Light emitting device including organometallic compound, electronic device and electronic apparatus including same, and organometallic compound
By using organometallic compounds and auxiliary dopants as emission layer materials in the light emitting device, the problems of insufficient color purity, luminous efficiency and lifetime in the prior art are solved, and the goal of high-performance light emitting devices is achieved.
Patent Information
- Application Number
- CN202410942135.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-08-07
- Filing Date
- 2024-07-15
- Publication Date
- 2025-02-14
AI Technical Summary
Existing light emitting devices have shortcomings in color purity, luminous efficiency and lifetime, and it is difficult to meet high-performance requirements.
Organometallic compounds represented by Formula 1-1 or Formula 1-2 are used as the emission layer material, combined with auxiliary dopants to improve luminescence efficiency and color purity, and to extend device life by optimizing electrode structure and intermediate layer design.
It realizes high color purity of light emitting devices, improves luminous efficiency, and extends the service life of the device, meeting the needs of high-performance light emitting devices.
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Figure CN119451531A_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0103126 filed in the Korean Intellectual Property Office on August 7, 2023, the contents of which are incorporated herein by reference in their entirety. Technical Field
[0002] One or more aspects of the embodiments of the present disclosure relate to a light emitting device including an organic metal compound, an electronic device and an electronic device including the light emitting device, and the organic metal compound. Background Art
[0003] Among light emitting devices, self-emitting devices have relatively wide viewing angles, relatively high contrast ratios, relatively short response times, and excellent or suitable characteristics in terms of brightness, driving voltage, and response speed.
[0004] In the light-emitting device, a first electrode may be arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode may be arranged sequentially on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. Excitons may transition (i.e., relax) from an excited state to a ground state, thereby generating light. Summary of the invention
[0005] One or more aspects of the embodiments of the present disclosure relate to a light emitting device including an organic metal compound, an electronic device and an electronic device including the light emitting device, and the organic metal compound.
[0006] 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 disclosed.
[0007] According to one or more embodiments, a light emitting device includes:
[0008] a first electrode;
[0009] a second electrode facing the first electrode; and
[0010] an intermediate layer, arranged between the first electrode and the second electrode and including an emission layer,
[0011] Wherein, the light-emitting device further comprises an organic metal compound represented by Formula 1-1 or Formula 1-2:
[0012] Formula 1-1
[0013]
[0014] Formula 1-2
[0015]
[0016] Among them, in formula 1-1 and formula 1-2,
[0017] M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm),
[0018] X 1 To X 4 can all independently be C or N,
[0019] Cyclo 1 CY 2 CY 31 To Ring CY 33 and CY 4 can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0020] L 1 To L 3 can be independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*', where * and *' both represent the binding sites with adjacent atoms,
[0021] n1 to n3 may each independently be an integer from 1 to 5,
[0022] T 1 Can be *-C(Z 1 )(Z 2 )-*'、*-Si(Z 1 )(Z 2 )-*'or*-Ge(Z 1 )(Z 2 )-*', where * and *' both represent the binding sites with adjacent atoms,
[0023] R 1 , R 2 , R 31 To R 33 , R 4 , R 1a and R 1b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, -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 ),
[0024] a1, a2, a31 to a33 and a4 may each independently be an integer from 1 to 20,
[0025] Z 1 and Z 2 may be independently unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, -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 ),
[0026] R with quantity a1 1 , the number of R is a2 2 , the number of R is a31 31 , the number of R is a32 32 , the number of R is a33 33 and R with quantity a4 4 Two or more adjacent groups in may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0027] Z 1 and Z 2 may optionally be combined with each other to form unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0028] Z 1 or Z 2 Can optionally be combined with R 31 To R 33 One or more rings CY 31 To Ring CY 33 to form an unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0029] R 10a It can be:
[0030] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,
[0031] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, -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 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy,
[0032] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, -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 3 -C60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 arylthio, or
[0033] -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
[0034] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, or
[0035] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0036] According to one or more embodiments, an electronic device includes a light emitting device.
[0037] According to one or more embodiments, an electronic device includes a light emitting device.
[0038] According to one or more embodiments, an organometallic compound represented by Formula 1-1 or Formula 1-2 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0039] The accompanying drawings are included to provide a further understanding of the foregoing and other aspects, features and advantages of certain embodiments of the present disclosure, and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate example 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:
[0040] Figure 1 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0041] Figure 2 is a schematic cross-sectional view of a structure of an electronic device according to one or more embodiments of the present disclosure;
[0042] Figure 3 is a schematic cross-sectional view of a structure of an electronic device according to one or more embodiments of the present disclosure;
[0043] Figure 4 is a schematic perspective view of a structure of an electronic device including a light emitting device according to one or more embodiments of the present disclosure;
[0044] Figure 5 is a perspective view of the exterior of a vehicle as an electronic device including a light emitting device according to one or more embodiments of the present disclosure; and
[0045] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle including an electronic device including a light emitting device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0046] Reference will now be made in more detail to embodiments of the present disclosure, examples of which are shown in the accompanying drawings, wherein the same reference numerals always refer to the same elements, and a repeated description thereof may not be provided. In this regard, the embodiments provided may have different forms and should not be construed as being limited to the descriptions set forth herein. Therefore, the embodiments are described only by reference to the accompanying drawings to explain aspects of the present specification.
[0047] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one of...", "one of...", and "selected from...", when preceding / preceding a list of elements, modify the entire list of elements, not the individual elements of the list. For example, throughout the disclosure, the expression "at least one of a, b, and c" means only a, only b, only c, (e.g., simultaneously) both a and b, (e.g., simultaneously) both a and c, (e.g., simultaneously) both b and c, all of a, b, and c, or variations thereof.
[0048] The term used herein is for the purpose of describing the embodiment, and is not intended to limit the embodiments described herein. Unless otherwise defined, all chemical names, technical terms and scientific terms and the terms defined in the common dictionary should be interpreted as having the meaning consistent with their meaning in the context of the relevant field, and should not be interpreted with idealized or overly formalized meanings. It will be understood that, although the term first and / or second etc. can be used to describe various elements here, 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.
[0049] 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.
[0050] It will also be understood that when the terms "includes," "has," "comprising" and / or variations thereof are used in this specification, it indicates the presence of stated features, steps, operations, elements and / or components, but does not preclude the presence or addition of one or more other features, steps, operations, elements, components and / or groups thereof.
[0051] As used herein, the term "use" and variations thereof may be considered synonymous with the term "utilize" and variations thereof, respectively.
[0052] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.
[0053] The term "may" will be understood to mean that some of the "one or more embodiments of the present disclosure" include the described elements, and some of them exclude the elements and / or include alternative elements. Similarly, alternative language such as "or" means that the "one or more embodiments of the present disclosure" each include the corresponding listed items.
[0054] It will be understood that when an element is referred to as being "on," "connected to," or "coupled to" another element, it can be directly on, directly connected to, or directly coupled to the other element, or one or more intervening elements may be present. When an element is referred to as being "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements.
[0055] 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 of one element or feature to another (additional) element or feature as shown in the accompanying drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the accompanying drawings. For example, if the device in the accompanying drawings is turned over, an element described as "below" or "beneath" other elements or features will subsequently be positioned as "above" or "on" the other elements or features. Thus, the term "under" may include both orientations above and below. The device may be otherwise positioned (rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
[0056] As used herein, "consisting essentially of" means that any additional components will not substantially affect the chemical, physical, optical, or electrical properties of the semiconductor film.
[0057] Furthermore, in this specification, the phrase "on a plane" or "plan view" means viewing a target portion from the top, and the phrase "on a cross section" means viewing a cross section formed by vertically cutting the target portion from the side.
[0058] The disclosed aspect provides a light emitting device, the light emitting device comprising:
[0059] a first electrode;
[0060] a second electrode facing the first electrode; and
[0061] an intermediate layer, arranged between the first electrode and the second electrode and including an emission layer,
[0062] Wherein, the light-emitting device further comprises an organic metal compound represented by Formula 1-1 or Formula 1-2:
[0063] Formula 1-1
[0064]
[0065] Formula 1-2
[0066]
[0067] Wherein, Formula 1-1 and Formula 1-2 may both be as described herein.
[0068] In one or more embodiments,
[0069] The first electrode of the light emitting device may be an anode,
[0070] The second electrode of the light emitting device may be a cathode,
[0071] The intermediate layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode.
[0072] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0073] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0074] In one or more embodiments, the intermediate layer of the light emitting device may include the organic metal compound represented by Formula 1-1 or Formula 1-2.
[0075] In one or more embodiments, the emission layer of the light emitting device may include the organic metal compound represented by Formula 1-1 or Formula 1-2.
[0076] In one or more embodiments, the emission layer of the light emitting device may include a dopant and a host, and the dopant may include an organic metal compound represented by Formula 1-1 or Formula 1-2. For example, the organic metal compound may act as a dopant. For example, the emission layer may emit (e.g., be configured to emit) blue light. The blue light may have a maximum emission wavelength in the range of, for example, about 430 nm to about 480 nm.
[0077] In one or more embodiments, the electron transport region of the light emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may directly contact the emission layer.
[0078] In one or more embodiments, the light emitting device may further include a nitrogen-containing C 1 -C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
[0079] The organometallic compound, the second compound, the third compound and the fourth compound in the light-emitting device may be different from each other:
[0080] Formula 3
[0081]
[0082] Among them, in formula 3,
[0083] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0084] X 71 can be a single bond or a linker comprising O, S, N, B, C, Si or any combination thereof, and
[0085] * represents a bonding position with any atom included in the remaining part other than the group represented by Formula 3 of the third compound.
[0086] In one or more embodiments, the organometallic compound can include at least one deuterium.
[0087] In one or more embodiments, the second to fourth compounds may each include at least one deuterium.
[0088] In one or more embodiments, the second compound may include at least one silicon.
[0089] In one or more embodiments, the third compound may include at least one silicon.
[0090] In one or more embodiments, in addition to the organic metal compound represented by Formula 1-1 or Formula 1-2, the light-emitting device may further include a second compound and a third compound, wherein at least one of the second compound and the third compound may include at least one deuterium, at least one silicon, or a combination thereof.
[0091] In one or more embodiments, in addition to the organometallic compound, the light emitting device (e.g., the emission layer in the light emitting device) may further include a second compound. At least one of the organometallic compound and the second compound may include at least one deuterium. For example, in addition to the organometallic compound and the second compound, 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.
[0092] In one or more embodiments, in addition to the organometallic compound, the light emitting device (e.g., the emission layer in the light emitting device) may further include a third compound. At least one of the organometallic compound and the third compound may include at least one deuterium. For example, in addition to the organometallic compound and the third compound, 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.
[0093] In one or more embodiments, in addition to the organometallic compound, the light emitting device (e.g., an emission layer in a light emitting device) may 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 serve to improve the color purity, luminous efficiency, and life characteristics of the light emitting device. For example, in addition to the organometallic compound and the fourth compound, the light emitting device (e.g., an emission layer in a light emitting device) may further include a second compound, a third compound, or any combination thereof.
[0094] In one or more embodiments, in addition to the organometallic compound, the light emitting device (e.g., an emission layer in the light emitting device) may further include a second compound and a third compound. The second compound and the third compound may form an exciplex. At least one of the organometallic compound, the second compound, and the third compound may include at least one deuterium.
[0095] In one or more embodiments, the emission layer of the light emitting device may include: i) an organic metal compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, wherein the emission layer may emit (eg, be configured to emit) blue light.
[0096] In one or more embodiments, the blue light can have a maximum emission wavelength in the range of about 430nm to about 480nm, 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, about 450nm to about 465nm, about 430nm to about 460nm, about 440nm to about 460nm, or about 450nm to about 460nm.
[0097] In one or more embodiments, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
[0098] In one or more embodiments, the following compounds may be excluded from the third compound (eg, the following compounds may not be included in the third compound):
[0099]
[0100] In the present disclosure, a "compound" that may be "not included in the 'compound'" and / or "excluded from the 'compound'", etc., means that the "compound" is not added, selected or used as a "compound" or component in the composition, but due to other impurities and / or external factors, the "excluded" compound may still be included in an appropriate amount.
[0101] In one or more embodiments, the difference between the triplet energy level (electron volts (eV)) of the fourth compound and the singlet energy level (eV) of the fourth compound may be 0 eV or more and 0.5 eV or less (or 0 eV or more and 0.3 eV or less).
[0102] In one or more embodiments, the fourth compound may be a compound including at least one ring group including boron (B) and nitrogen (N) as ring-constituting atoms.
[0103] In one or more embodiments, the fourth compound may be a C-containing compound including at least two condensed ring groups sharing boron (B). 8 -C 60 Polycyclic compounds.
[0104] In one or more embodiments, the fourth compound may include a condensed ring in which at least one third ring is condensed with at least one fourth ring,
[0105] 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
[0106] 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.
[0107] In one or more embodiments, the third compound may not include (eg, may exclude) the compound represented by Formula 3-1 described herein.
[0108] In one or more embodiments, the second compound may include a compound represented by Formula 2:
[0109] Formula 2
[0110]
[0111] Among them, in formula 2,
[0112] L 51 To L 53 may each independently be a single bond, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0113] b51 to b53 may each independently be an integer from 1 to 5,
[0114] 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 can be N, and
[0115] R 51 To R 56 and R 10a May be as described herein.
[0116] In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0117] Formula 3-1
[0118]
[0119] Formula 3-2
[0120]
[0121] Formula 3-3
[0122]
[0123] Formula 3-4
[0124]
[0125] Formula 3-5
[0126]
[0127] Among them, in Formula 3-1 to Formula 3-5,
[0128] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0129] 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 ),
[0130] X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0131] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0132] X 85 Can be C or Si,
[0133] L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or substituted with at least one R 10a The π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R10a A pyridine group, wherein Q 4 and Q 5 You can refer to Q 1 As described,
[0134] b81 to b85 may each independently be an integer from 1 to 5,
[0135] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b can be as described herein,
[0136] a71 to a74 may each independently be an integer from 0 to 20, and
[0137] R 10a May be as described herein.
[0138] In one or more embodiments, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0139] Formula 502
[0140]
[0141] Formula 503
[0142]
[0143] Among them, in equation 502 and equation 503,
[0144] Ring A 501 To Ring A 504 can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0145] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0146] Y 506 Can be O, S, N (R506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0147] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0148] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0149] Y 51 and Y 52 may be independently B, P(=O) or S(=O),
[0150] R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b may be as described herein, and
[0151] a501 to a504 may each independently be an integer of 0 to 20.
[0152] In one or more embodiments, the light emitting device may satisfy at least one of conditions 1 to 4 (for example, at least one selected from conditions 1 to 4):
[0153] Condition 1
[0154] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound > the LUMO energy level (eV) of the organometallic compound
[0155] Condition 2
[0156] LUMO energy level of the organometallic compound (eV) > LUMO energy level of the second compound (eV)
[0157] Condition 3
[0158] The highest occupied molecular orbital (HOMO) energy level (eV) of the organometallic compound is greater than the HOMO energy level (eV) of the third compound.
[0159] Condition 4
[0160] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.
[0161] 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.
[0162] 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 0.1 eV or greater and 1.0 eV or less, or 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 0.1 eV or greater and 1.0 eV or less, and 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 1.25 eV or less (e.g., 1.25 eV or less and 0.2 eV or greater), or the absolute value of the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the third compound may be 1.25 eV or less (e.g., 1.25 eV or less and 0.2 eV or greater).
[0163] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions as described, a balance between holes and electrons injected into the emission layer can be achieved.
[0164] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0165] First embodiment
[0166] According to a first embodiment, an organic metal compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may also include a host, the organic metal compound may be different from the host, and the emission layer may emit (e.g., be configured to emit) phosphorescence or fluorescence emitted from the organic metal compound. For example, according to the first embodiment, the organic metal compound may be a dopant or an emitter. For example, the organic metal compound may be a phosphorescent dopant or a phosphorescent emitter.
[0167] The phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
[0168] 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 efficiently transferring energy to the organometallic compound as a dopant or an emitter.
[0169] The auxiliary dopant may be different from the organometallic compound and the host.
[0170] In one or more embodiments, the auxiliary dopant may be a delayed fluorescence emission compound.
[0171] In one or more embodiments, the auxiliary dopant may be a compound including at least one ring group including boron (B) and nitrogen (N) as ring-forming atoms.
[0172] Second embodiment
[0173] According to a second embodiment, an organic metal compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may also 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 emit (e.g., be constructed to emit) phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
[0174] In one or more embodiments, the organometallic compound in the second embodiment may not be used as a dopant, but as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0175] In one or more embodiments, the organometallic compound in the second embodiment may be used as an emitter and may also be used as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0176] For example, phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0177] The dopant (or emitter) in the second embodiment can be a phosphorescent dopant material (e.g., an organic metal compound represented by Formula 1-1 or Formula 1-2 described herein, an organic metal compound represented by Formula 401 described herein, or any combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501 described herein, a compound represented by Formula 502 described herein, a compound represented by Formula 503 described herein, or any combination thereof).
[0178] The blue light in the first and second embodiments may be blue light having a maximum emission wavelength in the range 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.
[0179] The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0180] The host in the first and second embodiments may be any host material (eg, the compound represented by Formula 301, the compound represented by Formula 301-1, the compound represented by Formula 301-2, or any combination thereof).
[0181] In one or more embodiments, the subject in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
[0182] In one or more embodiments, the light emitting device may further include a cover layer disposed outside the first electrode and / or outside the second electrode.
[0183] In one or more embodiments, the light emitting device may further include at least one of a first covering layer arranged outside the first electrode and a second covering layer arranged outside the second electrode, wherein the organic metal compound represented by Formula 1-1 or Formula 1-2 may be included in at least one of the first covering layer and the second covering layer. The first covering layer and / or the second covering layer may be as described herein.
[0184] In one or more embodiments, the light emitting device may include:
[0185] A first covering layer disposed outside the first electrode and including an organic metal compound represented by Formula 1-1 or Formula 1-2;
[0186] A second covering layer disposed outside the second electrode and including an organic metal compound represented by Formula 1-1 or Formula 1-2; or
[0187] A first covering layer and a second covering layer.
[0188] The expression "(the intermediate layer and / or the covering layer) includes the organic metal compound represented by Formula 1-1 or Formula 1-2" as used herein may be understood as "(the intermediate layer and / or the covering layer) may include at least one organic metal compound represented by Formula 1-1 or Formula 1-2 or two or more different kinds of organic metal compounds both represented by Formula 1-1 or Formula 1-2".
[0189] In one or more embodiments, the intermediate layer and / or the covering layer may include 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 include compound 1 and compound 2 as organic metal compounds. In this regard, compound 1 and compound 2 may be present in substantially the same layer (e.g., both compound 1 and compound 2 may be present (e.g., simultaneously) 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).
[0190] The term "intermediate layer" as used herein refers to a single layer and / or all of a plurality of layers disposed between a first electrode and a second electrode of a light emitting device.
[0191] Another aspect of the disclosure provides an electronic device including a light emitting device. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. The electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. More details about the electronic device may be the same as described herein.
[0192] Another aspect of the disclosure provides an electronic device including a light emitting device.
[0193] For example, the electronic device can be at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor 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 stretchable display, a laser printer, a phone (e.g., a mobile phone, a tablet phone), a tablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display 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, a sign, and one or more combinations thereof.
[0194] Another aspect of the disclosure provides an organometallic compound represented by Formula 1-1 or Formula 1-2. Details regarding Formula 1-1 or Formula 1-2 may be as described herein.
[0195] By referring to the synthetic examples and / or examples provided, one of ordinary skill in the art can recognize methods for synthesizing organometallic compounds.
[0196] Description of Formula 1-1 and Formula 1-2
[0197] Formula 1-1
[0198]
[0199] Formula 1-2
[0200]
[0201] In Formula 1-1 and Formula 1-2, M can be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm).
[0202] In one or more embodiments, M may be Pt, Pd, or Au.
[0203] In one or more embodiments, M may be Pt.
[0204] In formula 1-1 and formula 1-2, X 1 To X 4 can all independently be C or N.
[0205] In one or more embodiments, X 1 It can be C.
[0206] In one or more embodiments, X 1 Can be C, and X 1 The bond with M may be a coordinate bond.
[0207] In one or more embodiments, X 1 It may be C of a carbene moiety.
[0208] In one or more embodiments, X 2 and X 3 Can be C, and X 4 Can be N.
[0209] In one or more embodiments, i) X 1 The bond between X and M may be a coordination bond, ii) 2 The key between M and X 3 The bond between M and X 4 One of the bonds to M may be a coordinate bond, and the other two may both be covalent bonds.
[0210] In one or more embodiments, X 1 The bond between M and X 4 The bonds between X and M can all be coordination bonds, and X 2The bond between M and X 3 The bonds with M may all be covalent bonds.
[0211] In one or more embodiments, X 1 , X 2 and X 3 Can be C, X 4 Can be N, X 1 The bond between M and X 4 The bonds between X and M can all be coordination bonds, and X 2 The bond between M and X 3 The bonds with M may all be covalent bonds.
[0212] In Formula 1-1 and Formula 1-2, ring CY 1 CY 2 CY 31 To Ring CY 33 and CY 4 can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group.
[0213] In one or more embodiments, CY 1 CY 2 CY 31 To Ring CY 33 and CY 4 can all independently be:
[0214] Benzene group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, 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 benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole 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, The invention also includes but is not limited to oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, dibenzooxasilane group, dibenzothiasilane group, dibenzodihydroazasilane group, dibenzodihydrodisilane group, dibenzodihydrosilane group, dibenzodioxane group, dibenzooxathiainene group, dibenzoxazine group, dibenzopyran group, dibenzodithiainene group, dibenzothiazine group, dibenzothiopyran group, dibenzocyclohexadiene group, dibenzodihydropyridine group or dibenzodihydropyrazine group.
[0215] In one or more embodiments, CY 1 It can be nitrogen-containing C 1 -C 60 Heterocyclic group.
[0216] In one or more embodiments, CY 1 It may be an imidazole group, a triazole group, a benzimidazole group, a naphthyimidazole group or an imidazopyridine group.
[0217] In one or more embodiments, X 1 Can be C, and
[0218] Cyclo 1 It may be an imidazole group, a triazole group, a benzimidazole group, a naphthimidazole group or an imidazopyridine group.
[0219] In one or more embodiments, X 1 may be C of the carbene portion, and
[0220] Cyclo 1 It may be an imidazole group, a triazole group, a benzimidazole group, a naphthimidazole group or an imidazopyridine group.
[0221] In one or more embodiments, CY 2It can be a phenyl group, a pyridine group, a pyrimidine group, a naphthalene 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 azadiphenylamine group, The present invention relates to an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group, an oxadiazine group
[0222] In one or more embodiments, CY 2 It may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group or a dibenzosilole group.
[0223] In one or more embodiments, CY 31 To Ring CY 33 can all independently be:
[0224] 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.
[0225] In one or more embodiments, CY 4 It can be nitrogen-containing C 1 -C 60 Heterocyclic group.
[0226] In one or more embodiments, CY 4 It may be 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, a benzopyrazole group, a benzimidazole group or a benzothiazole group.
[0227] In formula 1-1 and formula 1-2, L 1 To L 3 can be independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*'. * and *' both represent the binding sites with adjacent atoms.
[0228] In Formula 1-1 and Formula 1-2, n1 to n3 represent L 1 To L 3 The number of L can be independently an integer from 1 to 5. When n1 is 2 or more, L 1 Two or more of them may be the same or different from each other. When n2 is 2 or greater, L 2 Two or more of L may be the same as or different from each other, and when n3 is 2 or greater, L 3 Two or more of may be the same as or different from each other.
[0229] In one or more embodiments, L 1 and L 3 They can all be single bonds.
[0230] In one or more embodiments, L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0231] In one or more embodiments, L 1 and L 3 can all be single bonds, and
[0232] L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0233] In formula 1-1 and formula 1-2, R 1a and R 1b can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, -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 ).
[0234] R 10a and Q 1 To Q 3 May be as described herein.
[0235] In one or more embodiments, R 1a and R 1b can all independently be:
[0236] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20Alkoxy;
[0237] All substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0238] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q31 )(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 any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl; or
[0239] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0240] Q 1 To Q 3 and Q 31 To Q 33can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy; or
[0241] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0242] In formula 1-1 and formula 1-2, T 1 Can be *-C(Z 1 )(Z 2 )-*'、*-Si(Z 1 )(Z 2 )-*'or*-Ge(Z 1 )(Z 2 )-*'. * and *' both represent the binding sites with adjacent atoms.
[0243] In formula 1-1 and formula 1-2, Z 1 and Z 2 may be independently: unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, -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 ).
[0244] R 10a and Q 1 To Q 3 May be as described herein.
[0245] In one or more embodiments, Z 1 and Z 2 can all independently be:
[0246] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0247] All substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C1 -C 20 Alkoxy;
[0248] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl; or
[0249] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0250] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy; or
[0251] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C1 -C 60 Heterocyclic group.
[0252] In one or more embodiments, Z 1 and Z 2 can all independently be:
[0253] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0254] All substituted with deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0255] Unsubstituted or substituted with deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl; or
[0256] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -N(Q 1 )(Q 2 ),and
[0257] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen, deuterium, -F, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, or
[0258] All are unsubstituted or substituted with deuterium, -F, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0259] In one or more embodiments, Z 1 and Z 2 can all independently be:
[0260] C 1 -C 20 alkyl;
[0261] Substituted with deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1-C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl or any combination thereof 1 -C 20 alkyl;
[0262] All are unsubstituted or substituted with deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl or naphthyl; or
[0263] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0264] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen, deuterium, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl or C 2 -C 60 Alkynyl; unsubstituted or substituted with deuterium, C 1 -C 60 C alkyl, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic group.
[0265] In one or more embodiments, Z 1 and Z 2 may optionally be combined with each other to form unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1 -C 60 Heterocyclic group.
[0266] In formula 1-1 and formula 1-2, R 1 , R 2 and R 31 To R 33 can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, -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 ).
[0267] R 10aand Q 1 To Q 3 May be as described herein.
[0268] In one or more embodiments, R 1 , R 2 , R 31 To R 33 and R 4 can all independently be:
[0269] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0270] All substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0271] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl; or
[0272] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0273] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy; or
[0274] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0275] In one or more embodiments, R 1 , R 2 , R 31 To R 33 and R 4 can all independently be:
[0276] Hydrogen, deuterium, -F, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0277] All substituted with deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0278] Unsubstituted or substituted with deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl; or
[0279] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -N(Q 1 )(Q 2 ),and
[0280] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or unsubstituted or substituted with deuterium, -F, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0281] In one or more embodiments, R 1 , R 2 , R 31 To R 33 and R 4 can all independently be:
[0282] Hydrogen, deuterium or C 1 -C 20 alkyl;
[0283] Substituted with deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl or any combination thereof 1 -C 20 alkyl;
[0284] All are unsubstituted or substituted with deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q33 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl or naphthyl; or
[0285] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0286] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; or
[0287] Unsubstituted or substituted with deuterium, C 1 -C 60 C alkyl, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic group.
[0288] In one or more embodiments, at least one R 1 It may be a group represented by formula S1:
[0289]
[0290] Wherein, in Formula S1,
[0291] R 111 To R 113 Can be referred to as R 1 As described,
[0292] a111 can be an integer from 1 to 5,
[0293] a112 can be an integer from 1 to 3,
[0294] a113 can be an integer from 1 to 5, and
[0295] *Indicates the binding site with the adjacent atom.
[0296] In Formula 1-1 and Formula 1-2, a1, a2, a31 to a33 and a4 represent R 1 , R2 , R 31 To R 33 and R 4 and may be independently an integer from 1 to 20. When a1 is 2 or greater, R 1 Two or more of them may be the same or different from each other. When a2 is 2 or greater, R 2 Two or more of them may be the same or different from each other. When a31 is 2 or greater, R 31 Two or more of them may be the same or different from each other. When a32 is 2 or greater, R 32 Two or more of them may be the same or different from each other. When a33 is 2 or greater, R 33 Two or more of them may be the same or different from each other. When a4 is 2 or greater, R 4 Two or more of may be the same as or different from each other.
[0297] In one or more embodiments, the number of R 1 , the number of R is a2 2 , the number of R is a31 31 , the number of R is a32 32 , the number of R is a33 33 and R with quantity a4 4 Two or more adjacent groups in may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group.
[0298] In one or more embodiments, Z 1 or Z 2 Can optionally be combined with R 31 To R 33 One or more rings CY 31 To Ring CY 33 to form an unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group.
[0299] In formula 1-1 and formula 1-2, The group represented may be a group represented by at least one of formula CY1(1) to formula CY1(11):
[0300]
[0301]
[0302] Among them, in formula CY1(1) to formula CY1(11),
[0303] R 11 To R 17 Can be referred to as R 1 As described,
[0304] * represents the binding site with M in Formula 1-1 or Formula 1-2, and
[0305] *' represents the same as L in Formula 1-1 or Formula 1-2 1 The combination position.
[0306] In formula 1-1 and formula 1-2, The group represented may be a group represented by at least one of formula CY2(1) to formula CY2(13):
[0307]
[0308] Among them, in formula CY2(1) to formula CY2(13),
[0309] T 21 It can be B(Y 21 )、C(Y 21 )(Y 22 )、N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 It can be C(Y 21 ), N or Si(Y 21 ),
[0310] R 21 To R 26 , Y 21 and Y 22 Can be referred to as R 2 As described,
[0311] * represents the binding position with M in Formula 1-1 or Formula 1-2,
[0312] *' represents the same as L in Formula 1-1 or Formula 1-2 1 The binding site of
[0313] *" indicates the same as L in Formula 1-1 or Formula 1-2 2 The combination position.
[0314] In formula 1-1, The group represented by may be a group represented by at least one of Formula CY3-1(1) to Formula CY3-1(6), and
[0315] In formula 1-2, The group represented may be a group represented by formula CY3-2(1) or formula CY3-2(2):
[0316]
[0317] In Formula CY3-1(1) to Formula CY3-1(6), Formula CY3-2(1) and Formula CY3-2(2), X 311 It can be C(R 311 ) or N, and X 312 It can be C(R 312 ) or N,
[0318] X 321 It can be C(R 321 ) or N, X 322 It can be C(R 322 ) or N, X 323 It can be C(R 323 ) or N, and X 324 It can be C(R 324 ) or N,
[0319] X 331 It can be C(R 331 ) or N, X 332 It can be C(R 332 ) or N, X 333 It can be C(R 333 ) or N, and X 334 It can be C(R 334 ) or N,
[0320] T 1 As described herein,
[0321] R 311 and R 312 Can be referred to as R 31 As described,
[0322] R 321 To R 324 Can be referred to as R 32 As described,
[0323] R 331 To R 334 Can be referred to as R 33 As described,
[0324] R 311 , R 312 , R 321 To R 324 and R 331 To R 334 Two or more adjacent groups in may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0325] * represents the binding position with M in Formula 1-1 or Formula 1-2,
[0326] *" indicates the same as L in Formula 1-1 or Formula 1-2 2 The binding site of
[0327] *"' represents the same as L in Formula 1-1 or Formula 1-2 3 The combination position.
[0328] In formula 1-1, The group represented may be a group represented by at least one of Formula CY3-1(1A) to Formula CY3-1(6A), and
[0329] In formula 1-2, The group represented may be a group represented by the formula CY3-2(1A) or the formula CY3-2(2A):
[0330]
[0331]
[0332] Among them, in Formula CY3-1(1A) to Formula CY3-1(6A), Formula CY3-2(1A) and Formula CY3-2(2A),
[0333] T 1 As described herein,
[0334] R 311 and R 312 Can be referred to as R 31 As described,
[0335] R 321 To R 324 Can be referred to as R 32 As described,
[0336] R 331 To R334 Can be referred to as R 33 As described,
[0337] R 311 , R 312 , R 321 To R 324 and R 331 To R 334 Two or more adjacent groups in may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0338] * represents the binding position with M in Formula 1-1 or Formula 1-2,
[0339] *" indicates the same as L in Formula 1-1 or Formula 1-2 2 The binding site of
[0340] *"' represents the same as L in Formula 1-1 or Formula 1-2 3 The combination position.
[0341] In formula 1-1 and formula 1-2, The group represented may be a group represented by at least one of formula CY4(1) to formula CY4(29):
[0342]
[0343]
[0344] Among them, in formula CY4(1) to formula CY4(29),
[0345] R 41 To R 47 Can be referred to as R 4 As described,
[0346] * represents the binding site with M in Formula 1-1 or Formula 1-2, and
[0347] *"' represents the same as L in Formula 1-1 or Formula 1-2 3 The combination position.
[0348] In formula 1-1 and formula 1-2, T 1 It may be a group represented by formula T-1 or formula T-2:
[0349]
[0350] Wherein, in Formula T-1 and Formula T-2,
[0351] T 11 It can be C, Si or Ge,
[0352] T 12 Can be a single bond, *-C(Z 3 )(Z 4 )-*'、*-Si(Z 3 )(Z 4 )-*'or*-Ge(Z 3 )(Z 4 )-*', where * and *' both represent the binding sites with adjacent atoms,
[0353] X 51 It can be C(Z 11 ) or N, X 52 It can be C(Z 12 ) or N, X 53 It can be C(Z 13 ) or N, X 54 It can be C(Z 14 ) or N, X 55 It can be C(Z 15 ) or N,
[0354] X 61 It can be C(Z 21 ) or N, X 62 It can be C(Z 22 ) or N, X 63 It can be C(Z 23 ) or N, X 64 It can be C(Z 24 ) or N, X 65 It can be C(Z 25 ) or N,
[0355] Z 11 To Z 15 and Z 3 Can be as reference Z 1 As described,
[0356] Z 21 To Z 25 and Z 4 Can be as reference Z 2 As described,
[0357] Z 11 To Z 15 , Z 21 To Z 25 , Z 3 and Z 4Two or more adjacent groups in may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 a heterocyclic group, and
[0358] * and *' both indicate the binding sites with adjacent atoms.
[0359] The organic metal compound represented by Formula 1-1 may be a group represented by Formula 1-1(A1) or Formula 1-1(A2), and
[0360] The organic metal compound represented by Formula 1-2 may be a group represented by Formula 1-2(A1) or Formula 1-2(A2):
[0361] Formula 1-1 (A1)
[0362]
[0363] Formula 1-1(A2)
[0364]
[0365] Formula 1-2 (A1)
[0366]
[0367] Formula 1-2 (A2)
[0368]
[0369] Among them, in Formula 1-1(A1), Formula 1-1(A2), Formula 1-2(A1) and Formula 1-2(A2),
[0370] M, X 1 To X 4 and T 1 can be as described herein,
[0371] L 2 It can be *-O-*', *-S-*' or *-Se-*',
[0372] X 12 It can be C(R 12 ) or N, X 13 It can be C(R 13 ) or N, X 14 It can be C(R 14 ) or N, and X 15 It can be C(R15 ) or N,
[0373] 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,
[0374] X 311 It can be C(R 311 ) or N, X 312 It can be C(R 312 ) or N, X 321 It can be C(R 321 ) or N, X 322 It can be C(R 322 ) or N, X 323 It can be C(R 323 ) or N, X 324 It can be C(R 324 ) or N, X 331 It can be C(R 331 ) or N, X 332 It can be C(R 332 ) or N, X 333 It can be C(R 333 ) or N, and X 334 It can be C(R 334 ) or N,
[0375] 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,
[0376] R 11 To R 15 Can be referred to as R 1 As described,
[0377] R 21 To R 23 Can be referred to as R 2 As described,
[0378] R 311 and R 312 Can be referred to as R 31 As described,
[0379] R321 To R 324 Can be referred to as R 32 As described,
[0380] R 331 To R 334 Can be referred to as R 33 As described,
[0381] R 41 To R 44 Can be referred to as R 4 As described,
[0382] R 11 To R 15 , R 21 To R 23 , R 311 , R 312 , R 321 To R 324 , R 331 To R 334 , R 41 To R 44 , Z 1 and Z 2 Two or more adjacent groups in may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 a heterocyclic group, and
[0383] R 10a May be as described herein.
[0384] In the organometallic compound represented by Formula 1-1 or Formula 1-2, ring CY 31 CycloCY 32 By *-C(Z 1 )(Z 2 )-*'、*-Si(Z 1 )(Z 2 )-*'or*-Ge(Z 1 )(Z 2 )-*' represents T 1 The linker is connected to the ring CY 33 Thus, the (e.g., steric) hindrance of the organometallic compound may increase so that its interaction with other compounds (e.g., boron-based compounds) present nearby may decrease, thereby suppressing DexET energy transfer (a phenomenon in which excited electrons of one molecule are transferred to triplet energy of another molecule when the distance between molecules is short).
[0385] In some embodiments, in the organometallic compound represented by Formula 1-1 or Formula 1-2, the molecular rigidity is due to T 1 The linking group can be enlarged, so that the intramolecular motion can be suppressed or reduced, thereby suppressing the non-luminescent process of the molecule (reducing the Knr component), and reducing the Stoke shift, thereby increasing the photoluminescence quantum yield (PLQY). In addition, due to the increase in molecular rigidity, the structural deformation between the excited state and the ground state can be reduced.
[0386] Thus, when DexET energy transfer is suppressed or reduced and molecular rigidity is increased, the organometallic compound represented by Formula 1-1 or Formula 1-2 can improve luminous efficiency and device life. Therefore, by using the organometallic compound represented by Formula 1-1 or Formula 1-2, an electronic device (e.g., a light-emitting device) with reduced driving voltage, improved color purity and efficiency, and increased life can be realized.
[0387] Other descriptions
[0388] Formula 2
[0389]
[0390] In formula 2, L 51 To L 53 may each independently be a single bond, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group.
[0391] In Formula 2, b51 to b53 represent L 51 To L 53 The number of L can be an integer from 1 to 5. When b51 is 2 or greater, L 51 Two or more of them may be the same or different from each other. When b52 is 2 or greater, L 52 Two or more of L may be the same or different from each other, and when b53 is 2 or greater, L 53 Two or more of b51 to b53 may be the same as or different from each other. For example, b51 to b53 may each independently be 1 or 2.
[0392] In formula 2, L 51 To L 53 can all independently be:
[0393] a single key; or
[0394] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -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 any combination thereof, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene 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 azole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzoxinyl group, a dibenzothiinyl group, a dibenzodihydroazacyclohexyl group, a dibenzodihydrodicyclohexyl group, a dibenzodihydrocyclohexyl group, a dibenzodioxane group, a dibenzooxathiinyl group, a dibenzoxazine group, a dibenzopyran group, a dibenzodithiinyl group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group or a dibenzodihydropyrazine group, and
[0395] Q31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0396] In one or more embodiments, 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 key between 51 With X in Eq. 2 54 and X 55 The bonds between carbons, L 52 With X in Eq. 2 54 and X 56 The bonds between the carbons and L 53 With X in Eq. 2 55 and X 56 The bonds between the carbon atoms in the molecule may all be "carbon-carbon single bonds".
[0397] 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 can be as described herein. For example, X 54 To X 56 Two or three of them can all be N.
[0398] In formula 2, R 51 To R 56 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Heteroarylalkyl, -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 May be as described herein.
[0399] In formula 2, R 51 To R 56 can all independently be:
[0400] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0401] All substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0402] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl , benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91; or
[0403] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0404] Q 1 To Q 3 and Q 31 To Q 33 can all independently be:
[0405] -CH3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0406] None or substituted with deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl:
[0407] Formula 91
[0408]
[0409] Among them, in formula 91,
[0410] Cyclo 91 and CY 92 may be independently unsubstituted or substituted with at least one R 10a C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 30 Heterocyclic group,
[0411] 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 You can refer to R 82 , R 82a and R 82b As described,
[0412] R 10a may be as described herein, and
[0413] *Indicates the binding site with the adjacent atom.
[0414] For example, in Equation 91,
[0415] Cyclo 91 and CY 92 may be independently unsubstituted or substituted with at least one R 10a a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group or a triazine group, and
[0416] R 91 , R 91a and R 91b can all independently be:
[0417] Hydrogen or C 1 -C 10 Alkyl; or
[0418] None or substituted with deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0419] In formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented by may not all be phenyl.
[0420] In one or more embodiments, in Formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented may be the same as each other.
[0421] In one or more embodiments, in Formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L52 ) b52 -R 52 The groups represented may be different from each other.
[0422] In one or more embodiments, in Formula 2, b51 and b52 may both be 1, 2 or 3, and L 51 and L 52 may be independently unsubstituted or substituted with at least one R 10a A benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group.
[0423] For example, in Formula 2, R 51 and R 52 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),
[0424] Q 1 To Q 3 can be independently unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0425] In one or more embodiments,
[0426] 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
[0427] 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
[0428] In formula 2, *-(L 53 ) b53 -R 53 The group represented by may be a group represented by at least one of the formulas CY53-1 to CY53-27, -C(Q 1 )(Q 2 )(Q 3 ) and / or -Si(Q 1 )(Q 2 )(Q 3 ):
[0429]
[0430]
[0431]
[0432] 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,
[0433] 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 ),
[0434] 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 ),
[0435] 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 ), Y68 Can be single bond, O, S, N(R 68 )、B(R 68 )、C(R 68a )(R 68b ) or Si(R 68a )(R 68b ),
[0436] 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., concurrently),
[0437] 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., concurrently),
[0438] R 51a To R 51e , R 61 To R 64 , R 63a , R 63b , R 64a and R 64b Can be referred to as R 51 As described, R 51a To R 51e All of them may not be hydrogen,
[0439] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b Can be referred to as R 52 As described, R 52a To R 52e All of them may not be hydrogen,
[0440] R 53a To R 53e , R 69a and R 69b Can be referred to as R 53 As described, R 53a To R 53e may not be hydrogen, and
[0441] *Indicates the binding site with the adjacent atom.
[0442] For example,
[0443] In Formula CY51-1 to Formula CY51-26 and Formula CY52-1 to Formula CY52-26, R 51a To R 51e and R 52a To R 52e can all independently be:
[0444] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl , benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl , benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91; or
[0445] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),
[0446] Q 1 To Q 3 can be independently unsubstituted or substituted with deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl,
[0447] 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
[0448] 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 )(R 68b ), or ii) Y 67 It can be Si(R 67a )(R 67b ), and Y 68 Can be O or S.
[0449] Formula 3
[0450]
[0451] In Formula 3, ring CY 71 and CY 72 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridine group.
[0452] In formula 3, X 71 It may be a single bond or a linking group comprising O, S, N, B, C, Si or any combination thereof.
[0453] In Formula 3, * represents a bonding position with any atom included in the remaining part other than the group represented by Formula 3 of the third compound.
[0454] Formula 3-1
[0455]
[0456] Formula 3-2
[0457]
[0458] Formula 3-3
[0459]
[0460] Formula 3-4
[0461]
[0462] Formula 3-5
[0463]
[0464] In Formula 3-1 to Formula 3-5, ring CY 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridine group.
[0465] In Formula 3-1 to Formula 3-5, 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 ).
[0466] In Formula 3-1 to Formula 3-5, X 83 Can be single bond, O, S, N[(L83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ).
[0467] In Formula 3-1 to Formula 3-5, X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ).
[0468] In Formula 3-1 to Formula 3-5, X 85 It can be C or Si.
[0469] In Formula 3-1 to Formula 3-5, L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or substituted with at least one R 10a The π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a of the pyridine group.
[0470] Q 4 and Q 5 You can refer to Q 1 as described.
[0471] In Formulae 3-1 to 3-5, b81 to b85 may each independently be an integer of 1 to 5.
[0472] In Formula 3-1 to Formula 3-5, R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b May be as described herein.
[0473] In Formula 3-1 to Formula 3-5, a71 to a74 represent R 71 To R74 and may be independently an integer from 0 to 20. When a71 is 2 or greater, R 71 Two or more of them may be the same or different from each other. When a72 is 2 or greater, R 72 Two or more of them may be the same or different from each other. When a73 is 2 or greater, R 73 Two or more of may be the same or different from each other, and when a74 is 2 or greater, R 74 Two or more of a71 to a74 may be the same as or different from each other. a71 to a74 may each independently be an integer of 0 to 8.
[0474] R 10a May be the same as described herein.
[0475] In Formula 3-1 to Formula 3-5, L 81 To L 85 can all independently be:
[0476] a single key; or
[0477] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*';or
[0478] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -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 any combination thereof, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a thiorrole 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 benzothiorrole group, a dibenzothiorrole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothiorrole 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 pyrrol 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 thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group, and
[0479] Q 4 , Q 5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0480] In one or more embodiments, the formula 3-1 and the formula 3-2 are given by The group represented may be a group represented by at least one of Formula CY71-1(1) to Formula CY71-1(8), and / or
[0481] In formula 3-1 and formula 3-3, The group represented may be a group represented by at least one of Formula CY71-2(1) to Formula CY71-2(8), and / or
[0482] In formula 3-2 and formula 3-4, The group represented may be a group represented by at least one of Formula CY71-3(1) to Formula CY71-3(32), and / or
[0483] In formula 3-3 to formula 3-5, The group represented by may be a group represented by at least one of Formula CY71-4(1) to Formula CY71-4(32), and / or
[0484] In formula 3-5, The group represented may be a group represented by at least one of formula CY71-5(1) to formula CY71-5(8):
[0485]
[0486]
[0487]
[0488]
[0489] 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),
[0490] X 81 To X 85 , L 81 ,b81,R 81 and R 85 can be as described herein,
[0491] 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 ),
[0492] 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 key at the same time (e.g., concurrently),
[0493] 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(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0494] 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 single-key at the same time (e.g., concurrently), and
[0495] R 86 To R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b Can be referred to as R 81 as described.
[0496] Formula 502
[0497]
[0498] Formula 503
[0499]
[0500] In Formula 502 and Formula 503, ring A 501 To Ring A 504 can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0501] In equations 502 and 503, Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ).
[0502] In equations 502 and 503, Y 506 Can be O, S, N (R506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ).
[0503] In equations 502 and 503, Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ).
[0504] In equations 502 and 503, Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ).
[0505] In equations 502 and 503, Y 51 and Y 52 Each may independently be B, P(═O) or S(═O).
[0506] In equations 502 and 503, R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b May be as described herein.
[0507] In Formula 502 and Formula 503, a501 to a504 represent R 501 To R 504 and may be independently an integer from 0 to 20. When a501 is 2 or greater, R 501 Two or more of them may be the same or different from each other. When a502 is 2 or greater, R 502 Two or more of them may be the same or different from each other. When a503 is 2 or greater, R 503 Two or more of may be the same or different from each other, and when a504 is 2 or greater, R504 Two or more of a501 to a504 may be the same as or different from each other. a501 to a504 may each independently be an integer of 0 to 8.
[0508] The R used here 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a C 7 -C 60Arylalkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Heteroarylalkyl, -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 May be as described herein.
[0509] In one or more embodiments, i) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b and ii) R 10a can all independently be:
[0510] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0511] All substituted with deuterium, -F, -Cl, -Br, -I, -CD3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 C alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0512] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl , benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91; or
[0513] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0514] Q 1 To Q 3 and Q 31 To Q 33 can all independently be:
[0515] -CH 3 、-CD 3 、-CD2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0516] None or substituted with deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0517] In one or more embodiments, i) R in Formula 1-1 or Formula 1-2 1 , R 2 , R 31 To R 33 and R 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 , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R508a and R 508b and iii) R 10a can all independently be:
[0518] Hydrogen, deuterium, -F, cyano, nitro, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H or -CFH 2 ;
[0519] A group represented by at least one of Formula 9-1 to Formula 9-19; or
[0520] A group represented by at least one of Formula 10-1 to Formula 10-246, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) and / or -P(=O)(Q 1 )(Q 2 )(where Q 1 To Q 3 can be as described herein):
[0521]
[0522]
[0523]
[0524]
[0525]
[0526]
[0527]
[0528] In Formulae 9-1 to 9-19 and 10-1 to 10-246, * represents a bonding position with an adjacent atom, "Ph" represents a phenyl group, and "TMS" represents a trimethylsilyl group.
[0529] Examples of Compounds
[0530] In one or more embodiments, the organometallic compound represented by Formula 1-1 or Formula 1-2 may be at least one of Compound 1 to Compound 72:
[0531]
[0532]
[0533]
[0534]
[0535] For example, the second compound may be at least one of compounds ETH1 to ETH100:
[0536]
[0537]
[0538]
[0539]
[0540] For example, the third compound may be at least one of compound HTH1 to compound HTH40:
[0541]
[0542]
[0543] For example, the fourth compound may be at least one of compound DFD1 to compound DFD29:
[0544]
[0545]
[0546] In the compounds described, "Ph" means phenyl, "D 5 " means it is replaced by 5 deuterium atoms, and "D 4 " means replaced by 4 deuterium atoms. For example, The group represented by The groups represented are the same.
[0547] Figure 1 Description
[0548] 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 .
[0549] In the following, reference will be made to Figure 1A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described.
[0550] First electrode 110
[0551] exist Figure 1 In the embodiment, the substrate may be further arranged below the first electrode 110 or on the second electrode 150. In one or more embodiments, a glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include 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).
[0552] 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. As used herein, the term "high work function material" refers to a substance (e.g., a metal or a metal alloy) that requires a relatively large amount of energy to emit electrons from its surface.
[0553] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0554] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0555] Middle layer 130
[0556] The intermediate layer 130 is disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0557] 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 .
[0558] In addition to one or more suitable organic materials, the intermediate layer 130 may further include metal-containing compounds (such as organometallic compounds) and / or inorganic materials (such as quantum dots), etc.
[0559] 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 the two or more emission units. When the intermediate layer 130 includes two or more emission units and a charge generation layer, the light emitting device 10 may be a tandem light emitting device.
[0560] Hole transport region in the intermediate layer 130
[0561] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other; or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.
[0562] 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.
[0563] For example, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the constituent layers of each structure are stacked sequentially from the first electrode 110.
[0564] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, and / or any combination thereof:
[0565] Formula 201
[0566]
[0567] Formula 202
[0568]
[0569] Among them, in equation 201 and equation 202,
[0570] L 201 To L 204 may be independently unsubstituted or substituted with at least one R10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0571] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0572] xa1 to xa4 may each independently be an integer from 0 to 5,
[0573] xa5 can be an integer from 1 to 10,
[0574] R 201 To R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0575] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted with at least one R 10a C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted group having at least one R 10a C 8 -C 60 Polycyclic groups (eg, carbazole groups, etc.) (eg, see compound HT16),
[0576] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted with at least one R 10a C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted group having at least one R 10a C 8 -C 60 Polycyclic groups, and
[0577] na1 can be an integer from 1 to 4.
[0578] For example, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY217:
[0579]
[0580] Among them, in formula CY201 to formula CY217, R 10b and R 10c Can be referred to as R 10a As described, CY 201 To Ring CY 204 can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.
[0581] In one or more embodiments, ring CY in Formula CY201 to Formula CY217 201 To Ring CY 204 Each of them may independently be a benzene group, a naphthyl group, a phenanthrene group or an anthracene group.
[0582] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY203.
[0583] In one or more embodiments, Formula 201 may include at least one selected from among the groups represented by Formulas CY201 to CY203 and at least one selected from among the groups represented by Formulas CY204 to CY217.
[0584] In one or more embodiments, in Formula 201, xa1 may be 1, R201 can be one of the groups represented by the formula CY201 to the formula CY203, xa2 can be 0, R 202 It may be one of the groups represented by Formula CY204 to Formula CY207.
[0585] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY203.
[0586] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY203, and may include at least one of the groups represented by Formula CY204 to Formula CY217.
[0587] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY217.
[0588] For example, the hole transport region may include: at least one selected from the group consisting of compounds HT1 to HT46; m-MTDATA; TDATA; 2-TNATA; NPB (NPD); β-NPB; TPD; spiro-TPD; spiro-NPB; methylated NPB; TAPC; HMTPD; 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA); polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA); poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS); polyaniline / camphorsulfonic acid (PANI / CSA); polyaniline / poly(4-styrenesulfonate) (PANI / PSS); and / or any combination thereof:
[0589]
[0590]
[0591]
[0592]
[0593] The thickness of the hole transport region can be about 50 angstroms. 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 in the range of about to about (For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the described ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0594] 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.
[0595] p-dopant
[0596] In addition to the materials described, the hole transport region may also include charge generating materials for improving the conductive properties. The charge generating materials may be dispersed in the hole transport region uniformly or non-uniformly (eg, in the form of a single layer consisting of the charge generating materials).
[0597] The charge generating material may be, for example, a p-dopant.
[0598] For example, the p-dopant may have a LUMO level of -3.5 eV or less.
[0599] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0600] Examples of quinone derivatives are TCNQ and / or F 4 -TCNQ, etc.
[0601] Examples of cyano group-containing compounds are HAT-CN and / or compounds represented by Formula 221, etc.:
[0602]
[0603] Formula 221
[0604]
[0605] Among them, in formula 221,
[0606] R 221 To R 223 may be independently unsubstituted or substituted with at least one R 10a C 3 -C60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 a heterocyclic group, and
[0607] Selected from R 221 To R 223 At least one of them may be independently C substituted with the following groups 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0608] In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0609] Examples of metals are: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb) and / or cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and / or barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.) and / or lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and / or lutetium (Lu), etc.); etc.
[0610] Examples of metalloids are silicon (Si), antimony (Sb), and / or tellurium (Te), among others.
[0611] Examples of non-metals are oxygen (O) and / or halogens (eg, F, Cl, Br, and / or I, etc.), and the like.
[0612] For example, the compound including element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide and / or a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide and / or a metalloid iodide, etc.), a metal telluride, or any combination thereof.
[0613] Examples of metal oxides are tungsten oxide (e.g., WO, W 2 O 3 , WO 2 , WO 3 and / or W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 and / or V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 and / or Mo 2 O 5 etc.) and / or rhenium oxide (e.g., ReO 3 etc.
[0614] Examples of the metal halide are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides and / or lanthanide metal halides, and the like.
[0615] Examples of alkali metal halides are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI and / or CsI, etc.
[0616] An example of an alkaline earth metal halide is 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 ,BeI2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 wait.
[0617] Examples of transition metal halides are titanium halides (e.g., TiF 4 、TiCl 4 、TiBr 4 and / or TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 and / or ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 and / or HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 and / or VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 and / or NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 and / or TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 and / or CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 and / or MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 and / or WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 and / or MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 , TcBr 2 and / or TcI 2etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 and / or ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 and / or FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 and / or RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 and / or OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 and / or CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 and / or RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 and / or IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 and / or NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 and / or PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 and / or PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr and / or AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr and / or AuI, etc.), etc.
[0618] Examples of late transition metal halides are zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2and / or ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 etc.
[0619] Examples of lanthanide metal halides are YbF, YbF 2 , YbF 3 、SmF 3 、YbCl、YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and / or SmI 3 wait.
[0620] Examples of metalloid halides are antimony halides (e.g., SbCl 5 etc.
[0621] Examples of metal tellurides are alkali metal tellurides (e.g., Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te and / or Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe and / or Au 2Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.), etc.
[0622] Emission layer in the middle layer 130
[0623] 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 to emit white light, wherein the two or more layers are in contact with each other or separated from each other. 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 to emit white light, wherein the two or more materials are mixed with each other in a single layer.
[0624] In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In one or more embodiments, in addition to the host and the dopant (or emitter), the emission layer may also include an auxiliary dopant that promotes energy transfer to the dopant (or emitter). When the emission layer includes a dopant (or emitter) and an auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
[0625] The organometallic compound represented by Formula 1-1 or Formula 1-2 described herein may serve as a dopant (or emitter) or an auxiliary dopant.
[0626] The amount (weight) of the dopant (or emitter) in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0627] The organic metal compound represented by Formula 1-1 or Formula 1-2 may be included in the emission layer. The amount (weight) of the organic metal compound in the emission layer may be in the range of about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight based on 100 parts by weight of the emission layer.
[0628] In one or more embodiments, the emissive layer may include quantum dots.
[0629] In one or more embodiments, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emissive layer.
[0630] 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 described range, excellent or suitable light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0631] main body
[0632] The host in the emissive layer may include the second compound or the third compound described herein, or any combination thereof.
[0633] In one or more embodiments, the host may include a compound represented by Formula 301:
[0634] Formula 301
[0635] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0636] Wherein, in Formula 301,
[0637] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0638] xb11 can be 1, 2 or 3,
[0639] xb1 can be an integer from 0 to 5.
[0640] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0641] xb21 can be an integer from 1 to 5, and
[0642] Q 301 To Q 303 You can refer to Q 1 as described.
[0643] For example, when xb11 in Formula 301 is 2 or greater, Ar 301 Two or more of may be linked to each other via a single bond.
[0644] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0645] Formula 301-1
[0646]
[0647] Formula 301-2
[0648]
[0649] Among them, in Formula 301-1 and Formula 301-2,
[0650] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0651] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0652] xb22 and xb23 can each independently be 0, 1 or 2,
[0653] L 301 , xb1 and R 301 can be as described herein,
[0654] L 302 To L 304 Can be independently as reference L 301 As described,
[0655] xb2 to xb4 may each independently be as described with reference to xb1, and
[0656] R 302 To R 305 and R 311 To R 314 Can be referred to as R 301 as described.
[0657] In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0658] In one or more embodiments, the host may include: at least one selected from Compound H1 to Compound H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-tert-butylanthracene (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:
[0659]
[0660]
[0661]
[0662]
[0663]
[0664]
[0665] In one or more embodiments, the host can include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0666] The body may have one or more suitable modifications. For example, the body may include only one compound, or may include two or more different compounds.
[0667] Phosphorescent dopants
[0668] The emission layer may include the organic metal compound represented by Formula 1-1 or Formula 1-2 described herein as a phosphorescent dopant.
[0669] In one or more embodiments, when the emission layer includes the organic metal compound represented by Formula 1-1 or Formula 1-2 described herein, and the organic metal compound represented by Formula 1-1 or Formula 1-2 described herein acts as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0670] The phosphorescent dopant may include at least one transition metal as a central metal.
[0671] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0672] The phosphorescent dopant may be electrically neutral.
[0673] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0674] Formula 401
[0675] M(L 401 ) xc1 (L 402 ) xc2
[0676] Formula 402
[0677]
[0678] Among them, in equation 401 and equation 402,
[0679] 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)),
[0680] L 401 may be a ligand represented by formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, L 401 Two or more of may be the same or different from each other,
[0681] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, L 402 Two or more of may be the same or different from each other,
[0682] X 401 and X 402 may all independently be N or C,
[0683] Ring A 401 and Ring A 402 can all be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0684] 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=*',
[0685] X 403 and X 404 can each independently be a chemical bond (eg, 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 ),
[0686] Q 411 To Q 414 You can refer to Q 1 As described,
[0687] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a 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 ),
[0688] Q 401 To Q 403 You can refer to Q 1 As described,
[0689] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0690] The * and *' in formula 402 both represent the binding site with M in formula 401.
[0691] For example, in equation 402, i)X 401 may be nitrogen, and X 402 may be carbon; or ii) X 401 and X 402 Each of can be nitrogen.
[0692] In one or more embodiments, when xc1 in Formula 401 is 2 or greater, the compound selected from L 401 Two or more of the two rings A 401 It can be optionally connected via T as a linker 402 connected to each other and selected from L 401Two or more of the two rings A 402 It can be optionally connected via T as a linker 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be referred to as T 401 as described.
[0693] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinic acid salt group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group and / or a phosphite group, etc.), or any combination thereof.
[0694] The phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD39 or any combination thereof:
[0695]
[0696]
[0697]
[0698] Fluorescent dopants
[0699] In one or more embodiments, when the emission layer includes the organic metal compound represented by Formula 1-1 or Formula 1-2 described herein and the organic metal compound represented by Formula 1-1 or Formula 1-2 described herein acts as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0700] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1-1 or Formula 1-2 described herein and the organometallic compound represented by Formula 1-1 or Formula 1-2 described herein acts as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0701] 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.
[0702] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
[0703] Formula 501
[0704]
[0705] Wherein, in Formula 501,
[0706] Ar 501 , L 501 To L 503 , R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0707] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0708] xd4 can be 1, 2, 3, 4, 5 or 6.
[0709] In one or more embodiments, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed with each other (for example, anthracene group, group and / or pyrene group, etc.).
[0710] In one or more embodiments, xd4 in equation 501 may be 2.
[0711] For example, the fluorescent dopant and the auxiliary dopant may both include: one selected from the group consisting of compounds FD1 to FD37; DPVBi; DPAVBi; and / or any combination thereof:
[0712]
[0713]
[0714]
[0715]
[0716] Delayed fluorescence material
[0717] The emitting layer may include a delayed fluorescent material.
[0718] The delayed fluorescent material described herein may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0719] The delayed fluorescent material may include, for example, the fourth compound described herein.
[0720] The delayed fluorescent material included in the emission layer may act as a host or a dopant according to the types or kinds of other materials included in the emission layer.
[0721] In one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be 0 eV or more and 0.5 eV or less. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the described range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and therefore, the light emitting device 10 may have improved luminous efficiency.
[0722] For example, the delayed fluorescent material may include: i) a C-type molecule including at least one electron donor (eg, a π-electron-rich C-type molecule such as a carbazole group); 3 -C 60 ring group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group and / or a π-electron-poor nitrogen-containing C 1 -C 60 ii) a material comprising C wherein two or more cyclic groups are condensed while sharing boron (B); 8 -C 60 Polycyclic materials.
[0723] Examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF14:
[0724]
[0725]
[0726] quantum dots
[0727] The emissive layer may include quantum dots.
[0728] 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 suitable emission wavelengths depending on the size of the crystal.
[0729] The diameter of a quantum dot may, for example, be in the range of about 1 nanometer (nm) to about 10 nm.
[0730] The quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, and / or any process similar thereto.
[0731] 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. When the quantum dot particle crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal and controls the growth of the quantum dot particle crystal, so that the growth of the quantum dot particle crystal can be controlled or selected by a process that is less expensive and easier than a vapor deposition method such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0732] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.
[0733] Examples of II-VI semiconductor compounds are: binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS, etc.; 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, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe, etc.; or any combination thereof.
[0734] Examples of III-V semiconductor compounds are binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs and / or InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs and / or InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and / or InAlPSb, etc.; or any combination thereof. In one or more embodiments, the III-V semiconductor compounds may also include Group II elements. Examples of Group III-V semiconductor compounds also including Group II elements are InZnP, InGaZnP, and / or InAlZnP, and the like.
[0735] Examples of III-VI semiconductor compounds are: binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and / or InTe, etc.; ternary compounds such as InGaS 3 and / or InGaSe 3 etc.; or any combination thereof.
[0736] Examples of Group I-III-VI semiconductor compounds are: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and / or AgAlO 2 wait.
[0737] Examples of IV-VI semiconductor compounds are: 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.
[0738] Examples of Group IV elements or compounds are: simple substances such as Si and / or Ge, etc.; binary compounds such as SiC and / or SiGe, etc.; or any combination thereof.
[0739] Each element included in the multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present in the particle at a substantially uniform concentration or a non-substantially uniform concentration.
[0740] In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or may have a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
[0741] 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 act as a charged layer to impart electrophoretic properties to the quantum dot. The shell can be single-layer or multi-layer. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.
[0742] Examples of the shell of a quantum dot are oxides of metals, metalloids or nonmetals, semiconductor compounds and / or combinations thereof. Examples of oxides of metals, metalloids or nonmetals are: 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, etc.; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4、NiFe 2 O 4 and / or CoMn 2 O 4 etc.; or any combination thereof. Examples of semiconductor compounds are: as described herein, II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; and / or any combination thereof. Examples of semiconductor compounds are 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.
[0743] The quantum dots may have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or, for example, about 30 nm or less. When the FWHM of the quantum dots is within these ranges, the quantum dots may have improved color purity or improved color reproducibility. In some embodiments, because the light emitted by the quantum dots is emitted in all directions, the wide viewing angle may be improved.
[0744] In some embodiments, quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, and / or nanoplates, among others.
[0745] Because the band gap can be adjusted by controlling the size of the quantum dots, light with one or more suitable wavelengths 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 by combining one or more suitable colors of light.
[0746] Electron transport region in the intermediate layer 130
[0747] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other; or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.
[0748] 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.
[0749] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked sequentially from the emission layer.
[0750] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C 1 -C 60 Metal-free compounds of heterocyclic groups.
[0751] For example, the electron transport region may include a compound represented by Formula 601:
[0752] Formula 601
[0753] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0754] Wherein, in Formula 601,
[0755] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,
[0756] xe11 can be 1, 2 or 3,
[0757] xe1 can be 0, 1, 2, 3, 4, or 5,
[0758] R 601 may be unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0759] Q 601 To Q 603 You can refer to Q 1 As described,
[0760] xe21 can be 1, 2, 3, 4, or 5, and
[0761] Selected from Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted with at least one R 10a The π-electron-poor nitrogen-containing C 1 -C 60 Heterocyclic group.
[0762] In one or more embodiments, when xe11 in Formula 601 is 2 or greater, Ar 601 Two or more of may be linked to each other via a single bond.
[0763] In one or more embodiments, Ar in Formula 601 601 The anthracene group may be substituted or unsubstituted.
[0764] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
[0765] Formula 601-1
[0766]
[0767] Among them, in formula 601-1,
[0768] 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 selected from X 614 To X 616 At least one of them may be N,
[0769] L 611 To L 613 Can be referred to as L 601 As described,
[0770] xe611 to xe613 can all be as described with reference to xe1,
[0771] R 611 To R 613 Can be referred to as R 601 described, and
[0772] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group.
[0773] For example, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each independently be 0, 1, or 2.
[0774] The electron transport region may include: at least one selected from the group consisting of Compound ET1 to Compound ET45; 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:
[0775]
[0776]
[0777]
[0778] The thickness of the electron transport region can be about to about (For example, about to about ). When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be about to about (For example, about to about ), and the thickness of the electron transport layer can be in the range of about to about (For example, about to about ). When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within the described range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0779] In addition to the described materials, the electron transport region (eg, an electron transport layer in the electron transport region) can also include a metal-containing material.
[0780] The metal-containing material can include alkali metal complex, alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex can be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of the alkaline earth metal complex can be Be ion, Mg ion, Ca ion, Sr ion or Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0781] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compounds ET-D1 (Liq) or ET-D2:
[0782]
[0783] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0784] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other; or iii) a multilayer structure including a plurality of layers including (e.g., consisting of) a plurality of materials different from each other.
[0785] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0786] The alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0787] The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound may be oxides, halides (e.g., fluorides, chlorides, bromides, and / or iodides, etc.) or tellurides of alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.
[0788] The alkali metal-containing compound may include: alkali metal oxides, such as Li 2 O, Cs 2 O, and / or K 2 O, etc.; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and / or RbI, etc.; or any combination thereof. The alkaline earth metal-containing compound may include alkaline earth metal oxides or compounds (such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc.). The rare earth metal-containing compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm2 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 wait.
[0789] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include: i) at least one metal ion selected from alkali metals, alkaline earth metals and rare earth metals; and ii) a ligand (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof) that binds to the metal ion (i.e., the selected metal ion).
[0790] In one or more embodiments, the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described (e.g., composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described). In one or more embodiments, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).
[0791] In one or more embodiments, the electron injection layer may include: i) an alkali metal compound (e.g., an alkali metal halide); or ii) a) an alkali metal compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof (e.g., consisting of i) an alkali metal compound (e.g., an alkali metal halide); or ii) a) an alkali metal compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof). For example, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.
[0792] When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0793] 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 described range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0794] The second electrode 150
[0795] The second electrode 150 is arranged on the intermediate layer 130 having the structure as described. The second electrode 150 may be a cathode as an electron injection electrode, and metals, alloys, conductive compounds, or any combination thereof, each having a low work function, may be used as a material for forming the second electrode 150. The term "low work function material" as used herein refers to a substance (e.g., a metal or a metal alloy) that requires a relatively small or low amount of energy to emit electrons from its surface.
[0796] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0797] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
[0798] Covering
[0799] The first cover layer may be disposed outside the first electrode 110 (and, for example, on the first electrode 110), and / or the second cover layer may be disposed 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 cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150 are sequentially stacked in the stated order; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the stated order; or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the stated order.
[0800] Light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 can be extracted toward the outside through the first electrode 110 (which is a semi-transmissive electrode or a transmissive electrode) and the first cover layer. Light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 can be extracted toward the outside through the second electrode 150 (which is a semi-transmissive electrode or a transmissive electrode) and the second cover layer.
[0801] According to the principle of constructive interference, the first cover layer and the second cover layer can increase the external emission efficiency. Therefore, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be enhanced or improved.
[0802] Each of the first cover layer and the second cover layer may include a material having a refractive index of 1.6 or greater (at 589 nm).
[0803] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0804] At least one selected from the first cover layer and the second cover layer may independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from the first cover layer and the second cover layer may independently include an amine-containing compound.
[0805] In one or more embodiments, at least one selected from among the first cover layer and the second cover layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0806] In one or more embodiments, at least one selected from the first covering layer and the second covering layer may each independently include one selected from compounds HT28 to HT33, one selected from compounds CP1 to CP6, β-NPB, and / or any combination thereof:
[0807]
[0808] membrane
[0809] The organometallic compound represented by Formula 1-1 or Formula 1-2 may be included in one or more suitable films. Therefore, another aspect of the disclosure provides a film comprising an organometallic compound represented by Formula 1-1 or Formula 1-2. The film may be, for example, an optical member (or light control member or component) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer and / or a quantum dot layer, etc.), a light blocking member (e.g., a light reflecting layer and / or a light absorbing layer, etc.), and / or a protective member (e.g., an insulating layer and / or a dielectric layer, etc.).
[0810] Electronic Devices
[0811] The light emitting device may be included in one or more suitable electronic devices. For example, the electronic device including the light emitting device may be a lighting device and / or an authentication device, etc.
[0812] In addition to the light emitting device, the electronic device (e.g., a light emitting device) may further include: i) a color filter; ii) a color conversion layer; or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in at least one direction 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. Details about the light emitting device may be as described herein. In one or more embodiments, the color conversion layer may include quantum dots.
[0813] 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.
[0814] A pixel defining film (hereinafter, may also be referred to as a 'pixel defining layer') may be disposed between the sub-pixel regions to define each of the sub-pixel regions.
[0815] 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.
[0816] A plurality of color filter regions (or a plurality of color conversion regions) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, a plurality of color filter regions (or a plurality of 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. Details about quantum dots may be as described herein. The first region, the second region, and / or the third region may also each include a scatterer.
[0817] For example, the light emitting device may emit (e.g., be configured to emit) a first light, the first region may absorb (e.g., be configured to absorb) the first light to emit a first-first color light, the second region may absorb (e.g., be configured to absorb) the first light to emit a second-first color light, and the third region may absorb (e.g., be configured to absorb) the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In detail, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0818] In addition to the light emitting device as described, 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.
[0819] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.
[0820] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.
[0821] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside while (e.g., concurrently) preventing ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0822] In addition to the color filter and / or color conversion layer, various functional layers may be additionally arranged on the sealing portion according to the use of the electronic device. Examples of functional layers may include a touch screen layer and / or a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., a fingertip and / or a pupil, etc.).
[0823] In addition to the light emitting device as described, the authentication device may also include a biometric information collector.
[0824] 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, ultrasound diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), and / or projectors, etc.
[0825] Electronic devices
[0826] The light emitting device may be included in one or more suitable electronic devices.
[0827] For example, an electronic device including a light-emitting device can be at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor 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 stretchable display, a laser printer, a phone (e.g., a mobile phone, a tablet phone), a tablet computer, a PDA, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality display or an augmented reality display, a vehicle, a video wall with multiple displays spliced together, a theater screen or a stadium screen, a light therapy device, a sign, and one or more combinations thereof.
[0828] The light emitting device may have excellent or appropriate light emitting efficiency and a long lifespan, and thus, an electronic device including the light emitting device may have characteristics such as high brightness, high resolution, and low power consumption.
[0829] Figure 2 and Figure 3 Description
[0830] Figure 2 is a cross-sectional view of a light emitting apparatus as an example of an electronic device according to one or more embodiments.
[0831] 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.
[0832] 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 the substrate 100, and may provide a flat surface on the substrate 100.
[0833] 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.
[0834] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0835] 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 .
[0836] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the electrodes from each other.
[0837] The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source and drain regions of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed portions of the source and drain regions of the active layer 220.
[0838] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device may be disposed on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0839] 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.
[0840] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a specific region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic organic film. In one or more embodiments, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.
[0841] The second electrode 150 may be disposed on the intermediate layer 130, and the second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0842] The encapsulation part 300 may be disposed on the second cover layer 170. The encapsulation part 300 may be disposed on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic films and organic films.
[0843] Figure 3 is a cross-sectional view of a light emitting apparatus as an example of an electronic device according to another embodiment.
[0844] In addition to the light shielding pattern 500 and the functional region 400 being additionally arranged on the packaging portion 300, Figure 3 Light emitting devices and Figure 2 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 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. Figure 3 The light emitting devices in the light emitting device may be series light emitting devices.
[0845] Figure 4 Description
[0846] Figure 4is a schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments. As a device for displaying moving images or still images, the electronic device 1 may be a portable electronic device (such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an e-book, a portable multimedia player (PMP), a navigation or ultra-mobile PC (UMPC)) and one or more suitable products (such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device). The electronic device 1 may be such a product as described herein or a part 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 glasses-like display or a head-mounted display (HMD)) or a part of a wearable device. However, the embodiments are not limited thereto. For example, the electronic device 1 may include a dashboard of a vehicle, a central instrument panel of a vehicle, a central information display (CID) arranged on the dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle or a display arranged behind a front seat, a head-up display (HUD) mounted in front of the vehicle or projected on a front windshield, or a computer-generated hologram augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 A case is shown in which the electronic device 1 is a smartphone.
[0847] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.
[0848] The non-display area NDA is an area where no image is displayed, and may entirely surround the display area DA. A driver for providing an electrical signal or power to a display device arranged in the display area DA may be arranged in the non-display area NDA. A pad (also called a "pad" or "solder pad"), which is an area to which an electronic component or a printed circuit board can be electrically connected, may be arranged in the non-display area NDA.
[0849] In the electronic device 1, the length in the x-axis direction (or x direction) and the length in the y-axis direction (or y direction) may be different from each other, and the z-axis direction (or z direction) may be the thickness direction of the electronic device 1. In one or more embodiments, as Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be the same as the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0850] Figure 5 and FIG. 6A to FIG. 6C Description
[0851] Figure 5 is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to one or more embodiments. FIG. 6A to FIG. 6C 1 and 2 are schematic diagrams of the interior of a vehicle 1000 according to one or more embodiments.
[0852] Reference Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable devices for moving an object to be transported (such as a person, an object, or an animal) from a starting point to a destination. The vehicle 1000 may include a vehicle (e.g., a car) traveling on a road or track, a ship moving on an ocean or a river, and / or an airplane flying in the sky using the action of air, etc.
[0853] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train running on a track.
[0854] The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical equipment required for driving is installed as other components in addition to the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or a column provided at a boundary between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front wheels and rear wheels, and / or left wheels and right wheels, etc.
[0855] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , a cluster 1400 , a central instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0856] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0857] 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 the plurality of side window glasses 1100 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 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0858] In one or more embodiments, the side window glass 1100 can be separated and / or separated from each other in the x-direction or in the direction opposite to the x-direction. For example, the first side window glass 1110 and the second side window glass 1120 can be separated and / or separated from each other in the x-direction or in the direction opposite to the x-direction. In other words, the imaginary straight line L connecting the side window glass 1100 can extend in the x-direction or in the direction opposite to the x-direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 can extend in the x-direction or in the direction opposite to the x-direction.
[0859] 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.
[0860] The side view mirror 1300 can provide a rear view of the vehicle 1000. The side view mirror 1300 can be installed 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.
[0861] Cluster 1400 may be arranged in front of the steering wheel. Cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, an automatic shift selector indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0862] The central instrument panel 1500 may include a control panel on which a plurality of keys for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The central instrument panel 1500 may be arranged at one side of the cluster 1400 .
[0863] The passenger seat instrument panel 1600 may be separated and / or apart from the cluster 1400, and the central instrument panel 1500 may be arranged between the passenger seat instrument panel 1600 and the cluster 1400. In one or more embodiments, the cluster 1400 may be arranged to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be arranged to correspond to the passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0864] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the central instrument panel 1500, and the passenger seat instrument panel 1600.
[0865] The display device 2 may include an organic light-emitting display device, an inorganic light-emitting display device, and / or a quantum dot display device, etc. Hereinafter, as the display device 2 according to one or more disclosed embodiments, an organic light-emitting display device including a light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described may be used in the disclosed embodiments.
[0866] Reference Fig. 6A , the display device 2 may be arranged on the central instrument panel 1500. In one or more embodiments, the display device 2 may display navigation information. In one or more embodiments, the display device 2 may display audio, video, or information about vehicle settings.
[0867] Reference Figure 6B , the display device 2 may be arranged on the cluster 1400. When the display device 2 is arranged on the cluster 1400, the cluster 1400 may display driving information and the like through the display device 2. For example, the cluster 1400 may be implemented digitally. The digital cluster 1400 may display vehicle information and driving information as images. For example, the needle and range of a tachometer and one or more suitable warning light icons may be displayed through digital signals.
[0868] Reference 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 1400 and / or the information displayed on the central instrument 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 1400 and / or the information displayed on the central instrument panel 1500.
[0869] Manufacturing method
[0870] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region by using one or more suitable methods (such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and / or laser induced thermal imaging, etc.).
[0871] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be within a range of about 100° C. to about 500° C., the deposition temperature may be ... -8 About 10 -3 The vacuum level is in the range of 10 torr and the speed is about 0.01 angstrom per second. to about The vacuum deposition is performed at a deposition rate within a range of .
[0872] Definition of terms
[0873] As used herein, the term "C 3 -C 60 "Carbocyclyl" refers to a cyclic group consisting of only carbon as a ring atom and having 3 to 60 carbon atoms, and the term "C 1 -C 60 The term "heterocyclic group" refers to a ring group having 1 to 60 carbon atoms and having a hetero atom as a ring-forming atom in addition to carbon. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. 1 -C 60 The number of ring-forming atoms of the heterocyclic group can be 3 to 61.
[0874] As used herein, a "cyclic group" may (for example, simultaneously) include C3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups.
[0875] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-poor nitrogen-containing C 1 -C 60 The term "heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.
[0876] For example,
[0877] C 3 -C 60 The carbocyclic group may be: i) a group T1; or ii) a condensed ring group in which two or more of the group T1 are condensed with 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 acenaphthene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, a benzophenone group, a fluorene group, a spirobifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),
[0878] C 1 -C 60The heterocyclic group may be: i) a group T2; ii) a condensed ring group in which two or more of the groups T2 are condensed with each other; or iii) a condensed ring group in which at least one group T2 and at least one group T1 are condensed with 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 benzothiophene group, a 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, benzofurandibenzo thiophene 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, benzo quinoline 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 and / or azadibenzofuran group, etc.),
[0879] Pi-electron-rich C 3 -C 60 The cyclic group may be: i) a group T1; ii) a condensed ring group in which two or more of the groups T1 are condensed with each other; iii) a group T3; iv) a condensed ring group in which two or more of the groups T3 are condensed with each other; or v) a condensed ring group in which at least one group T3 and at least one group T1 are condensed with each other (e.g., C 3 -C 60a 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 benzothiololcarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiol group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group and / or a benzothiophenodibenzothiophene group, etc.),
[0880] π-electron-poor nitrogen-containing C 1 -C 60 The heterocyclic group may be: i) a group T4; ii) a condensed ring group in which two or more of the groups T4 are condensed with each other; iii) a condensed ring group in which at least one group T4 and at least one group T1 are condensed with each other; iv) a condensed ring group in which at least one group T4 and at least one group T3 are condensed with each other; or v) a condensed ring group in which at least one group T4, at least one group T1 and at least one group T3 are condensed with 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 , benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline 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 and / or azadibenzofuran group, etc.),
[0881] 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,
[0882] 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,
[0883] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a thiole group or a borole group, and
[0884] 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.
[0885] As used herein, the term "cyclic group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic, π-electron-rich C 3 -C 60 Ring-based or π-electron-poor nitrogen-containing C 1 -C 60 The “heterocyclic group” may refer to a group condensed to any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group and / or a tetravalent group, etc.) according to the structure of the formula used for the corresponding term. For example, the “phenyl group” may be a benzo group, a phenyl group and / or a phenylene group, etc., which can be easily understood by a person of ordinary skill in the art based on the structure of the formula including the “phenyl group”.
[0886] Depending on the context, a divalent group may refer to or may be a multivalent group (eg, trivalent, tetravalent, etc., not just divalent) based on, for example, the structure of the formula associated with the term used.
[0887] Unit Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 An example of a heterocyclic group is C 3 -C 10 Cycloalkyl, C 1 -C10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 An example of a heterocyclic group is C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 heteroarylene groups, divalent non-aromatic condensed polycyclic groups and divalent non-aromatic condensed heteropolycyclic groups.
[0888] As used herein, the term "C 1 -C 60 The term “alkyl” refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and / or tert-decyl, etc. As used herein, the term “C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl groups are divalent groups of substantially the same structure.
[0889] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 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 end of the alkyl group, and examples thereof are ethenyl, propenyl and / or butenyl, etc. 2 -C 60"Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of substantially the same structure.
[0890] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 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 end of the alkyl group, and examples thereof are ethynyl and / or propynyl, etc. 2 -C 60 "Alkyne" refers to a 2 -C 60 Alkynyl is a divalent group of substantially the same structure.
[0891] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 It is C 1 -C 60 The invention further comprises a monovalent group represented by an alkyl group, and examples thereof are a methoxy group, an ethoxy group and / or an isopropoxy group and the like.
[0892] As used herein, the term "C 3 -C 10 The term "cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[ 3 -C 10 "Cycloalkylene" refers to a cycloalkylene group having a 3 -C 10 Cycloalkyl is a divalent group of substantially the same structure.
[0893] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof are 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl, etc. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of substantially the same structure.
[0894] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof are cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of substantially the same structure.
[0895] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms in its ring structure and has at least one double bond (eg, carbon-carbon double bond). 1 -C 10 Examples of heterocycloalkenyl groups are 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term "C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of substantially the same structure.
[0896] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups are phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, corynyl and / or ovaphenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be condensed with each other.
[0897] As used herein, the term "C 1 -C 60The term "heteroaryl" as used herein refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 Examples of heteroaryl groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and / or naphthyridinyl, etc. When C 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the rings may be condensed with each other.
[0898] As used herein, the term "monovalent non-aromatic condensed polycyclic radical" refers to a monovalent group having two or more rings condensed to each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms and no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic condensed polycyclic radicals are indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. As used herein, the term "divalent non-aromatic condensed polycyclic radical" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic radical.
[0899] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group having two or more rings condensed to each other, including at least one heteroatom as a ring-constituting atom in addition to carbon atoms (for example, having 1 to 60 carbon atoms), and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzo The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
[0900] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 It is C 6 -C 60 aryl), and as used herein the term "C 6 -C 60 "Arylthio" refers to -SA 103 (Among them, A 103 It is C 6 -C 60 aryl).
[0901] As used herein, the term "C 7 -C 60 "Arylalkyl" refers to -A 104 A 105 (Among them, A 104 It is C 1 -C 54 Alkylene, and A 105 It is C 6 -C 59 aryl), and as used herein the term "C2 -C 60 "Heteroarylalkyl" refers to -A 106 A 107 (Among them, A 106 It is C 1 -C 59 Alkylene, and A 107 It is C 1 -C 59 heteroaryl).
[0902] As used herein, the term " 10a ” can be:
[0903] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0904] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -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 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;
[0905] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -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 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl; or
[0906] -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 ).
[0907] The Q used here 1To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group; C 7 -C 60 Arylalkyl; or C 2 -C 60 Heteroarylalkyl.
[0908] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms are O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0909] The term "third row transition metal" as used herein includes Hf, Ta, W, Re, Os, Ir, Pt and / or Au, among others.
[0910] As used herein, "Ph" refers to phenyl, as used herein, "Me" refers to methyl, as used herein, "Et" refers to ethyl, as used herein, "tert-Bu", " t "Bu" or "Bu t " refers to tert-butyl, and "OMe" as used herein refers to methoxy.
[0911] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". In other words, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0912] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" may be a phenyl group substituted with a C 6-C 60 Aryl C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0913] Unless otherwise defined, as used herein, *, *', *", and *'" all refer to binding sites with adjacent atoms in the corresponding formula or moiety.
[0914] The x-axis, y-axis, and z-axis used herein are not limited to the three axes in the orthogonal coordinate system, and can be interpreted in a broad sense including the three axes. For example, the x-axis, y-axis, and z-axis can refer to axes that are orthogonal to each other, or can refer to axes in different directions that are not orthogonal to each other.
[0915] Hereinafter, the compound according to the embodiment and the light emitting device according to the embodiment will be described in more detail with reference to Synthesis Examples and Examples. The phrase "using B instead of A" used in describing Synthesis Examples means using the same molar equivalent of B instead of the same molar equivalent of A.
[0916] Terms such as "substantially", "about", and "approximately" are used as relative terms rather than terms of degree, and are intended to account for the inherent deviations in measured or calculated values that one of ordinary skill in the art will recognize. They may include the stated value and an acceptable range of deviations as 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 standard deviations, or ±30%, ±20%, ±10%, ±5% of the stated value.
[0917] The numerical ranges disclosed herein include and are intended to disclose all subranges contained within the same numerical precision. For example, a range of "1.0 to 10.0" includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Therefore, the applicant reserves the right to amend this specification (including the claims) to explicitly list any subranges contained within the ranges explicitly listed herein.
[0918] The light emitting device and / or any other related device or component according to the embodiments of the present disclosure described herein can be implemented using any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the light emitting device can be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device can 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 can 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 to perform various functions described herein. The computer program instructions are stored in a memory, which can 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 can also be stored in other non-temporary computer-readable media (such as a CD-ROM, a flash drive, etc. as an example). In addition, it should be appreciated by those skilled in the art that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices can be combined or integrated into a single computing device, or the functions of a specific computing device can be distributed across one or more other computing devices.
[0919] In the present disclosure, when the particles are spherical, "diameter" means the average particle diameter, and when the particles are non-spherical, "diameter" means the length of the major axis. The diameter (or size) of the particles can be measured by particle size analysis, dynamic light scattering, scanning electron microscopy and / or transmission electron microscopy photography. When the size of the particles is measured using a particle size analyzer, the average particle diameter (or particle size) can be referred to as D50. The term "D50" as used herein refers to the average diameter (or size) of the particles corresponding to the cumulative volume of 50% by volume in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle in a distribution curve accumulated in the order of the smallest particle size to the largest particle size when the total number of particles is 100%. Particle size analysis can be performed with a HORIBALA-950 laser particle size analyzer.
[0920] Example
[0921] Synthesis Example 1: Synthesis of Compound 4
[0922]
[0923] 1) Synthesis of intermediate 4-1
[0924] 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,8'-indeno[2,1-c]carbazole] (1.0 equivalent), compound 4-a (1.0 equivalent), Pd2 (dba) 3 (5 mol%), Xphos (7 mol%) and sodium tert-butoxide (NaO t Bu, 2.0 equivalents) was dissolved in dioxane (0.1M) and stirred at 110°C for 3 hours to prepare a reaction mixture. After the reaction mixture was cooled at room temperature, the solvent was removed therefrom by distillation under reduced pressure at 8 mbar, the mixture was diluted with water, and an organic layer was obtained by subjecting it to three extraction processes using dichloromethane (MC). The obtained organic layer was dried and concentrated using anhydrous magnesium sulfate, and column chromatography (MC: hexane) was used to obtain intermediate 4-1 (yield 75%).
[0925] 2) Synthesis of intermediate 4-2
[0926] Intermediate 4-1 (1.0 equivalent) was dissolved in triethyl orthoformate ((OEt) 3 CHCl (30 equivalents), 37% HCl (1.5 equivalents) was added thereto, followed by stirring at 80°C for 18 hours to prepare a reaction mixture. After the reaction mixture was cooled at room temperature, triethyl orthoformate therein was concentrated, the mixture was diluted with water, and an organic layer was obtained by subjecting it to three extraction processes using MC. The obtained organic layer was dried and concentrated by using anhydrous magnesium sulfate, and column chromatography (MC: methanol) was used to obtain intermediate 4-2 (yield: 87%).
[0927] 3) Synthesis of compound 4
[0928] Intermediate 4-2 (1.0 equivalent), potassium platinum (II) chloride (K 2 PtCl 4 , 1.1 equivalents) and 2,6-lutidine (4.0 equivalents) were dissolved in 1,2-dichlorobenzene (0.05M) and stirred at 120 ° C for 3 days under nitrogen conditions to prepare a reaction mixture. After the reaction mixture was cooled at room temperature, 1,2-dichlorobenzene was concentrated and removed, the mixture was diluted with water, and an organic layer was obtained by three extraction processes using dichloromethane. The obtained organic layer was dried and concentrated by using anhydrous magnesium sulfate, and column chromatography (MC: hexane) was used to obtain compound 4 (yield 46%).
[0929] ESI-LCMS:[M]+:C 80 H 69 N 4 OPt,1297.9
[0930] Synthesis Example 2: Synthesis of Compound 3
[0931]
[0932] Compound 3 was synthesized in substantially the same manner as for the synthesis of Intermediate 4-1, Intermediate 4-2, and Compound 4, except that 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,12'-indeno[1,2-c]carbazole] was used instead of 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,8'-indeno[2,1-c]carbazole].
[0933] ESI-LCMS:[M]+:C 80 H 69 N 4 OPt,1297.7
[0934] Synthesis Example 3: Synthesis of Compound 34
[0935]
[0936] Compound 34 was synthesized in substantially the same manner as for the synthesis of Intermediate 4-1, Intermediate 4-2 and Compound 4, except that 3'-(3-bromo-5-(methyl-d3)phenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,12'-indeno[1,2-c]carbazole] was used instead of 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,8'-indeno[2,1-c]carbazole] and Compound 34-a was used instead of Compound 4-a.
[0937] ESI-LCMS:[M]+:C 84 H 72 D 3 N 4 OPt,1354.2
[0938] Synthesis Example 4: Synthesis of Compound 35
[0939]
[0940] Compound 35 was synthesized in essentially the same manner as for the synthesis of Intermediate 4-1, Intermediate 4-2 and Compound 4, except that 7'-(5-bromo-2-(methyl-d3)phenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,12'-indeno[1,2-c]carbazole] was used instead of 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,8'-indeno[2,1-c]carbazole] and Compound 35-a was used instead of Compound 4-a.
[0941] ESI-LCMS:[M]+:C 84 H 72 D 3 N 4 OPt,1354.2
[0942] Synthesis Example 5: Synthesis of Compound 63
[0943]
[0944] Compound 63 was synthesized in substantially the same manner as for the synthesis of Intermediate 4-1, Intermediate 4-2 and Compound 4, except that 7-(3-bromophenoxy)-5-(4-(methyl-d3)-5-(4-(methyl-d3)phenyl)pyridin-2-yl)-12,12-diphenyl-5,12-dihydrobenzo[4,5]thiorrolo[3,2-c]carbazole was used instead of 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,8'-indeno[2,1-c]carbazole] and Compound 63-a was used instead of Compound 4-a.
[0945] ESI-LCMS:[M]+:C 79 H 54 D 9 N 4 OPtSi,1316.1
[0946] Synthesis Example 6: Synthesis of Compound 70
[0947]
[0948] Compound 70 was synthesized in substantially the same manner as for the synthesis of Intermediate 4-1, Intermediate 4-2 and Compound 4, except that 3-(3-bromophenoxy)-5-(4-(tert-butyl)-5-(phenyl-d5)pyridin-2-yl)-12,12-diphenyl-5,12-dihydrobenzo[4,5]thiorrolo[3,2-c]carbazole was used instead of 7'-(3-bromophenoxy)-5'-(4-(tert-butyl)pyridin-2-yl)-5'H-spiro[fluorene-9,8'-indeno[2,1-c]carbazole] and Compound 70-a was used instead of Compound 4-a.
[0949] ESI-LCMS:[M]+:C 80 H 58 D 5 N 4 OPtSi,1324.3
[0950] LC / MS of the compounds synthesized in the Synthesis Examples are shown in Table 1. Those skilled in the art can easily recognize the synthesis methods of compounds other than the compounds synthesized in the Synthesis Examples by referring to the synthesis routes and source materials.
[0951] Table 1
[0952]
[0953] Example 1
[0954] As an anode, a 15 ohm per square centimeter (Ω / cm 2 )(1,200 Angstroms ) A glass substrate for an ITO electrode (product of Corning Inc.) was cut into a size of 50 millimeters (mm) × 50 mm × 0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, cleaned by irradiating ultraviolet rays and exposing to ozone for 30 minutes, and then mounted on a vacuum deposition device.
[0955] NPD is deposited on the anode to form a A hole injection layer having a thickness of 1000 mm is formed, and HT3 is deposited on the hole injection layer to form a A hole transport layer having a thickness of , and CzSi is deposited on the hole transport layer to form a The thickness of the emission auxiliary layer is .
[0956] A premixed host of HTH30 and ETH2, compound 3, and compound DF9 were co-deposited on the emission auxiliary layer in a weight ratio of 85:14:1 to form a The emission layer is formed by depositing TSPO1 on the emission layer to form a A hole blocking layer with a thickness of 1000 Å is formed, and TPBI is deposited on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is deposited on the electron injection layer to form a A cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.
[0957]
[0958]
[0959] Examples 2 to 6 and Comparative Examples 1 and 2
[0960] A light emitting device was manufactured in substantially the same manner as in Example 1, except that the compound for forming the emission layer was changed as shown in Table 2.
[0961] Evaluation Example 1
[0962] The brightness of each of the light emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 and 2 at 1,000 (cd / m 2 The driving voltage (V), efficiency (cd / A), maximum emission wavelength (nm) and device life (hours (h)) at the brightness of the device are shown in Table 2. In Table 2, the device life (T 95 ) is a measure of the time (h) it takes until the brightness drops to 95% of the initial brightness.
[0963] Table 2
[0964]
[0965]
[0966]
[0967] It is confirmed from Table 2 that the light emitting devices according to Examples 1 to 6 have driving voltage, luminous efficiency, and device lifespan superior to those of the light emitting devices according to Comparative Examples 1 and 2.
[0968] According to one or more embodiments, by using an organic metal compound, a light emitting device having reduced driving voltage, improved color purity and efficiency, and increased lifespan, and a high-quality electronic device including the same may be manufactured.
[0969] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for the purpose of limitation. The description of features or aspects within each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.
Claims
1. A light emitting device, comprising: a first electrode; a second electrode, facing the first electrode; as well as an intermediate layer, located between the first electrode and the second electrode and including an emission layer, Wherein, the light emitting device further comprises an organic metal compound represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 Among them, in formula 1-1 and formula 1-2, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 to X4 are independently C or N, CycloCY1, CycloCY2, CycloCY 31 To Ring CY 33 and ring CY4 are independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1 to L3 are independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', where * and *' both represent the binding sites with adjacent atoms, n1 to n3 are each independently an integer from 1 to 5, T1 is *-C(Z1)(Z2)-*', *-Si(Z1)(Z2)-*' or *-Ge(Z1)(Z2)-*', wherein * and *' both represent the binding sites with adjacent atoms, R1, R2, R 31 To R 33 , R4, R 1a and R 1b are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C6-C 60 arylthio, -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, a2, a31 to a33 and a4 are each independently an integer from 1 to 20, Z1 and Z2 are each independently unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C6-C 60 arylthio, -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), R1 with quantity a1, R2 with quantity a2, R 31 , the number of R is a32 32 , the number of R is a33 33 and two or more adjacent groups in the number a4 of R4 may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, Z1 and Z2 may be optionally combined with each other to form an unsubstituted or substituted with at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, Z1 or Z2 can be optionally combined with R 31 To R 33 One or more rings CY 31 To Ring CY 33 to form an unsubstituted or substituted with at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, R 10a yes: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy or C6-C 60 arylthio; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or Unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C4 alkyl, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
2. The light emitting device according to claim 1, wherein: The emission layer includes a host and a dopant, and The dopant includes the organometallic compound.
3. The light emitting device according to claim 1, further comprising a nitrogen-containing C1-C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound emitting delayed fluorescence, or any combination thereof, in, The organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 3 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 linker comprising O, S, N, B, C, Si or any combination thereof, and * represents a bonding position with any atom included in the remaining part other than the group represented by Formula 3 of the third compound.
4. The light emitting device according to claim 3, wherein: The second compound includes a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or any combination thereof, and The fourth compound is a compound including a ring group including boron and nitrogen as ring-constituting atoms.
5. The light emitting device according to claim 3, wherein: The transmitting layer comprises: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound or any combination thereof, and The emitting layer is configured to emit blue light. 6 . An electronic device comprising the light emitting device according to claim 1 .
7. The electronic device according to claim 6, further comprising a thin film transistor, in, The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode of the thin film transistor.
8. The electronic device of claim 6, further comprising a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. 9 . An electronic device comprising the light emitting device according to claim 1 .
10. The electronic device according to claim 9, wherein: The electronic device 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 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 stretchable display, a laser printer, a phone, a tablet computer, 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 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, a sign, and combinations thereof.
11. An organic metal compound, the organic metal compound is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 in, In formula 1-1 and formula 1-2, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 to X4 are independently C or N, CycloCY1, CycloCY2, CycloCY 31 To Ring CY 33 and ring CY4 are independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1 to L3 are independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', where * and *' both represent the binding sites with adjacent atoms, n1 to n3 are each independently an integer from 1 to 5, T1 is *-C(Z1)(Z2)-*', *-Si(Z1)(Z2)-*' or *-Ge(Z1)(Z2)-*', wherein * and *' both represent the binding sites with adjacent atoms, R1, R2, R 31 To R 33 , R4, R 1a and R 1b are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C6-C 60 arylthio, -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, a2, a31 to a33 and a4 are each independently an integer from 1 to 20, Z1 and Z2 are each independently unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C6-C 60 arylthio, -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), R1 with quantity a1, R2 with quantity a2, R 31 , the number of R is a32 32 , the number of R is a33 33 and two or more adjacent groups in the number a4 of R4 may optionally be combined with each other to form an unsubstituted or substituted group having at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, Z1 and Z2 may be optionally combined with each other to form an unsubstituted or substituted with at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, Z1 or Z2 can be optionally combined with R 31 To R 33 One or more rings CY 31 To Ring CY 33 to form an unsubstituted or substituted with at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, R 10a yes: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy or C6-C 60 arylthio; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or Unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C4 alkyl, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
12. The organometallic compound according to claim 11, wherein X1, X2 and X3 are all C, and X4 is N, The bond between X1 and M and the bond between X4 and M are both coordination bonds, and The bond between X2 and M and the bond between X3 and M are both covalent bonds.
13. The organometallic compound according to claim 11, wherein CycloCY1, CycloCY2, CycloCY 31 To Ring CY 33 and ring CY4 are independently: a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene 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 benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole 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, The invention also includes but is not limited to oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, dibenzooxasilane group, dibenzothiasilane group, dibenzodihydroazasilane group, dibenzodihydrodisilane group, dibenzodihydrosilane group, dibenzodioxane group, dibenzooxathiainene group, dibenzoxazine group, dibenzopyran group, dibenzodithiainene group, dibenzothiazine group, dibenzothiopyran group, dibenzocyclohexadiene group, dibenzodihydropyridine group or dibenzodihydropyrazine group.
14. The organometallic compound according to claim 11, wherein R1, R2, R 31 To R 33 and R4 are independently: Hydrogen, Deuterium, -F, C1-C 20 Alkyl or C1-C 20 Alkoxy; All are substituted with deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 10 C1-C12 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof 20 Alkyl or C1-C 20 Alkoxy; All are unsubstituted or substituted with deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 are independently: hydrogen, deuterium, -F, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or All are unsubstituted or substituted with deuterium, -F, C1-C 60 Alkyl, C1-C 60 C3-C4 alkyl, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
15. The organometallic compound according to claim 11, wherein At least one R1 is a group represented by formula S1: Wherein, in Formula S1, R 111 To R 113 are as defined with reference to R1 in Formula 1-1 or Formula 1-2, a111 is an integer from 1 to 5, a112 is an integer from 1 to 3, a113 is an integer from 1 to 5, and *Indicates the binding site with the adjacent atom.
16. The organometallic compound according to claim 11, wherein Z1 and Z2 are independently: C1-C 20 Alkyl or C1-C 20 Alkoxy; All are substituted with deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 10 C1-C12 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof 20 Alkyl or C1-C 20 Alkoxy; All are unsubstituted or substituted with deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 are independently: hydrogen, deuterium, -F, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or unsubstituted or substituted with deuterium, -F, C1-C 60 Alkyl, C1-C 60 C3-C4 alkyl, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
17. The organometallic compound according to claim 11, wherein In formula 1-1, The group represented by is a group represented by one of the formulas CY3-1(1) to CY3-1(6), and In formula 1-2, The group represented is a group represented by the formula CY3-2(1) or the formula CY3-2(2): Among them, in Formula CY3-1(1) to Formula CY3-1(6), Formula CY3-2(1) and Formula CY3-2(2), X 311 is C(R 311 ) or N, and X 312 is C(R 312 ) or N, X 321 is C(R 321 ) or N, X 322 is C(R 322 ) or N, X 323 is C(R 323 ) or N, and X 324 is C(R 324 ) or N, X 331 is C(R 331 ) or N, X 332 is C(R 332 ) or N, X 333 is C(R 333 ) or N, and X 334 is C(R 334 ) or N, T1 is as defined in Formula 1-1 or Formula 1-2, R 311 and R 312 All are as shown in R in Formula 1-1 or Formula 1-2 31 As defined, R 321 To R 324 All are as shown in R in Formula 1-1 or Formula 1-2 32 As defined, R 331 To R 334 All are as shown in R in Formula 1-1 or Formula 1-2 33 As defined, R 311 , R 312 , R 321 To R 324 and R 331 To R 334 Two or more adjacent groups in the formula (R) may be optionally combined with each other to form an unsubstituted or substituted group having at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, * represents the binding position with M in Formula 1-1 or Formula 1-2, *" represents the binding site with L2 in Formula 1-1 or Formula 1-2, and *"' represents the binding site with L3 in Formula 1-1 or Formula 1-2.
18. The organometallic compound according to claim 11, wherein In formula 1-1 and formula 1-2, Depend on The group represented by is a group represented by one of the formulas CY1(1) to CY1(11), Depend on The group represented by is a group represented by one of the formulas CY2(1) to CY2(13), and Depend on The group represented is a group represented by one of the formulas CY4(1) to CY4(29): Among them, in Formula CY1(1) to Formula CY1(11), Formula CY2(1) to Formula CY2(13) and Formula CY4(1) to Formula CY4(29), T 21 is B(Y 21 ), C(Y 21 )(Y 22 ), N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 is C(Y 21 ), N or Si(Y 21 ), R 11 To R 17 are as defined with reference to R1 in Formula 1-1 or Formula 1-2, R 21 To R 26 , Y 21 and Y 22 As defined with reference to R2 in Formula 1-1 or Formula 1-2, R 41 To R 47 are as defined with reference to R4 in Formula 1-1 or Formula 1-2, * represents the binding site with M in Formula 1-1 or Formula 1-2, *' represents the binding site with L1 in Formula 1-1 or Formula 1-2, *" represents the binding site with L2 in Formula 1-1 or Formula 1-2, and *"' represents the binding site with L3 in Formula 1-1 or Formula 1-2.
19. The organometallic compound according to claim 11, wherein In Formula 1-1 and Formula 1-2, T1 is a group represented by Formula T-1 or Formula T-2: Wherein, in Formula T-1 and Formula T-2, T 11 is C, Si or Ge, T 12 is a single bond, *-C(Z3)(Z4)-*', *-Si(Z3)(Z4)-*' or *-Ge(Z3)(Z4)-*', wherein * and *' both represent the binding sites with adjacent atoms, X 51 C(Z 11 ) or N, X 52 C(Z 12 ) or N, X 53 C(Z 13 ) or N, X 54 C(Z 14 ) or N, X 55 C(Z 15 ) or N, X 61 is C(Z 21 ) or N, X 62 is C(Z 22 ) or N, X 63 is C(Z 23 ) or N, X 64 is C(Z 24 ) or N, X 65 is C(Z 25 ) or N, Z 11 To Z 15 and Z3 are defined as Z1 in Formula 1-1 or Formula 1-2, Z 21 To Z 25 and Z4 are defined as Z2 in Formula 1-1 or Formula 1-2, Z 11 To Z 15 , Z 21 To Z 25 Two or more adjacent groups among Z3 and Z4 may be optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 a heterocyclic group, and * and *' both indicate the binding sites with adjacent atoms.
20. The organometallic compound according to claim 11, wherein The organic metal compound represented by Formula 1-1 is a group represented by Formula 1-1(A1) or Formula 1-1(A2), and The organic metal compound represented by Formula 1-2 is a group represented by Formula 1-2(A1) or Formula 1-2(A2): Formula 1-1 (A1) Formula 1-1(A2) Formula 1-2 (A1) Formula 1-2 (A2) Among them, in Formula 1-1(A1), Formula 1-1(A2), Formula 1-2(A1) and Formula 1-2(A2), M, X1 to X4 and T1 are all as defined in Formula 1-1 or Formula 1-2, L2 is *-O-*', *-S-*' or *-Se-*', X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, and X 15 is C(R 15 ) or N, 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, X 311 is C(R 311 ) or N, X 312 is C(R 312 ) or N, X 321 is C(R 321 ) or N, X 322 is C(R 322 ) or N, X 323 is C(R 323 ) or N, X 324 is C(R 324 ) or N, X 331 is C(R 331 ) or N, X 332 is C(R 332 ) or N, X 333 is C(R 333 ) or N, and X 334 is C(R 334 ) or N, 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 11 To R 15 are as defined with reference to R1 in Formula 1-1 or Formula 1-2, R 21 To R 23 are as defined with reference to R2 in Formula 1-1 or Formula 1-2, R 311 and R 312 All are as shown in R in Formula 1-1 or Formula 1-2 31 As defined, R 321 To R 324 All are as shown in R in Formula 1-1 or Formula 1-2 32 As defined, R 331 To R 334 All are as shown in R in Formula 1-1 or Formula 1-2 33 As defined, R 41 To R 44 are as defined with reference to R4 in Formula 1-1 or Formula 1-2, R 11 To R 15 , R 21 To R 23 , R 311 , R 312 , R 321 To R 324 , R 331 To R 334 , R 41 To R 44 Two or more adjacent groups among Z1 and Z2 may be optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C1-C 60 a heterocyclic group, and R 10a As defined in Formula 1-1 or Formula 1-2.
21. The organometallic compound according to claim 11, wherein The organometallic compound is selected from Compound 1 to Compound 72:
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