Composition, light-emitting device, electronic device, electronic equipment, and organometallic compound
The color purity, luminescence efficiency and service life of the luminescent device are improved by using specific compositions, including organometallic compounds and nitrogen-containing heterocyclic groups, and these shortcomings in the prior art are solved.
Patent Information
- Application Number
- CN202411261907.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-09-12
- Filing Date
- 2024-09-10
- Publication Date
- 2025-03-14
AI Technical Summary
There is room for improvement in existing luminescent devices in terms of color purity, luminous efficiency and service life.
A composition consisting of specific organometallic compounds, nitrogen-containing C1-C60 heterocyclic groups, π-electron-rich C3-C60 cyclic groups or pyridine groups is used to improve the performance of the light emitting device.
The luminescent device is realized to improve color purity, luminous efficiency and service life.
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Figure CN119613458A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0121344 filed in the Korean Intellectual Property Office on September 12, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more aspects of embodiments of the present disclosure relate to a composition, a light-emitting device, electronic devices and electronic equipment each including the light-emitting device, and an organometallic compound. Background Art
[0004] So-called "self-emissive" devices among light-emitting devices (eg, organic light-emitting devices) have relatively wide viewing angles, relatively high contrast, relatively short response times, and excellent or suitable characteristics in terms of brightness, driving voltage, and / or response speed.
[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 by the first electrode move toward the emission layer through the hole transport region, and electrons provided by the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons can then transition (ie, relax) from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] One or more aspects of the embodiments of the present disclosure relate to compositions and organometallic compounds capable of providing improved color purity, improved luminous efficiency and / or improved service life, light-emitting devices having improved color purity, improved luminous efficiency and / or improved service life, and electronic devices and electronic equipment each comprising the light-emitting device.
[0007] 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.
[0008] According to one or more embodiments,
[0009] The composition comprises:
[0010] an organometallic compound represented by Formula 1; and
[0011] Contains at least one nitrogen-containing C with a π-deficient 1 -C 60a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or a (for example, any) combination thereof,
[0012] The organometallic compound, the second compound, the third compound and the fourth compound may be different from each other.
[0013] Formula 1
[0014]
[0015] Formula 1A
[0016]
[0017] Ar in Formula 1 1 It may be a group represented by Formula 1A,
[0018] The * in Formula 1A represents the ring CY in Formula 1 1 The binding site
[0019] In Formula 1 and Formula 1A,
[0020] M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag) or copper (Cu),
[0021] X 1 To X 4 can each independently be C or N,
[0022] i)X 1 The bond between M and X may be a coordination bond, ii) selected from 2 The key between M and X 3 The bond between M and X 4 One of the bonds to M may be a coordination bond and is selected from X 2 The key between M and X 3 The bond between M and X 4 Two of the bonds between X and M are each covalent bonds (eg, the other two bonds may each be covalent bonds), for example, 2 The key between M and X 3 The bond between M and X 4 Each of the bonds between M and M may be a coordinate bond or a covalent bond, wherein one of the bonds is a coordinate bond,
[0023] Cyclo 1 To Ring CY 4 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60Heterocyclic group,
[0024] X 51 can be a single bond, *-N(Z 51a ), *-B(Z 51a ), *-P(Z 51a ), *-C(Z 51a )(Z 51b ), *-Si(Z 51a )(Z 51b ), *-Ge(Z 51a )(Z 51b ), *-S-*, *-Se-*, *-O-*, *-C(=O)-*, *-S(=O)-*, *-S(=O) 2 ), *-C(Z 51a ), =*, *=C(Z 51a ), *-C(Z 51a ), =C(Z 51b ), *-C(=S)-* or *-C≡C-*,
[0025] X 52 can be a single bond, *-N(Z 52a ), *-B(Z 52a ), *-P(Z 52a ), *-C(Z 52a )(Z 52b ), *-Si(Z 52a )(Z 52b ), *-Ge(Z 52a )(Z 52b ), *-S-*, *-Se-*, *-O-*, *-C(=O)-*, *-S(=O)-*, *-S(=O) 2 ), *-C(Z 52a ), =*, *=C(Z 52a ), *-C(Z 52a ), =C(Z 52b ), *-C(=S)-* or *-C≡C-*,
[0026] R 1 to R 4 , Z 51a , Z 51b , Z 52a , Z 52b and T 1 to T 4can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroarylalkyl group, -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 ),
[0027] a1 to a4 may each independently be an integer from 0 to 10,
[0028] c1 can be an integer from 1 to 3.
[0029] c2 and c4 can each independently be an integer from 1 to 5,
[0030] c3 can be an integer from 1 to 4,
[0031] In Formula 1A, The groups represented by The groups represented may be different from each other,
[0032] Selected from R 1 , R 2 , R 3 , R 4 , Z 51a , Z 51b , Z 52a , Z 52b 、T 1 、T 2 、T 3 and T 4 Two or more of the 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 groups,
[0033] * and *' each represent a binding site with an adjacent atom,
[0034] R 10a It can be:
[0035] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group,
[0036] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or (for example, any) combination thereof substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups,
[0037] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -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 (for example, any) combination thereof substituted C 3 -C 60 Carbocyclic group, C1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group or C 2 -C 60 a heteroarylalkyl group, or
[0038] -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 ),as well as
[0039] 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; a hydroxyl group; a cyano group; a nitro group; or each is unsubstituted or substituted with deuterium, -F, a cyano group, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group or (for example, any) combination thereof 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0040] Formula 3
[0041]
[0042] In formula 3,
[0043] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0044] X 71 may be a single bond, or a linking group comprising O, S, N, B, C, Si, or (e.g., any) combination thereof, and
[0045] * in Formula 3 represents a binding site with an atom in the third compound not included in Formula 3 (eg, an (eg, arbitrary) atom included in the remaining portion of the third compound other than Formula 3).
[0046] According to one or more embodiments,
[0047] The light emitting device comprises a first electrode,
[0048] a second electrode facing the first electrode,
[0049] an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, and
[0050] The organic metal compound represented by Formula 1.
[0051] According to one or more embodiments, an electronic device comprises the light emitting device.
[0052] According to one or more embodiments, an electronic equipment comprises the light emitting device.
[0053] According to one or more than one embodiment, the organometallic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0054] The accompanying drawings are included to provide a further understanding of the previous aspects and other aspects, and the features and advantages of certain embodiments of the present disclosure are incorporated into and constitute a part of this specification. The accompanying drawings illustrate exemplary embodiments and together with the following description in conjunction with the accompanying drawings, serve to make the principles of the present disclosure more apparent. In the drawings:
[0055] Figure 1 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0056] Figure 2 and Figure 3each being a schematic diagram of a structure of a light emitting device as one of electronic devices according to one or more embodiments of the present disclosure; and
[0057] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to one or more embodiments of the present disclosure;
[0058] Figure 5 is a schematic perspective view of an exterior of a vehicle as an electronic equipment including a light emitting device according to one or more embodiments of the present disclosure; and
[0059] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle including electronic equipment including a light emitting device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0060] Now will refer to the embodiment in more detail, the example of the embodiment is illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the text, and the description thereof may not be provided in this specification. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the embodiment is only described with reference to the accompanying drawings to explain the aspects of this description. As used herein, the term "and / or" includes any combination and all combinations of one or more than one of the related listed items. Statements such as "at least one (kind) in ...", "one (kind) in ..." and "selected from" when before a column of elements modify the elements of the entire column and do not modify the single element of the column. For example, throughout the disclosure, the statement "at least one of a, b and c" means only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all a, b and c, or its variants.
[0061] Unless otherwise defined, all chemical names, technical and scientific terms and terms defined in common dictionaries should be interpreted as having a meaning consistent with the background of the relevant technology, and should not be interpreted with an ideal or overly formal meaning. It should 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.
[0062] As used herein, singular forms such as "a", "an" and "the" are intended to include plural forms as well, unless the context clearly indicates otherwise.
[0063] It should be further understood that the terms “comprise,” “comprises,” “comprising,” “has,” “have,” “having,” “include,” “includes,” and / or “including,” when used in the present specification, specify the presence of specified features, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and / or groups thereof.
[0064] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0065] The term "may" should be understood to refer to "one or more than one embodiments of the present disclosure," some of which include the described element, and some of which exclude the element and / or include alternative elements. Similarly, alternative wordings such as "or" refer to "one or more than one embodiments of the present disclosure," each of which includes the corresponding listed items.
[0066] It should be understood that when an element is referred to as being "on," "connected to," or "on" another element, it may be directly on, directly connected to, or directly coupled to the other element, or there may be one or more intervening elements. When an element is referred to as being "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements.
[0067] For ease of description, spatially relative terms such as "under", "below", "down", "above", "up", "bottom", "top", etc. may be used herein to describe the relationship between one element or feature and another element or feature as illustrated in the accompanying drawings. It should be understood that spatially relative terms are intended to cover different orientations of the device when in use or operation in addition to the orientation depicted in the accompanying drawings. For example, if the device in the accompanying drawings is turned over, the elements described as being "under" or "under" other elements or features will be oriented "above" or "on" other elements or features. Therefore, the term "below" can cover both the directions above and below. The device can be oriented in other ways (rotated 90 degrees or in other directions), and the spatially relative descriptors used herein should be interpreted accordingly.
[0068] In the present context, "consisting essentially of" means that any additional components will not substantially affect the chemical, physical, optical or electrical properties of the semiconductor film.
[0069] In the present disclosure, "does not include (or does not include (not including)) 'component' or any 'component'", "excludes (or excludes (excluding)) 'component' or any 'component'", "does not contain 'component'" and the like mean that the 'component' is not added, selected or used as a component in an element / composition, but due to other impurities and / or external factors, less than an appropriate amount of the 'component' may still be included.
[0070] Furthermore, in this specification, the phrase “in plan view” or “plan view” means observing the 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.
[0071] Composition
[0072] According to one or more embodiments,
[0073] The composition comprises: an organometallic compound represented by Formula 1; and
[0074] Contains at least one nitrogen-containing C with a π-deficient 1 -C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or a (for example, any) combination thereof,
[0075] wherein the organometallic compound, the second compound, the third compound and the fourth compound may be different from each other:
[0076] Formula 1
[0077]
[0078] Formula 3
[0079]
[0080] Among them, in formula 3,
[0081] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0082] X 71 can be a single bond, or a linking group comprising O, S, N, B, C, Si or any combination thereof, and
[0083] * in Formula 3 represents a binding site with an atom not included in the third compound in Formula 3 (eg, an (eg, arbitrary) atom included in the remaining portion of the third compound other than Formula 3).
[0084] As used herein, the organometallic compound represented by Formula 1 may be referred to as a “first compound”.
[0085] Formula 1 and Formula 3 are each as described herein.
[0086] In one or more embodiments, the composition can be contained in a layer. A "layer comprising a composition" can include a mixture comprising 1) an organometallic compound and 2) a second compound, a third compound, a fourth compound, or any combination thereof. Thus, a "layer comprising a composition" is clearly distinguished from, for example, a bilayer comprising 1) a first layer comprising an organometallic compound and 2) a second layer comprising a second compound, a third compound, a fourth compound, or any combination thereof.
[0087] In one or more embodiments, the composition can be a composition prepared for forming a layer comprising 1) an organometallic compound and 2) a second compound, a third compound, a fourth compound, or any combination thereof by using one or more suitable methods (e.g., a deposition method, a wet method, etc.). In one or more embodiments, the composition can be a premixed mixture prepared for a deposition method (e.g., a vacuum deposition method). For example, the premixed mixture can be loaded into a deposition source within a vacuum chamber, and two or more compounds contained in the premixed mixture can be co-deposited.
[0088] In one or more embodiments, the weight ratio of the organometallic compound to the second compound in the composition can be from 10:90 to 90:10 or from 20:80 to 80:20.
[0089] According to one or more embodiments,
[0090] The light emitting device comprises: a first electrode;
[0091] a second electrode facing the first electrode;
[0092] an intermediate layer disposed between the first electrode and the second electrode and including an emission layer; and
[0093] An organometallic compound represented by Formula 1.
[0094] Formula 1 is as described herein.
[0095] The light emitting device includes the organometallic compound represented by Formula 1 and thus may have improved color purity, improved light emitting efficiency, and improved lifespan characteristics.
[0096] In one or more than one embodiments, an intermediate layer in a light emitting device may comprise an organometallic compound.
[0097] In one or more than one embodiments, the emissive layer in the light emitting device may comprise an organometallic compound.
[0098] In one or more embodiments, the light emitting device may further include at least one π-electron-deficient nitrogen-containing C 1 -C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or a (for example, any) combination thereof, and
[0099] The organometallic compound, the second compound, the third compound, and the fourth compound in the light-emitting device may be different from each other.
[0100] The second to fourth compounds in the composition and the light-emitting device are each as described herein.
[0101] In one or more than one embodiment, the organometallic compound may comprise at least one deuterium.
[0102] In one or more than one embodiments, the second to fourth compounds can each comprise at least one deuterium.
[0103] In one or more embodiments, the second compound may include at least one silicon.
[0104] In one or more than one embodiment, the third compound may include at least one silicon.
[0105] 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 and a third compound, and 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.
[0106] In one or more embodiments, in addition to the organometallic compound, 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 and the second compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound and the second compound, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof.
[0107] In one or more embodiments, in addition to the organometallic 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. At least one of the organometallic compound and the third compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound 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.
[0108] In one or more embodiments, in addition to the organometallic compound, the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may each further include a fourth compound. At least one of the organometallic compound and the fourth compound may include at least one deuterium. The fourth compound may be used to improve the color purity, luminous efficiency and service life characteristics of the light-emitting device. In one or more embodiments, in addition to the organometallic compound 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.
[0109] In one or more than one embodiment, in addition to the organometallic compound, the composition and the light-emitting device (e.g., the emissive layer in the light-emitting device) may each further include a second compound and a third compound. The second compound and the third compound may form an exciplex. At least one of the organometallic compound, the second compound, and the third compound may include at least one deuterium.
[0110] In one or more embodiments, the organometallic compound can have a highest occupied molecular orbital (HOMO) energy level of about -5.35 electron volts (eV) to about -5.15 eV or about -5.30 eV to about -5.20 eV.
[0111] In one or more embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound can be from about -2.20 eV to about -1.80 eV or from about -2.15 eV to about -1.90 eV.
[0112] HOMO and LUMO energy levels can be evaluated via cyclic voltammetry analysis of the organometallic compound (eg, as described in Evaluation Example 1 herein).
[0113] In one or more embodiments, the maximum emission wavelength (or emission peak wavelength) of the photoluminescence (PL) spectrum in the film of the organometallic compound can be from about 430 nanometers (nm) to about 475 nm, from about 440 nm to about 475 nm, from about 450 nm to about 475 nm, from about 430 nm to about 470 nm, from about 440 nm to about 470 nm, from about 450 nm to about 470 nm, from about 430 nm to about 465 nm, from about 440 nm to about 465 nm, from about 450 nm to about 465 nm, from about 430 nm to about 460 nm, from about 440 nm to about 460 nm, or from about 450 nm to about 460 nm.
[0114] In one or more embodiments, the emission full width at half maximum (FWHM) of the PL spectrum in the film of the organometallic compound can be 40 nm or less, about 5 nm to about 40 nm, about 10 nm to about 40 nm, about 15 nm to about 40 nm, about 20 nm to about 40 nm, about 5 nm to about 38 nm, about 10 nm to about 38 nm, about 15 nm to about 38 nm, or about 20 nm to about 38 nm.
[0115] In one or more embodiments, the photoluminescence quantum yield (PLQY) in the film of the organometallic compound can be from about 50% to about 99% or from about 55% to about 90%.
[0116] In one or more embodiments, the decay time of the organometallic compound can be from about 1.80 microseconds (μs) to about 3.00 μs, from about 1.90 μs to about 2.70 μs, or from about 1.90 μs to about 2.50 μs.
[0117] For the film containing the organometallic compound, the maximum emission wavelength, emission FWHM, PLQY, and decay time of the organometallic compound were evaluated, and the evaluation method thereof was as described with respect to, for example, Evaluation Example 2 and Evaluation Example 3 described herein.
[0118] In one or more embodiments, the emission layer of the light emitting device may include: i) an organometallic compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, and the emission layer may be designed to emit blue light.
[0119] In one or more embodiments, the maximum emission wavelength of blue light can be about 430nm to about 475nm, about 440nm to about 475nm, about 450nm to about 475nm, about 430nm to about 470nm, about 440nm to about 470nm, about 450nm to about 470nm, about 430nm to about 465nm, about 440nm to about 465nm, or about 450nm to about 465nm.
[0120] In one or more embodiments, the emission FWHM of blue light can be 40 nm or less, about 5 nm to about 40 nm, about 10 nm to about 40 nm, about 15 nm to about 40 nm, about 20 nm to about 40 nm, about 5 nm to about 38 nm, about 10 nm to about 38 nm, about 15 nm to about 38 nm, or about 20 nm to about 38 nm.
[0121] In one or more embodiments, the blue light can be deep blue light.
[0122] In one or more embodiments, the CIEx coordinate of blue light (eg, bottom emission CIEx coordinate) can be about 0.125 to about 0.140 or about 0.130 to about 0.140.
[0123] In one or more embodiments, the CIE y coordinate of blue light (eg, bottom emission CIE y coordinate) can be about 0.100 to about 0.130.
[0124] Examples of maximum emission wavelengths and CIEy coordinates for blue light are described in Tables 7 and 9 herein.
[0125] In one or more than one embodiment, the second compound can include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
[0126] In one or more than one embodiment, the following compounds may be excluded from the third compound.
[0127]
[0128] In one or more embodiments, the difference between the triplet energy level (eV) of the fourth compound and the singlet energy level (eV) of the fourth compound can be about 0 eV or higher and about 0.5 eV or lower (or, about 0 eV or higher and about 0.3 eV or lower).
[0129] In one or more than one embodiment, the fourth compound may include at least one cyclic group containing each of boron (B) and nitrogen (N) as ring-forming atoms.
[0130] In one or more than one embodiment, the fourth compound may be a C-containing fused cyclic group comprising at least two common boron (B) groups. 8 -C 60 Polycyclic compounds.
[0131] In one or more than one embodiment, the fourth compound can comprise a fused ring, wherein at least one third ring and at least one fourth ring are fused together.
[0132] The third ring may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group, and
[0133] The fourth ring may be a 1,2-azaborinyl group, a 1,3-azaborinyl group, a 1,4-azaborinyl group, a 1,2-dihydro-1,2-azaborinyl group, a 1,4-oxaborinyl group, a 1,4-thiaborinyl group, or a 1,4-dihydroborinyl group.
[0134] In one or more than one embodiments, the third compound may not include (eg, may exclude) the compound represented by Formula 3-1 described herein.
[0135] In one or more than one embodiments, the second compound may include a compound represented by Formula 2:
[0136] Formula 2
[0137]
[0138] Among them, in formula 2,
[0139] L 51 To L 53 may be independently a single bond, unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0140] b51 to b53 may each independently be an integer from 1 to 5,
[0141] 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 X56 At least one of may be N, and
[0142] R 51 To R 56 and R 10a Each is as described herein.
[0143] In one or more than one 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:
[0144] Formula 3-1
[0145]
[0146] Formula 3-2
[0147]
[0148] Formula 3-3
[0149]
[0150] Formula 3-4
[0151]
[0152] Formula 3-5
[0153]
[0154] Among them, in Formula 3-1 to Formula 3-5,
[0155] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0156] 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 ),
[0157] X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R83b ) or Si(R 83a )(R 83b ),
[0158] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ), X 85 Can be C or Si,
[0159] 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 divalent π-electron-rich C 3 -C 60 Cyclic groups, either unsubstituted or substituted with at least one R 10a A substituted pyridinylene group wherein Q 4 and Q 5 Each as about Q 1 Description, * and *' each represent the binding site with the adjacent atom,
[0160] b81 to b85 may each independently be an integer from 1 to 5,
[0161] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b Each as described herein,
[0162] a71 to a74 may each independently be an integer from 0 to 20, and
[0163] R 10a As described herein.
[0164] In one or more than one embodiments, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or a (eg, any) combination thereof:
[0165] Formula 502
[0166]
[0167] Formula 503
[0168]
[0169] Among them, in equation 502 and equation 503,
[0170] Ring A 501 To Ring A 504 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0171] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0172] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0173] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0174] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0175] Y 51 and Y 52 may be each independently B, P(=O) or S(=O),
[0176] R500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b each as described herein, and
[0177] a501 to a504 may each independently be an integer of 0 to 20.
[0178] In one or more than one embodiments, the light emitting device may satisfy at least one of conditions 1 to 4 (e.g., selected from at least one of conditions 1 to 4):
[0179] Condition 1
[0180] The LUMO energy level (eV) of the third compound is greater than the LUMO energy level (eV) of the organometallic compound;
[0181] Condition 2
[0182] The LUMO energy level (eV) of the organometallic compound> the LUMO energy level (eV) of the second compound;
[0183] Condition 3
[0184] The HOMO energy level (eV) of the organometallic compound> the HOMO energy level (eV) of the third compound; and
[0185] Condition 4
[0186] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.
[0187] Each of the HOMO energy level and the LUMO energy level of each of the organometallic compound, 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).
[0188] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the organic metal compound and the LUMO energy level of the second compound may be about 0.1 eV or more and about 1.0 eV or less, the absolute value of the difference between the LUMO energy level of the organic metal compound and the LUMO energy level of the third compound may be about 0.1 eV or more and about 1.0 eV or less, the absolute value of the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the second compound may be about 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or more), and the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the third compound may be about 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or more).
[0189] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions as described herein, a balance between holes and electrons injected into the emission layer may be achieved.
[0190] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0191] First embodiment
[0192] According to a first embodiment, the organometallic compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may further include a host, the organometallic compound and the host may be different from each other, and the emission layer may be intended to emit phosphorescence or fluorescence emitted from the organometallic compound. In other words, according to a first embodiment, the organometallic compound may be a dopant or an emitter. In one or more than one embodiments, the organometallic compound may be a phosphorescent dopant or a phosphorescent emitter.
[0193] The phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
[0194] The emission layer may further include an auxiliary dopant. The auxiliary dopant may be used to improve the light emission efficiency from the organometallic compound by effectively transferring the dopant or the organometallic compound as an emitter.
[0195] The auxiliary dopant may be different from each of the organometallic compound and the host.
[0196] In one or more than one embodiments, the auxiliary dopant may be a compound that emits delayed fluorescence.
[0197] In one or more than one embodiments, the auxiliary dopant may be a compound including at least one cyclic group including each of boron (B) and nitrogen (N) as a ring-forming atom.
[0198] Second embodiment
[0199] According to a second embodiment, the organic metal compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may further include a host and a dopant, the organic metal compound, the host and the dopant may be different from each other, and the emission layer may be intended to emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
[0200] In one or more than one embodiment, the organometallic compound in the second embodiment may be used as an auxiliary dopant that transfers energy to the dopant (or emitter) rather than as a dopant.
[0201] In one or more than one embodiment, the organometallic compound of the second embodiment can be used as an emitter and as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0202] For example, the phosphorescence or fluorescence emitted by the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0203] The dopant (or emitter) in the second embodiment can be a 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 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).
[0204] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
[0205] The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0206] The host in the first and second embodiments may be 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).
[0207] In one or more than one embodiments, the host in the first embodiment and the second embodiment can be the second compound, the third compound, or any combination thereof.
[0208] In one or more than one embodiments, the light emitting device may further include a covering layer located outside the first electrode and / or outside the second electrode.
[0209] In one or more embodiments, the light-emitting device may further include at least one of a first covering layer located outside the first electrode and a second covering layer located outside the second electrode, and at least one of the first covering layer and the second covering layer may include an organic metal compound represented by Formula 1. The first covering layer and / or the second covering layer are each as described herein.
[0210] In one or more than one embodiments, the light emitting device may further comprise:
[0211] a first covering layer located outside the first electrode and comprising an organic metal compound represented by Formula 1;
[0212] a second covering layer located outside the second electrode and including an organic metal compound represented by Formula 1; or
[0213] A first covering layer and a second covering layer.
[0214] The expression “(the intermediate layer and / or the covering layer) contains an organic metal compound represented by Formula 1” as used herein may be intended to mean that (the intermediate layer and / or the covering layer) may contain one kind of organic metal compound represented by Formula 1 or two or more different kinds of organic metal compounds each represented by Formula 1.
[0215] In one or more embodiments, the intermediate layer and / or the covering layer may contain only compound 1 as an organic metal compound. In this regard, compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the intermediate layer may contain compound 1 and compound 2 as organic metal compounds. In this regard, compound 1 and compound 2 may be substantially present in the same layer (e.g., compound 1 and compound 2 may all 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).
[0216] The term “intermediate layer” as used herein refers to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of a light emitting device.
[0217] According to one or more embodiments, the electronic device includes a light emitting device. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor, the thin film transistor includes a source electrode and a drain electrode, and 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 of the electronic device, reference may be made to the description provided herein.
[0218] According to one or more embodiments, an electronic equipment comprises the light emitting device.
[0219] For example, the electronic equipment can be selected from at least one or a combination of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a signal light, a head-up display, a fully transparent display or 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 or an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen or a stadium screen, a light therapy device, and a sign.
[0220] According to one or more embodiments, there is provided an organometallic compound represented by Formula 1. Formula 1 is as described herein.
[0221] Methods for synthesizing organometallic compounds can be easily understood by one of ordinary skill in the art by referring to the synthesis examples and / or embodiments described herein.
[0222] Description of Formula 1
[0223] Ar in Formula 1 1 It may be a group represented by Formula 1A:
[0224] Formula 1A
[0225]
[0226] Wherein the * in Formula 1A represents the ring CY in Formula 1 1 binding site.
[0227] Description of Formula 1A (or Ar in Formula 1 1 Description of ) as provided herein.
[0228] In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
[0229] In one or more than one embodiments, M may be Pt.
[0230] In formula 1, X 1 To X 4 can each independently be C or N.
[0231] In one or more than one embodiment, X in Formula 11 Can be C. In one or more than one embodiment, X in Formula 1 1 It may be C, and C may be the carbon of a carbene moiety.
[0232] In one or more than one embodiment, X in Formula 1 1 It can be N.
[0233] In one or more than one embodiments, X 2 and X 3 can each be C, and X 4 It can be N.
[0234] In formula 1, i)X 1 The bond between M and X may be a coordination bond, ii) selected from 2 The key between M and X 3 The bond between M and X 4 One of the bonds to M may be a coordination bond and is selected from X 2 The key between M and X 3 The bond between M and X 4 Two of the bonds between X and M are each covalent bonds, for example, and the other two may each be covalent bonds. 2 The key between M and X 3 The bond between M and X 4 Each of the bonds with M may be a coordinate bond or a covalent bond, wherein one of the bonds is a coordinate bond.
[0235] In one or more than one embodiment, X 2 The bond between M and X 3 The bonds between X and M may each be covalent bonds, and X 4 The bond with M may be a coordinate bond.
[0236] In one or more than one embodiments, X 4 Can be N, and X 4 The bond with M may be a coordinate bond.
[0237] In Formula 1, ring CY 1 To Ring CY 4 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0238] For example, CY 1 Can be nitrogen-containing C 1 -C 60 Heterocyclic group.
[0239] Ring CY in Formula 1 1 Can be i) containing X 1 ii) wherein at least one 6-membered ring containing X is fused 1 iii) a 5-membered ring containing X 1 6-membered ring.
[0240] In one or more than one embodiment, ring CY in formula 1 1 Can be i) containing X 1 or ii) wherein at least one 6-membered ring is fused to a ring containing X 1 For example, the CY 1 This can include 1 Bonded to the 5-membered ring of M in Formula 1. Here, 1 The 5-membered ring of may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group or a thiadiazole group, and contains X 1 The 6-membered ring may be optionally fused to a ring containing X 1 The 5-membered ring and the 6-membered ring of may each independently be a phenyl group, a pyridine group or a pyrimidine group.
[0241] In one or more than one embodiment, CY 1 Can contain X 1 A 5-membered ring containing X 1 The 5-membered ring may be an imidazole group or a triazole group.
[0242] In one or more than one embodiment, CY 1 It may be a X-containing 1 A 5-membered ring, wherein at least one 6-membered ring containing X is fused 1 The 5-membered ring may be a benzimidazole group or a pyrimidopyridine group.
[0243] In one or more than one embodiment, CY 1 It may be an imidazole group, a triazole group, a benzimidazole group, a naphthimidazole group or an imidazopyridine group.
[0244] In one or more than one embodiments, X 1 Can be C, and ring CY 1 It may be an imidazole group, a triazole group, a benzimidazole group, a naphthimidazole group or an imidazopyridine group.
[0245] In one or more than one embodiment, CY 2 CY 3 and CY 4The benzophenone group, the benzofluorene group, the benzothiophene group, the benzofuran group, the benzothiophene group, the benzocarbazole ... A group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group or an azadinaphthosilole group.
[0246] In one or more than one embodiment, CY 2 It may be a benzene group, a pyridine group, a pyrimidine group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group or a dibenzosilole group.
[0247] In one or more than one embodiment, CY 3 It may be a benzene group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group or an azadinaphthosilole group.
[0248] In one or more than one embodiment, CY 3 It may be a carbazole group, a benzocarbazole group, a dibenzocarbazole group, an azacarbazole group, an azabenzocarbazole group or an azadibenzocarbazole group.
[0249] In one or more than one embodiment, CY 4 It may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group or an isoquinoline group.
[0250] X in Formula 1 51 Can be a single bond, *-N(Z51a )-*'、*-B(Z 51a )-*'、*-P(Z 51a )-*'、*-C(Z 51a )(Z 51b )-*'、*-Si(Z 51a )(Z 51b )-*'、*-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(Z 51a )=*'、*=C(Z 51a )-*'、*-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*'. 51a and Z 51b Each as described herein. 51a and Z 51b may be optionally bonded together to form an unsubstituted or substituted group with at least one R 10a Substituted C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0251] For example, X 51 Can be *-N(Z 51a )-*'、*-B(Z 51a )-*'、*-P(Z 51a )-*'、*-C(Z 51a )(Z 51b )-*'、*-Si(Z 51a )(Z 51b )-*'、*-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*' or *-O-*'.
[0252] X in Formula 1 52 Can be a single bond, *-N(Z 52a )-*'、*-B(Z 52a )-*'、*-P(Z 52a )-*'、*-C(Z 52a )(Z 52b )-*'、*-Si(Z 52a )(Z52b )-*'、*-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(Z 52a )=*'、*=C(Z 52a )-*'、*-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*'. 52a and Z 52b Each as described herein. 52a and Z 52b may be optionally bonded together to form an unsubstituted or substituted group with at least one R 10a Substituted C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0253] X in Formula 1 52 Can be a single bond, *-N(Z 52a )-*'、*-B(Z 52a )-*'、*-P(Z 52a )-*'、*-C(Z 52a )(Z 52b )-*'、*-Si(Z 52a )(Z 52b )-*'、*-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*' or *-O-*'. * and *' each represent a binding site with an adjacent atom. R 10a Can be the same as described herein.
[0254] In one or more than one embodiment, in Formula 1,
[0255] i)X 52 can be a single bond, and in Formula 1 is represented by The group represented by may be a group represented by the formula CY3A or the formula CY3B,
[0256] ii)X 52 may not be a single bond, and in Formula 1 is represented by The group represented by may be a group represented by the formula CY3C, or
[0257] iii)X52 Can be *-N(R 52a )-*', and R 52a and R 3 may be bonded together to form an unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups:
[0258]
[0259] Among them, in Formula CY3A to Formula CY3C,
[0260] X 3 and X 31 To X 33 can each independently be C or N,
[0261] Cyclo 31 CY 32 and CY 33 Each is C 2 -C 8 Monocyclic groups,
[0262] X 31 With X 3 The key between 3 With X 32 The key between and X 32 With X 33 The bonds between them can each be chemical bonds,
[0263] "*" indicates the same as X 51 The binding site
[0264] * represents the binding site with M in Formula 1, and
[0265] *' indicates that 52 The binding site of R 10a Can be the same as described herein.
[0266] In one or more than one embodiment, in Formula CY3A and Formula CY3B, X 31 , X 3 and X 32 can each be C, and X 33 It can be N.
[0267] In one or more than one embodiment, X in formula CY3C 31 , X 3 and X 32They can each be C.
[0268] In Formula 1 and Formula 1A, R 1 To R 4 , Z 51a , Z 51b , Z 52a , Z 52b and T 1 To T 4 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroarylalkyl group, -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)(Q1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each is as described herein. 10a Can be the same as described herein.
[0269] In one or more than one embodiment, R in Formula 1 and Formula 1A 1 To R 4 , Z 51a , Z 51b , Z 52a , Z 52b and T 1 To T 4 Can be independently:
[0270] hydrogen, deuterium, -F or a cyano group;
[0271] unsubstituted or deuterated, -F, cyano group, phenyl group, deuterated phenyl group, fluorophenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C 1 -C 20 C substituted with an alkyl) biphenyl group or a (for example, any) combination thereof 1 -C 20 an alkyl group; or
[0272] Each is unsubstituted or substituted with deuterium, -F, cyano group, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, phenyl group, deuterated phenyl group, fluorophenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C 1 -C 20 C substituted with an alkyl) biphenyl group or a (for example, any) combination thereof 3 -C 10 a cycloalkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group or a dibenzothienyl group.
[0273] In one or more than one embodiment, R in Formula 1 4 It can be:
[0274] hydrogen, deuterium, -F or a cyano group; or
[0275] unsubstituted or deuterated, -F, cyano group, phenyl group, deuterated phenyl group, fluorophenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C 1 -C 20 C substituted with an alkyl) biphenyl group or a (for example, any) combination thereof 1 -C 20 Alkyl group.
[0276] In one or more than one embodiment, R in Formula 1 4 It can be:
[0277] hydrogen, deuterium, -F or a cyano group; or
[0278] C unsubstituted or substituted with deuterium, -F, cyano group or (for example, any) combination thereof 1 -C 20 Alkyl group.
[0279] In one or more than one embodiment, T in Formula 1A 1 To T 4 Can be independently:
[0280] hydrogen, deuterium, -F or a cyano group; or
[0281] C unsubstituted or substituted with deuterium, -F, cyano group or (for example, any) combination thereof 1 -C 20 Alkyl group.
[0282] As used herein, "C 1 -C 60 "alkyl group" and "C 1 -C 20 The “alkyl group” may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group or a tert-decyl group, each of which is unsubstituted or substituted with at least one deuterium.
[0283] In one or more than one embodiment, "C 1 -C 60 "alkyl group" and "C 1 -C 20 An "alkyl group" may 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:
[0284]
[0285] In Formulae X-1 to X-30, * represents a binding site with an adjacent atom.
[0286] As used herein, "deuterated C 1 -C 60 alkyl group", "C substituted by (at least one) deuterium 1 -C 60 Alkyl group", "deuterated C 1 -C 20 "alkyl group" or "C 1 -C 20 "Alkyl group" may refer to a straight or branched C 1 -C 60 Alkyl group (either straight chain or branched C 1 -C 20The group may be a group represented by an alkyl group) and may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each of which is substituted with 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 Formulas X-2 to X-6, X-8 to X-10, X-12 to X-22, and X-23 to X-30 (for example, a group selected from one of Formulas X-2 to X-6, X-8 to X-10, X-12 to X-22, and X-23 to X-30).
[0287] a1, a2, a3, a4, c1, c2, c3 and c4 in Formula 1 and Formula 1A represent R 1 , R 2 , R 3 , R 4 、T 1 、T 2 、T 3 and T 4 wherein a1 to a4 may each independently be an integer from 0 to 10 (e.g., an integer from 0 to 6), c1 may be an integer from 1 to 3, c2 and c4 may each independently be an integer from 1 to 5, and c3 may be an integer from 1 to 4. When a1 is 2 or more, two or more R1 may be the same as or different from each other. When a2 is 2 or greater than 2, two or more R 2 may be the same as or different from each other. When a3 is 2 or greater than 2, two or more R 3 may be the same as or different from each other. When a4 is 2 or greater than 2, two or more R 4 can be the same as or different from each other. When c1 is 2 or greater than 2, two or more T 1 can be the same as or different from each other. When c2 is 2 or greater than 2, two or more T 2 can be the same as or different from each other. When c3 is 2 or greater than 2, two or more T 3 may be the same as or different from each other, and when c4 is 2 or greater than 2, two or more T 4 May be the same as or different from each other.
[0288] In one or more than one embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions A1 to A4 (eg, at least one selected from Conditions A1 to A4):
[0289] Condition A1
[0290] a1 is not 0, and R 1 It is not hydrogen;
[0291] Condition A2
[0292] a2 is not 0, and R 2 It is not hydrogen;
[0293] Condition A3
[0294] a3 is not 0, and R 3 is not hydrogen; and
[0295] Condition A4
[0296] a4 is not 0, and R 4 Not hydrogen.
[0297] In one or more than one embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
[0298] In one or more than one embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions B1 to B4 (eg, at least one selected from Conditions B1 to B4):
[0299] Condition B1
[0300] a1 is not 0, and at least one R 1 is deuterium or a deuterium-containing group;
[0301] Condition B2
[0302] a2 is not 0, and at least one R 2 is deuterium or a deuterium-containing group;
[0303] Condition B3
[0304] a3 is not 0, and at least one R 3 is deuterium or a deuterium-containing group; and
[0305] Condition B4
[0306] a4 is not 0, and at least one R 4 It is deuterium or a deuterium-containing group.
[0307] As used herein, a "deuterium-containing group" refers to a (eg, any) group containing at least one deuterium, and may be further substituted with a substituent other than deuterium. For example, a deuterium-containing group may be a C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, phenyl group, fluorophenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, fluorobiphenyl group, (C 1 -C 20 Alkyl) biphenyl group, C 3 -C 10 A cycloalkyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group (e.g., -CH 2 D. -CHD 2 、-CD 3 , -C 6 D 5 wait).
[0308] In Formula 1A, The groups represented by The groups represented by may be different from each other. In other words, the group represented by Formula 1A has an asymmetric structure.
[0309] In one or more than one embodiments, Formula 1A may satisfy one of Conditions C1 to C3 (eg, selected from one of Conditions C1 to C3):
[0310] Condition C1
[0311] T 1 is hydrogen or deuterium;
[0312] Condition C2
[0313] T 1 One of them is:
[0314] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0315] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0316] (e.g., any) remaining T 1 is hydrogen or deuterium; and
[0317] Condition C3
[0318] T 1 The two of them can be independently:
[0319] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0320] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0321] (e.g., any) remaining T 1 It is hydrogen or deuterium.
[0322] In one or more than one embodiments, Formula 1A may satisfy one of Conditions D1 to D4 (eg, selected from one of Conditions D1 to D4):
[0323] Condition D1
[0324] T 2 is hydrogen or deuterium;
[0325] Condition D2
[0326] T 2 One of them is:
[0327] C unsubstituted or substituted with at least one deuterium 1 -C 20an alkyl group; or
[0328] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0329] (e.g., any) remaining T 2 is hydrogen or deuterium;
[0330] Condition D3
[0331] T 2 The two of them can be independently:
[0332] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0333] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0334] (e.g., any) remaining T 2 is hydrogen or deuterium; and
[0335] Condition D4
[0336] T 2 The three of them can each independently be:
[0337] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0338] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0339] (e.g., any) remaining T 2 It is hydrogen or deuterium.
[0340] In one or more than one embodiments, Formula 1A may satisfy one of Conditions E1 to E3 (eg, selected from one of Conditions E1 to E3):
[0341] Condition E1
[0342] T 3 is hydrogen or deuterium;
[0343] Condition E2
[0344] T 3 One of them is:
[0345] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0346] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0347] (e.g., any) remaining T 3 is hydrogen or deuterium; and
[0348] Condition E3
[0349] T 3 The two of them can be independently:
[0350] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0351] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0352] (e.g., any) remaining T 3 It is hydrogen or deuterium.
[0353] In one or more than one embodiments, Formula 1A may satisfy one of Conditions F1 to F4 (eg, selected from one of Conditions F1 to F4):
[0354] Condition F1
[0355] T 4 is hydrogen or deuterium;
[0356] Condition F2
[0357] T 4 One of them is:
[0358] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0359] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0360] (e.g., any) remaining T 4 is hydrogen or deuterium;
[0361] Condition F3
[0362] T 4 The two of them can be independently:
[0363] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0364] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0365] (e.g., any) remaining T 4 is hydrogen or deuterium; and
[0366] Condition F4
[0367] T 4 The three of them can each independently be:
[0368] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0369] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0370] (e.g., any) remaining T 4 It is hydrogen or deuterium.
[0371] In one or more than one embodiments, Formula 1A may satisfy one selected from Conditions C1 to C3, one selected from Conditions D1 to D4, one selected from Conditions E1 to E3, one selected from Conditions F1 to F4, or (e.g., any) combination thereof.
[0372] In one or more than one embodiment, when in Formula 1A T 1 、T 3 and T 4 are each hydrogen, c2 is 1, and T 2 When it is a tert-butyl group, Formula 1 satisfies Condition G1:
[0373] Condition G1
[0374] R 4 yes:
[0375] hydrogen, deuterium, -F or a cyano group; or
[0376] C unsubstituted or substituted with deuterium, -F, cyano group or (for example, any) combination thereof 1 -C 20 Alkyl group.
[0377] In one or more than one embodiment, in Formula 1A, The groups represented can be:
[0378] i) one of the groups represented by formula A1-1 to A1-8; or
[0379] ii) one of the groups represented by formula A1-1 to formula A1-8 in which at least one hydrogen is replaced by deuterium:
[0380]
[0381] Among them, in Formula A1-1 to Formula A1-8,
[0382] T 11 To T 13 Can be independently:
[0383] C unsubstituted or substituted with at least one deuterium 1 -C 20an alkyl group; or
[0384] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (e.g., a phenyl group),
[0385] *' represents the same as in Formula 1A represents the binding site of the group, and
[0386] *" indicates the same as in Formula 1A Represents the binding site of the group.
[0387] In one or more than one embodiment, in Formula 1A, The groups represented can be:
[0388] i) one of the groups represented by formula A2-1 to formula A2-14; or
[0389] ii) one of the groups represented by formula A2-1 to formula A2-14 in which at least one hydrogen is replaced by deuterium:
[0390]
[0391] Among them, in Formula A2-1 to Formula A2-14,
[0392] T 21 To T 25 Can be independently:
[0393] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0394] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0395] *' represents the same as in Formula 1A Represents the binding site of the group.
[0396] In one or more than one embodiment, in Formula 1A, The groups represented can be:
[0397] i) one of the groups represented by formula A3-1 to A3-6; or
[0398] ii) one of the groups represented by formula A3-1 to formula A3-6 in which at least one hydrogen is replaced by deuterium:
[0399]
[0400] Among them, in Formula A3-1 to Formula A3-6,
[0401] T 31 To T 34 Can be independently:
[0402] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0403] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (e.g., a phenyl group),
[0404] *" indicates the same as in Formula 1A represents the binding site of the group, and
[0405] In formula 1A, Represents the binding site of the group.
[0406] Formula A3-3 and Formula A3-7 same.
[0407] In one or more than one embodiment, in Formula 1A, The groups represented can be:
[0408] i) one of the groups represented by formula A4-1 to formula A4-14; or
[0409] ii) one of the groups represented by formula A4-1 to formula A4-14 in which at least one hydrogen is replaced by deuterium:
[0410]
[0411] Among them, in Formula A4-1 to Formula A4-14,
[0412] T 41 To T 45 Can be independently:
[0413] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0414] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0415] In formula 1A, Represents the binding site of the group.
[0416] In one or more than one embodiment, Ar 1 (or a group represented by Formula 1A) may be unsubstituted or substituted with at least one deuterium. 4 -C 10 Alkyl (e.g., an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each of which is unsubstituted or substituted with at least one deuterium, or in one or more than one embodiments, a group represented by one of Formulas X-7 to X-30), and included in Ar 1 unsubstituted or substituted with at least one deuterium in 4 -C 10 The number of the alkyl groups may be 2 or more (eg, 2 to 15).
[0417] In one or more than one embodiment, Ar in Formula 1 1 It can be:
[0418] i) one of the groups represented by Formula TP-1 to Formula TP-228 (eg, one selected from the groups represented by Formula TP-1 to Formula TP-228); or
[0419] ii) one of the groups represented by Formula TP-1 to Formula TP-228 in which at least one hydrogen is replaced by deuterium (for example, one selected from the groups represented by Formula TP-1 to Formula TP-228):
[0420]
[0421]
[0422]
[0423]
[0424]
[0425]
[0426]
[0427]
[0428]
[0429]
[0430] Among them, in Formula TP-1 to Formula TP-228,
[0431] T 11 To T 13 、T 21 To T 24 、T 31 To T 33 and T 41 To T 45 Can be independently:
[0432] C unsubstituted or substituted with at least one deuterium 1 -C 20 an alkyl group; or
[0433] Unsubstituted or deuterated, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 C substituted with an alkyl group or (for example, any) combination thereof 6 -C 20 an aryl group (eg, a phenyl group), and
[0434] *' represents the ring CY in formula 1 1 binding site.
[0435] The expression "one of the groups represented by formula X in which at least one hydrogen is substituted with deuterium" refers to a group in which at least one of "all" hydrogens present in formula X is substituted with deuterium.
[0436] For example, examples of the “group represented by the formula TP-51 in which at least one hydrogen is substituted with deuterium” may include (for example, represented by the formula TP-51(1) to the formula TP-51(6)):
[0437]
[0438] wherein R is selected from Formula 1 and Formula 1A 1 , R 2 , R 3 , R 4 , Z 51a , Z 51b , Z 52a , Z 52b 、T 1 、T 2 、T 3 and T 4 Two or more of the 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. 10a Can be the same as described herein.
[0439] Unless otherwise stated, "*" as used herein indicates a binding site to an adjacent atom.
[0440] In one or more than one embodiments, the organometallic compound represented by Formula 1 may be an organometallic compound represented by Formula 1-1 or an organometallic compound represented by Formula 1-2:
[0441] Formula 1-1
[0442]
[0443] Formula 1-2
[0444]
[0445] M, X 1 To X 4 , X 51 、T 1 To T 4 and c1 to c4 are each as described herein,
[0446] X 11 It can be C(R 11 ) or N, X 12 It can be C(R 12 ) or N, X 13 It can be C(R 13 ) or N, and X 14 It can be C(R 14 ) or N,
[0447] R 11 To R 14 Each as about R 1 Description, and R 11 To R 14 Two or more of the 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 groups,
[0448] X 21 It can be C(R 21 ) or N, X 22 It can be C(R 22 ) or N, and X 23 It can be C(R 23 ) or N,
[0449] R 21 To R 23 Each as about R 2 Description, and R 21 To R 23 Two or more of the R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Heterocyclic groups,
[0450] X 31 It can be C(R 31 ) or N, X 32 It can be C(R 32 ) or N, X 33 It can be C(R 33 ) or N, X 34 It can be C(R 34 ) or N, X 35It can be C(R 35 ) or N, and X 36 It can be C(R 36 ) or N,
[0451] R 31 To R 36 Each as about R 3 Description, and R 31 To R 36 Two or more of the R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Heterocyclic groups,
[0452] X 41 It can be C(R 41 ) or N, X 42 It can be C(R 42 ) or N, X 43 It can be C(R 43 ) or N, and X 44 It can be C(R 44 ) or N,
[0453] R 41 To R 44 Each as about R 4 Description, and R 41 To R 44 Two or more of the R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Heterocyclic groups,
[0454] Depend on The groups represented by The groups represented may be different from each other, and
[0455] * indicates the binding site with the adjacent atom. 10a Can be the same as described herein.
[0456] The description of Formula 1 can be applied to Formula 1-1 and Formula 1-2.
[0457] Ar 1 The description of and the description of Formula 1A can be applied to Formula 1-1 and Formula 1-2 where Represents the group.
[0458] In one or more than one embodiment, X in Formula 1-1 and 1-2 is 43 It can be C(R 43 ), where R 43 It can be:
[0459] hydrogen, deuterium, -F or a cyano group; or
[0460] C unsubstituted or substituted with deuterium, -F, cyano group or (for example, any) combination thereof 1 -C 20 Alkyl group.
[0461] In one or more than one embodiment, when T in Formula 1-1 and Formula 1-2 1 、T 3 and T 4 are each hydrogen, c2 is 1, and T 2 When it is a tert-butyl group, Formula 1-1 and Formula 1-2 satisfy Condition G2:
[0462] Condition G2
[0463] X 43 is C(R 43 ),
[0464] Where R 43 yes:
[0465] hydrogen, deuterium, -F or a cyano group; or
[0466] C unsubstituted or substituted with deuterium, -F, cyano group or (for example, any) combination thereof 1 -C 20 Alkyl group.
[0467] In one or more than one embodiment, in Formula 1-1 and Formula 1-2, X 11 It can be C(R 11 ), X 12 It can be C(R 12 ), X 13 It can be C(R 13 ), X 14 It can be C(R 14 ), X 21 It can be C(R 21 ), X 22 It can be C(R 22 ), X 23 It can be C(R 23 ), X 31 It can be C(R 31 ), X32 It can be C(R 32 ), X 33 It can be C(R 33 ), X 34 It can be C(R 34 ), X 35 It can be C(R 35 ), X 36 It can be C(R 36 ), X 41 It can be C(R 41 ), X 42 It can be C(R 42 ), and X 43 It can be C(R 43 ), R 11 To R 14 , R 21 To R 23 , R 31 To R 36 and R 41 To R 43 can be the same as described herein, and
[0468] Each of Formula 1-1 and Formula 1-2 may satisfy at least one selected from Conditions H1 to H4:
[0469] Condition H1
[0470] R in Formula 1-1 11 To R 14 At least one of is deuterium or a deuterium-containing group, and R in Formula 1-2 11 and R 12 At least one of is deuterium or a deuterium-containing group;
[0471] Condition H2
[0472] R 21 To R 23 At least one of is deuterium or a deuterium-containing group;
[0473] Condition H3
[0474] R 31 To R 36 At least one of is deuterium or a deuterium-containing group; and
[0475] Condition H4
[0476] R 41 To R 44 At least one of the is deuterium or a deuterium-containing group.
[0477] In one or more than one embodiment, the The group represented may be a group represented by one of the formulas CY1-1 to CY1-42:
[0478]
[0479] Among them, in Formula CY1-1 to Formula CY1-42,
[0480] X 1 As described in this article,
[0481] Y 1 may contain O, S, N, C or Si,
[0482] * represents the binding site with M in Formula 1, and
[0483] *' represents the binding site to the nitrogen atom in Formula 1.
[0484] In one or more than one embodiment, X in Formula CY1-1 to Formula CY1-8 is 1 may be C, and X in formula CY1-9 to CY1-42 is 1 It can be N.
[0485] In one or more than one embodiment, the The group represented may be a group represented by one of the formulas CY2-1 to CY2-11:
[0486]
[0487] Among them, in Formula CY2-1 to Formula CY2-11,
[0488] X 2 As described in this article,
[0489] Y 2 may contain O, S, N, C or Si,
[0490] * represents the binding site with M in Formula 1,
[0491] *' represents the ring CY in formula 1 1 binding sites, and
[0492] *" indicates the same as X in Formula 1 51 binding site.
[0493] In one or more than one embodiment, in Formula 1, The groups represented by and in Formula 1-1 and Formula 1-2 are represented by The groups represented may each independently be a group represented by one of the formulas CY2(1) to CY2(26):
[0494]
[0495] Among them, in formula CY2(1) to formula CY2(26),
[0496] X 2 As described in this article,
[0497] X 21 Can be O, S, N (R 20 )、C(R 20a )(R 20b ) or Si(R 20a )(R 20b ),
[0498] R 20 , R 20a , R 20b and R 21 To R 23 Each as about R 2 Description, and R 21 To R 23 Each of them may not be hydrogen,
[0499] * represents the binding site with M in Formula 1,
[0500] *' represents the ring CY in formula 1 1 binding sites, and
[0501] *" indicates the same as X in Formula 1 51 binding site.
[0502] In one or more than one embodiment, the The group represented may be a group represented by one of the formulas CY3-1 to CY3-23:
[0503]
[0504] Among them, in Formula CY3-1 to Formula CY3-23,
[0505] X 3 As described in this article,
[0506] Y 3 may contain O, S, N, C or Si,
[0507] * represents the binding site with M in Formula 1,
[0508] *' represents the X in formula 1 52 binding sites, and
[0509] *" indicates the same as X in Formula 1 51 binding site.
[0510] In one or more than one embodiment, in Formula 1, The group represented by may be a group represented by one of the formulas CY3(1) to CY3(20), and in formulas 1-1 and 1-2, The group represented by may be a group represented by one of the formulas CY3(1) to CY3(12):
[0511]
[0512]
[0513] Among them, in formula CY3(1) to formula CY3(20),
[0514] X 3 As described in this article,
[0515] R 31 To R 36 Each as about R 3 Description, where R 31 To R 36 Each of them may not be hydrogen,
[0516] * represents the binding site with M in Formula 1,
[0517] *' represents the X in formula 1 52 binding sites, and
[0518] *" indicates the same as X in Formula 1 51 binding site.
[0519] In one or more than one embodiment, the The group represented may be a group represented by one of formula CY4(1) to formula CY4(16):
[0520]
[0521] Among them, in formula CY4(1) to formula CY4(16),
[0522] X 4 As described in this article,
[0523] R 41 To R 44 Each as about R 4 Description, and R 41 To R 44 may each be other than hydrogen, * represents a binding site with M in Formula 1, and
[0524] *' represents the X in formula 1 52binding site.
[0525] Ar in Formula 1 1 It may be a group represented by Formula 1A:
[0526] Formula 1A
[0527]
[0528] Wherein, Formula 1A comprises a "phenyl group 4" bonded to the para position in "phenyl group 3" relative to the carbon bonded to "phenyl group 1". In some embodiments, in Formula 1A, The groups represented by The groups represented by may be different from each other. In other words, Formula 1A has an asymmetric structure with respect to the symmetry axis.
[0529] Therefore, 1) the intramolecular movement of Formula 1A is suppressed or reduced and the Stoke shift is reduced, thereby increasing the PLQY of the organometallic compound represented by Formula 1, 2) during the formation of a film containing the organometallic compound, the intramolecular stacking effect is reduced, thereby reducing the sublimation temperature and the deposition temperature, and 3) the interference between other substituents in the molecule of the organometallic compound is minimized or reduced by "phenyl group 3" and "phenyl group 4". Therefore, the non-radiative decay rate (Knr) and Dexter energy transfer of the light-emitting device containing the organometallic compound represented by Formula 1 are reduced, and therefore, the luminous efficiency and / or service life of the light-emitting device can be improved.
[0530] In one or more than one embodiment, Formula 1A may further comprise at least one unsubstituted or deuterated C 1 -C 20 Therefore, the asymmetry and volume of Formula 1A may be increased, and thus, the luminous efficiency and / or lifetime of a light-emitting device including the organometallic compound may be further improved.
[0531] In one or more than one embodiment, b51 to b53 in Formula 2 represent L 51 Quantity to L 53 When b51 is 2 or more, two or more L 51 can be the same or different from each other. When b52 is 2 or greater than 2, 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 53 In one or more than one embodiment, b51 to b53 may each independently be 1 or 2.
[0532] L in Formula 251 To L 53 Can be independently:
[0533] a single key; or
[0534] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazine group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzosilyl group, a dimethyldibenzosilyl group, a diphenyldibenzosilyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or (for example, any) combination thereof substituted with a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzothioole group, a dibenzothioole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothioole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group a divalent group selected from the group consisting of a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasilinyl group, a dibenzothiasilinyl group, a dibenzodihydroazasilinyl group, a dibenzodihydrodisilinyl group, a dibenzodihydrosilinyl group, a dibenzodioxane group, a dibenzooxathiasilinyl group, a dibenzoxazine group, a dibenzopyran group, a dibenzodithiainyl group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group or a dibenzodihydropyrazine group, and
[0535] Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0536] In one or more than one embodiment, in Formula 2, L 51 With R 51 The key between 52 With R 52 The key between 53 With 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 253 With X 55 and X 56 The bonds between the carbon atoms in the carbon atoms may each be a "carbon-carbon single bond".
[0537] In formula 2, 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. R 54 To R 56 Each is as described herein. In one or more than one embodiment, X 54 To X 56 Two or three of them can be N.
[0538] As used in this paper, 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 each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C60 Alkoxy groups, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroarylalkyl group, -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 is as described herein. 10a Can be the same as described herein.
[0539] For example, i) R in Formula 1 1 To R 4 , Z 51a , Z 51b , Z 52a , Z 52b and T 1 To T 4 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 and 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 , and iii) R 10a Can be independently:
[0540] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0541] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or (for example, any) combination thereof 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0542] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C 1 -C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or (for example, any) combination thereof substituted with a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C 1 -C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine 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 azadibenzosilyl group, or a group represented by Formula 91; or
[0543] -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 ),as well as
[0544] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0545] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0546] Each is unsubstituted or replaced by deuterium, C 1 -C 10 An n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, pyridyl group, pyrimidyl group, pyridazinyl group, pyrazinyl group or triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group, for example, in any combination thereof:
[0547] Formula 91
[0548]
[0549] Among them, in formula 91,
[0550] 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 groups,
[0551] 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 ), R 91 , R 91a and R 91b Each of them is as follows 82 , R 82a and R 82b describe,
[0552] R 10a As described herein, and
[0553] * indicates the binding site with the adjacent atom.
[0554] For example, in Equation 91,
[0555] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a a substituted phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group or a triazine group,
[0556] R 91 , R 91a and R 91b Can be independently:
[0557] Hydrogen or C 1 -C 10 an alkyl group; or
[0558] Each is unsubstituted or replaced by deuterium, C 1 -C 10 A phenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, or (e.g., any) combination thereof.
[0559] In one or more than one embodiment, i) R in Formula 1 1 To R 4 , Z 51a , Z 51b , Z 52a , Z 52b and T 1 To T 4 ,ii)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 and 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 R508b , and iii) R 10a can each independently be hydrogen, deuterium, -F, a cyano group, a nitro group, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a group represented by one of Formula 9-1 to Formula 9-19, a group represented by one of Formula 10-1 to Formula 10-246, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -P(=O)(Q 1 )(Q 2 )(Q 1 To Q 3 each as described herein):
[0560]
[0561]
[0562]
[0563]
[0564]
[0565]
[0566]
[0567] Wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-246, * represents a binding site with an adjacent atom, "D" represents a deuterium atom, "Ph" represents a phenyl group, and "TMS" represents a trimethylsilyl group.
[0568] In Formulas 3-1 to 3-5, Formula 502, and Formula 503, a71 to a74 and a501 to a504 represent R 71 To R 74 The number and R 501 To R 504 and may be independently an integer from 0 to 20. When a71 is 2 or greater, two or more R 71can be the same as or different from each other. When a72 is 2 or greater than 2, two or more R 72 can be the same as or different from each other. When a73 is 2 or greater than 2, two or more R 73 can be the same or different from each other. When a74 is 2 or greater than 2, two or more R 74 can be the same as or different from each other. When a501 is 2 or greater than 2, two or more R 501 can be the same as or different from each other. When a502 is 2 or greater than 2, two or more R 502 can be the same or different from each other. When a503 is 2 or greater than 2, 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 of 0 to 8.
[0569] In formula 2, *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 Each of the groups represented may be other than a phenyl group.
[0570] In one or more than one embodiment, the *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented may be the same as each other.
[0571] In one or more than one embodiment, the *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented may be different from each other.
[0572] In one or more than one embodiment, 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 A substituted phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group. 10aCan be the same as described herein.
[0573] In one or more than one embodiment, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ), R 10a can be the same as described herein, and
[0574] Q 1 To Q 3 may be each independently unsubstituted or substituted with deuterium, -F, a cyano group, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group or (for example, any) combination thereof 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0575] In one or more than one embodiments,
[0576] 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
[0577] 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
[0578] 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 )(Q 1 To Q 3 Can be the same as described in this article):
[0579]
[0580]
[0581]
[0582] 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,
[0583] 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 ),
[0584] 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 ),
[0585] 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 ), Y 68 Can be single bond, O, S, N(R 68 )、B(R 68 )、C(R 68a )(R 68b ) or Si(R68a )(R 68b ),
[0586] Y in formula CY51-16 and formula CY51-17 63 and Y 64 Each of may not be a single key at the same time (e.g., simultaneously),
[0587] Y in formula CY52-16 and formula CY52-17 67 and Y 68 Each of may not be a single key at the same time (e.g., simultaneously),
[0588] R 51a To R 51e , R 61 To R 64 , R 63a , R 63b , R 64a and R 64b Each as about R 51 Description, where R 51a To R 51e Each of them may not be hydrogen,
[0589] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b Each as about R 52 Description, where R 52a To R 52e Each of them may not be hydrogen,
[0590] R 53a To R 53e , R 69a and R 69b Each as about R 53 Description, and R 53a To R 53e may each be other than hydrogen, and
[0591] * indicates the binding site with the adjacent atom.
[0592] In one or more than one embodiments,
[0593] R in Formula CY51-1 to Formula CY51-26 and Formula CY52-1 to Formula CY52-26 51a To R 51e and R 52a To R 52e Can be independently:
[0594] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C 1 -C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiophenyl group, a benzoimidazole group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoindolyl ... substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C 1 -C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine 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 azadibenzosilyl group, or a group represented by Formula 91; or
[0595] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),as well as
[0596] Q 1 To Q 3 may be each independently unsubstituted or substituted with deuterium, C 1 -C 10 a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, or (for example, any) combination thereof,
[0597] In formula CY51-16 and formula CY51-17, i) Y 63 Can be O or S, and Y 64 It can be Si(R 64a )(R 64b ), or ii) Y 63 It can be Si(R 63a )(R 63b ), and Y 64 Can be O or S, and
[0598] In formula CY52-16 and formula CY52-17, i) Y 67 Can be O or S, and Y 68 It can be Si(R 68a )(R68b ), or ii) Y 67 It can be Si(R 67a )(R 67b ), and Y 68 Can be O or S.
[0599] In Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0600] a single key; or
[0601] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*', * and *' each represent a binding site with an adjacent atom; or
[0602] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazine group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzosilyl group, a dimethyldibenzosilyl group, a diphenyldibenzosilyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or (for example, any) combination thereof substituted with a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, group, cyclopentadiene group, furan group, thiophene group, silole group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzosilole group, dibenzosilole group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, pyridine group, pyrimidine group, pyrazine group a divalent group selected from the group consisting of a benzopyrazole group, a benzoimidazole group, a benzoxazole group, a benzothiazole group, a benzooxadiazole group, or a benzothiadiazole group; and
[0603] Q 4 , Q 5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0604] In one or more than one embodiment, the The group represented may be a group represented by one of the formulas CY71-1(1) to CY71-1(8), and / or
[0605] In formula 3-1 and formula 3-3, The group represented may be a group represented by one of the formulas CY71-2(1) to CY71-2(8), and / or
[0606] In formula 3-2 and formula 3-4, The group represented may be a group represented by one of the formulas CY71-3(1) to CY71-3(32), and / or
[0607] In formula 3-3 to formula 3-5, The group represented may be a group represented by one of the formulas CY71-4(1) to CY71-4(32), and / or
[0608] In formula 3-5, The group represented may be a group represented by one of the formulas CY71-5(1) to CY71-5(8):
[0609]
[0610]
[0611]
[0612]
[0613] 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),
[0614] X 81 To X 85 , L 81 ,b81,R 81 and R 85 Each as described herein,
[0615] 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 ), 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 ),
[0616] In Formula CY71-1(1) to Formula CY71-1(8) and Formula CY71-4(1) to Formula CY71-4(32), X 86 and X 87 Each of may not be a single bond at the same time,
[0617] 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 ), X 89 Can be single bond, O, S, N(R 89 )、B(R89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0618] In Formulas CY71-2(1) to CY71-2(8), Formulas CY71-3(1) to CY71-3(32), and Formulas CY71-5(1) to CY71-5(8), X 88 and X 89 Each of may not be a single bond at the same time, and
[0619] R 86 To R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b Each as about R 81 describe.
[0620] Examples of Compounds
[0621] In one or more than one embodiments, the organometallic compound represented by Formula 1 may be at least one of Compound 1 to Compound 344:
[0622]
[0623]
[0624]
[0625]
[0626]
[0627]
[0628]
[0629]
[0630]
[0631]
[0632]
[0633]
[0634]
[0635]
[0636]
[0637] In one or more than one embodiments, the second compound may be at least one of compounds ETH1 to ETH100:
[0638]
[0639]
[0640]
[0641]
[0642] In one or more than one embodiments, the third compound can be at least one of compound HTH1 to compound HTH46:
[0643]
[0644]
[0645] In one or more than one embodiments, the fourth compound can be at least one of compound DFD1 to compound DFD29 and compound DFD051:
[0646]
[0647]
[0648] In the previous compounds described herein, Ph represents a phenyl group, D 5 means substitution with five deuteriums, and D 4 means substitution with four deuterium. For example, The group represented by The groups represented are the same.
[0649] Figure 1 Description
[0650] Figure 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 intermediate layer 130 , and a second electrode 150 .
[0651] In the following, reference will be made to Figure 1The structure of the light emitting device 10 and the method of manufacturing the light emitting device 10 according to one or more embodiments are described.
[0652] First electrode 110
[0653] exist Figure 1 In the embodiment, the substrate may be additionally arranged under the first electrode 110 or on the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be used. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0654] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0655] The first electrode 110 may be a reflective electrode, a semi-transmissive reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In one or more than one embodiments, when the first electrode 110 is a semi-transmissive reflective 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.
[0656] 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. In one or more than one embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.
[0657] Middle layer 130
[0658] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0659] The intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 150 .
[0660] In addition to one or more than one suitable organic materials, the intermediate layer 130 may further include a metal-containing compound (eg, an organometallic compound), an inorganic material (eg, quantum dots), or the like.
[0661] In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between two adjacent emission units. When the intermediate layer 130 includes an emission unit and a charge generation layer as described herein, the light-emitting device 10 may be a tandem light-emitting device.
[0662] Hole transport region in the intermediate layer 130
[0663] The hole transport region may have: i) a single-layer structure including (e.g., consisting of): a single layer containing a single material (e.g., consisting of a single material), ii) a single-layer structure including (e.g., consisting of): a single layer containing multiple materials different from each other (e.g., consisting of multiple materials different from each other); or iii) a multi-layer structure including multiple layers containing multiple materials different from each other.
[0664] 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.
[0665] In one or more embodiments, the hole transport zone may have a multilayer structure, comprising a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the constituent layers of each structure are stacked in sequence from the first electrode 110.
[0666] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, and / or any combination thereof:
[0667] Formula 201
[0668]
[0669] Formula 202
[0670]
[0671] Among them, in equation 201 and equation 202,
[0672] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0673] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene group, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene group, unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic group, * and *' each represent a binding site with an adjacent atom,
[0674] xa1 to xa4 may each independently be an integer from 0 to 5,
[0675] xa5 can be an integer from 1 to 10,
[0676] 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 groups,
[0677] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted 10a Substituted C 8 -C 60Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16),
[0678] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted 10a Substituted C 8 -C 60 Polycyclic groups, and
[0679] na1 can be an integer from 1 to 4. 10a Can be the same as described herein.
[0680] In one or more than one embodiments, each of Formula 201 and Formula 202 may include at least one of the groups represented by Formula CY201 to Formula CY217:
[0681]
[0682] In formula CY201 to formula CY217, R 10b and R 10c Each as about R 10a Description, Cyclic Cy 201 To Ring CY 204 Can be C independently 3 -C 20 Carbocyclic group or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R as described herein 10a replace.
[0683] In one or more than one embodiment, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each may independently be a benzene group, a naphthyl group, a phenanthrene group or an anthracene group.
[0684] In one or more than one embodiments, each of Formula 201 and Formula 202 may include at least one of the groups represented by Formula CY201 to Formula CY203.
[0685] In one or more than one embodiments, Formula 201 may include at least one of the groups represented by Formula CY201 to Formula CY203 and at least one of the groups represented by Formula CY204 to Formula CY217.
[0686] In one or more than one embodiments, in Formula 201, xa1 may be 1, R 201 may be a group represented by one of the formulas CY201 to CY203, xa2 may be 0, and R 202 It may be a group represented by one of Formula CY204 to Formula CY207.
[0687] In one or more than one embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY203.
[0688] In one or more than one embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) one of the groups represented by Formula CY201 to Formula CY203, and may include at least one of the groups represented by Formula CY204 to Formula CY217.
[0689] In one or more than one embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) groups represented by Formula CY201 to Formula CY217.
[0690] In one or more than one embodiments, 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), and / or any combination thereof:
[0691]
[0692]
[0693]
[0694]
[0695]
[0696] 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 can be 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 the ranges described herein, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.
[0697] 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 material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0698] p-dopant
[0699] In addition to these materials, the hole transport region may further include a charge generating material for improving the conductive properties. The charge generating 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 generating material).
[0700] The charge generating material may be, for example, a p-dopant.
[0701] For example, the LUMO level of the p-dopant may be less than or equal to -3.5 eV.
[0702] In one or more than one embodiments, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound containing element EL1 and element EL2, or any combination thereof.
[0703] Examples of the quinone derivative may include TCNQ and / or F4-TCNQ.
[0704] Examples of the cyano group-containing compound may include HAT-CN and / or a compound represented by Formula 221.
[0705]
[0706] Formula 221
[0707]
[0708] In formula 221,
[0709] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a can be the same as described herein, and
[0710] R 221 To R 223 At least one of the following may be independently: each of which is substituted by a cyano group; -F; -Cl; -Br; -I; a C substituted by a cyano group, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 Alkyl group; or any combination thereof substituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0711] In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a nonmetal, a metalloid, or a combination thereof.
[0712] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt ( (e.g., tantalum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium, etc.).
[0713] Examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te).
[0714] Examples of non-metals may include oxygen (O) and / or halogens (eg, F, Cl, Br, I, etc.).
[0715] Examples of compounds containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), and metal tellurides or a combination of one or more thereof.
[0716] Examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.), and / or rhenium oxide (e.g., ReO 3 wait).
[0717] 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.
[0718] 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.
[0719] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2, CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 .
[0720] Examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, Ta Br3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, etc.), , ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr 2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), and / or gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).
[0721] Examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.), and / or tin halides (e.g., SnI 2 wait).
[0722] 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 、SmI 3 wait.
[0723] Examples of metalloid halides may include antimony halides (e.g., SbCl 5 wait).
[0724] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, 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, LuTe, etc.).
[0725] Emission layer in the middle layer 130
[0726] When the light-emitting device 10 is a full-color light-emitting device, the emission layer can 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.
[0727] In one or more embodiments, the emissive 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 emissive layer may further include an auxiliary dopant that facilitates energy transfer to the dopant (or emitter). When the emissive layer includes a dopant (or emitter) and an auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
[0728] The organometallic compound represented by Formula 1 may serve as a dopant (or emitter), or may serve as an auxiliary dopant.
[0729] The amount (weight) of the dopant (or emitter) in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0730] The emission layer may include an organic metal compound represented by Formula 1. The amount (weight) of the organic metal compound in the emission layer may be 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.
[0731] 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 the range, excellent or suitable light emission characteristics may be obtained without a significant increase in driving voltage.
[0732] main body
[0733] The host in the emissive layer may include the second compound or the third compound described herein, or any combination thereof.
[0734] In one or more embodiments, the host can include a compound represented by Formula 301.
[0735] Formula 301
[0736] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0737] In formula 301,
[0738] Ar 301 may be 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, L 301 may be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0739] xb11 can be 1, 2 or 3,
[0740] xb1 can be an integer from 0 to 5.
[0741] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q303 )、-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 ),
[0742] xb21 can be an integer from 1 to 5, and
[0743] Q 301 To Q 303 Each as about Q 1 Description. 10a Can be the same as described herein.
[0744] In one or more than one embodiment, when xb11 in Formula 301 is 2 or greater than 2, two or more Ar 301 can be connected to each other via a single bond.
[0745] In one or more than one embodiments, the host may comprise at least one compound represented by Formula 301-1, at least one compound represented by Formula 301-2, or any combination thereof:
[0746] Formula 301-1
[0747]
[0748] Formula 301-2
[0749]
[0750] Among them, in Formula 301-1 and Formula 301-2,
[0751] 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 groups,
[0752] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R305 ) or Si(R 304 )(R 305 ),
[0753] xb22 and xb23 can each independently be 0, 1 or 2,
[0754] L 301 , xb1, and R 301 Each as described herein,
[0755] L 302 To L 304 can be independently determined as 301 describe,
[0756] xb2 to xb4 may each independently be as described with respect to xb1, and
[0757] R 302 To R 305 and R 311 To R 314 Each and About R 301 Description. 10a Can be the same as described herein.
[0758] In one or more embodiments, the host may comprise an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In one or more embodiments, the host may comprise a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0759] In one or more than one 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), and / or any combination thereof:
[0760]
[0761]
[0762]
[0763]
[0764]
[0765]
[0766] In one or more than one embodiments, the host can include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0767] The subject may have one or more than one suitable modification. For example, the subject may include only one type of compound, or may include two or more than two types of different compounds.
[0768] Phosphorescent dopants
[0769] The emission layer may include the organometallic compound represented by Formula 1 as described herein as a phosphorescent dopant.
[0770] In one or more than one embodiments, when the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein acts as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0771] The phosphorescent dopant may include at least one transition metal as a central metal.
[0772] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or a (eg, any) combination thereof.
[0773] The phosphorescent dopant may be electrically neutral.
[0774] In one or more than one embodiments, the phosphorescent dopant may include at least one organometallic compound represented by Formula 401:
[0775] Formula 401
[0776] M(L 401 ) xc1 (L 402 ) xc2
[0777] Formula 402
[0778]
[0779] Among them, in equation 401 and equation 402,
[0780] 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)),
[0781] 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 can be the same or different from each other,
[0782] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater than 2, two or more L 402 can be the same or different from each other,
[0783] X 401 and X 402 may each independently be nitrogen or carbon,
[0784] Ring A 401 and Ring A 402 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0785] 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=*', * and *' each represent the binding site with the adjacent atom,
[0786] X 403 and X 404 can each independently be 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 ),
[0787] Q 411 To Q 414 Each as about Q 1 describe,
[0788] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R10a Substituted C 1 -C 20 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy groups, 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 ), R 10a can be the same as described in this article,
[0789] Q 401 To Q 403 Each as about Q 1 describe,
[0790] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0791] * and *' in Formula 402 may each represent a binding site with M in Formula 401.
[0792] In one or more than one embodiment, in Formula 402, i) X 401 can be nitrogen, and X 402 It can be carbon, or ii) X 401 and X 402 Each of can be nitrogen.
[0793] In one or more than one embodiment, when xc1 in Formula 401 is 2 or greater than 2, two or more than two selected from L 401 The two rings A 401 Optionally, the linkage group may be T 402 Connected to each other, or two rings A 402 Optionally, the linkage group may be T 403are connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Each as about T 401 describe.
[0794] L in Formula 401 402 Can be an organic ligand. In one or more than one embodiment, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, -CN, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0795] The phosphorescent dopant may include, for example, at least one of Compound PD1 to Compound PD25 or a (for example, any) combination thereof:
[0796]
[0797] Fluorescent dopants
[0798] When the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0799] In one or more than one embodiments, when the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein acts as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0800] The fluorescent dopant and the auxiliary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0801] In one or more than one embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
[0802] Formula 501
[0803]
[0804] Wherein, in Formula 501,
[0805] Ar 501 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 501 To L 503 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic group, R 10a can be the same as described in this article,
[0806] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0807] xd4 can be 1, 2, 3, 4, 5 or 6.
[0808] In one or more than one embodiment, Ar in Formula 501 501 It may be a fused cyclic group in which three or more monocyclic groups are fused together (for example, anthracene groups, group, pyrene group, etc.).
[0809] In one or more embodiments, xd4 in formula 501 can be 2.
[0810] In one or more than one embodiments, the fluorescent dopant and the auxiliary dopant may each include at least one of compounds FD1 to FD36, DPVBi, DPAVBi and / or any combination thereof:
[0811]
[0812]
[0813]
[0814] In one or more than one embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a fourth compound represented by Formula 502 or Formula 503 as described herein.
[0815] quantum dots
[0816] The emissive layer may comprise quantum dots.
[0817] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light at one or more than one suitable emission wavelength depending on the size of the crystal.
[0818] The diameter of the quantum dot can be, for example, about 1 nm to about 10 nm.
[0819] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0820] The wet chemical process is a method that includes mixing a precursor material with an organic solvent and then growing a quantum dot particle crystal. As the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal, so that the growth of the quantum dot particles can be controlled or selected by a lower cost and easier process than a vapor deposition method such as metal organic chemical vapor deposition (MOCVD) and / or molecular beam epitaxy (MBE).
[0821] Quantum dots may include one or more than one Group II-VI semiconductor compound; Group III-V semiconductor compound; Group III-VI semiconductor compound; Group I-III-VI semiconductor compound; Group IV-VI semiconductor compound; Group IV element or compound; or any combination thereof.
[0822] Examples of II-VI semiconductor compounds may include (e.g., may be): binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and / or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS , CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe; or any combination thereof.
[0823] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; or any combination thereof. In some embodiments, the III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include (eg, may be) InZnP, InGaZnP, InAlZnP, and the like.
[0824] Examples of III-VI semiconductor compounds may include (for example, may be): binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and / or InTe; ternary compounds such as InGaS 3 and / or InGaSe 3 ; and any combination thereof.
[0825] Examples of Group I-III-VI semiconductor compounds may include (for example, may be): ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and / or AgAlO 2 ; or any combination thereof.
[0826] Examples of IV-VI semiconductor compounds may include (for example, may be): binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and / or SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe and / or SnPbSTe; or any combination thereof.
[0827] The Group IV elements or compounds may include: single element materials, such as Si or Ge; binary compounds, such as SiC and / or SiGe; or any combination thereof.
[0828] Each element contained in the multi-element compound (eg, binary compound, ternary compound, and quaternary compound) may be present in the particle in a substantially uniform concentration or a substantially non-uniform concentration.
[0829] In some embodiments, the quantum dot may have a single structure, in which the concentration of each element in the quantum dot is substantially uniform, or a core-shell dual structure. For example, the material contained in the core and the material contained in the shell may be different from each other.
[0830] The shell of a quantum dot can act as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties and / or a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, where the concentration of the element present in the shell decreases toward the center of the core.
[0831] Examples of the shell of the quantum dot may be metal, metalloid or non-metal oxides, semiconductor compounds and any combination thereof. Examples of metal, metalloid or non-metal oxides may include (for example, may be) binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and / or NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe2 O 4 and / or CoMn 2 O 4 ; and any combination thereof. Examples of semiconductor compounds may include (e.g., may be) II-VI semiconductor compounds as described herein; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; and any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0832] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dots can be about 45 nm or less, such as about 40 nm or less, or about 30 nm or less, and within these ranges, color purity or color reproducibility can be increased. In some embodiments, because the light emitted by the quantum dots is emitted in all directions, the wide viewing angle can be improved.
[0833] In some embodiments, quantum dots can be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0834] Because the band gap can be adjusted by controlling the size of the quantum dots, light with one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths can be realized. In one or more embodiments, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In some embodiments, the size of the quantum dots can be configured to emit white light through a combination of one or more suitable colors of light.
[0835] Electron transport region in the intermediate layer 130
[0836] The electron transport region may have: i) a single-layer structure including (e.g., consisting of): a single layer containing (e.g., consisting of): a single material, ii) a single-layer structure including (e.g., consisting of): a single layer containing a plurality of different materials, or iii) a multi-layer structure including a plurality of layers containing a plurality of different materials.
[0837] 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.
[0838] In one or more than one embodiments, 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 constituent layers of each structure are stacked in a prescribed order from the emission layer.
[0839] 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 at least one π-electron-deficient nitrogen-containing C 1 -C 60 Metal-free compounds of heterocyclic groups.
[0840] In one or more than one embodiments, the electron transport region can include a compound represented by Formula 601.
[0841] Formula 601
[0842] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0843] In formula 601,
[0844] Ar 601 may be 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, L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0845] xe11 can be 1, 2 or 3,
[0846] xe1 can be 0, 1, 2, 3, 4, or 5,
[0847] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60Carbocyclic 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 ),
[0848] Q 601 To Q 603 Each as about Q 1 describe,
[0849] xe21 can be 1, 2, 3, 4, or 5, and
[0850] At least one of the following conditions can be met: 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group; R 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 a heterocyclic group; and L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group.
[0851] In one or more than one embodiment, when xe11 in Formula 601 is 2 or greater than 2, two or more Ar 601 Can be connected together via a single bond.
[0852] In one or more than one embodiment, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracene group. 10a Can be the same as described herein.
[0853] In one or more than one embodiments, the electron transport region may comprise a compound represented by Formula 601-1:
[0854] Formula 601-1
[0855]
[0856] Among them, in formula 601-1,
[0857] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and X 614 To X 616 At least one of may be N,
[0858] L 611 To L 613 Each as about L 601 Description,
[0859] xe611 to xe613 are each as described with respect to xe1,
[0860] R 611 To R 613 Each as about R 601 Description, and
[0861] R 614 To R 616 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group. 10a Can be the same as described herein.
[0862] In one or more than one embodiments, xe1 in formula 601 and xe611 to xe613 in formula 601-1 can each independently be 0, 1 or 2.
[0863] The electron transport region may include a compound 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 and / or any combination thereof:
[0864]
[0865]
[0866]
[0867]
[0868] The thickness of the electron transport region may 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 each independently about to about For example, about to about And the thickness of the electron transport layer can be 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 may be obtained without a significant increase in driving voltage.
[0869] In addition to the materials described herein, the electron transport region (eg, an electron transport layer in the electron transport region) can further include a metal-containing material.
[0870] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may include at least one and / or any combination thereof selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene.
[0871] In one or more than one embodiment, 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:
[0872]
[0873] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
[0874] The electron injection layer may have: i) a single-layer structure that includes (e.g., consists of): a single layer containing a single material (e.g., consisting of a single material), ii) a single-layer structure that includes (e.g., consists of): a single layer containing multiple different materials, or iii) a multi-layer structure that includes multiple layers containing multiple different materials.
[0875] The electron injection layer may contain an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0876] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0877] The compounds containing an alkali metal, the compounds containing an alkaline earth metal, and the compounds containing a rare earth metal may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, and / or any combination thereof.
[0878] The compound containing an alkali metal may include an alkali metal oxide, such as Li 2 O, Cs 2 O, or K 2 O; an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or RbI; or any combination thereof. The compound containing an alkaline earth metal may include an alkaline earth metal oxide, such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1), or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1). The compound containing a rare earth metal may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3, TbI 3 Or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, LaTe, 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 Lu 2 Te 3 .
[0879] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may contain: i) one metal ion selected from alkali metals, alkaline earth metals and rare earth metals, and ii) a ligand bonded to the metal ion (e.g., a selected metal ion), such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene and / or any combination thereof.
[0880] The electron injection layer may comprise (e.g., consist 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 than one embodiments, the electron injection layer may further comprise an organic material (e.g., a compound represented by Formula 601).
[0881] In one or more embodiments, the electron injection layer may include (e.g., consisting of); i) an alkali metal-containing compound (e.g., an alkali metal halide), ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In one or more embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, a LiF:Yb co-deposition layer, etc.
[0882] When the electron injection layer further comprises an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in a matrix comprising an organic material.
[0883] The thickness of the electron injection layer can be about to about For example, about to about When the thickness of the electron injection layer is within the range as described herein, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.
[0884] The second electrode 150
[0885] The second electrode 150 is disposed on the intermediate layer 130. 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.
[0886] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode.
[0887] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
[0888] Covering
[0889] The first covering layer may be arranged outside the first electrode 110 (and, for example, on the first electrode 110) and / or the second covering layer may be arranged outside 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 covering layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are sequentially stacked in this prescribed order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150 and the second covering layer are sequentially stacked in this prescribed order, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150 and the second covering layer are sequentially stacked in this prescribed order.
[0890] The light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be led out toward the outside through the first electrode 110 (which is a semi-transmissive reflective electrode or a transmissive electrode) and the first covering layer, or the light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be led out toward the outside through the second electrode 150 (which is a semi-transmissive reflective electrode or a transmissive electrode) and the second covering layer.
[0891] The first cover layer and the second cover layer can increase the external emission efficiency according to the principle of constructive interference, thereby increasing the light extraction efficiency of the light emitting device 10, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0892] Each of the first cover layer and the second cover layer may include a material having a refractive index of 1.6 or more (at 589 nm).
[0893] The first covering layer and the second covering layer may each independently be an organic covering layer including an organic material, an inorganic covering layer including an inorganic material, or an organic-inorganic composite covering layer including an organic material and an inorganic material.
[0894] At least one selected from the first covering layer and the second covering layer may each independently contain a carbocyclic compound, a heterocyclic compound, a compound containing an amine group, 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 compound containing an amine group may optionally be substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I or any combination thereof. In one or more than one embodiments, at least one selected from the first covering layer and the second covering layer may each independently contain a compound containing an amine group.
[0895] In one or more than one embodiments, at least one selected from the first covering layer and the second covering layer may each independently contain a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0896] In one or more than one embodiments, at least one selected from the first cover layer and the second cover layer may each independently comprise at least one selected from compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB and / or any combination thereof:
[0897]
[0898] Electronic devices
[0899] The light emitting device may be included in one or more suitable electronic devices. In one or more embodiments, the electronic device including the light emitting device may be a light emitting device, a verification device, and the like.
[0900] 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 located in at least one direction of travel of the light emitted from the light emitting device. For example, the light emitted from the light emitting device may be blue light, green light, or white light. The light emitting device may be as described herein. In one or more embodiments, the color conversion layer may include quantum dots.
[0901] 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 sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the sub-pixel regions.
[0902] A pixel defining film may be disposed between the sub-pixel regions to define each of the sub-pixel regions.
[0903] The color filter may further include a plurality of color filter regions and a light shielding pattern disposed between the color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern disposed between the color conversion regions.
[0904] The plurality of color filter regions (or 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. In one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In one or more embodiments, the plurality of color filter regions (or color conversion regions) may include quantum dots. In detail, 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. A detailed description of quantum dots is provided herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0905] In one or more embodiments, the light emitting device may be intended to emit a first light, the first region may be intended to absorb the first light to emit a first-1 color light, the second region may be intended to absorb the first light to emit a second-1 color light, and the third region may be intended to absorb the first light to emit a third-1 color light. In this case, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. In detail, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.
[0906] In addition to the light emitting device described herein, 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.
[0907] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0908] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0909] The electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be located between the color filter and / or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be led out to the outside while (e.g., simultaneously) preventing or reducing the penetration of ambient air and moisture 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.
[0910] Depending on the purpose of the electronic device, in addition to the color filter and / or color conversion layer, various functional layers may be additionally arranged on the sealing portion. The functional layer may include a touch screen layer, 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 verification device may be, for example, a biometric verification device that verifies an individual by using biometric information of a living being (e.g., a fingertip, a pupil, etc.).
[0911] In addition to the light emitting device, the authentication device may further include a biometric information collector.
[0912] The electronic device can be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft and ships), projectors, etc.
[0913] Figure 2 and Figure 3 Description
[0914] Figure 2 is a cross-sectional view of a light emitting device as one of the electronic devices according to one or more embodiments.
[0915] Figure 2 The light emitting apparatus includes a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation part 300 sealing the light emitting device.
[0916] 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 impurities from penetrating through the substrate 100, and may provide a flat surface on the substrate 100.
[0917] 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.
[0918] The active layer 220 may include an inorganic semiconductor (eg, silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0919] 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 .
[0920] 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 be insulated from each other.
[0921] Source electrode 260 and drain electrode 270 may be disposed on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may be disposed to contact exposed portions of the source and drain regions of active layer 220.
[0922] The TFT is electrically connected to the light emitting device to drive the light emitting device, and may be covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light emitting device is provided on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0923] 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.
[0924] A pixel defining film 290 including an insulating material may be disposed on the first electrode 110. The pixel defining film 290 may expose a certain area of the first electrode 110, and the intermediate layer 130 may be formed in the exposed area of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic acid organic film. In one or more than one embodiments, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining film 290 to be arranged in the form of a common layer.
[0925] The second electrode 150 may be positioned on the intermediate layer 130, and a 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.
[0926] The encapsulation part 300 may be located on the second cover layer 170. The encapsulation part 300 may be located 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, an acrylic-based resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.
[0927] Figure 3 is a cross-sectional view of a light emitting device as one of electronic devices according to another embodiment.
[0928] Figure 3 Light emitting devices and Figure 2 The light emitting device is the same as that of the embodiment of the present invention, but the light shielding pattern 500 and the functional area 400 are additionally arranged on the packaging part 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 shielding pattern 500 and the functional area 400 are additionally arranged on the packaging part 300. Figure 3 The light emitting devices in the light emitting apparatus may be series light emitting devices.
[0929] Figure 4 Description
[0930] Figure 4 1 is a schematic perspective view of an electronic device 1 including a light emitting device according to one or more embodiments. The electronic device 1 may be a device for displaying a moving image or a still image, and may be any product, such as a television, a laptop computer, a monitor, a sign, or an Internet of Things (IoT) device, and a portable electronic device, such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic diary, an electronic book, and a portable multimedia player (PMP) or a navigation, an ultra mobile PC (UMPC) or a component thereof. In some embodiments, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type or similar display, or a head-mounted display (HMD), or a component of a wearable device. However, the embodiments are not limited thereto. In one or more embodiments, the electronic device 1 may be a dashboard of a vehicle, a central information display arranged on a central panel or dashboard of a vehicle, an interior mirror display of a vehicle replacing a side mirror, entertainment for a rear seat of a vehicle, a display arranged on the back of a front seat of a vehicle, a head-up display (HUD) mounted in front of the vehicle or projected on a front windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 A case in which the electronic equipment 1 is a smartphone is exemplified.
[0931] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.
[0932] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. On the non-display area NDA, a driver for providing an electrical signal or power to a display device arranged on the display area DA may be arranged. On the non-display area NDA, a pad may be arranged, which is an area to which an electronic component or a printed circuit board may be electrically connected.
[0933] 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, Figure 4 , the length in the x-axis direction may be less 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 greater than the length in the y-axis direction.
[0934] Figure 5 and FIG. 6A to FIG. 6C Description
[0935] Figure 5 is a schematic diagram of an exterior of a vehicle 1000 as an electronic device including a lighting 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.
[0936] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable devices for moving a transported individual such as a person, an object, or an animal from a departure point to a destination point. The vehicle 1000 may include a vehicle traveling on roads or tracks, a ship moving on the sea or a river, and an airplane flying in the air using the action of air.
[0937] The vehicle 1000 can travel on a road or track. The vehicle 1000 can move in a specific direction according to the rotation of at least one wheel. In one or more than one embodiments, the vehicle 1000 can include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0938] The vehicle 1000 may include a vehicle body having an interior and an exterior, and a chassis in which mechanical equipment necessary for driving as the remaining components other than the vehicle body is installed. The exterior of the vehicle body may include a front plate, a bonnet, a top plate, a rear plate, a luggage compartment, and 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, left and right wheels, etc.
[0939] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster piece 1400 , a center panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0940] The side window glass 1100 and the front window glass 1200 may be separated by a filler disposed between the side window glass 1100 and the front window glass 1200 .
[0941] 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 the 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 cluster piece 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0942] In one or more embodiments, the side window glass 1100 may be spaced apart from each other and / or separated from each other in the x direction or the -x direction. In one or more embodiments, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other and / or separated from each other in the x direction or the -x direction. In other words, the virtual straight line L connecting the side window glass 1100 may extend in the x direction or the -x direction. In an embodiment, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x direction or the -x direction.
[0943] 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.
[0944] The side view mirror 1300 can provide a rear view of the vehicle 1000. The side view mirror 1300 can be mounted on the outside of the vehicle body. In one or more embodiments, a plurality of side view mirrors 1300 can be provided. Any one of the plurality of side view mirrors 1300 can be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 can be arranged outside the second side window glass 1120.
[0945] Cluster piece 1400 may be arranged in front of the steering wheel. Cluster piece 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, an automatic transmission selector lever indicator light, a door open warning light, an oil warning light, and / or a low fuel warning light.
[0946] The center panel 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 panel 1500 may be disposed on one side of the cluster piece 1400 .
[0947] The passenger seat instrument panel 1600 may be spaced apart and / or separated from the cluster piece 1400 with the center panel 1500 disposed therebetween. In one or more embodiments, the cluster piece 1400 may be disposed to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be disposed to correspond to the passenger seat. In one or more embodiments, the cluster piece 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.
[0948] 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 the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster piece 1400, the center panel 1500, and the passenger seat instrument panel 1600.
[0949] The display device 2 may include an organic light emitting display, an inorganic electroluminescent (EL) light emitting display (inorganic light emitting display), and a quantum dot display. Hereinafter, an organic light emitting display including a light emitting device according to one or more embodiments is described as an example of a display device 2 according to one or more embodiments, but in an embodiment, one or more suitable types (kinds) of display devices as described herein may be used.
[0950] refer to Fig. 6A, the display device 2 can be arranged on the central panel 1500. In one or more embodiments, the display device 2 can display navigation information. In one or more embodiments, the display device 2 can display audio, video or information about vehicle settings.
[0951] refer to Figure 6B , the display device 2 may be arranged on the clusterware 1400. In this case, the clusterware 1400 may display driving information and the like through the display device 2. In other words, the clusterware 1400 may be implemented digitally. The clusterware 1400 may display vehicle information and driving information as images. In one or more embodiments, the needle and gauge of the tachometer and one or more suitable warning light icons may be displayed through digital signals.
[0952] refer to Figure 6C , the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display an image related to the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 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 cluster piece 1400 and / or the information displayed on the center panel 1500.
[0953] Manufacturing method
[0954] 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 suitable methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging, etc.).
[0955] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and about 0.01 angstrom / second to about Deposition is carried out at a deposition rate of .
[0956] Definition of terms
[0957] As used herein, the term "C 3 -C60 A "carbocyclic group" refers to a cyclic group consisting only of carbon as a ring atom and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms), and the term "C 1 -C 60 The term "heterocyclic group" refers to a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and further including heteroatoms other than carbon atoms as ring-forming atoms. 3 -C 60 Carbocyclic groups and C 1 -C 60 The heterocyclic groups 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 (eg, 3 to 30, 3 to 20, 3 to 15, or 3 to 10).
[0958] As used herein, a "cyclic group" may include C 3 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups both (eg, simultaneously).
[0959] As used herein, the term "π-electron-rich C 3 -C 60 "Cyclic group" refers to a cyclic group having three to sixty carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms) and not containing *-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 one to sixty carbon atoms (eg, 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and containing *-N=*' as a ring-forming portion.
[0960] In one or more than one embodiments,
[0961] C 3 -C 60The carbocyclic group may be i) a group T1 or ii) a fused cyclic group in which two or more groups T1 are fused to each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a benzophenone group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),
[0962] C 1 -C 60 The heterocyclic group may be i) a group T2, ii) a fused cyclic group in which two or more groups T2 are fused to each other, or iii) a fused cyclic group in which at least one group T2 and at least one group T1 are fused to each other (e.g., a pyrrole group, a thiophene group, a furan group, an indole group, a benzindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzosilole group, a benzo Thiophene group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolecarbazole group, benzofurancarbazole group, benzothiophenecarbazole group, benzosilolecarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofurandibenzofuran group, benzofurandibenzofuran group benzothiophene group, benzothienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),
[0963] Pi-electron-rich C 3 -C 60The cyclic group may be i) a group T1, ii) a fused cyclic group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused cyclic group in which two or more groups T3 are fused to each other, or v) a fused cyclic 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 a carbocyclic group, a 1H-pyrrole group, a thiol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiol group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiol group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothioylcarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiol group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophenodibenzothiophene group, and the like),
[0964] π-electron-deficient nitrogen-containing C 1 -C 60 The cyclic group may be i) a group T4, ii) a fused cyclic group in which two or more groups T4 are fused to each other, iii) a fused cyclic group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused cyclic group in which at least one group T4 and at least one group T3 are fused to each other (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a pyridine group, a pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, or the like), or v) a condensed cyclic group in which at least one group T4, at least one group T1, and at least one group T3 are condensed with each other,
[0965] The group T1 can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,
[0966] The group T2 can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borocyclopentadiene group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,
[0967] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group or a borole group, and
[0968] The group T4 can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
[0969] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group", "C 1 -C 60 Heterocyclic groups", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 A "heterocyclic group" may refer to a group fused to any cyclic group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula associated with the term used. In one or more than one embodiments, the "phenyl group" may be a benzo group, a phenyl group, a phenylene group, etc., which may be easily understood by a person of ordinary skill in the art based on the structure of the formula including the "phenyl group".
[0970] Depending on the context, a divalent group may refer to or be a multivalent group (eg, trivalent, tetravalent, etc., and not just divalent), depending on, for example, the structure of the formula associated with the term used.
[0971] In one or more than one embodiment, the monovalent C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups, and divalent C 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene group, C 1 -C 10 Heterocycloalkylene group, C 3 -C 10 Cycloalkenylene group, C 1 -C 10 Heterocycloalkenylene group, C 6 -C 60 Arylene group, C 1 -C 60 heteroarylene group, a divalent non-aromatic condensed polycyclic group and a divalent non-aromatic condensed heteropolycyclic group.
[0972] As used herein, the term "C 1 -C 60The term “alkyl group” refers to a straight or branched aliphatic hydrocarbon monovalent group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms), and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. As used herein, the term “C 1 -C 60 "Alkylene group" refers to a group having 1 -C 60 A divalent group of the same structure as an alkyl group.
[0973] As used herein, the term "C 2 -C 60 "Alkenyl group" means a 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof include a vinyl group, a propenyl group, and a butenyl group. 2 -C 60 "Alkenylene group" refers to a 2 -C 60 Alkenyl groups are divalent groups of the same structure.
[0974] As used herein, the term "C 2 -C 60 "Alkynyl group" means a 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof include an ethynyl group and a propynyl group. 2 -C 60 "Alkyne group" refers to a 2 -C 60 Alkynyl groups are divalent groups of the same structure.
[0975] As used herein, the term "C 1 -C 60 "Alkoxy group" refers to a group consisting of -OA 101 (A 101 It is C 1 -C60 The invention further comprises a monovalent group represented by an alkyl group (eg, an alkyl group), and examples thereof include a methoxy group, an ethoxy group and an isopropoxy group.
[0976] As used herein, the term "C 3 -C 10 The term "cycloalkyl group" refers to a monovalent saturated hydrocarbon ring group having three to ten carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. As used herein, the term "C 3 -C 10 "Cycloalkylene group" refers to a group having a 3 -C 10 Cycloalkyl groups are divalent groups of the same structure.
[0977] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl group" as used herein refers to a monovalent cyclic group having one to ten carbon atoms and further containing at least one heteroatom other than carbon atoms as a ring-forming atom, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group and a tetrahydrothienyl group. 1 -C 10 The term "heterocycloalkylene group" refers to a 1 -C 10 Heterocycloalkyl groups are divalent groups of the same structure.
[0978] As used herein, the term "C 3 -C 10 A "cycloalkenyl group" refers to a monovalent cyclic group having three to ten carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. As used herein, the term "C 3 -C 10 "Cycloalkenylene group" refers to a group having a 3 -C 10 Cycloalkenyl groups are divalent groups of the same structure.
[0979] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent cyclic group of one to ten carbon atoms which further contains at least one heteroatom other than carbon atoms as a ring-forming atom in its ring and has at least one double bond. 1 -C 10Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups and 2,3-dihydrothienyl groups. 1 -C 10 The term "heterocycloalkenylene group" refers to a 1 -C 10 Heterocycloalkenyl groups are divalent groups of the same structure.
[0980] As used herein, the term "C 6 -C 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing six to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms), and the term "C 6 -C 60 "Arylene group" refers to a divalent group having a carbocyclic aromatic system containing six to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms). 6 -C 60 Examples of the aryl group include 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 triphenylenyl group, a pyrenyl group, The phenyl groups include phenyl groups, peryl groups, pentaphenyl groups, heptaphenyl groups, tetraphenyl groups, naphthacene groups, hexaphenyl groups, pentacene groups, rubidinyl groups, corynyl groups and ovaphenyl groups. 6 -C 60 Aryl groups and C 6 -C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other.
[0981] As used herein, the term "C 1 -C 60 The term "heteroaryl group" refers to a monovalent group having a heterocyclic aromatic system having one to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms) and further containing at least one heteroatom other than a carbon atom as a ring-forming atom. As used herein, the term "C 1 -C 60The "heteroarylene group" may be a divalent group having a heterocyclic aromatic system having one to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms) and further containing at least one heteroatom other than a carbon atom as a ring-forming atom. 1 -C 60 Examples of heteroaryl groups include pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, benzoquinolyl groups, isoquinolyl groups, benzoisoquinolyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinnolinyl groups, phenanthrolinyl groups, phthalazinyl groups and naphthyridinyl groups. 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other.
[0982] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, only carbon atoms (e.g., eight to sixty carbon atoms, e.g., 8 to 30, 8 to 20, 8 to 15, or 8 to 10 carbon atoms) as ring atoms, and no aromaticity in its molecular structure when viewed as a whole. Examples of monovalent non-aromatic fused polycyclic groups include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenophenanthryl groups, and indenoanthryl groups. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.
[0983] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group which has two or more rings fused to each other, further contains at least one heteroatom other than carbon atoms (e.g., one to sixty carbon atoms, e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) as a ring-constituting atom, and does not have aromaticity in its molecular structure when viewed as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thienyl group, a furanyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothiorolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group , thiadiazolyl group, benzopyrazolyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazine group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazolyl group, indolecarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzothiorrolocarbazolyl group, benzoindolecarbazolyl group, benzocarbazolyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthothiophenyl group, benzonaphthothiophenyl group, benzofuranodibenzofuranyl group, benzofuranodibenzothiophenyl group and benzothiophenylodibenzothiophenyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0984] As used herein, the term "C 6 -C 60 "Aryloxy group" means -OA 102 (A 102 It is C 6 -C 60 aryl group), and as used herein, the term "C 6 -C 60 "Arylthio group" means -SA 103 (A 103 It is C 6 -C 60 aryl group).
[0985] As used herein, the term "C 7 -C60 "Arylalkyl group" refers to -A 104 A 105 (A 104 It is C 1 -C 54 An alkylene group, and A 105 It is C 6 -C 59 aryl group), and as used herein, the term "C 2 -C 60 A "heteroarylalkyl group" refers to an -A 106 A 107 (A 106 It is C 1 -C 59 An alkylene group, and A 107 It is C 1 -C 59 heteroaryl group).
[0986] R 10a It can be:
[0987] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group,
[0988] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -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 substituted C 1 -C 60 Alkyl group, C 2 -C60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups,
[0989] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -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 substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group or C 2 -C 60 a heteroarylalkyl group; or
[0990] -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 ).
[0991] As used in this paper, 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; a hydroxyl group; a cyano group; a nitro group; or each is unsubstituted or substituted with deuterium, -F, a cyano group, C 1 -C 60 Alkyl group, C 1 -C 60 Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0992] As used herein, the term "heteroatom" refers to any atom other than a carbon atom, and the number of heteroatoms may be 1 to 10, for example 1, 2, 3, 4 or 5. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se or any combination thereof.
[0993] The term "transition metal" as used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
[0994] The term "Ph" as used herein refers to a phenyl group, the term "Me" as used herein refers to a methyl group, the term "Et" as used herein refers to an ethyl group, the term "tert-Bu" or "Bu" as used herein refers to an ethyl group.t ” refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
[0995] As used herein, the term "biphenyl group" refers to a "phenyl group substituted by a phenyl group". In other words, a "biphenyl group" is a 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0996] As used herein, the term "terphenyl group" refers to a "phenyl group substituted by a biphenyl group". 6 -C 60 Aryl-substituted C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0997] Unless otherwise defined, *, *' and *" as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0998] Terms such as "substantially", "about" and "approximately" are used as relative terms rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. They may include the stated value and an acceptable range of deviation determined by one of ordinary skill in the art, taking into account the limitations and errors associated with the measurement of the quantity. For example, "about" may refer to one or more than one standard deviation, or ±30%, ±20%, ±10%, ±5% of the stated value.
[0999] The numerical ranges disclosed herein include and are intended to disclose all sub-ranges of the same numerical precision. For example, a range of "1.0 to 10.0" includes all sub-ranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Applicants therefore reserve the right to amend this specification (including the claims) to explicitly list any sub-ranges that are included in the ranges explicitly listed herein.
[1000] Any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware, and hardware may be used to implement 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. For example, the various components of the light emitting device and / or light emitting element may be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the light emitting device and / or light emitting element may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device and / or element may be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact 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 memory device (such as a random access memory (RAM) as an example). The computer program instructions may also be stored in other non-temporary computer-readable media, such as a CD-ROM, a flash drive, etc. as an example. 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 that the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[1001] Hereinafter, an organometallic compound and a light emitting device according to one or more embodiments will be described in more detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used to describe a synthesis example means using B instead of A in an equimolar equivalent.
[1002] Example
[1003] Synthesis Example 1: Synthesis of Compound 14
[1004]
[1005]
[1006] Synthesis of Intermediate 14-1
[1007] 4-Bromo-1,1'-biphenyl (1.0 equivalent), silver carbonate (Ag 2 CO 3 , 0.2 equivalent), cyclohexyldiphenylphosphine (Ph 2 PCy, 0.5 equivalent), K 2 CO 3 (1 equivalent) and deuterium oxide (D 2O, 20 equivalents) was dissolved in toluene, stirred at 120°C for 24 hours, cooled to room temperature, and then quenched by using ammonium chloride (NH 3 Next, the solvent was removed by distillation under reduced pressure at a pressure of 8 mbar, the organic layer obtained by three extraction processes using dichloromethane (MC) and water was dried using magnesium sulfate, and then concentrated and column chromatography (n-hexane only) was performed to synthesize intermediate 14-1 (yield: 94%).
[1008] Synthesis of intermediate 14-2
[1009] Intermediate 14-1 (1.0 equivalent), bis(diphenylphosphino)ferrocene palladium dichloride (0.05 equivalent), bis(pinacolato)diboron (1.5 equivalent) and potassium acetate (3 equivalent) were dissolved in 1,4-dioxane, stirred at 100° C. for 24 hours, and then cooled to room temperature. Next, the solvent was removed by distillation under reduced pressure at a pressure of 8 mbar, and the organic layer obtained by performing three extraction processes using MC and water was dried by using magnesium sulfate, and then concentrated and column chromatography (MC: hexane) was performed to synthesize Intermediate 14-2 (yield: 87%).
[1010] Synthesis of intermediate 14-3
[1011] Intermediate 14-2 (1.0 equiv), CX31 Umicore (0.05 equiv), 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine (1.5 equiv) and potassium acetate (3 equiv) were dissolved in 1,4-dioxane and H 2 O (volume ratio 3: 1), stirred at 100 ° C for 24 hours, and then cooled to room temperature. Next, the solvent was removed by distillation under reduced pressure at a pressure of 8 mbar, and the organic layer obtained by performing three extraction processes using MC and water was dried using magnesium sulfate, and then concentrated and column chromatography (MC: hexane) was performed to synthesize Intermediate 14-3 (yield: 76%).
[1012] Synthesis of Intermediate 14-4
[1013] Intermediate 14-3 (1.0 equivalent), 1-bromo-2-nitrobenzene (2 equivalents), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos, 0.10 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3, 0.05 equivalent) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in toluene, stirred at 110° C. for 24 hours, and then cooled to room temperature. Next, the solvent was removed by distillation under reduced pressure at a pressure of 8 mbar, and the organic layer obtained by performing three extraction processes using MC and water was dried by using magnesium sulfate, and then concentrated and column chromatography (MC: hexane) was performed to synthesize Intermediate 14-4 (yield: 78%).
[1014] Synthesis of Intermediate 14-5
[1015] Intermediate 14-4 (1.0 equivalent) and tin (5 equivalent) were dissolved in ethanol (EtOH), and then stirred. Hydrogen chloride (12M) was injected into the mixture obtained therefrom, stirred at 80°C for 6 hours, and then cooled to room temperature. Next, the solvent was removed by distillation under reduced pressure at a pressure of 8mbar, and the organic layer obtained by performing three extraction processes using MC and water was dried using magnesium sulfate, and then concentrated and column chromatography (MC: hexane) was performed to synthesize intermediate 14-5 (yield: 81%).
[1016] Synthesis of Intermediate 14-6
[1017] Intermediate 14-5 (1.0 equivalent), 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (0.05 equivalent), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) (0.10 equivalent) and sodium tert-butoxide (2.0 equivalent) were dissolved in toluene (0.1M), stirred at 110°C for 2 hours, and then cooled to room temperature. Next, the solvent was removed by distillation under reduced pressure at a pressure of 8 mbar, and the organic layer obtained by performing three extraction processes using MC and water was dried by using magnesium sulfate, and then concentrated and column chromatography (MC: hexane) was performed to synthesize Intermediate 14-6 (yield: 77%).
[1018] Synthesis of Intermediate 14-7
[1019] Intermediate 14-6 (1.0 equivalent) was dissolved in triethyl orthoformate (30 equivalents), and 37% DCl (1.5 equivalents) was added thereto, stirred at 80° C. for 24 hours, and then cooled to room temperature to concentrate and remove triethyl orthoformate. Next, the organic layer obtained by performing three extraction processes using MC and water was dried using magnesium sulfate, and then concentrated and column chromatography (MC: methanol) was performed to synthesize Intermediate 14-7 (yield: 85%).
[1020] Synthesis of compound 14
[1021] Intermediate 14-7 (1.0 equivalent), potassium chloroplatinate (II) acid (1.1 equivalent) and 2,6-lutidine (4.0 equivalent) were dissolved in 1,2-dichlorobenzene (0.05M), stirred at 120°C for 18 hours under nitrogen, and then cooled to room temperature to concentrate and remove 1,2-dichlorobenzene. Next, the organic layer obtained by performing three extraction processes using dichloromethane and water was dried using magnesium sulfate, and concentrated and column chromatography (MC: hexane) was performed to synthesize compound 14 (yield: 51%).
[1022] ESI-LCMS of compound 14: [M]+: C 67 H 54 D 6 N 4 OPt,1138.4.
[1023] Synthesis Example 2: Synthesis of Compound 54
[1024]
[1025]
[1026] Synthesis of Intermediate 54-0
[1027] Intermediate 54-0 was synthesized in substantially the same manner as used to synthesize Intermediate 14-1 of Synthesis Example 1, except that 1-bromo-4-iodobenzene was used instead of 4-bromo-1,1′-biphenyl.
[1028] Synthesis of Intermediate 54-1
[1029] Intermediate 54-1 was synthesized in substantially the same manner as used to synthesize Intermediate 14-3 of Synthesis Example 1, except that Intermediate 54-0 and 1-bromo-4-(tert-butyl)benzene were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine, respectively.
[1030] Synthesis of Intermediate 54-2, Intermediate 54-3, Intermediate 54-4 and Intermediate 54-5
[1031] Intermediate 54-2, intermediate 54-3, intermediate 54-4 and intermediate 54-5 were synthesized sequentially in substantially the same manner as that used to sequentially synthesize intermediate 14-2, intermediate 14-3, intermediate 14-4 and intermediate 14-5 of Synthesis Example 1, except that intermediate 54-1, intermediate 54-2, intermediate 54-3 and intermediate 54-4 were used instead of intermediate 14-1, intermediate 14-2, intermediate 14-3 and intermediate 14-4, respectively.
[1032] Synthesis of Intermediate 54-6
[1033] Intermediate 54-6 was synthesized in substantially the same manner as that used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 54-5 and 2-(3-bromophenoxy)-9-(5-(tert-butyl)pyridin-2-yl)-9H-carbazole were used instead of Intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d2)pyridin-2-yl)-9H-carbazole, respectively.
[1034] Synthesis of Intermediate 54-7
[1035] Intermediate 54-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 54-6 was used instead of Intermediate 14-6.
[1036] Synthesis of compound 54
[1037] Compound 54 (yield: 54%) was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1, except that Intermediate 54-7 was used instead of Intermediate 14-7.
[1038] ESI-LCMS of compound 54: [M]+: C 70 H 62 D 4 N 4 OPt,1178.5.
[1039] Synthesis Example 3: Synthesis of Compound 197
[1040]
[1041]
[1042] Synthesis of Intermediate 197-1
[1043] 4-Bromo-1-iodo-2-(methyl-d 3 )benzene (1.0 equivalent), (2-(methyl-d 3 )phenyl)boronic acid (1.2 equiv), Pd(OAc) 2(5mol%), PPh 3 (10 mol%) and Na 2 CO 3 (2.0 equivalents) dissolved in acetone and H 2 O (volume ratio of 1:3, 0.1M) mixture, and then stirred at 60 ° C for 24 hours, and then cooled to room temperature. Next, the solvent was removed by distillation under reduced pressure at a pressure of 8 mbar, the organic layer obtained by performing three extraction processes using MC and water was dried by using magnesium sulfate, and then concentrated and column chromatography (n-hexane only) was performed to synthesize Intermediate 197-1 (yield: 73%).
[1044] Synthesis of Intermediate 197-2
[1045] Intermediate 197-2 was synthesized in substantially the same manner as used to synthesize Intermediate 14-2 of Synthesis Example 1, except that Intermediate 197-1 was used instead of Intermediate 14-1.
[1046] Synthesis of Intermediate 197-3
[1047] Intermediate 197-3 was synthesized in substantially the same manner as used to synthesize Intermediate 14-3 of Synthesis Example 1, except that Intermediate 197-2 and Compound 197(1) were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine.
[1048] Synthesis of Intermediate 197-4 and Intermediate 197-5
[1049] Intermediate 197-4 and Intermediate 197-5 were synthesized sequentially in substantially the same manner as for sequentially synthesizing Intermediate 14-4 and Intermediate 14-5 of Synthesis Example 1 except that Intermediate 197-3 and Intermediate 197-4 were used instead of Intermediate 14-3 and Intermediate 14-4, respectively.
[1050] Synthesis of Intermediate 197-6
[1051] Intermediate 197-6 was synthesized in substantially the same manner as used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 197-5 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole were used instead of Intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole.
[1052] Synthesis of Intermediate 197-7
[1053] Intermediate 197-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 197-6 was used instead of Intermediate 14-6.
[1054] Synthesis of compound 197
[1055] Compound 197 was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1 (yield: 50%), except that Intermediate 197-7 was used instead of Intermediate 14-7.
[1056] ESI-LCMS of compound 197: [M]+: C 64 H 44 D 10 N 4 OPt,1100.4.
[1057] Synthesis Example 4: Synthesis of Compound 219
[1058]
[1059]
[1060] Synthesis of Intermediate 219-1
[1061] Intermediate 219-1 was synthesized in substantially the same manner as used to synthesize Intermediate 197-1 of Synthesis Example 3, except that Compound 219(2) and Compound 219(3) were used instead of 4-bromo-1-iodo-2-(methyl-d 3 )benzene and (2-(methyl-d 3 )phenyl)boronic acid.
[1062] Synthesis of Intermediate 219-2
[1063] Intermediate 219-2 was synthesized in substantially the same manner as used to synthesize Intermediate 14-2 of Synthesis Example 1, except that Intermediate 219-1 was used instead of Intermediate 14-1.
[1064] Synthesis of intermediate 219-3
[1065] Intermediate 219-3 was synthesized in substantially the same manner as used to synthesize Intermediate 14-3 of Synthesis Example 1, except that Intermediate 219-2 and Compound 219(1) were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine.
[1066] Synthesis of Intermediate 219-4 and Intermediate 219-5
[1067] Intermediate 219-4 and Intermediate 219-5 were synthesized sequentially in substantially the same manner as for sequentially synthesizing Intermediate 14-4 and Intermediate 14-5 of Synthesis Example 1 except that Intermediate 219-3 and Intermediate 219-4 were used instead of Intermediate 14-3 and Intermediate 14-4, respectively.
[1068] Synthesis of Intermediate 219-6
[1069] Intermediate 219-6 was synthesized in substantially the same manner as that used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 219-5 and 2-(3-bromophenoxy)-9-(4-(methyl-d 3 )pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 Substituting intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole.
[1070] Synthesis of Intermediate 219-7
[1071] Intermediate 219-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 219-6 was used instead of Intermediate 14-6.
[1072] Synthesis of compound 219
[1073] Compound 219 was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1 (yield: 53%), except that Intermediate 219-7 was used instead of Intermediate 14-7.
[1074] ESI-LCMS of compound 219: [M]+: C 64 H 21 D 33 N 4 OPt,1123.5.
[1075] Synthesis Example 5: Synthesis of Compound 281
[1076]
[1077]
[1078] Synthesis of Intermediate 281-2
[1079] Intermediate 281-2 was synthesized in substantially the same manner as that used to synthesize Intermediate 14-2 of Synthesis Example 1, except that the compound 4-bromo-1,1′-biphenyl-2′,3′,4′,5′,6′-d 5 Replace intermediate 14-1.
[1080] Synthesis of Intermediate 281-3
[1081] Intermediate 281-3 was synthesized in substantially the same manner as used to synthesize Intermediate 14-3 of Synthesis Example 1, except that Intermediate 281-2 and Compound 281(1) were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine.
[1082] Synthesis of Intermediate 281-4 and Intermediate 281-5
[1083] Intermediate 281-4 and Intermediate 281-5 were synthesized sequentially in substantially the same manner as for sequentially synthesizing Intermediate 14-4 and Intermediate 14-5 of Synthesis Example 1 except that Intermediate 281-3 and Intermediate 281-4 were used instead of Intermediate 14-3 and Intermediate 14-4, respectively.
[1084] Synthesis of Intermediate 281-6
[1085] Intermediate 281-6 was synthesized in substantially the same manner as used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 281-5 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole were used instead of Intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole.
[1086] Synthesis of Intermediate 281-7
[1087] Intermediate 281-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 281-6 was used instead of Intermediate 14-6.
[1088] Synthesis of compound 281
[1089] Compound 281 was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1 (yield: 56%), except that Intermediate 281-7 was used instead of Intermediate 14-7.
[1090] ESI-LCMS of compound 281: [M]+: C 66 H 44 D 14 N 4 OPt,1132.5.
[1091] Synthesis Example 6: Synthesis of Compound 299
[1092]
[1093]
[1094] Synthesis of Intermediate 299-2
[1095] Intermediate 299-2 was synthesized in substantially the same manner as used to synthesize Intermediate 14-2 of Synthesis Example 1, except that the compound 4-bromo-2,4′-di-tert-butyl-1,1′-biphenyl was used instead of Intermediate 14-1.
[1096] Synthesis of Intermediate 299-3
[1097] Intermediate 299-3 was synthesized in substantially the same manner as used to synthesize Intermediate 14-3 of Synthesis Example 1, except that Intermediate 281-2 and Compound 299(1) were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine.
[1098] Synthesis of Intermediate 299-4 and Intermediate 299-5
[1099] Intermediate 299-4 and Intermediate 299-5 were synthesized sequentially in substantially the same manner as for sequentially synthesizing Intermediate 14-4 and Intermediate 14-5 of Synthesis Example 1 except that Intermediate 299-3 and Intermediate 299-4 were used instead of Intermediate 14-3 and Intermediate 14-4, respectively.
[1100] Synthesis of Intermediate 299-6
[1101] Intermediate 299-6 was synthesized in substantially the same manner as that used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 299-5 and 2-(5-bromo-2-(methyl-d 3 )phenoxy)-9-(4-(2-(methyl-d 3 )propan-2-yl-1,1,1,3,3,3-d 6 )pyridin-2-yl)-9H-carbazole instead of intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole.
[1102] Synthesis of Intermediate 299-7
[1103] Intermediate 299-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 299-6 was used instead of Intermediate 14-6.
[1104] Synthesis of compound 299
[1105] Compound 299 was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1 (yield: 48%), except that Intermediate 299-7 was used instead of Intermediate 14-7.
[1106] ESI-LCMS of compound 299: [M]+: C 71 H 56 D 12 N 4 OPt,1200.6.
[1107] Synthesis Example 7: Synthesis of Compound 1
[1108]
[1109] Synthesis of intermediate 1-3
[1110] Intermediate 1-3 was synthesized in substantially the same manner as Intermediate 14-3 of Synthesis Example 1, except that 2-([1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 3-bromo-[1,1'-biphenyl]-2-amine were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine.
[1111] Synthesis of Intermediates 1-4 and 1-5
[1112] Intermediate 1-4 and Intermediate 1-5 were sequentially synthesized in substantially the same manner as for sequentially synthesizing Intermediate 14-4 and Intermediate 14-5 of Synthesis Example 1 except that Intermediate 1-3 and Intermediate 1-4 were used instead of Intermediate 14-3 and Intermediate 14-4, respectively.
[1113] Synthesis of intermediates 1-6
[1114] Intermediate 1-6 was synthesized in substantially the same manner as used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 1-5 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole were used instead of Intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole.
[1115] Synthesis of intermediates 1-7
[1116] Intermediate 1-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 1-6 was used instead of Intermediate 14-6.
[1117] Synthesis of compound 1
[1118] Compound 1 was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1 (yield: 59%), except that Intermediate 1-7 was used instead of Intermediate 14-7.
[1119] ESI-LCMS of compound 1: [M]+: C 58 H 42 N 4 OPt,1006.1.
[1120] Synthesis Example 8: Synthesis of Compound 337
[1121]
[1122] Synthesis of Intermediate 337-3
[1123] Intermediate 337-3 was synthesized in substantially the same manner as Intermediate 14-3 of Synthesis Example 1, except that 2-(4'-(tert-butyl)-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 3-bromo-4'-(tert-butyl)-[1,1'-biphenyl]-2-amine were used instead of Intermediate 14-2 and 3-bromo-3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine.
[1124] Synthesis of Intermediate 337-4 and Intermediate 337-5
[1125] Intermediate 337-4 and Intermediate 337-5 were sequentially synthesized in substantially the same manner as for sequentially synthesizing Intermediate 14-4 and Intermediate 14-5 of Synthesis Example 1 except that Intermediate 337-3 and Intermediate 337-4 were used instead of Intermediate 14-3 and Intermediate 14-4, respectively.
[1126] Synthesis of Intermediate 337-6
[1127] Intermediate 337-6 was synthesized in substantially the same manner as used to synthesize Intermediate 14-6 of Synthesis Example 1, except that Intermediate 337-5 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole were used instead of Intermediate 14-5 and 2-(3-bromophenoxy)-9-(4-(2,2-dimethylpropyl-1,1-d 2 )pyridin-2-yl)-9H-carbazole.
[1128] Synthesis of Intermediate 337-7
[1129] Intermediate 337-7 was synthesized in substantially the same manner as used to synthesize Intermediate 14-7 of Synthesis Example 1, except that Intermediate 337-6 was used instead of Intermediate 14-6.
[1130] Synthesis of compound 337
[1131] Compound 337 was synthesized in substantially the same manner as used to synthesize Compound 14 of Synthesis Example 1 (yield: 48%), except that Intermediate 337-7 was used instead of Intermediate 14-7.
[1132] ESI-LCMS of compound 337: [M]+: C 66 H 58 N 4 OPt,1118.4.
[1133] For the compounds synthesized in Synthesis Examples 1 to 8, high resolution mass (HR-MS) was measured, and the results thereof are shown in Table 1. By referring to the synthesis routes and raw materials, a person of ordinary skill in the art can easily recognize the synthesis methods of other compounds than the compounds synthesized in Synthesis Examples 1 to 8.
[1134] Table 1
[1135]
[1136] Evaluation Example 1
[1137] According to the method in Table 2, the HOMO and LUMO energy levels of each of Compound 14, Compound 54, Compound 197, Compound 219, Compound 281, Compound 299, Compound 1, Compound 337, Compound A, Compound B and Compound C were evaluated, and the results are shown in Table 3.
[1138] Table 2
[1139]
[1140] Table 3
[1141] Compound No. HOMO(eV) LUMO(eV) 14 -5.30 -2.05 54 -5.29 -2.09 197 -5.32 -2.12 219 -5.30 -2.08 281 -5.26 -2.06 299 -5.28 -2.08 1 -5.28 -2.08 337 -5.26 -2.06 A -5.30 -2.18 B -5.32 -2.23 C -5.26 -1.89
[1142]
[1143] Evaluation Example 2
[1144] After compound 14 (2 mg), compound ETH2 (10 mg), compound HTH29 (10 mg) and CH 2 Cl 2After mixing with PMMA (the weight of PMMA is 50 mg) in MgSO4, the resultant thus obtained was coated on a quartz substrate by using a spin coater, heat-treated at 80° C. in an oven, and then cooled to room temperature to prepare a film 14 having a thickness of 40 nanometers (nm). Next, films 54, 197, 219, 281, 299, 1, 337, A, B, and C were prepared in substantially the same manner as for preparing film 14, but each of compound 54, compound 197, compound 219, compound 281, compound 299, compound 1, compound 337, compound A, compound B, and compound C were used instead of compound 14.
[1145] The photoluminescence (PL) spectrum of each of Film 14, Film 54, Film 197, Film 219, Film 281, Film 299, Film 1, Film 337, Film A, Film B, and Film C was measured by a Quantaurus-QY absolute PL quantum yield spectrometer of Hamamatsu Company (equipped with a xenon light source, a monochromator, a photon multichannel analyzer, and an integrating sphere, and using the photoluminescence quantum yield (PLQY) measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, the excitation wavelength was scanned from 320 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 organic metal compound contained in each film, which are shown in Table 4.
[1146] Next, the PLQY of each of Film 14, Film 54, Film 197, Film 219, Film 281, Film 299, Film 1, Film 337, Film A, Film B, and Film C was measured by scanning the excitation wavelength from 300 nm to 380 nm at intervals of 10 nm using a Quantaurus-QY absolute PL quantum yield spectrometer of Hamamatsu Corporation, and then, the PLQY measured at an excitation wavelength of 330 nm was taken to obtain the PLQY of the organic metal compound contained in each film. The results are shown in Table 4.
[1147] Table 4
[1148]
[1149]
[1150] It can be confirmed from Table 4 that each of Compound 14, Compound 54, Compound 197, Compound 219, Compound 281, Compound 299, Compound 1, and Compound 337 has improved PLQY and emits blue light with a relatively small FWHM compared to Compound A to Compound C.
[1151] Evaluation Example 3
[1152] Subsequently, the PL spectrum of each of Film 14, Film 54, Film 197, Film 219, Film 281, Film 299, Film 1, Film 337, Film A, Film B, and Film C was evaluated at room temperature using FluoTime 300, which is a time-resolved photoluminescence (TRPL) measurement system of PicoQuant Inc., and PLS340, which is a pump source of PicoQuant Inc. (excitation wavelength = 340 nm, spectrum width = 20 nm), and then, the wavelength of the main peak of the spectrum was determined. Based on time-correlated single photon counting (TCSPC) according to time, PLS340 repeatedly measures the number of photons emitted from each film at the wavelength of the main peak by applying a photon pulse (pulse width = 500 picoseconds) to each film to obtain a TRPL curve sufficient for fitting. The results thus obtained are fitted with one or more exponential decay functions to obtain the T of each of Film 14, Film 54, Film 197, Film 219, Film 281, Film 299, Film 1, Film 337, Film A, Film B, and Film C. 衰减 (Ex), that is, decay time. The results are shown in Table 5. The function used for fitting is shown in Equation 1, and T obtained from each exponential decay function used for fitting 衰减 , obtained as T 衰减 In this regard, the same measurement is performed during the same measurement time as that for obtaining the TRPL curve in the dark state (wherein the pump signal entering the set or predetermined membrane is blocked) to obtain a baseline or background signal curve, which is used as a baseline for fitting.
[1153] Equation 1
[1154]
[1155] Table 5
[1156]
[1157] It can be confirmed from Table 5 that each of Compound 14, Compound 54, Compound 197, Compound 219, Compound 281, Compound 299, Compound 1, and Compound 337 has a relatively small emission decay time compared to Compound A to Compound C.
[1158] Example 1
[1159] As the anode, it will have a resistance of 15 ohms / cm2 (Ω / cm 2 )(1,200 Angstroms )A glass substrate (product of Corning Inc.) on which ITO was formed was cut into a size of 50 mm x 50 mm x 0.7 mm, was washed by ultrasonicating with isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet rays and exposed to ozone for 30 minutes, and then fixed on a vacuum deposition apparatus.
[1160] 2-TNATA was vacuum deposited on the anode to form a A hole injection layer having a thickness of 1000 Å was formed, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as “NPB”) was vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .
[1161] The first compound (compound 14), the second compound (compound ETH2), the third compound (compound HTH29) and the fourth compound (compound DFD051) are vacuum deposited on the hole transport layer to form a In this regard, the amount of the first compound is 13wt% based on the total amount of the emission layer (100wt%), the amount of the fourth compound is 1.3wt% based on the total amount of the emission layer (100wt%), and the weight ratio of the second compound to the third compound is adjusted to 4:6.
[1162] The compound ETH34 was vacuum deposited on the emission layer to form a hole blocking layer having a thickness of 50 μm, and ET46 and Liq were vacuum deposited on the hole blocking layer at a weight ratio of 4:6 to form a hole blocking layer having a thickness of 50 μm. Next, Yb is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and then Mg is vacuum deposited thereon to form A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[1163]
[1164] Examples 2 to 8 and Comparative Examples A to C
[1165] Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that when forming the emission layer, the compounds shown in Table 6 were each used instead of Compound 14 as the first compound. The weight in brackets in Table 6 represents the weight of the corresponding compound based on 100 wt % of the emission layer.
[1166] Evaluation Example 4
[1167] The organic light-emitting devices manufactured in Examples 1 to 8 and Comparative Examples A to C were measured using a Keithley MU 236 and a luminance meter PR650 at 1,000 (cd / m 2 )), driving voltage (V), color coordinate value (CIE (y)), color conversion efficiency (cd / A / y), maximum emission wavelength (nanometer (nm)) and service life (T 95 ) and the results are shown in Table 7. In Table 7, the service life (T 95 ) is a measure of the time (hours (h)) taken until the brightness reaches 95% of the initial brightness, and is expressed as a relative value (%).
[1168] Table 6
[1169]
[1170]
[1171] Table 7
[1172]
[1173]
[1174] It can be confirmed from Table 7 that the organic light-emitting devices of Examples 1 to 6 each emit deep blue light and have excellent or suitable driving voltage, excellent or suitable color purity, excellent or suitable luminous efficiency, excellent or suitable color conversion efficiency, and excellent or suitable service life characteristics. It can also be confirmed that the organic light-emitting devices of Examples 7 and 8 each emit deep blue light and have improved characteristics in terms of driving voltage, color purity, color conversion efficiency, and service life compared to Comparative Examples A to C.
[1175] Examples 11 to 18 and Comparative Examples 1A to 1C
[1176] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, but when forming the emission layer, the compounds shown in Table 8 were each used as the first compound and the fourth compound, and the amounts of the first compound and the fourth compound and the weight ratio of the second compound to the third compound were each adjusted to those shown in Table 8. The weight in brackets in Table 8 represents the weight of the corresponding compound based on 100 wt % of the emission layer.
[1177] Evaluation Example 5
[1178] The organic light-emitting devices manufactured in Examples 11 to 18 and Comparative Examples 1A to 1C were measured in substantially the same manner as used in Evaluation Example 4 at 1,000 cd / m 2 The driving voltage (V), color coordinate value (CIE (y)), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and service life (T 95 ) and the results are shown in Table 9. In Table 9, the service life (T 95 ) is a measure of the time (h) taken until the brightness reaches 95% of the initial brightness, and is expressed as a relative value (%).
[1179] Table 8
[1180]
[1181]
[1182] Table 9
[1183]
[1184] It can be confirmed from Table 9 that the organic light-emitting devices of Examples 11 to 16 each emit deep blue light and have excellent or suitable driving voltage, excellent or suitable color purity, excellent or suitable luminous efficiency, excellent or suitable color conversion efficiency, and excellent or suitable service life characteristics. It can also be confirmed that the organic light-emitting devices of Examples 17 and 18 each emit deep blue light and have improved characteristics in terms of driving voltage, color purity, color conversion efficiency, and service life compared to Comparative Examples 1A to 1C.
[1185] The organometallic compound has excellent or suitable processability and excellent or suitable electrical characteristics, and thus a light-emitting device including the organometallic compound may have improved color purity, improved luminous efficiency, and improved lifetime.
[1186] 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 the 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 than one embodiment has been described with reference to the accompanying drawings, it should be understood by those of ordinary skill in the art that one or more than one suitable changes in form and detail may be made herein without departing from the subject 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 Contains at least one nitrogen-containing C1-C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or a combination thereof, wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 1 Formula 1A Wherein Ar1 in Formula 1 is a group represented by Formula 1A, * in Formula 1A represents the binding site with ring CY1 in Formula 1, In Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, X1 to X4 are each independently C or N, i) The bond between X1 and M is a coordination bond, ii) one selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and two selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M are each covalent bonds, Ring CY1 to Ring CY4 are each independently C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, X 51 is a single bond, *-N(Z 51a )-*', *-B(Z 51a )-*', *-P(Z 51a )-*', *-C(Z 51a )(Z 51b )-*', *-Si(Z 51a )(Z 51b )-*', *-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 51a )=*', *=C(Z 51a )-*', *-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*', X 52 is a single bond, *-N(Z 52a )-*', *-B(Z 52a )-*', *-P(Z 52a )-*', *-C(Z 52a )(Z 52b )-*', *-Si(Z 52a )(Z 52b )-*', *-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 52a )=*', *=C(Z 52a )-*', *-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*', R1 to R4, Z 51a , Z 51b , Z 52a , Z 52b and T1 to T4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -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 a4 are each independently an integer from 0 to 10, c1 is an integer from 1 to 3, c2 and c4 are each independently an integer from 1 to 5, c3 is an integer from 1 to 4, In Formula 1A, The groups represented by The groups represented are different from each other, Selected from R1, R2, R3, R4, Z 51a , Z 51b , Z 52a , Z 52b , T1, T2, T3 and T4 are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, * and *' each represent a binding site with an adjacent atom, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; 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; a hydroxyl group; a cyano group; a nitro group; or each is unsubstituted or substituted with deuterium, -F, a cyano group, a C1-C 60 Alkyl groups, C1-C 60 C1-C2-substituted alkyl groups, phenyl groups, biphenyl groups or a combination thereof 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, Formula 3 as well as Among them, in formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 a cyclic group or a pyridine group, X 71 is a single bond, or a linking group comprising O, S, N, B, C, Si or a combination thereof, and * in Formula 3 represents a bonding site with an atom not included in the third compound in Formula 3.
2. A light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; as well as An organometallic compound represented by Formula 1: Formula 1 Formula 1A Wherein Ar1 in Formula 1 is a group represented by Formula 1A, * in Formula 1A represents the binding site with ring CY1 in Formula 1, In Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, X1 to X4 are each independently C or N, i) The bond between X1 and M is a coordination bond, ii) one selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and two selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M are each covalent bonds, Ring CY1 to Ring CY4 are each independently C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, X 51 is a single bond, *-N(Z 51a )-*', *-B(Z 51a )-*', *-P(Z 51a )-*', *-C(Z 51a )(Z 51b )-*', *-Si(Z 51a )(Z 51b )-*', *-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 51a )=*', *=C(Z 51a )-*', *-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*', X 52 is a single bond, *-N(Z 52a )-*', *-B(Z 52a )-*', *-P(Z 52a )-*', *-C(Z 52a )(Z 52b )-*', *-Si(Z 52a )(Z 52b )-*', *-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 52a )=*', *=C(Z 52a )-*', *-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*', R1 to R4, Z 51a , Z 51b , Z 52a , Z 52b and T1 to T4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -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 a4 are each independently an integer from 0 to 10, c1 is an integer from 1 to 3, c2 and c4 are each independently an integer from 1 to 5, c3 is an integer from 1 to 4, In Formula 1A, The groups represented by The groups represented are different from each other, Selected from R1, R2, R3, R4, Z 51a , Z 51b , Z 52a , Z 52b , T1, T2, T3 and T4 are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, * and *' each represent a binding site with an adjacent atom, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; 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 each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or each is unsubstituted or substituted with deuterium, -F, a cyano group, a C1-C 60 Alkyl groups, C1-C 60 C1-C2-substituted alkyl groups, phenyl groups, biphenyl groups or a combination thereof 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.
3. The light emitting device of claim 2, further comprising a nitrogen-containing C1-C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 3 as well as in, In formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 a cyclic group or a pyridine group, X 71 is a single bond, or a linking group comprising O, S, N, B, C, Si or a combination thereof, and * in Formula 3 represents a bonding site with an atom not included in the third compound in Formula 3.
4. The light-emitting device of claim 3, wherein the second compound comprises a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a combination thereof, and 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 of claim 3, wherein the emitting layer comprises: i) the organometallic compound represented by Formula 1; and ii) the second compound, the third compound, the fourth compound or a combination thereof, and The emitting layer is configured to emit blue light. 6 . The light emitting device of claim 3 , comprising the second compound and the third compound, wherein at least one of the second compound and the third compound comprises 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 of claim 7, further comprising a color filter, a color conversion layer, a touch screen layer, a polarization layer, or a combination thereof.
9. Electronic equipment comprising the light emitting device according to any one of claims 2 to 6.
10. The electronic equipment of claim 9, wherein the electronic equipment is selected from at least one of 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 stitched together, a theater screen, a stadium screen, a light therapy device, and a sign, or a combination thereof.
11. An organometallic compound represented by Formula 1: Formula 1 Formula 1A Wherein Ar1 in Formula 1 is a group represented by Formula 1A, * in Formula 1A represents the binding site with ring CY1 in Formula 1, In Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, X1 to X4 are each independently C or N, i) The bond between X1 and M is a coordination bond, ii) one selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and two selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M are each covalent bonds, Ring CY1 to Ring CY4 are each independently C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, X 51 is a single bond, *-N(Z 51a )-*', *-B(Z 51a )-*', *-P(Z 51a )-*', *-C(Z 51a )(Z 51b )-*', *-Si(Z 51a )(Z 51b )-*', *-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 51a )=*', *=C(Z 51a )-*', *-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*', X 52 is a single bond, *-N(Z 52a )-*', *-B(Z 52a )-*', *-P(Z 52a )-*', *-C(Z 52a )(Z 52b )-*', *-Si(Z 52a )(Z 52b )-*', *-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 52a )=*', *=C(Z 52a )-*', *-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*', R1 to R4, Z 51a , Z 51b , Z 52a , Z 52b and T1 to T4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, 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 groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -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 a4 are each independently an integer from 0 to 10, c1 is an integer from 1 to 3, c2 and c4 are each independently an integer from 1 to 5, c3 is an integer from 1 to 4, In Formula 1A, The groups represented by The groups represented are different from each other, Selected from R1, R2, R3, R4, Z 51a , Z 51b , Z 52a , Z 52b , T1, T2, T3 and T4 are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, * and *' each represent a binding site with an adjacent atom, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; 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; a hydroxyl group; a cyano group; a nitro group; or each is unsubstituted or substituted with deuterium, -F, a cyano group, a C1-C 60 Alkyl groups, C1-C 60 C1-C2-substituted alkyl groups, phenyl groups, biphenyl groups or a combination thereof 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.
12. The organometallic compound of claim 11, wherein X1 is C, and Ring CY1 is an imidazole group, a triazole group, a benzimidazole group, a naphthimidazole group or an imidazopyridine group.
13. The organometallic compound according to claim 11, wherein R1 to R4, Z 51a , Z 51b , Z 52a , Z 52b and T1 to T4 are each independently: hydrogen, deuterium, -F or a cyano group; unsubstituted or deuterated, -F, cyano group, phenyl group, deuterated phenyl group, fluorophenyl group, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C1-C 20 an alkyl group; or Each unsubstituted or deuterated, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl groups, fluorinated C1-C 20 Alkyl group, phenyl group, deuterated phenyl group, fluorophenyl group, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C3-C 10 a cycloalkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group or a dibenzothienyl group.
14. The organometallic compound of claim 11, wherein T1 to T4 are each independently: hydrogen, deuterium, -F or a cyano group; or C1-C2- 20 Alkyl group.
15. The organometallic compound of claim 11, comprising at least one deuterium.
16. The organometallic compound according to claim 11, wherein Formula 1A satisfies one selected from Condition C1 to Condition C3: Condition C1 T1 is hydrogen or deuterium; Condition C2 The one in T1 is: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T1 is hydrogen or deuterium; and Condition C3 The two in T1 are independently: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T1 is hydrogen or deuterium.
17. The organometallic compound according to claim 11, wherein Formula 1A satisfies one selected from Condition D1 to Condition D4: Condition D1 T2 is hydrogen or deuterium; Condition D2 One of T2 is: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T2 is hydrogen or deuterium; Condition D3 The two in T2 are independently: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T2 is hydrogen or deuterium; and Condition D4 The three in T2 are independently: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T2 is hydrogen or deuterium.
18. The organometallic compound according to claim 11, wherein Formula 1A satisfies one selected from Conditions E1 to E3: Condition E1 T3 is hydrogen or deuterium; Condition E2 One of the T3 ones is: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T3 is hydrogen or deuterium; and Condition E3 The two in T3 are independently: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T3 is either hydrogen or deuterium.
19. The organometallic compound according to claim 11, wherein Formula 1A satisfies one selected from Conditions F1 to F4: Condition F1 T4 is hydrogen or deuterium; Condition F2 One of the T4 ones is: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T4 is hydrogen or deuterium; Condition F3 The two in T4 are independently: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T4 is hydrogen or deuterium; and Condition F4 The three in T4 are independently: C1-C2 unsubstituted or substituted with at least one deuterium 20 an alkyl group; or Unsubstituted or deuterated, C1-C 20 Alkyl groups, deuterated C1-C 20 C6-C 20 Aryl groups, and Any remaining T4 is either hydrogen or deuterium.
20. The organometallic compound according to claim 11, wherein the organometallic compound is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 And among them, In formula 1-1 and formula 1-2, M, X1 to X4, X 51 , T1 to T4 and c1 to c4 are each as described in Formula 1 and Formula 1A, X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, and X 14 is C(R 14 ) or N, R 11 To R 14 Each is as described for R1 of Formula 1, wherein R 11 To R 14 Two or more of the R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, and X 23 is C(R 23 ) or N, R 21 To R 23 Each is as described for R2 of Formula 1, wherein R 21 To R 23 Two or more of the R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Heterocyclic groups, X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, X 34 is C(R 34 ) or N, X 35 is C(R 35 ) or N, and X 36 is C(R 36 ) or N, R 31 To R 36 Each is as described for R3 of Formula 1, wherein R 31 To R 36 Two or more of the R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Heterocyclic groups, X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N, R 41 To R 44 Each is as described for R4 of Formula 1, wherein R 41 To R 44 Two or more of the R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Heterocyclic groups, Depend on The groups represented by The groups represented are different from each other, and * indicates the binding site with the adjacent atom, R 10a Same as defined in claim 11.
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