallic compound represented by Formula 1. The results are summarized in Table 4.
[0862] Table 4
[0863]
[0864]
[0865] Referring to Table 4, it is confirmed that Compounds 77, 93, 96, 2, 3, and 31 each emit blue light having a relatively narrow FWHM while having improved PLQY compared to Compounds A to C.
[0866] Example 1
[0867] A 15 ohm per square centimeter (Ω / cm 2 )(1,200 Angstroms )ITO glass substrate (product of Corning Incorporated) was cut into a size of 50 millimeters (mm)×50 mm×0.7 mm, washed by ultrasonication using isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet rays and exposed to ozone for 30 minutes, and then mounted on a vacuum deposition device.
[0868] 2-TNATA was vacuum deposited on the anode to form a layer with a thickness of A hole injection layer is formed, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as "NPB") is vacuum deposited on the hole injection layer to form a layer with a thickness of hole transport layer.
[0869] The first compound (compound 77), the second compound (compound ETH2) and the third compound (compound HTH29) are vacuum deposited on the hole transport layer to form a layer with a thickness of Here, the amount of the first compound is 13 wt % of the total weight (100 wt %) of each emission layer, and the weight ratio of the second compound to the third compound is adjusted to 3.5:6.5.
[0870] The compound ETH34 is vacuum deposited on the emission layer to form a layer with a thickness of The hole blocking layer is formed by vacuum depositing ET46 and Liq at a weight ratio of 4:6 on the hole blocking layer to form a layer having a thickness of Next, Yb is vacuum deposited on the electron transport layer to form a layer with a thickness of and then Mg is vacuum deposited thereon to form an electron injection layer with a thickness of The cathode of the organic light-emitting device is thus completed.
[0871]
[0872]
[0873] Examples 2 to 6 and Comparative Examples A to C
[0874] Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 5 were each used as the first compound instead of Compound 77 when forming the emission layer. In Table 5, the weight in parentheses indicates the weight of the corresponding compound per 100 wt % of the emission layer.
[0875] Evaluation Example 3
[0876] The organic light-emitting devices of Examples 1 to 6 and Comparative Examples A to C were 1,000 candela per square meter (cd / m 2 )), driving voltage (V), y color coordinate (CIEy), color conversion efficiency (cd / A / y), maximum emission wavelength (nm), and lifetime (T 95 ) were each measured by using a Keithley SMU 236 meter and a luminance meter PR650, and the results are shown in Table 6. In Table 6, the lifespan (T 95 ) is a measured value of the time (hr) taken for the brightness to reach 95% of the initial brightness expressed as a relative value (%) relative to Comparative Example A.
[0877] Table 5
[0878]
[0879]
[0880]
[0881] Table 6
[0882]
[0883]
[0884] See Table 6 to confirm that:
[0885] 1) The organic light-emitting devices of Example 1 and Example 2 each emit blue light and have comparable driving voltage, excellent or appropriate color conversion efficiency, and excellent or appropriate lifespan characteristics compared to the organic light-emitting device of Comparative Example A;
[0886] 2) The organic light-emitting device of Example 4 emits blue light and has a comparable driving voltage, excellent or appropriate color conversion efficiency, and excellent or appropriate lifespan characteristics compared to the organic light-emitting device of Comparative Example B;
[0887] 3) The organic light-emitting devices of Example 5 and Example 6 each emit blue light and have comparable driving voltage, excellent or appropriate color conversion efficiency, and excellent or appropriate lifespan characteristics as compared to the organic light-emitting device of Comparative Example C; and
[0888] 4) The organic light-emitting device of Example 3 emits blue light and has excellent or appropriate driving voltage, excellent or appropriate color conversion efficiency, and excellent or appropriate lifespan characteristics.
[0889] Example 11 and Example 12
[0890] Organic light-emitting devices were each manufactured in substantially the same manner as in Example 1, except that the amounts of the first compound, the second compound, and the third compound were changed and the fourth compound was further added when the emission layer was formed as shown in Table 7. In Table 7, the weight in parentheses indicates the weight of the corresponding compound per 100 wt % of the emission layer.
[0891] Evaluation Example 4
[0892] The organic light-emitting devices of Examples 11 and 12 were measured at 1,000 cd / m 2 The driving voltage (V), y color coordinate (CIEy), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and lifetime (T 95 ), and the results are shown in Table 8. In Table 8, the lifespan (T 95 ) is a measured value of the time (hr) taken for the luminance to reach 95% of the initial luminance expressed as a relative value (%) with respect to Comparative Example A. For comparison, data of the organic light-emitting device of Comparative Example A are also provided in Table 8.
[0893] Table 7
[0894]
[0895]
[0896] Table 8
[0897]
[0898] Referring to Table 8, it is confirmed that the organic light-emitting devices of Example 11 and Example 12 each emit blue light and have excellent or appropriate driving voltage, excellent or appropriate color conversion efficiency, and excellent or appropriate lifespan characteristics compared to the organic light-emitting device of Comparative Example A.
[0899] According to one or more embodiments, the organometallic compound represented by Formula 1 may have excellent or appropriate processability and electrical properties, and thus a light-emitting device including the organometallic compound represented by Formula 1 may have improved color purity, improved luminous efficiency, and / or improved lifespan characteristics.
[0900] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more appropriate changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. A composition comprising: An organometallic compound represented by Formula 1; as well as Includes at least one π-electron-deficient nitrogen-containing C1-C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound emitting delayed fluorescence, or any combination thereof, The organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 1 Formula 1A In Formula 1, Ar1 and Ar2 are each independently a group represented by Formula 1A, Wherein, in Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, L1 is a monodentate ligand, X1 to X3 and Y1 to Y3 are each independently C or N, Ring CY1 to Ring CY3 and Ring A1 to Ring A4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, Two of the four bonds selected from the bond between X1 and M, the bond between X2 and M, the bond between X3 and M, and the bond between L1 and M are each coordinate bonds, and two of the four bonds are each covalent bonds, n1 and n2 are each independently 0 or 1, R1 to R3 and T1 to T4 are each 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), a1 to a3 and b1 to b4 are each independently an integer selected from 0 to 20, At least two selected from ring CY1, ring CY2, ring A2, ring A3, R1 to R3 and T1 to T4 are not bonded to each other or bonded to each other to form an unsubstituted or substituted ring. 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, * indicates the binding site with adjacent atoms, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 any combination thereof; Each unsubstituted or substituted 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 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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 any 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 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Formula 3 In formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 Cyclic group or pyridyl group, X 71 is a single bond, or is a linking group comprising O, S, N, B, C, Si or any combination thereof, and * indicates a binding site with an atom not including Formula 3 in the third compound.
2. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emitting layer; as well as An organometallic compound represented by Formula 1: Formula 1 Formula 1A Wherein, in Formula 1, Ar1 and Ar2 are each independently a group represented by Formula 1A, and Wherein, in Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, L1 is a monodentate ligand, X1 to X3 and Y1 to Y3 are each independently C or N, Ring CY1 to Ring CY3 and Ring A1 to Ring A4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, Two of the four bonds selected from the bond between X1 and M, the bond between X2 and M, the bond between X3 and M, and the bond between L1 and M are each coordination bonds, and two of the four bonds are each covalent bonds, n1 and n2 are each independently 0 or 1, R1 to R3 and T1 to T4 are each 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), a1 to a3 and b1 to b4 are each independently an integer selected from 0 to 20, At least two selected from ring CY1, ring CY2, ring A2, ring A3, R1 to R3 and T1 to T4 are not bonded to each other or bonded to each other to form an unsubstituted or substituted ring. 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, * indicates the binding site with adjacent atoms, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 any combination thereof; Each unsubstituted or substituted 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 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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 any 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 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.
3. The light emitting device according to claim 2, further comprising: Includes at least one π-electron-deficient nitrogen-containing C1-C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound emitting delayed fluorescence, or any combination thereof, the organometallic compound, the second compound, the third compound and the fourth compound are different from each other, Formula 3 In formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 Cyclic group or pyridyl group, X 71 is a single bond, or is a linking group comprising O, S, N, B, C, Si or any combination thereof, and * indicates a binding site with an atom not including Formula 3 in the third compound.
4. The light emitting device according to claim 3, The second compound includes a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group or any combination thereof, The fourth compound is a compound including at least one cyclic group including each of boron and nitrogen as a ring-constituting atom.
5. The light emitting device according to claim 3, wherein The transmitting layer comprises: i) the organometallic compound; as well as ii) the second compound, the third compound, the fourth compound or any combination thereof, wherein The emission layer emits blue light.
6. The light emitting device according to claim 3, further comprising: The second compound and the third compound, At least one selected from the second compound and the third compound includes at least one deuterium, at least one silicon, or a combination thereof.
7. An electronic device comprising the light emitting device according to any one of claims 2 to 6.
8. The electronic device according to claim 7, further comprising: Color filters, color conversion layers, touch screen layers, polarizing layers, or any combination thereof.
9. An electronic device comprising the light emitting device according to any one of claims 2 to 6.
10. The electronic device of claim 9, wherein the electronic device is at least one selected from 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 retractable display, a laser printer, a phone, a portable 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 tiled together, a theater screen, a stadium screen, a light therapy device, and a sign.
11. An organometallic compound represented by Formula 1: Formula 1 Formula 1A in, In Formula 1, Ar1 and Ar2 are each independently a group represented by Formula 1A, and Wherein, in Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, L1 is a monodentate ligand, X1 to X3 and Y1 to Y3 are each independently C or N, Ring CY1 to Ring CY3 and Ring A1 to Ring A4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, Two of the four bonds selected from the bond between X1 and M, the bond between X2 and M, the bond between X3 and M, and the bond between L1 and M are each coordinate bonds, and two of the four bonds are each covalent bonds, n1 and n2 are each independently 0 or 1, R1 to R3 and T1 to T4 are each 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), a1 to a3 and b1 to b4 are each independently an integer selected from 0 to 20, At least two selected from ring CY1, ring CY2, ring A2, ring A3, R1 to R3 and T1 to T4 are not bonded to each other or bonded to each other to form an unsubstituted or substituted ring. 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, * indicates the binding site with adjacent atoms, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 any combination thereof; Each unsubstituted or substituted 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 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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 any 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 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.
12. The organometallic compound according to claim 11, wherein Ring CY1 is: imidazolyl fused to phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or any combination thereof; or imidazolyl or triazolyl, and Ring CY2 is: imidazolyl, oxazolyl or thiazolyl, each fused to phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or any combination thereof; or imidazolyl, oxazolyl, thiazolyl or triazolyl.
13. The organometallic compound according to claim 11, wherein the ring CY3 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, naphthyl, quinolyl or isoquinolyl.
14. The organometallic compound according to claim 11, wherein Ring A1 to Ring A4 are each independently: phenyl, pyridyl, pyrimidinyl, pyridazinyl or pyrazinyl; or Phenyl, pyridyl, pyrimidyl, pyridazinyl or pyrazinyl, each fused to a cyclohexyl, adamantyl or norbornyl group.
15. The organometallic compound according to claim 11, wherein The bond between X1 and M and the bond between X2 and M are each coordinate bonds, and The bond between X3 and M and the bond between L1 and M are each covalent bonds.
16. The organometallic compound according to claim 11, wherein R1 to R3 and T1 to T4 are each independently: Hydrogen, deuterium, -F or cyano; Unsubstituted or substituted with C1-C 20 Alkyl: deuterium, -F, cyano, C3-C 10 Cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 Cycloalkyl, (C1-C 20 Alkyl) C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl or any combination thereof; or Each unsubstituted or substituted C3-C 10 Cycloalkyl, phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C3-C 10 Cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 Cycloalkyl, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl, carbazolyl, deuterated carbazolyl, fluorinated carbazolyl, (C1-C 20 alkyl)carbazolyl or any combination thereof.
17. The organometallic compound of claim 11, wherein the organometallic compound comprises at least one deuterium.
18. The organometallic compound according to claim 11, wherein condition A1 or condition A2 is satisfied: Condition A1 In formula 1A, n1 is 0. Ring A3 in Formula 1A and Ring CY1 in Formula 1 are linked together via a single bond, and The ring formed by the ring-forming atoms in the ring CY1, Y1, Y3 and the ring-forming atoms in the ring A3 in Formula 1 and Formula 1A is a 7-membered ring; and Condition A2 In formula 1A, n1 is 1. Ring A3 in Formula 1A and Ring CY1 in Formula 1 are linked together via a single bond, and The ring formed by the ring-forming atoms in ring CY1, Y1, Y3, the ring-forming atoms in ring A4 and the ring-forming atoms in ring A3 in Formula 1 and Formula 1A is a 9-membered ring.
19. The organometallic compound according to claim 11, wherein condition B1 or condition B2 is satisfied: Condition B1 In formula 1, n2 is 1. In formula 1A, n1 is 0. Ring A3 in Formula 1A and Ring CY2 in Formula 1 are linked together via a single bond, and The ring formed by the ring-forming atoms in the ring CY2 in Formula 1 and Formula 1A, Y1, Y3 and the ring-forming atoms in the ring A3 is a 7-membered ring; and Condition B2 In formula 1, n2 is 1. In formula 1A, n1 is 1. Ring A3 in Formula 1A and Ring CY2 in Formula 1 are linked together via a single bond, and The ring formed by the ring-forming atoms in ring CY2, Y1, Y3, the ring-forming atoms in ring A4 and the ring-forming atoms in ring A3 in Formula 1 and Formula 1A is a 9-membered ring.
20. The organometallic compound according to claim 11, wherein the organometallic compound is represented by one selected from Formula 1-1 to Formula 1-10: in, In Formula 1-1 to Formula 1-10, X 20 N(R 20 ), N(Ar2), O or S, M, L1, Ar1, Ar2 and X1 to X3 are each as defined in Formula 1, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, and X 14 C(R 14 ) or N, where R 11 To R 14 Each is as defined for R1 in Formula 1, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, X 23 C(R 23 ) or N, and X 24 C(R 24 ) or N, where R 20 To R 24 Each is as defined for R2 in Formula 1, X 31 C(R 31 ) or N, X 32 C(R 32 ) or N, and X 33 C(R 33 ) or N, where R 31 To R 33 Each is as defined for R3 in Formula 1, Y 11 C(T 11 ) or N, Y 12 C(T 12 ) or N, and Y 13 C(T 13 ) or N, where T 11 To T 13 Each is as defined for T1 in Formula 1A, Y 21 C(T 21 ) or N, Y 22 C(T 22 ) or N, Y 23 C(T 23 ) or N, Y 24 C(T 24 ) or N, and Y 25 C(T 25 ) or N, where T 21 To T 25 Each is as defined for T2 in Formula 1A, Y 31 C(T 31 ) or N, Y 32 C(T 32 ) or N, Y 33 C(T 33 ) or N, and Y 34 C(T 34 ) or N, where T 31 To T 34 Each is as defined for T3 in Formula 1A, Y 41 C(T 41 ) or N, Y 42 C(T 42 ) or N, Y 43 C(T 43 ) or N, and Y 44 C(T 44 ) or N, where T 41 To T 44 Each is as defined for T4 in Formula 1A, Y 51 C(T 51 ) or N, Y 52 C(T 52 ) or N, and Y 53 C(T 53 ) or N, where T 51 To T 53 Each is as defined for T1 in Formula 1A, Y 61 C(T 61 ) or N, Y 62 C(T 62 ) or N, Y 63 C(T 63 ) or N, Y 64 C(T 64 ) or N, Y 65 C(T 65 ) or N, and T 61 To T 65 Each is as defined for T2 in Formula 1A, Y 71 C(T 71 ) or N, Y 72 C(T 72 ) or N, Y 73 C(T 73 ) or N, and Y 74 C(T 74 ) or N, where T 71 To T 74 Each is as defined for T3 in Formula 1A, and Y 81 C(T 81 ) or N, Y 82 C(T 82 ) or N, Y 83 C(T 83 ) or N, and Y 84 C(T 84 ) or N, where T 81 To T 84 Each is as defined for T4 in Formula 1A.
Citation Information
Patent Citations
Electric furnace with video equipment attached
KR1020230132834A