Composition, light-emitting device, electronic device and electronic device including light-emitting device, and
By using specific organometallic compounds and nitrogen-containing heterocyclic group compositions as the emission layer material in the light emitting device, the problem of insufficient color purity, luminous efficiency and lifetime characteristics in the prior art is solved, and more efficient and longer-lasting luminous properties are achieved.
Patent Information
- Application Number
- CN202411544557.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-11-03
- Filing Date
- 2024-10-31
- Publication Date
- 2025-05-06
AI Technical Summary
There is room for improvement in existing luminescent devices in terms of color purity, luminous efficiency and lifetime characteristics, especially in terms of improving color purity and extending lifetime.
The composition of the luminescent device is used as the emission layer material of the light emitting device using an organometallic compound represented by Formula 1 and a second compound containing a nitrogen-containing C1-C60 heterocyclyl group containing π electron-deficient, a third compound of a group represented by Formula 3 or a fourth compound capable of emitting a delayed fluorescence.
Improved color purity, luminous efficiency and lifetime characteristics of the luminescent device are achieved, specifically manifested as higher photoluminescent quantum yield (PLQY), shorter attenuation time and narrower full width of the emission spectrum.
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Figure CN119930700A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0151024 filed on November 3, 2023 in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments of the present disclosure relate to a composition, a light-emitting device, an electronic device and an electronic equipment including the light-emitting device, and an organometallic compound. Background Art
[0004] Self-emissive devices among light-emitting devices (eg, organic light-emitting devices, etc.) have relatively wide viewing angles, relatively high contrast ratios, relatively short response times, and excellent or appropriate characteristics in terms of brightness, driving voltage, and / or response speed.
[0005] In the light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode in the order described. Holes provided by the first electrode move toward the emission layer through the hole transport region, and electrons provided by the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to generate excitons. Excitons can transition and decay from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] One or more aspects of the embodiments of the present disclosure relate to compositions capable of providing improved color purity, improved luminous efficiency and / or improved lifetime characteristics for light-emitting devices, organometallic compounds, light-emitting devices with improved color purity, improved luminous efficiency and / or improved lifetime characteristics, and / or electronic devices and electronic equipment including light-emitting devices.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments of the disclosure.
[0008] According to one or more embodiments of the present disclosure, the composition includes:
[0009] an organometallic compound represented by Formula 1; and
[0010] Includes at least one π-electron-deficient nitrogen-containing C 1 -C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof,
[0011] wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other:
[0012] Formula 1
[0013]
[0014] Formula 1A
[0015]
[0016] Among them, Ar in formula 1 1 may be a group represented by Formula 1A,
[0017] The * in Formula 1A indicates the same ring as in Formula 1 1 The binding site
[0018] Wherein, in Formula 1 and Formula 1A,
[0019] M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag) or copper (Cu),
[0020] X 1 To X 4 can be independently C or N,
[0021] i)X 1 The bond between and M may be a coordination bond, and ii) is selected from X 2 The bond between M and X 3 The key between M and X 4 One of the bonds between and M is a coordinate bond, and the other two may each be a covalent bond,
[0022] Cyclo 1 To Ring CY 4 and Ring W 4 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0023] Ring W 2 Can be saturated C 3 -C 8 Carbocyclic group,
[0024] n4 can be 0, 1 or 2, wherein when n4 is 0, the The group represented by may be a single bond,
[0025] X 51 Can be a single bond, *-N(Z 51a )-*'、*-B(Z 51a)-*'、*-P(Z 51a )-*'、*-C(Z 51a )(Z 51b )-*'、*-Si(Z 51a )(Z 51b )-*'、*-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(Z 51a )=*'、*=C(Z 51a )-*'、*-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*',
[0026] X 52 Can be a single bond, *-N(Z 52a )-*'、*-B(Z 52a )-*'、*-P(Z 52a )-*'、*-C(Z 52a )(Z 52b )-*'、*-Si(Z 52a )(Z 52b )-*'、*-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(Z 52a )=*'、*=C(Z 52a )-*'、*-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*',
[0027] R 1 To R 4 , Z 51a , Z 51b , Z 52a and Z 52b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0028] T 1 , T 2 , T 31 To T 35 and T 4 Can be independently:
[0029] Hydrogen, deuterium, -F or cyano;
[0030] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; or
[0031] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl) biphenyl or phenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl substituted by (for example, any appropriate) combination thereof,
[0032] a1 to a4 may each independently be an integer selected from 0 to 10,
[0033] c1 can be an integer selected from 1 to 3,
[0034] c2 may be an integer selected from 1 to 15,
[0035] c4 may be an integer selected from 1 to 10,
[0036] Formula 1A may satisfy at least one selected from Condition A and Condition B:
[0037] Condition A
[0038] T 31 and T 35 may be different from each other; and
[0039] Condition B
[0040] T 32 and T 34 Can be different from each other,
[0041] In Formula 1A, The groups represented by The groups represented by may be different from each other,
[0042] Selected from Cyclo 1 CY 2 CY 3 CY 4 , R 1 , R 2 , R3 , R 4 , Z 51a , Z 51b , Z 52a , Z 52b , T 1 , T 2 , T 31 , T 32 , T 33 , T 34 , T 35 and T 4 Two or more of the may be optionally bonded together to form (or provide) unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0043] * indicates the binding site with the neighboring atoms,
[0044] R 10a Can be:
[0045] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0046] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12)、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or (for example, any appropriate) combination thereof;
[0047] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or (for example, any appropriate) combination thereof;
[0048] -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 );or
[0049] (e.g., any suitable) combination thereof, and
[0050] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any suitable combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0051] Formula 3
[0052]
[0053] Among them, in formula 3,
[0054] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0055] X 71may be a single bond, or a linking group comprising O, S, N, B, C, Si or a combination thereof (e.g., any appropriate one), and
[0056] * indicates a bonding site with an arbitrary atom included in the remaining part other than the group represented by Formula 3 in the third compound.
[0057] According to one or more embodiments of the present disclosure, a light emitting device includes:
[0058] a first electrode;
[0059] a second electrode facing (e.g., opposite and confronting) the first electrode;
[0060] an interlayer between the first electrode and the second electrode and including an emissive layer; and
[0061] An organometallic compound represented by Formula 1.
[0062] According to one or more embodiments of the present disclosure, an electronic device includes a light emitting device.
[0063] According to one or more embodiments of the present disclosure, an electronic device includes a light emitting device.
[0064] One or more aspects of embodiments of the present disclosure relate to an organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS
[0065] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and together with the description are used to explain the principles of the present disclosure. The above and other aspects, features and advantages of certain embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:
[0066] Figure 1 A diagram schematically showing the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0067] Figure 2 and Figure 3 Each is a diagram schematically showing a structure of a light emitting device as an electronic device according to one or more embodiments of the present disclosure; and
[0068] Figure 4 , Figure 5 , Fig. 6A , Figure 6B and Figure 6C Each is a diagram schematically showing a structure of an electronic device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0069] The embodiments in the accompanying drawings will now be explained in more detail with reference to their examples, wherein the same reference numerals refer to the same elements throughout the present disclosure, and for the sake of brevity, their repeated description may not be provided. In this regard, the embodiments of the present disclosure may have different forms and should not be interpreted as being limited to the descriptions stated herein. Accordingly, by referring to the accompanying drawings, the embodiments of the present disclosure are only described to explain the various aspects of the present disclosure. As used herein, the term "and / or" or "or" may include any and all combinations of one or more related enumerated items. Throughout the present disclosure, expressions such as "at least one of ...", "one of ..." and "selected from ...", when before / after the list of elements, modify the entire list of elements without modifying the individual elements of the list. For example, "at least one of a, b and c", "selected from at least one of a, b and c", "selected from at least one of a to c", etc., may indicate only a, only b, only c, both a and b (e.g., a and b at the same time), both a and c (e.g., a and c at the same time), both b and c (e.g., b and c at the same time), all a, b and c, or variations thereof. As used herein, “ / ” may be interpreted as “and” or as “or” depending on the specific circumstances.
[0070] According to one or more embodiments of the present disclosure, the composition includes:
[0071] an organometallic compound represented by Formula 1; and
[0072] Includes at least one π-electron-deficient nitrogen-containing C 1 -C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof,
[0073] wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other:
[0074] Formula 1
[0075]
[0076] Formula 3
[0077]
[0078] Among them, in formula 3,
[0079] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0080] X 71may be a single bond, or a linking group comprising O, S, N, B, C, Si or a combination thereof (e.g., any appropriate one), and
[0081] * indicates a bonding site with an arbitrary atom included in the remaining part other than the group represented by Formula 3 in the third compound.
[0082] In the present disclosure, the organometallic compound represented by Formula 1 may be referred to as a “first compound”.
[0083] For the description of each of Formula 1 and Formula 3, reference may be made to the present disclosure.
[0084] In one or more embodiments, the composition may be included in a layer comprising 1) an organometallic compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof. The phrase "a layer comprising a composition" may refer to a layer comprising a mixture comprising 1) an organometallic compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof. Therefore, the phrase "a layer comprising a composition" may, for example, be clearly distinguished from a bilayer comprising (e.g., consisting of) 1) a first layer comprising an organometallic compound represented by Formula 1 and 2) a second layer comprising a second compound, a third compound, a fourth compound, or any combination thereof.
[0085] In one or more embodiments, the composition may be a composition prepared by using one or more appropriate methods (such as a deposition process and / or a wet process, etc.) to form (or provide) the following layer, which includes 1) an organic metal compound represented by Formula 1 and 2) a second compound, a third compound, a fourth compound, or any combination thereof. For example, the composition may be a premixed mixture prepared for use in a deposition process (e.g., a vacuum deposition process). The premixed mixture may, for example, be filled into a deposition source in a vacuum chamber, and two or more compounds included in the premixed mixture may be co-deposited.
[0086] In one or more embodiments, a weight ratio of the organometallic compound represented by Formula 1 to the second compound in the composition may be in a range of about 10:90 to about 90:10 or about 20:80 to about 80:20.
[0087] According to one or more embodiments of the present disclosure, a light emitting device may include:
[0088] a first electrode;
[0089] a second electrode facing (e.g., opposite and confronting) the first electrode;
[0090] an interlayer between the first electrode and the second electrode and including an emissive layer; and
[0091] An organometallic compound represented by Formula 1.
[0092] For the description of Formula 1, reference may be made to the present disclosure.
[0093] The light-emitting device includes the organometallic compound represented by Formula 1, and may accordingly have improved color purity, improved luminous efficiency, and / or improved lifespan characteristics.
[0094] In one or more embodiments, an interlayer in a light-emitting device may include an organic metal compound represented by Formula 1.
[0095] In one or more embodiments, an emission layer in a light emitting device may include the organometallic compound represented by Formula 1.
[0096] 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,
[0097] The organometallic compound represented by Formula 1, the second compound, the third compound, and the fourth compound in the light-emitting device may be different from each other:
[0098] Regarding the description of each of the second compound to the fourth compound in the composition, reference may be made to the present disclosure.
[0099] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
[0100] In one or more embodiments, the second to fourth compounds may each include at least one deuterium.
[0101] In one or more embodiments, the second compound may include at least one silicon.
[0102] In one or more embodiments, the third compound may include at least one silicon.
[0103] In one or more embodiments, in addition to the organic metal compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound and a third compound, wherein at least one of the second compound and the third compound may include at least one deuterium, at least one silicon, or any combination thereof.
[0104] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound. At least one of the organometallic compound represented by Formula 1 and the second compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound represented by Formula 1 and the second compound, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof.
[0105] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound. At least one of the organometallic compound represented by Formula 1 and the third compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound represented by Formula 1 and the third compound, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a fourth compound, or any combination thereof.
[0106] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a fourth compound. At least one of the organometallic compound represented by Formula 1 and the fourth compound may include at least one deuterium. The fourth compound may have a role in improving the color purity, luminous efficiency and / or life characteristics of the light-emitting device. In one or more embodiments, in addition to the organometallic compound represented by Formula 1 and the fourth compound, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a third compound, or any combination thereof.
[0107] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, each of the composition and the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound and a third compound. The second compound and the third compound may form (or provide) an excited complex. At least one of the organometallic compound represented by Formula 1, the second compound, and the third compound may include at least one deuterium.
[0108] In one or more embodiments, the highest occupied molecular orbital (HOMO) energy level of the organometallic compound represented by Formula 1 may be in the range of about -5.35 eV to about -5.15 eV or about -5.30 eV to about -5.20 eV.
[0109] In one or more embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound represented by Formula 1 may be in the range of about -2.20 eV to about -1.80 eV or about -2.15 eV to about -1.90 eV.
[0110] The HOMO energy level and the LUMO energy level can be evaluated by cyclic voltammetry analysis of the organometallic compound represented by Formula 1 (see Evaluation Example 1).
[0111] In one or more embodiments, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of the film including the organic metal compound represented by Formula 1 may be in the range of about 430 nanometers (nm) to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
[0112] In one or more embodiments, the full width at half maximum (FWHM) of the emission spectrum of the film including the organic metal compound represented by Formula 1 may be 40 nm or less, for example, about 5 nm to about 40 nm, about 10 nm to about 40 nm, about 15 nm to about 40 nm, about 20 nm to about 40 nm, about 5 nm to about 38 nm, about 10 nm to about 38 nm, about 15 nm to about 38 nm, or about 20 nm to about 38 nm.
[0113] In one or more embodiments, the photoluminescence quantum yield (PLQY) of the film including the organometallic compound represented by Formula 1 may be in the range of about 50% to about 99%, about 55% to about 95%, about 60% to about 95%, about 65% to about 95%, about 70% to about 95%, about 55% to about 90%, about 60% to about 90%, about 65% to about 90%, or about 70% to about 90%.
[0114] In one or more embodiments, the decay time of the film including the organometallic compound represented by Formula 1 may be in a range of about 1.80 to about 3.00 μs, about 1.90 to about 2.70 μs, about 1.90 to about 2.50 μs, or about 1.90 to about 2.30 μs.
[0115] The maximum emission wavelength, FWHM, PLQY and decay time of the organometallic compound represented by Formula 1 were evaluated for the film including the organometallic compound represented by Formula 1. For description of the evaluation method thereof, reference may be made to, for example, Evaluation Examples 2 and 3.
[0116] In one or more embodiments, an emission layer in a light emitting device may include: i) an organometallic compound represented by Formula 1; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, wherein the emission layer may emit blue light.
[0117] In one or more embodiments, the maximum emission wavelength (e.g., emission peak wavelength) of blue light may be 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, about 455 nm to about 470 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
[0118] In one or more embodiments, the full width at half maximum of the blue light may be 40 nm or less, or may be in the range of about 5 nm to about 40 nm, about 10 nm to about 40 nm, about 15 nm to about 40 nm, about 20 nm to about 40 nm, about 5 nm to about 38 nm, about 10 nm to about 38 nm, about 15 nm to about 38 nm, or about 20 nm to about 38 nm.
[0119] In one or more embodiments, the blue light may be deep blue light.
[0120] In one or more embodiments, the CIEx coordinate of blue light (eg, the CIEx coordinate of bottom emission) may be in a range of about 0.125 to about 0.140 or about 0.130 to about 0.140.
[0121] In one or more embodiments, the CIEy coordinate of blue light (eg, the CIEy coordinate of bottom emission) may be in the range of about 0.100 to about 0.130.
[0122] For examples of the maximum emission wavelength and CIEy coordinate of blue light, reference may be made to Table 7 and Table 9 in the present disclosure.
[0123] In one or more embodiments, the second compound may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or (eg, any suitable) combinations thereof.
[0124] In one or more embodiments, the third compound may not include (eg, may exclude) the following compounds:
[0125]
[0126] In one or more embodiments, the fourth compound may be a compound in which the difference between its triplet energy level (unit: eV) and its singlet energy level (eV) is in the range of about 0 eV or more to about 0.5 eV or less (or about 0 eV or more to about 0.3 eV or less).
[0127] In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including (eg, simultaneously) both boron (B) and nitrogen (N) as ring-constituting atoms.
[0128] In one or more embodiments, the fourth compound may be C-containing 8 -C 60 A compound of a polycyclic group, which includes two or more cyclic groups fused while sharing B (for example, one is the third ring, and the other is the fourth ring).
[0129] In one or more embodiments, the fourth compound may include a fused ring in which at least one third ring is fused with at least one fourth ring, for example, to form a fused ring including four or more rings.
[0130] wherein the third ring of the fourth compound can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and
[0131] The fourth ring of the fourth compound can be 1,2-azaborinyl, 1,3-azaborinyl, 1,4-azaborinyl, 1,2-dihydro-1,2-azaborinyl, 1,4-oxaborinyl, 1,4-thiaborinyl or 1,4-dihydroborinyl.
[0132] In one or more embodiments, the third compound may not include (eg, may exclude) (eg, any suitable) compound represented by Formula 3-1 described herein.
[0133] In one or more embodiments, the second compound may include a compound represented by Formula 2:
[0134] Formula 2
[0135]
[0136] Among them, in formula 2,
[0137] L 51 To L 53 may be independently a single bond, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0138] b51 to b53 may each independently be an integer selected from 1 to 5,
[0139] 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 selected from X 54 To X 56 At least one of may be N, and
[0140] R 51 To R 56 and R 10a Each may be the same as described herein.
[0141] 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 a combination thereof (e.g., any appropriate combination):
[0142] Formula 3-1
[0143]
[0144] Formula 3-2
[0145]
[0146] Formula 3-3
[0147]
[0148] Formula 3-4
[0149]
[0150] Formula 3-5
[0151]
[0152] Among them, in Formula 3-1 to Formula 3-5,
[0153] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0154] 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 ),
[0155] 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 ),
[0156] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0157] X 85 Can be C or Si,
[0158] L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a Substituted pyridyl, wherein Q 4 and Q 5 can be independently compared with Q 1 Same as described,
[0159] b81 to b85 may each independently be an integer selected from 1 to 5,
[0160] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may each independently be the same as described herein,
[0161] a71 to a74 may each independently be an integer selected from 0 to 20, and
[0162] R 10a May be the same as described herein.
[0163] In one or more embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or a combination thereof (eg, any appropriate combination):
[0164] Formula 502
[0165]
[0166] Formula 503
[0167]
[0168] Among them, in equation 502 and equation 503,
[0169] Ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0170] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0171] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0172] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0173] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0174] Y 51 and Y 52 may be independently B or P(=O),
[0175] R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b may each be the same as described herein, and
[0176] a501 to a504 may each independently be an integer selected from 0 to 20.
[0177] In one or more embodiments, the light emitting device may satisfy at least one selected from Condition 1 to Condition 4:
[0178] Condition 1
[0179] The LUMO energy level (eV) of the third compound> the LUMO energy level (eV) of the organic metal compound represented by Formula 1; Condition 2
[0180] The LUMO energy level (eV) of the organic metal compound represented by Formula 1> the LUMO energy level (eV) of the second compound; Condition 3
[0181] The HOMO energy level (eV) of the organometallic compound represented by Formula 1> the HOMO energy level (eV) of the third compound; and
[0182] Condition 4
[0183] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.
[0184] Here, each of the HOMO level and the LUMO level of each of the organometallic compound represented by Formula 1, the second compound, and the third compound may be a negative value and may be measured according to an appropriate method, for example, the method described in Evaluation Example 1 in the present disclosure.
[0185] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the organic metal compound represented by Formula 1 and the LUMO energy level of the second compound may be in the range of about 0.1 eV or greater to about 1.0 eV or less, the absolute value of the difference between the LUMO energy level of the organic metal compound represented by Formula 1 and the LUMO energy level of the third compound may be in the range of about 0.1 eV or greater to about 1.0 eV or less, the absolute value of the difference between the HOMO energy level of the organic metal compound represented by Formula 1 and the HOMO energy level of the second compound may be 1.25 eV or less (e.g., about 0.2 eV or greater to about 1.25 eV or less) and / or the absolute value of the difference between the HOMO energy level of the organic metal compound represented by Formula 1 and the HOMO energy level of the third compound may be about 1.25 eV or less (e.g., about 0.2 eV or greater to about 1.25 eV or less).
[0186] When the relationship between the LUMO energy level and the HOMO energy level satisfies the aforementioned conditions, a balance between holes and electrons injected into the emission layer can be achieved.
[0187] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0188] First embodiment
[0189] According to the first embodiment, the emission layer of the interlayer in the light-emitting device may include an organic metal compound represented by Formula 1, and may further include a host, wherein the organic metal compound represented by Formula 1 and the host may be different from each other, and the emission layer may emit phosphorescence or fluorescence emitted by the organic metal compound represented by Formula 1. For example, according to the first embodiment, the organic metal compound represented by Formula 1 may be a dopant or an emitter. For example, in some embodiments, the organic metal compound represented by Formula 1 may be a phosphorescent dopant or a phosphorescent emitter.
[0190] Phosphorescence or fluorescence emitted from the organometallic compound represented by Formula 1 may be blue light.
[0191] In one or more embodiments, the emission layer may further include an auxiliary dopant. The auxiliary dopant may effectively transfer energy to the organic metal compound represented by Formula 1 used as a dopant or emitter, and in this regard, the auxiliary dopant may be used to improve the luminous efficiency of the organic metal compound represented by Formula 1.
[0192] The auxiliary dopant may be different from the organometallic compound represented by Formula 1 and the host.
[0193] In one or more embodiments, the auxiliary dopant may be a compound capable of emitting delayed fluorescence.
[0194] In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0195] Second embodiment
[0196] According to a second embodiment, the emission layer of the interlayer in the light-emitting device may include an organic metal compound represented by Formula 1, and may further include a host and a dopant, wherein the organic metal compound represented by Formula 1, the host and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted by the dopant.
[0197] In one or more embodiments, the organometallic compound represented by Formula 1 in the second embodiment is not a dopant but may be used as an auxiliary dopant that transfers energy to a dopant (or an emitter).
[0198] In one or more embodiments, the organometallic compound represented by Formula 1 in the second embodiment may be used as an emitter, and may also be used as an auxiliary dopant that transfers energy to a dopant (or emitter).
[0199] For example, in some embodiments, the phosphorescence or fluorescence emitted by the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0200] The dopant (or emitter) in the second embodiment may be any phosphorescent dopant material (e.g., an organic metal compound represented by Formula 1, an organic metal compound represented by Formula 401, or a (e.g., any appropriate) combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or a (e.g., any appropriate) combination thereof).
[0201] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength (e.g., emission peak 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, about 455 nm to about 470 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
[0202] The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503.
[0203] In one or more embodiments, the host in the first embodiment and the second embodiment may be any host material (eg, a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or a combination thereof (eg, any appropriate combination).
[0204] In one or more embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or a combination thereof (eg, any appropriate one).
[0205] In one or more embodiments, the light emitting device may further include a capping layer disposed outside the first electrode (eg, on the first electrode) and / or outside the second electrode (eg, on the second electrode).
[0206] In one or more embodiments, the light-emitting device may further include at least one of a first capping layer disposed outside the first electrode (e.g., on the first electrode) and a second capping layer disposed outside the second electrode (e.g., on the second electrode), wherein at least one of the first capping layer and the second capping layer may include an organic metal compound represented by Formula 1. For more details about the first capping layer and / or the second capping layer, reference may be made to the description provided herein.
[0207] In one or more embodiments, the light emitting device may include:
[0208] a first capping layer disposed outside the first electrode (eg, on the first electrode) and including an organic metal compound represented by Formula 1;
[0209] a second capping layer disposed outside the second electrode (eg, on the second electrode) and including an organic metal compound represented by Formula 1; or
[0210] A first capping layer and a second capping layer.
[0211] The phrase “(the interlayer and / or the capping layer) includes the organic metal compound represented by Formula 1” as used herein may be understood as “(the interlayer and / or the capping layer) may include one kind of the organic metal compound represented by Formula 1 or two or more different kinds of organic metal compounds each represented by Formula 1”.
[0212] In one or more embodiments, the interlayer and / or the capping layer may include only Compound 1, which is an organic metal compound represented by Formula 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include Compound 1 and Compound 2, which are organic metal compounds represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in substantially the same layer (e.g., both Compound 1 and Compound 2 (e.g., simultaneously) may be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0213] The term "interlayer" as used herein refers to a single layer and / or multiple layers between a first electrode and a second electrode of a light emitting device.
[0214] According to one or more embodiments of the present disclosure, the electronic device may include a light emitting device. In one or more embodiments, the electronic device may further include a thin film transistor. For example, in some embodiments, the electronic device may further include: a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. In some embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or a combination thereof (e.g., any appropriate). For more details about the electronic device, reference may be made to the description provided herein.
[0215] According to one or more embodiments of the present disclosure, electronic equipment may include a light emitting device.
[0216] For example, the electronic device may be at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a portable phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, and a billboard.
[0217] According to one or more embodiments of the present disclosure, there is provided an organometallic compound represented by Formula 1. Details regarding Formula 1 may refer to the description provided herein.
[0218] The synthesis method of the organometallic compound represented by Formula 1 can be recognized by one of ordinary skill in the art by referring to the Synthesis Examples and / or Examples provided herein.
[0219] Description of chemical formula
[0220] In formula 1, Ar 1 It may be a group represented by Formula 1A:
[0221] Formula 1A
[0222]
[0223] The * in Formula 1A indicates the same ring as in Formula 1 1 For example, in one or more embodiments, the * in Formula 1A may indicate a binding site with ring CY in Formula 1 1 The binding site of the nitrogen atom in .
[0224] Description of Formula 1A (or Ar in Formula 1 1 ), please refer to the present disclosure.
[0225] In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
[0226] In one or more embodiments, M may be Pt.
[0227] In formula 1, X 1 To X 4 They may each independently be C or N.
[0228] In one or more embodiments, X 1Can be C. In some embodiments, X in Formula 1 1 may be C, and C may be the carbon of the carbene portion.
[0229] In one or more embodiments, X in Formula 1 1 Can be N.
[0230] In one or more embodiments, X 2 and X 3 can each be C, and X 4 Can be N.
[0231] In formula 1, i)X 1 The bond between and M may be a coordination bond, and ii) selected from X 2 The key between M and X 3 The key between M and X 4 Any one of the bonds between and M may be a coordinate bond, and the other two bonds may each be a covalent bond.
[0232] In one or more embodiments, X 2 The key between M and X 3 The bonds between X and M may each be covalent bonds, and X 4 The bond between M and R may be a coordinate bond.
[0233] In one or more embodiments, X 4 Can be N, and X 4 The bond between M and R may be a coordinate bond.
[0234] In Formula 1 and Formula 1A, ring CY 1 To Ring CY 4 and Ring W 4 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0235] For example, in one or more embodiments, CY 1 Can be nitrogen-containing C 1 -C 60 Heterocyclic group.
[0236] In Formula 1, ring CY 1 i) containing X 1 ii) a 5-membered ring fused with at least one 6-membered ring containing X 1 5-membered ring, or iii) containing X 1 6-membered ring.
[0237] In one or more embodiments, ring CY in Formula 1 1 i) containing X1 or ii) a 5-membered ring fused with at least one 6-membered ring containing X 1 For example, in some embodiments, ring CY 1 May include X 1 A 5-membered ring bonded to M in Formula 1. Here, X 1 The 5-membered ring may be pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl or thiadiazolyl, and contains X 1 The 6-membered ring may be optionally fused to a ring containing X 1 The 5-membered ring and the 6-membered ring of can each independently be phenyl, pyridyl or pyrimidinyl.
[0238] In one or more embodiments, CY 1 Can be X 1 A 5-membered ring containing X 1 The 5-membered ring may be an imidazolyl group or a triazolyl group.
[0239] In one or more embodiments, CY 1 It may be an X-containing 1 A 5-membered ring, and a 6-membered ring fused to at least one X 1 The 5-membered ring of may be a benzimidazolyl group or an imidazopyridinyl group.
[0240] In one or more embodiments, CY 1 It may be imidazolyl, triazolyl, benzimidazolyl, naphthoimidazolyl or imidazopyridinyl.
[0241] In one or more embodiments, X 1 Can be C, and the ring CY 1 It may be imidazolyl, triazolyl, benzimidazolyl, naphthoimidazolyl or imidazopyridinyl.
[0242] In one or more embodiments, CY 2 CY 3 CY 4 and Ring W 4The phenyl groups may be independently phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl, quinolyl, isoquinolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzocarbazolyl, benzofluorenyl, naphthobenzosilyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzocarbazolyl, dibenzofluorenyl, dibenzosilyl, a naphthothirolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothirolyl group, an azanaphthobenzofuranyl group, an azanaphthobenzothiophenyl group, an azabenzocarbazolyl group, an azabenzofluorenyl group, an azanaphthobenzothirolyl group, an azadinaphthofuranyl group, an azadinaphthothiophenyl group, an azadibenzocarbazolyl group, an azadibenzofluorenyl group, an azadinaphthobenzothirolyl group, an azadinaphthofuranyl group, an azadinaphthothiophenyl group, an azadinabenzocarbazolyl group, an azadinabenzofluorenyl group, or an azadinaphthothirolyl group.
[0243] In one or more embodiments, CY 2 It may be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl or dibenzosilyl.
[0244] In one or more embodiments, CY 3 The phenyl group may be phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, dibenzothioyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzocarbazolyl, benzofluorenyl, naphthobenzothioyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzocarbazolyl, dibenzofluorenyl, dinaphthothioyl, azadibenzofuranyl, azadibenzothiophenyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azanaphthobenzofuranyl, azanaphthobenzothiophenyl, azabenzocarbazolyl, azabenzofluorenyl, azanaphthobenzothioyl, azadinaphthofuranyl, azadinaphthothiophenyl, azadibenzocarbazolyl, azadibenzofluorenyl or azadinaphthothioyl.
[0245] In one or more embodiments, CY 3 It may be a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an azacarbazolyl group, an azabenzocarbazolyl group or an azadibenzocarbazolyl group.
[0246] In one or more embodiments, CY 4 It may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl or isoquinolyl.
[0247] In one or more embodiments, the ring W 4 It may be phenyl.
[0248] In Formula 1A, ring W 2 Can be saturated C 3 -C 8 For example, in one or more embodiments, ring W2 It may be cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
[0249] In Formula 1A, n4 may be 0, 1 or 2. When n4 is 0, The group represented by may be a single bond.
[0250] In one or more embodiments, n4 of Formula 1A may be 0 or 1.
[0251] In formula 1, X 51 Can be a single bond, *-N(Z 51a )-*'、*-B(Z 51a )-*'、*-P(Z 51a )-*'、*-C(Z 51a )(Z 51b )-*'、*-Si(Z 51a )(Z 51b )-*'、*-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(Z 51a )=*'、*=C(Z 51a )-*'、*-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*'. 51a and Z 51b Each may be the same as described herein. 51a and Z 51b may be optionally bonded to each other to form (or provide) unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0252] For example, in some embodiments, X 51 Can be *-N(Z 51a )-*'、*-B(Z 51a )-*'、*-P(Z 51a )-*'、*-C(Z 51a )(Z 51b )-*'、*-Si(Z 51a )(Z 51b )-*'、*-Ge(Z51a )(Z 51b )-*', *-S-*', *-Se-*' or *-O-*'.
[0253] In formula 1, X 52 Can be a single bond, *-N(Z 52a )-*'、*-B(Z 52a )-*'、*-P(Z 52a )-*'、*-C(Z 52a )(Z 52b )-*'、*-Si(Z 52a )(Z 52b )-*'、*-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(Z 52a )=*'、*=C(Z 52a )-*'、*-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*'. 52a and Z 52b Each may be the same as described herein. 52a and Z 52b may be optionally bonded to each other to form (or provide) unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0254] In some embodiments, in Formula 1, X 52 Can be a single bond, *-N(Z 52a )-*'、*-B(Z 52a )-*'、*-P(Z 52a )-*'、*-C(Z 52a )(Z 52b )-*'、*-Si(Z 52a )(Z 52b )-*'、*-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*' or *-O-*'.
[0255] In one or more embodiments, in Formula 1,
[0256] i)X 52 may be a single bond, and in Formula 1 The group represented by may be a group represented by formula CY3A or formula CY3B,
[0257] ii)X 52 may not be a single bond, and in Formula 1 The group represented by may be a group represented by the formula CY3C, or
[0258] iii)X 52 Can be *-N(R 52a )-*', and R 52a and R 3 may be bonded to form (or provide) unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group:
[0259]
[0260] Among them, in Formula CY3A to Formula CY3C,
[0261] X 3 and X 31 To X 33 can be independently C or N,
[0262] Cyclo 31 CY 32 and CY 33 Each can be C 2 -C 8 Monocyclic groups,
[0263] X 31 and X 3 The key between 3 and X 32 The key between 32 and X 33 The bonds between them can each be chemical bonds,
[0264] *" indicates that 51 The binding site
[0265] * indicates the binding site with M in Formula 1, and
[0266] *' indicates that 52 binding site.
[0267] In one or more embodiments, in Formula CY3A and Formula CY3B, X 31 , X 3 and X 32 can each be C, and X 33 Can be N.
[0268] In one or more embodiments, X in Formula CY3C 31 , X 3 and X 32 Can each be C.
[0269] In formula 1, R 1 To R 4 , Z 51a , Z 51b , Z 52a and Z 52b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each may be the same as described herein.
[0270] In one or more embodiments, in Formula 1, R 1 To R 4 , Z 51a , Z 51b , Z 52a and Z 52b Can be independently:
[0271] Hydrogen, deuterium, -F or cyano;
[0272] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; or
[0273] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 3 -C 10 Cycloalkyl, phenyl, naphthyl, dibenzofuranyl or dibenzothienyl.
[0274] In one or more embodiments, R in Formula 1 4Can be:
[0275] hydrogen, deuterium, -F or cyano; or
[0276] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 alkyl.
[0277] In one or more embodiments, R in Formula 1 4 Can be:
[0278] hydrogen, deuterium, -F or cyano; or
[0279] unsubstituted or substituted with deuterium, -F, cyano or (e.g., any suitable) combination thereof 1 -C 20 alkyl.
[0280] In Formula 1A, T 1 , T 2 , T 31 To T 35 and T 4 Can be independently:
[0281] Hydrogen, deuterium, -F or cyano;
[0282] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; or
[0283] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C20 alkyl)biphenyl or phenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl substituted with (for example, any suitable) combination thereof.
[0284] In one or more embodiments, in Formula 1A, T 1 , T 2 , T 31 To T 35 and T 4 Can be independently:
[0285] Hydrogen, deuterium, -F or cyano;
[0286] unsubstituted or substituted with deuterium, -F, cyano or (e.g., any suitable) combination thereof 1 -C 20 Alkyl; or
[0287] Unsubstituted or deuterated, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl)biphenyl or phenyl substituted with (for example, any appropriate) combination thereof.
[0288] In one or more embodiments, Formula 1A may not include (eg, may exclude) silicon (Si).
[0289] As used herein, the term "C 1 -C 60 "alkyl" and "unsubstituted or substituted with at least one deuterium C 1 -C 20 The “alkyl” radicals may each be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl or tert-decyl, each of which is unsubstituted or substituted by at least one deuterium.
[0290] In one or more embodiments, the term "unsubstituted or substituted with at least one deuterium" as used herein1 -C 60 "alkyl" and "unsubstituted or substituted with at least one deuterium C 1 -C 20 "Alkyl" may each be -CH 3 、-CDH 2 、-CD 2 H.-CD 3 、-CH 2 CH 3 、-CDHCH 3 、-CD 2 CH 3 、-CH 2 CDH 2 、-CDHCDH 2 、-CD 2 CDH 2 、-CH 2 CD 2 H, -CDHCD 2 H.-CD 2 CD 2 H, -CH 2 CD 3 、-CDHCD 3 、-CD 2 CD 3 , or a group represented by one selected from Formula X-1 to Formula X-30:
[0291]
[0292] In Formulae X-1 to X-30, * indicates a binding site with an adjacent atom.
[0293] As used herein, the term "deuterated C 1 -C 60 Alkyl", "C substituted by (at least one) deuterium 1 -C 60 Alkyl", "deuterated C 1 -C 20 "alkyl" or "C 1 -C 20 "Alkyl" may refer to a linear or branched C 1 -C 60 Alkyl (either straight chain or branched chain C 1 -C 20alkyl) in which at least one hydrogen atom is replaced by deuterium, and non-limiting examples thereof may be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl or tert-decyl, each of which is substituted by at least one deuterium (e.g., -CDH 2 、-CD 2 H.-CD 3 、-CDHCH 3 、-CD 2 CH 3 、-CH 2 CDH 2 、-CDHCDH 2 、-CD 2 CDH 2 、-CH 2 CD 2 H, -CDHCD 2 H.-CD 2 CD 2 H, -CH 2 CD 3 、-CDHCD 3 、-CD 2 CD 3 , or a group represented by one selected from Formula X-2 to Formula X-6, Formula X-8 to Formula X-10, Formula X-12 to Formula X-22, and Formula X-24 to Formula X-30).
[0294] In Formula 1 and Formula 1A, a1, a2, a3, a4, c1, c2, and c4 respectively represent R 1 , R 2 , R 3 , R 4 , T 1 , T 2 and T 4 wherein a1 to a4 may each independently be an integer selected from 0 to 10 (e.g., an integer selected from 0 to 6), c1 may be an integer selected from 1 to 3, c2 may be an integer selected from 1 to 15, and c4 may be an integer selected from 1 to 10. When a1 is 2 or more, two or more R 1 may be the same as or different from each other. When a2 is 2 or greater, two or more R 2 may be the same as or different from each other. When a3 is 2 or greater, two or more R 3 may be the same as or different from each other. When a4 is 2 or greater, two or more R 4may be the same as or different from each other. When c1 is 2 or greater, two or more T 1 may be the same as or different from each other. When c2 is 2 or greater, two or more T 2 may be the same as or different from each other, and when c4 is 2 or greater, two or more T 4 Can be the same as or different from each other.
[0295] Formula 1A (or Formula 1) may satisfy at least one selected from Condition A and Condition B:
[0296] Condition A
[0297] T 31 and T 35 are different from each other; and
[0298] Condition B
[0299] T 32 and T 34 Different from each other.
[0300] In one or more embodiments, Formula 1A (or Formula 1) may satisfy Condition A, and may further satisfy one selected from Condition A-1 to Condition A-3:
[0301] Condition A-1
[0302] T 31 is hydrogen, deuterium or -F,
[0303] T 35 for:
[0304] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; or
[0305] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20alkyl)biphenyl or phenyl, naphthyl, dibenzofuranyl or dibenzothienyl substituted with (for example, any appropriate) combination thereof;
[0306] Condition A-2
[0307] T 31 and T 35 are different from each other, and
[0308] T 31 and T 35 may be each independently unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; and
[0309] Condition A-3
[0310] T 31 is unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl, and
[0311] T 35 are each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl)biphenyl or phenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl substituted with (for example, any suitable) combination thereof.
[0312] In one or more embodiments, Formula 1A (or Formula 1) may satisfy Condition B, and may further satisfy one of Conditions B-1 to B-3:
[0313] Condition B-1
[0314] T 32 is hydrogen, deuterium or -F,
[0315] T 34 for:
[0316] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; or
[0317] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl)biphenyl or phenyl, naphthyl, dibenzofuranyl or dibenzothienyl substituted with (for example, any appropriate) combination thereof;
[0318] Condition B-2
[0319] T 32 and T 34 are different from each other, and
[0320] T 32 and T 34 may be each independently unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl, and
[0321] Condition B-3
[0322] T 32is unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl, and
[0323] T 34 are each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl)biphenyl or phenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl substituted with (for example, any suitable) combination thereof.
[0324] In one or more embodiments, Formula 1A (or Formula 1) may satisfy Condition A and / or Condition B, and may further satisfy one selected from Conditions A-1 to A-3 and one selected from Conditions B-1 to B-3.
[0325] In one or more embodiments, the group represented by Formula 1A may be one selected from the group represented by Formula 1A(1) to Formula 1A(4):
[0326] Formula 1A (1)
[0327]
[0328] Formula 1A (2)
[0329]
[0330] Formula 1A (3)
[0331]
[0332] Formula 1A (4)
[0333]
[0334] Wherein, in Formula 1A(1) to Formula 1A(4),
[0335] * indicates the same ring as CY in formula 1 1 The binding site
[0336] Ring W 2 , T 1 , T 2 , T 31 To T 35 , c1 and c2 may each be the same as described herein, and
[0337] T 41 To T 45 Can be independently compared with T 4 Same as described.
[0338] The description of Formula 1A is applicable to each of Formula 1A(1) to Formula 1A(4).
[0339] In one or more embodiments, the group represented by Formula 1A may be a group represented by one selected from Formula 5-1 to Formula 5-100:
[0340]
[0341]
[0342]
[0343]
[0344]
[0345]
[0346]
[0347]
[0348] Wherein, in Formula 5-1 to Formula 5-100, * indicates the same as the ring CY in Formula 1. 1 binding site.
[0349] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium. For example, in one or more embodiments, R 1 To R 4 , Z 51a , Z 51b , Z 52a and Z 52b And T in Formula 1A 1 , T 2 , T 31 To T 35 and T4 and may each independently be deuterium or a deuterium-containing group.
[0350] As used herein, the term "deuterium-containing group" refers to any group containing at least one deuterium and may be additionally substituted with substituents other than deuterium. For example, a deuterium-containing group may include C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, fluorinated biphenyl, (C 1 -C 20 Alkyl) biphenyl, C 3 -C 10 Cycloalkyl, naphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl (e.g., -CH 2 D. -CHD 2 、-CD 3 and / or -C 6 D 5 wait).
[0351] In Formula 1A, The groups represented by The groups represented may be different from each other.
[0352] In one or more embodiments, Ar 1 (or a group represented by Formula 1A) may include unsubstituted or at least one deuterium-substituted C 4 -C 10 Alkyl (for example, i) each unsubstituted or substituted with at least one deuterium-substituted n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl or tert-decyl, etc., or ii) a group represented by Formula X-7 to Formula X-30, etc.) Here, Ar is included 1 unsubstituted or substituted with at least one deuterium in 4 -C 10 The number of the alkyl groups may be 2 or more (eg, 2 to 15).
[0353] In Formula 1 and Formula 1A, a ring selected from CY 1 CY 2 CY 3 CY 4 , R 1 , R2 , R 3 , R 4 , Z 51a , Z 51b , Z 52a , Z 52b , T 1 , T 2 , T 31 , T 32 , T 33 , T 34 , T 35 and T 4 Two or more of the may be optionally bonded together to form (or provide) unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0354] Unless otherwise stated herein, "*" indicates a binding site to an adjacent atom.
[0355] In one or more embodiments, the organometallic compound represented by Formula 1 may be an organometallic compound represented by Formula 1-1 or an organometallic compound represented by Formula 1-2:
[0356] Formula 1-1
[0357]
[0358] Formula 1-2
[0359]
[0360] Among them, in formula 1-1 and formula 1-2,
[0361] M, X 1 To X 4 、Ring W 4 、Ring W 2 、n4、X 51 , T 1 , T 2 , T 31 To T 35 , T 4 , c1, c2 and c4 may each be the same as described herein,
[0362] X 11 Can be C(R 11 ) or N, X 12 Can be C(R 12 ) or N, X 13Can be C(R 13 ) or N, and X 14 Can be C(R 14 ) or N,
[0363] R 11 To R 14 Can be independently compared with R 1 Same as described, and selected from R 11 To R 14 Two or more of the may be optionally bonded together to form (or provide) unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0364] X 21 Can be C(R 21 ) or N, X 22 Can be C(R 22 ) or N, and X 23 Can be C(R 23 ) or N,
[0365] R 21 To R 23 Can be independently compared with R 2 Same as described, and selected from R 21 To R 23 Two or more of the may be optionally bonded together to form (or provide) unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0366] X 31 Can be C(R 31 ) or N, X 32 Can be C(R 32 ) or N, X 33 Can be C(R 33 ) or N, X 34 Can be C(R 34 ) or N, X 35 Can be C(R 35 ) or N, and X 36 Can be C(R 36 ) or N,
[0367] R31 To R 36 can be independently compared with the same R as described for 3 , and selected from R 31 To R 36 Two or more of the may be optionally bonded together to form (or provide) unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0368] X 41 Can be C(R 41 ) or N, X 42 Can be C(R 42 ) or N, X 43 Can be C(R 43 ) or N, and X 44 Can be C(R 44 ) or N,
[0369] R 41 To R 44 Can be respectively with respect to R 4 Same as described, and selected from R 41 To R 44 Two or more of the may be optionally bonded together to form (or provide) unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and
[0370] Formula 1-1 and Formula 1-2 may satisfy at least one selected from Condition A and Condition B:
[0371] Condition A
[0372] T 31 and T 35 are different from each other; and
[0373] Condition B
[0374] T 32 and T 34 Different from each other.
[0375] In formula 1-1 and formula 1-2, The groups represented by The groups represented are different from each other, and
[0376] *Indicates the binding site with the neighboring atoms.
[0377] All descriptions of Formula 1 in the present disclosure may be applied to Formula 1-1 and Formula 1-2.
[0378] In this disclosure, Ar 1 All descriptions of Formula 1A can be applied to Formula 1-1 and Formula 1-2 in which Represents the group.
[0379] In one or more embodiments, in Formula 1-1 and Formula 1-2, X 43 Can be C(R 43 ), and R 43 Can be:
[0380] hydrogen, deuterium, -F or cyano; or
[0381] unsubstituted or substituted with deuterium, -F, cyano or (e.g., any suitable) combination thereof 1 -C 20 alkyl.
[0382] In one or more embodiments, in Formula 1-1 and Formula 1-2, X 42 Can be C(R 42 ), X 43 Can be C(R 43 ), and R 42 and R 43 At least one of may not be hydrogen.
[0383] In one or more embodiments, in Formula 1-1 and Formula 1-2, X 11 Can be C(R 11 ), X 12 Can be C(R 12 ), X 13 Can be C(R 13 ), X 14 Can be C(R 14 ), X 21 Can be C(R 21 ), X 22 Can be C(R 22 ), X 23 Can be C(R 23 ), X 31 Can be C(R 31 ), X 32 Can be C(R 32 ), X 33 Can be C(R 33 ), X 34 Can be C(R 34 ), X 35 Can be C(R35 ), X 36 Can be C(R 36 ), X 41 Can be C(R 41 ), X 42 Can be C(R 42 ), X 43 Can be C(R 43 ), and X 44 Can be C(R 44 ).
[0384] Each of Formula 1-1 and Formula 1-2 may satisfy at least one selected from Conditions H1 to H4:
[0385] Condition H1
[0386] R selected from formula 1-1 11 To R 14 At least one of them is deuterium or a deuterium-containing group, and is selected from R in Formula 1-2 11 and R 12 At least one of is deuterium or a deuterium-containing group;
[0387] Condition H2
[0388] Selected from R 21 To R 23 At least one of is deuterium or a deuterium-containing group;
[0389] Condition H3
[0390] Selected from R 31 To R 36 At least one of is deuterium or a deuterium-containing group; and
[0391] Condition H4
[0392] Selected from R 41 To R 44 At least one of the above is deuterium or a deuterium-containing group.
[0393] In one or more embodiments, the The group represented may be a group represented by one selected from the group consisting of Formula CY1-1 to Formula CY1-42:
[0394]
[0395] Among them, in Formula CY1-1 to Formula CY1-42,
[0396] X 1 may be the same as described herein,
[0397] Y 1 may include O, S, N, C or Si,
[0398] * indicates the binding site with M in Formula 1, and
[0399] *' indicates the ring CY in formula 1 2 binding site.
[0400] In one or more embodiments, X in Formula CY1-1 to Formula CY1-8 1 may be C, and X in Formula CY1-9 to Formula CY1-42 1 Can be N.
[0401] In one or more embodiments, the The group represented may be a group represented by one selected from Formula CY2-1 to Formula CY2-11:
[0402]
[0403] Among them, in Formula CY2-1 to Formula CY2-11,
[0404] X 2 may be the same as described herein,
[0405] Y 2 may include O, S, N, C or Si,
[0406] * indicates the binding site with M in Formula 1,
[0407] *' indicates the ring CY in formula 1 1 binding site, and
[0408] *" indicates the same as X in Formula 1 51 binding site.
[0409] In one or more embodiments, the The group represented by and the group represented by in Formula 1-1 and Formula 1-2 The groups represented may each independently be a group represented by one selected from the group consisting of Formula CY2(1) to Formula CY2(26):
[0410]
[0411] Among them, in formula CY2(1) to formula CY2(26),
[0412] X 2 may be the same as described herein,
[0413] Y 2 Can be O, S, N (R 20 )、C(R 20a )(R20b ) or Si(R 20a )(R 20b ),
[0414] R 20 , R 20a , R 20b and R 21 To R 23 Can be independently compared with R 2 Same as described, where R 21 To R 23 Each of may not be hydrogen,
[0415] * indicates the binding site with M in Formula 1,
[0416] *' indicates the ring CY in formula 1 1 binding site, and
[0417] *" indicates the same as X in Formula 1 51 binding site.
[0418] In one or more embodiments, the The group represented may be a group represented by one selected from the group consisting of Formula CY3-1 to Formula CY3-23:
[0419]
[0420] Among them, in Formula CY3-1 to Formula CY3-23,
[0421] X 3 may be the same as described herein,
[0422] Y 3 may include O, S, N, C or Si,
[0423] * indicates the binding site with M in Formula 1,
[0424] *' indicates the difference with X in Formula 1 52 binding site, and
[0425] *" indicates the same as X in Formula 1 51 binding site.
[0426] In one or more embodiments, the The group represented by may be a group represented by one selected from Formula CY3(1) to Formula CY3(20), and the group represented by in Formula 1-1 and Formula 1-2 The group represented by may be a group represented by one selected from the group consisting of Formula CY3(1) to Formula CY3(12):
[0427]
[0428]
[0429] Among them, in formula CY3(1) to formula CY3(20),
[0430] X 3 may be the same as described herein,
[0431] R 31 To R 36 Can be independently compared with R 3 Same as described, where R 31 To R 36 Each of may not be hydrogen,
[0432] * indicates the binding site with M in Formula 1,
[0433] *' indicates the difference with X in Formula 1 52 binding site, and
[0434] *" indicates the same as X in Formula 1 51 binding site.
[0435] In one or more embodiments, the The group represented by may be a group represented by one selected from the group consisting of Formula CY4(1) to Formula CY4(16):
[0436]
[0437] Among them, in formula CY4(1) to formula CY4(16),
[0438] X 4 may be the same as described herein,
[0439] R 41 To R 44 Can be independently compared with R 4 Same as described, where R 41 To R 44 Each of may not be hydrogen,
[0440] * indicates the binding site with M in Formula 1, and
[0441] *' indicates the difference with X in Formula 1 52 binding site.
[0442] In formula 1, Ar 1 It may be a group represented by Formula 1A:
[0443] Formula 1A
[0444]
[0445] Wherein, in Formula 1A, ring W 2 For non-conjugated "saturated" C 3 -C 8 The carbocyclic group allows the intermolecular interaction of the organometallic compound represented by Formula 1 to be effectively suppressed or reduced.
[0446] In one or more embodiments, T in Formula 1A 1 , T 2 , T 31 To T 35 and T 4 Can be independently:
[0447] Hydrogen, deuterium, -F or cyano;
[0448] unsubstituted or deuterated, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 C substituted with alkyl) biphenyl or (for example, any appropriate) combination thereof 1 -C 20 Alkyl; or
[0449] Each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C 1 -C 20 alkyl) biphenyl or its (for example, any appropriate) combination substituted phenyl, naphthyl, dibenzofuranyl or dibenzothiophene. For example, in one or more embodiments, Formula 1A may not include (for example, may exclude) Si. In this regard, the organometallic compound represented by Formula 1 may have excellent or appropriate thermal stability.
[0450] In addition, in one or more embodiments, Formula 1A may have
[0451] i) Due to The structure represented by the group is asymmetric with respect to the first axis,
[0452] ii) a structure that is asymmetric with respect to the second axis by satisfying at least one selected from Condition A and Condition B, and
[0453] iii) When The groups represented by When the groups represented are different from each other, the structure is asymmetric with respect to the third axis.
[0454] Three different asymmetric structures can be formed (or provided) by including the group represented by 1A,
[0455] 1) the intermolecular interaction of the organometallic compound represented by Formula 1 can be further suppressed or reduced, so that Dexter energy transfer can be effectively suppressed or reduced, and
[0456] 2) The stacking effect between molecules of the organic metal compound represented by Formula 1 can be reduced, so that the sublimation temperature and the deposition temperature can be lowered.
[0457] Accordingly, a light-emitting device including the organometallic compound represented by Formula 1 may have improved light-emitting efficiency and / or improved lifespan characteristics.
[0458] In one or more embodiments, Formula 1A may further include unsubstituted or deuterium-substituted C 1 -C 20 In these embodiments, the asymmetry and bulkiness of Formula 1A may be increased, so that a light-emitting device including the organometallic compound represented by Formula 1 may have further improved luminous efficiency and / or lifetime characteristics.
[0459] In Formula 2, b51 to b53 respectively indicate L 51 Quantity to L 53 and each may be an integer selected from 1 to 5. When b51 is 2 or greater, two or more L 51 may be the same or different from each other. When b52 is 2 or greater, two or more L 52 may be the same as or different from each other, and when b53 is 2 or greater, two or more L 53 In one or more embodiments, b51 to b53 may be 1 or 2, respectively.
[0460] In one or more embodiments, in Formula 2, L 51 To L 53 Can be independently:
[0461] a single key; or
[0462] phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isoxazolyl thiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilyl, dibenzothiosilyl, dibenzodihydroazosilyl, dibenzodihydrodisilyl, dibenzodihydrosilyl, dibenzodioxanyl, dibenzothioxanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithioinyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -Si(Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or (for example, any suitable) combination, and
[0463] 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.
[0464] In an embodiment, in Formula 2, L 51 and R 51 The key between 52 and R 52 The key between 53 and R 53 The key between the two L 51 The key between the two L 52 The key between the two L 53 The bond between 51 With X 54 and X 55 The bonds between the carbons, L in Formula 2 52 With X 54 and X 56 The bonds between the carbons and L in Formula 2 53 With X 55 and X 56 The bonds between the carbon atoms in between may each be a "carbon-carbon single bond".
[0465] In formula 2, X 54 Can be N or C(R 54 ), X 55 Can be N or C(R 55 ), and X 56 Can be N or C(R 56 ), where X 54 To X 56 At least one of may be N. 54 To R 56 Each may be the same as described herein. In one or more embodiments, selected from X 54 To X 56 Two or three of them can each be N.
[0466] R in this disclosure 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 , R507a , R 507b , R 508a and R 508b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3Each may be the same as described herein.
[0467] For example, in one or more embodiments, i) R in Formula 1 1 To R 4 , Z 51a , Z 51b , Z 52a and Z 52b , and ii) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b Can be independently:
[0468] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0469] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or (e.g., any appropriate) combination thereof;
[0470] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, phenyl a dibenzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzothiorol group, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or (for example, any appropriate) combination thereof; or
[0471] -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
[0472] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0473] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH2 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
[0474] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or (for example, any appropriate) combination thereof:
[0475] Formula 91
[0476]
[0477] Among them, in formula 91,
[0478] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group,
[0479] 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 ),
[0480] R 91 , R 91a and R 91b Can be respectively with respect to R 82 , R82a and R 82b Same as described,
[0481] R 10a may be the same as described herein, and
[0482] *Indicates the binding site with the neighboring atoms.
[0483] For example, in one or more embodiments, in Formula 91,
[0484] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a substituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, and
[0485] R 91 , R 91a and R 91b Can be independently:
[0486] Hydrogen or C 1 -C 10 Alkyl; or
[0487] phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or (eg, any appropriate) combination thereof.
[0488] In one or more embodiments, i) R in Formula 1 1 To R 4 , Z 51a , Z 51b , Z 52a and Z 52b , and ii) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b, R 506a , R 506b , R 507a , R 507b , R 508a and R 508b can be independently hydrogen, deuterium, -F, cyano, nitro, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a group represented by one selected from Formula 9-1 to Formula 9-19, a group represented by one selected from Formula 10-1 to Formula 10-246, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -P(=O)(Q 1 )(Q 2 )(Among which about Q 1 To Q 3 More details can be found in the description provided in this article):
[0489]
[0490]
[0491]
[0492]
[0493]
[0494]
[0495]
[0496] Wherein, in Formulae 9-1 to 9-19 and Formulae 10-1 to 10-246, * indicates a bonding site with an adjacent atom, "Ph" represents a phenyl group, "D" represents deuterium, and "TMS" represents a trimethylsilyl group.
[0497] In Formulas 3-1 to 3-5, Formula 502, and Formula 503, a71 to a74 and a501 to a504 each indicate R 71 To R 74 The number and R 501 To R 504and may each independently be an integer selected from 0 to 20. When a71 is 2 or greater, two or more R 71 may be the same as or different from each other. When a72 is 2 or greater, two or more R 72 may be the same as or different from each other. When a73 is 2 or greater, two or more R 73 may be the same or different from each other. When a74 is 2 or greater, two or more R 74 may be the same as or different from each other. When a501 is 2 or greater, two or more R 501 may be the same or different from each other. When a502 is 2 or greater, two or more R 502 may be the same or different from each other. When a503 is 2 or greater, two or more R 503 may be the same as or different from each other, and when a504 is 2 or greater, two or more R 504 In some embodiments, a71 to a74 and a501 to a504 may each independently be an integer selected from 0 to 8.
[0498] In formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented by may each be other than phenyl.
[0499] In one or more embodiments, the formula 2 is represented by *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented may be the same as each other.
[0500] In one or more embodiments, the formula 2 is represented by *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented may be different from each other.
[0501] In one or more embodiments, in Formula 2, b51 and b52 may each be 1, 2 or 3, and L 51 and L 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0502] In one or more embodiments, R in Formula 2 51 and R 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0503] Q 1 To Q 3 may be each independently unsubstituted or substituted by the following C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or (eg, any suitable) combination thereof.
[0504] In one or more embodiments,
[0505] In formula 2, *-(L 51 ) b51 -R 51 The group represented by may be a group represented by one selected from the group consisting of Formula CY51-1 to Formula CY51-26, and / or
[0506] In formula 2, *-(L 52 ) b52 -R 52 The group represented by may be a group represented by one selected from the group consisting of Formula CY52-1 to Formula CY52-26, and / or
[0507] In formula 2, *-(L 53 )b53 -R 53 The group represented by may be a group represented by one selected from the group consisting of Formula CY53-1 to Formula CY53-27, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ):
[0508]
[0509]
[0510]
[0511]
[0512] 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,
[0513] 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 ),
[0514] 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 ),
[0515] 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 ),
[0516] Y 68 Can be single bond, O, S, N(R 68 )、B(R 68 )、C(R 68a )(R 68b ) or Si(R 68a)(R 68b ),
[0517] Y in formula CY51-16 and formula CY51-17 63 and Y 64 Each of may not be a single bond at the same time,
[0518] Y in formula CY52-16 and formula CY52-17 67 and Y 68 Each of may not be a single bond at the same time,
[0519] R 51a To R 51e , R 61 To R 64 , R 63a , R 63b , R 64a and R 64b Can be independently compared with R 51 Same as described, where R 51a To R 51e Each of them may not be hydrogen,
[0520] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b Can be independently compared with R 52 Same as described, where R 52a To R 52e Each of them may not be hydrogen,
[0521] R 53a To R 53e , R 69a and R 69b Can be independently compared with R 53 Same as described, where R 53a To R 53e each may not be hydrogen, and
[0522] *Indicates the binding site with the neighboring atoms.
[0523] For example, in one or more embodiments,
[0524] 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 be independently:
[0525] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, phenyl a dibenzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzothiorol group, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, 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, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl or (for example, any appropriate) combination thereof; or
[0526] -C(Q 1 )(Q 2)(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0527] Q 1 To Q 3 may be each independently phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or (e.g., any appropriate) combination thereof,
[0528] In some embodiments, in Formula CY51-16 and Formula CY51-17, i) Y 63 Can be O or S, and Y 64 Can be Si(R 64a )(R 64b ), or ii) Y 63 Can be Si(R 63a )(R 63b ), and Y 64 can be O or S, and
[0529] In some embodiments, in Formula CY52-16 and Formula CY52-17, i) Y 67 Can be O or S, and Y 68 Can be Si(R 68a )(R 68b ), or ii) Y 67 Can be Si(R 67a )(R 67b ), and Y 68 Can be O or S.
[0530] In one or more embodiments, in Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0531] a single key; or
[0532] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*';or
[0533] phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, pyridyl, pyrrolyl, benzoxadiazolyl or benzothiadiazolyl, each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -Si(Q) 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or a combination thereof (e.g., any suitable combination), and
[0534] 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.
[0535] In one or more embodiments, the formula 3-1 and the formula 3-2 are represented by The group represented by may be a group represented by one selected from the group consisting of Formula CY71-1(1) to Formula CY71-1(8), and / or
[0536] In formula 3-1 and formula 3-3, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-2(1) to Formula CY71-2(8), and / or
[0537] In formula 3-2 and formula 3-4, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-3(1) to Formula CY71-3(32), and / or
[0538] In formula 3-3 to formula 3-5, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-4(1) to Formula CY71-4(32), and / or
[0539] In formula 3-5, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-5(1) to Formula CY71-5(8):
[0540]
[0541]
[0542]
[0543]
[0544] 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),
[0545] X 82 To X 85 , L 81 ,b81,R 81 and R 85 may each be the same as described herein,
[0546] 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 ),
[0547] 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 ),
[0548] X in Formula CY71-1(2) to Formula CY71-1(4), Formula CY71-4(2) to Formula CY71-4(4), Formula CY71-4(10) to Formula CY71-4(12), Formula CY71-4(18) to Formula CY71-4(20), and Formula CY71-4(26) to Formula CY71-4(28) 86 and X 87 Each of may not be a single bond at the same time,
[0549] 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 ),
[0550] 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 ),
[0551] X in formula CY71-2(2) to formula CY71-2(4), formula CY71-3(2) to formula CY71-3(4), formula CY71-3(10) to formula CY71-3(12), formula CY71-3(18) to formula CY71-3(20), formula CY71-3(26) to formula CY71-3(28), and formula CY71-5(2) to formula CY71-5(4) 88 and X 89 Each of may not be a single bond at the same time, and
[0552] R 86 To R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b Can be independently compared with R 81 Same as described.
[0553] Examples of Compounds
[0554] In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from Compound 1 to Compound 267:
[0555]
[0556]
[0557]
[0558]
[0559]
[0560]
[0561]
[0562]
[0563]
[0564]
[0565]
[0566]
[0567] In one or more embodiments, the second compound may be one selected from compound ETH1 to compound ETH101:
[0568]
[0569]
[0570]
[0571]
[0572] In one or more embodiments, the third compound may be one selected from compound HTH1 to compound HTH47:
[0573]
[0574]
[0575] In one or more embodiments, the fourth compound may be one selected from compound DFD1 to compound DFD31:
[0576]
[0577]
[0578] In the above compounds, Ph represents phenyl, D 5 means substitution with five deuteriums, and D 4 means substitution with four deuteriums. For example, The group represented by The groups represented are the same.
[0579] Figure 1 Description
[0580] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments. The light emitting device 10 may include a first electrode 110 , an interlayer 130 , and a second electrode 150 .
[0581] In the following, reference will be made to Figure 1 A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described.
[0582] First electrode 110
[0583] exist Figure 1 In one or more embodiments, a substrate may be additionally provided and arranged under the first electrode 110 and / 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 appropriate heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide or a combination thereof (e.g., any appropriate combination).
[0584] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming (or providing) the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming (or providing) the first electrode 110 may be a high work function material that facilitates injection of holes.
[0585] The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, the material used to form (or provide) the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), or (for example, any appropriate) combination thereof. In one or more embodiments, when the first electrode 110 is a transflective electrode or a reflective electrode, the material used to form (or provide) 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 (for example, any appropriate) combination thereof.
[0586] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.
[0587] Mezzanine 130
[0588] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0589] In one or more embodiments, the interlayer 130 may further include: a hole transport region between the first electrode 110 and the emission layer; and an electron transport region between the emission layer and the second electrode 150 .
[0590] In one or more embodiments, the interlayer 130 may further include metal-containing compounds (such as organometallic compounds, for example, organometallic compounds represented by Formula 1) and / or inorganic materials (such as quantum dots), etc., in addition to one or more suitable organic materials.
[0591] In one or more embodiments, the interlayer 130 may include i) two or more light emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer disposed between two adjacent light emitting units. When the interlayer 130 includes two or more light emitting units and a charge generation layer, the light emitting device 10 may be a tandem light emitting device.
[0592] Hole transport region in interlayer 130
[0593] 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 (e.g., consisting of) a plurality of materials different from each other.
[0594] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or (eg, any appropriate) combinations thereof.
[0595] For example, in some embodiments, the hole transport region may have a multi-layer structure, including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the constituent layers in each structure are stacked in sequence from the first electrode 110 in the order described.
[0596] In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof (eg, any appropriate combination):
[0597] Formula 201
[0598]
[0599] Formula 202
[0600]
[0601] Among them, in equation 201 and equation 202,
[0602] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0603] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0604] xa1 to xa4 may each independently be an integer selected from 0 to 5,
[0605] xa5 may be an integer selected from 1 to 10,
[0606] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0607] R 201 and R 202 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form (or provide) an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (eg, carbazole groups, etc.) (eg, see compound HT16),
[0608] R 203 and R 204 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form (or provide) an unsubstituted or substituted R 10a Substituted C 8 -C 60 polycyclic groups, and
[0609] na1 may be an integer selected from 1 to 4.
[0610] For example, in some embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY217:
[0611]
[0612] Among them, in formula CY201 to formula CY217, R 10b and R 10c Can be respectively with respect to R10a Same 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.
[0613] In one or more embodiments, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.
[0614] 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.
[0615] In one or more embodiments, Formula 201 may include at least one selected from the group represented by Formulas CY201 to CY203 and at least one selected from the group represented by Formulas CY204 to CY217.
[0616] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be one of the groups represented by the formula CY201 to the formula CY203, xa2 may be 0, and R 202 It may be one selected from the group represented by the formula CY204 to the formula CY207.
[0617] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any group represented by Formula CY201 to Formula CY203.
[0618] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any group represented by Formula CY201 to Formula CY203, and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.
[0619] In one or more embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) any group represented by Formula CY201 to Formula CY217. In the present disclosure, "does not include one or any 'component'", "excludes one or any 'component'" and / or "does not contain a 'component'", etc., means that the "component" is not added, selected or used as a component in the composition / chemical formula / structure, but, in some embodiments, due to other impurities and / or external factors, the "component" may still be included in an appropriate amount.
[0620] For example, in one or more embodiments, the hole transport region may include: at least one selected from the group consisting of Compound HT1 to Compound HT46; 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA); 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA); 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA); N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB (NPD)); β-NPB; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD) ; spiro-TPD; spiro-NPB; methylated NPB; 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC); 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD); 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA); polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA); poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS); polyaniline / camphorsulfonic acid (PANI / CSA); polyaniline / poly(4-styrenesulfonate) (PANI / PSS); or (e.g., any suitable) combination thereof:
[0621]
[0622]
[0623]
[0624]
[0625]
[0626] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof (for example, any appropriate combination), the thickness of the hole injection layer may be about to about For example, about to about and the thickness of the hole transport layer may be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0627] The emission auxiliary layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The materials that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0628] p-dopant
[0629] In one or more embodiments, in addition to one or more of the aforementioned materials, the hole transport region may further include a charge generation material for improved conductive properties. The charge generation material may be uniformly (substantially uniformly) or non-uniformly (substantially non-uniformly) dispersed in the hole transport region (e.g., in the form of a monolayer composed of the charge generation material).
[0630] The charge generating material may be, for example, a p-dopant.
[0631] For example, in one or more embodiments, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0632] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound containing the element EL1 and the element EL2, or (eg, any appropriate) combinations thereof.
[0633] Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and the like.
[0634] Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or a compound represented by Formula 221, and the like:
[0635]
[0636] Formula 221
[0637]
[0638] Among them, in formula 221,
[0639] R 221 To R 223 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and
[0640] Selected from R 221 To R 223 At least one of them may be independently C each substituted by 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any suitable combination thereof 1 -C 20 alkyl; or (eg, any suitable) combinations thereof.
[0641] In a compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or (eg, any appropriate) combination thereof, and element EL2 may be a nonmetal, a metalloid, or (eg, any appropriate) combination thereof.
[0642] Non-limiting examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb) and / or cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and / or barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt ( Co), 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.
[0643] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te), among others.
[0644] Non-limiting examples of non-metals may include oxygen (O) and / or halogens (eg, F, Cl, Br, and / or I, etc.), and the like.
[0645] For example, the compound containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides and / or metalloid iodides, etc.), metal tellurides or their (e.g., any appropriate) combinations.
[0646] Non-limiting examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 and / or W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 and / or V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 and / or Mo 2 O5 etc.) and / or rhenium oxide (e.g., ReO 3 etc.
[0647] Non-limiting examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides, among others.
[0648] Non-limiting examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI, among others.
[0649] Non-limiting examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 wait.
[0650] Non-limiting examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 and / or TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 and / or ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 and / or HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3and / 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 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 and / or ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 and / or FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 and / or RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 and / or OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 and / or CoI 2etc.), 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.
[0651] Non-limiting examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 and / or ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 etc.
[0652] Non-limiting examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and / or SmI 3 wait.
[0653] Non-limiting examples of metalloid halides may include antimony halides (e.g., SbCl 5 etc.
[0654] Non-limiting examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te and / or Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe and / or Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.), etc.
[0655] Emission layer in interlayer 130
[0656] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from the red emission layer, the green emission layer and the blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from the red light-emitting material, the green light-emitting material and the blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).
[0657] In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In some embodiments, in addition to the host and the dopant (or emitter), the emission layer may further include an auxiliary dopant that promotes energy transfer to the dopant (or emitter). When the emission layer includes a dopant (or emitter) and an auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
[0658] The organometallic compound represented by Formula 1 in the present disclosure may be used as a dopant (or emitter), or may be used as an auxiliary dopant.
[0659] 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.
[0660] In one or more embodiments, the emission layer may include an organic metal compound represented by Formula 1. The amount of the organic metal compound represented by Formula 1 in the emission layer may be in a range of about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight based on 100 parts by weight of the emission layer.
[0661] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within these ranges, excellent or appropriate light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0662] main body
[0663] In one or more embodiments, the host in the emission layer may include the second compound, the third compound, or a combination thereof (eg, any suitable one).
[0664] In one or more embodiments, the host may include a compound represented by Formula 301:
[0665] Formula 301
[0666] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0667] Wherein, in Formula 301,
[0668] Ar 301 and L 301may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0669] xb11 can be 1, 2 or 3,
[0670] xb1 may be an integer selected from 0 to 5,
[0671] R 301 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0672] xb21 may be an integer selected from 1 to 5, and
[0673] Q 301 To Q 303 can be independently compared with Q 1 Same as described.
[0674] For example, in some embodiments, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 Can be connected to each other via a single bond.
[0675] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or a combination thereof (eg, any suitable combination):
[0676] Formula 301-1
[0677]
[0678] Formula 301-2
[0679]
[0680] Among them, in Formula 301-1 and Formula 301-2,
[0681] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0682] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0683] xb22 and xb23 can each independently be 0, 1 or 2,
[0684] L 301 , xb1 and R 301 may each be the same as described herein,
[0685] L 302 To L 304 Can be independently compared with L 301 Same as described,
[0686] xb2 to xb4 may each independently be the same as described for xb1, and
[0687] R 302 To R305 and R 311 To R 314 can be independently compared with the R 301 Same as described.
[0688] In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or a combination thereof (e.g., any suitable combination thereof). In one or more embodiments, the host may each independently include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or a combination thereof (e.g., any suitable combination thereof).
[0689] In one or more embodiments, the host may include at least one selected from Compound H1 to Compound H130, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(9H-carbazol-9-yl)benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or (for example, any appropriate) combination thereof:
[0690]
[0691]
[0692]
[0693]
[0694]
[0695]
[0696] In one or more embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or a combination thereof (eg, any suitable one).
[0697] The body may have one or more suitable variations. For example, the body may include only one type of compound, or may include two or more types of different compounds.
[0698] Phosphorescent dopants
[0699] The emission layer may include the organic metal compound represented by Formula 1 as a phosphorescent dopant.
[0700] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0701] The phosphorescent dopant may include at least one transition metal as a central metal.
[0702] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or (eg, any suitable) combinations thereof.
[0703] The phosphorescent dopant may be electrically neutral.
[0704] For example, in some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0705] M(L 401 ) xc1 (L 402 ) xc2 ,
[0706] Wherein, in Formula 401,
[0707] M may be a transition metal (e.g., Ir, Pt, Pd, Os, Ti, Au, Hf, Eu, Tb, Rh, Re, or Tm),
[0708] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,
[0709] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,
[0710] Formula 402
[0711]
[0712] In formula 401, X 401 and X 402 may each independently be nitrogen or carbon,
[0713] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0714] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411)-*'、*-C(Q 411 )(Q 412 )-*',
[0715] *-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C(Q 411 )-*',
[0716] X 403 and X 404 can be independently a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0717] Q 411 To Q 414 can be independently compared with Q 1 Same as described,
[0718] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 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 ),
[0719] Q 401 To Q 403 can be independently compared with Q 1 Same as described,
[0720] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0721] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0722] For example, in some embodiments, in Formula 402, i) X 401 may be nitrogen and X 402 Can be carbon, or ii) X 401 and X 402 Each of may be nitrogen.
[0723] In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two or more L 401 The two rings A 401 Optionally, T as a linker 402 Connected to each other and / or two rings A 402 Optionally, T as a linker 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be respectively with respect to T 401 Same as described.
[0724] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include a halogen, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group and / or a phosphite group, etc.), or a combination thereof (e.g., any appropriate one).
[0725] In one or more embodiments, the phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD25 or a combination thereof (for example, any appropriate combination):
[0726]
[0727]
[0728] Fluorescent dopants
[0729] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0730] In one or more embodiments, when the emission layer includes the organometallic compound represented by Formula 1 and the organometallic compound represented by Formula 1 is used as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0731] The fluorescent dopant and the auxiliary dopant may each independently include an aromatic amine compound, a styrylamine compound, a boron-containing compound, or a combination thereof (eg, any appropriate one).
[0732] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
[0733] Formula 501
[0734]
[0735] Wherein, in Formula 501,
[0736] Ar 501 , L 501 To L 503 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0737] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0738] xd4 can be 1, 2, 3, 4, 5 or 6.
[0739] For example, in some embodiments, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracenyl, 1,2-triphenylenyl and / or pyrene, etc.).
[0740] For example, in some embodiments, xd4 in equation 501 may be 2.
[0741] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include: at least one selected from the group consisting of Compound FD1 to Compound FD36; 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi); 4,4'-bis[4-(N,N-diphenylamino)phenylvinyl]biphenyl (DPAVBi); or (e.g., any appropriate) combination thereof:
[0742]
[0743]
[0744]
[0745] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a fourth compound represented by Formula 502 or Formula 503.
[0746] Electron transport region in interlayer 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 (eg, any appropriate) combinations thereof.
[0749] For example, in one or more embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers in each structure are stacked in sequence from the emission layer in the order described.
[0750] In one or more embodiments, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group.
[0751] For example, in some embodiments, 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 Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[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 Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0759] Q 601 To Q 603 can be independently compared with Q 1 Same 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 by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C60 Heterocyclic group.
[0762] For example, in some embodiments, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be connected to each other via a single bond.
[0763] In one or more embodiments, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[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 ), and X 616 Can be N or C(R 616 ), where X 614 To X 616 At least one of may be N,
[0769] L 611 To L 613 Can be independently compared with L 601 Same as described,
[0770] xe611 to xe613 can each independently be the same as described for xe1,
[0771] R 611 To R 613 Can be independently compared with R 601 Same as 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 Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R10a Substituted C 1 -C 60 Heterocyclic group.
[0773] For example, in some embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.
[0774] In one or more embodiments, the electron transport region may include: at least one selected from Compound ET1 to Compound ET46; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); tris(8-hydroxyquinoline)aluminum (Alq 3 ); bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq); 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ); 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ); or (e.g., any suitable) combination thereof:
[0775]
[0776]
[0777]
[0778]
[0779] 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 a combination thereof (for example, any appropriate combination), the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about to about For example, about to about and the thickness of the electron transport layer can be in the range of about to about For example, about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0780] In one or more embodiments, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material in addition to one or more of the aforementioned materials.
[0781] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or a combination thereof (e.g., any appropriate combination thereof). The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated to the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof (e.g., any appropriate combination thereof).
[0782] For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0783]
[0784] In one or more embodiments, the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0785] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other, or iii) a multilayer structure including a plurality of layers including a plurality of materials different from each other.
[0786] 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 (eg, any appropriate) combinations thereof.
[0787] The alkali metal may include Li, Na, K, Rb, Cs, or any suitable combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any suitable combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any suitable combination thereof.
[0788] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may be, respectively, oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of alkali metals, alkaline earth metals, and rare earth metals, or a (e.g., any suitable) combination thereof.
[0789] The alkali metal 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, and / or KI, etc.; or a (e.g., any suitable) combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 or a (e.g., any suitable) combination thereof. In one or more embodiments, the rare earth metal compound may include lanthanide metal tellurides. Non-limiting examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 、Gd 2 Te 3 、Tb2 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.
[0790] The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex may include i) one of the metal ions of the alkali metal, one of the metal ions of the alkaline earth metal and one of the metal ions of the rare earth metal, and ii) a ligand bonded to the metal ion (e.g., the respective metal ion), for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or (e.g., any appropriate) combination thereof.
[0791] In one or more embodiments, the electron injection layer may include (e.g., be composed of): an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or (e.g., any appropriate) combination thereof as described above. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0792] In one or more embodiments, the electron injection layer may include (e.g., consisting of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or a combination thereof (e.g., any appropriate combination). For example, in some embodiments, 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.
[0793] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or a combination thereof (e.g., any appropriate) may be uniformly (substantially uniformly) or non-uniformly (substantially non-uniformly) dispersed in a matrix including the organic material.
[0794] 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 these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0795] The second electrode 150
[0796] The second electrode 150 may be disposed on the interlayer 130 having the aforementioned structure. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for forming (or providing) the second electrode 150, metals, alloys, conductive compounds, or (for example, any appropriate) combinations thereof, each having a low work function, may be used.
[0797] The second electrode 150 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, Yb, Ag-Yb, ITO, IZO or any suitable combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode.
[0798] The second electrode 150 may have a single-layer structure, or a multi-layer structure including a plurality of layers.
[0799] Capping layer
[0800] The first capping layer may be disposed on the outer side of the first electrode 110 (e.g., on the first electrode 110), and / or the second capping layer may be disposed on the outer side of the second electrode 150 (e.g., on the second electrode 150). In one or more embodiments, the light emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
[0801] In some embodiments, light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first capping layer. In some embodiments, light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second capping layer.
[0802] The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, light extraction efficiency of the light emitting device 10 may be increased, and accordingly, light emitting efficiency of the light emitting device 10 may be improved.
[0803] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or greater (eg, at 589 nm).
[0804] 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.
[0805] At least one of the first capping layer and the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or (for example, any appropriate) combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or (for example, any appropriate) combination thereof. In one or more embodiments, at least one of the first capping layer and the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include an amine-containing compound.
[0806] In one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof (e.g., any appropriate combination).
[0807] In one or more embodiments, at least one of the first capping layer and the second capping layer may (for example, the first capping layer and the second capping layer may each independently) include: at least one selected from compounds HT28 to HT33; at least one selected from compounds CP1 to CP6; β-NPB; or (for example, any appropriate) combination thereof:
[0808]
[0809]
[0810] Electronic devices
[0811] The light emitting device may be included in one or more appropriate types of electronic devices. For example, the electronic device including the light emitting device may be a light emitting device and / or an authentication device, etc.
[0812] In one or more embodiments, 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 in which the light emitted from the light emitting device travels. For example, in some embodiments, the light emitted from the light emitting device may be blue light, green light, or white light (e.g., combined white light). For details about the light emitting device, reference may be made to the description provided herein. In some 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 plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.
[0814] A pixel defining layer may be disposed between the plurality of sub-pixel regions to define each sub-pixel region.
[0815] The color filter may further include a plurality of color filter regions and a light shielding pattern therebetween, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern therebetween.
[0816] The plurality of color filter regions (or the plurality of color conversion regions) may include: a first region configured to emit a first color light; a second region configured to emit a second color light; and / or a third region configured to emit 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, in one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, in one or more embodiments, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. In some embodiments, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) any quantum dots. Each of the first region, the second region, and / or the third region may further include a scatterer.
[0817] For example, in a light emitting device that emits a first light, the first region may absorb the first light to emit a first-first color light, the second region may absorb the first light to emit a second-first color light, and the third region may absorb the first light to emit a third-first color light. Here, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In some embodiments, 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 one or more embodiments, in addition to the aforementioned light-emitting device, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer (e.g., a semiconductor layer), wherein one of the source electrode and the drain electrode may be electrically connected to the first electrode or 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] In one or more embodiments, the electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and simultaneously (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0822] In one or more embodiments, in addition to the color filter and / or the color conversion layer, various functional layers may be additionally arranged on the sealing portion according to the purpose of the electronic device. Non-limiting examples of the functional layer may include a touch screen layer and / or a polarizing 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.
[0823] The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (eg, fingertips and / or pupils, etc.) In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.
[0824] The electronic device can be applied to one or more displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscope displays), fish finders, one or more appropriate measuring tools, instruments (e.g., instruments for vehicles, aircraft, and ships), and / or projectors, etc.
[0825] Figure 2 and Figure 3 Description
[0826] Figure 2is a cross-sectional view showing a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0827] Figure 2 The light emitting apparatus may include a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation portion 300 that seals the light emitting device.
[0828] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and provide a flat surface on the substrate 100.
[0829] The TFT may be 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.
[0830] 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.
[0831] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220 , and the gate electrode 240 may be on the gate insulating film 230 .
[0832] An interlayer insulating film 250 may be 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.
[0833] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be arranged to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0834] 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 a combination thereof (e.g., any appropriate one). The light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0835] The first electrode 110 (eg, as an anode) may be on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.
[0836] A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a certain area of the first electrode 110, and the interlayer 130 may be formed in the exposed area of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 and be arranged in the form of (or provided with) a common layer.
[0837] The second electrode 150 may be on the interlayer 130, and the second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0838] The encapsulation part 300 may be on the second capping layer 170. The encapsulation part 300 may be arranged 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 their (e.g., any appropriate) combination; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyaromatic ester, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.) or their (e.g., any appropriate) combination; or any combination of an inorganic film and an organic film.
[0839] Figure 3 is a cross-sectional view of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0840] Figure 3 The light-emitting device is basically the same as Figure 2 The light emitting device is the same as that of the light emitting device, except that the light shielding pattern 500 and the functional area 400 are additionally arranged on the encapsulation part 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, Figure 3 The light-emitting device included in the light-emitting apparatus may be a series light-emitting device.
[0841] Figure 4 Description
[0842] Figure 4Schematic perspective view of an electronic device 1 including a light emitting device according to one or more embodiments. The electronic device 1 may be a device for displaying moving images or still images, a portable electronic device (such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation and / or an ultra mobile PC (UMPC), etc.), and one or more suitable products (such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device), or a part of such one or more suitable products. In one or more embodiments, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a display of the type or kind of glasses or a head mounted display (HMD), or a part of such a wearable device. However, the embodiments of the present disclosure are not limited thereto. For example, the electronic device 1 may include a dashboard of a vehicle, a central instrument panel of a vehicle or a central information display on the dashboard, an interior rearview mirror display replacing a side mirror of a vehicle, an entertainment display arranged on a rear seat of a vehicle or on a backrest of a front seat thereof, a head-up display (HUD) mounted on the front of the vehicle or projected on the front windshield, and / or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For convenience of explanation, Figure 4 An embodiment is explained in which the electronic device 1 is a smart phone.
[0843] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device of the electronic equipment 1 may realize an image through a plurality of pixel arrays two-dimensionally arranged in the display area DA.
[0844] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to a display element arranged in the display area DA may be arranged. In the non-display area NDA, a pad may be arranged, which may be electrically connected to an electronic element or a printed circuit board.
[0845] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction (eg, the width) may be different from each other. Figure 4 , the length in the x-axis direction may be shorter than the length (e.g., width) in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be substantially the same as the length (e.g., width) in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length (e.g., width) in the y-axis direction.
[0846] Figure 5 and FIG. 6A to FIG. 6C Description
[0847] 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 of the present disclosure. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments of the present disclosure.
[0848] See also 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, object, or animal) from a starting point to a destination point. The vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on an ocean or river, and / or an airplane flying in the air using the action of air.
[0849] In one or more embodiments, the vehicle 1000 may travel on a road or track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel thereof. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover device, a bicycle, or a train traveling on a track.
[0850] The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical equipment required for driving is installed as other parts outside the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear wheels, and / or left and right wheels, etc.
[0851] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , an instrument cluster 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0852] The side window glass 1100 and the front window glass 1200 may be divided by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0853] The side window glass 1100 may be mounted on the side of the vehicle 1000. In some embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In some embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In some embodiments, the first side window glass 1110 may be arranged adjacent to the instrument cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0854] In one or more embodiments, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. In other words, the imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-axis direction or the -x-axis direction.
[0855] 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.
[0856] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In one embodiment, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be arranged outside the second side window glass 1120.
[0857] Instrument cluster 1400 may be arranged in front of the steering wheel. Instrument cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a tachometer, an automatic shift lever indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0858] The center console 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and / or a seat heater are arranged. The center console 1500 may be arranged on one side of the instrument cluster 1400 .
[0859] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, and the center console 1500 may be disposed between the passenger seat instrument panel 1600 and the instrument cluster 1400. In some embodiments, the instrument cluster 1400 may be disposed corresponding to the driver's seat, and the passenger seat instrument panel 1600 may be disposed corresponding to the passenger seat. In some embodiments, the instrument cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0860] 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 some embodiments, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the instrument cluster 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0861] The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, and / or a quantum dot display device, etc. Hereinafter, as a display device 2 according to one or more embodiments, an organic light-emitting display device including the aforementioned light-emitting device will be described as an example, but one or more appropriate types (kinds) of display devices described above may be used in the embodiments of the present disclosure.
[0862] See also Fig. 6A In one or more embodiments, the display device 2 may be arranged on the center console 1500. In some embodiments, the display device 2 may display navigation information. In some embodiments, the display device 2 may display audio, video, or information about vehicle settings.
[0863] See also Figure 6B In one or more embodiments, the display device 2 may be arranged on the instrument cluster 1400. When the display device 2 is arranged on the instrument cluster 1400, the instrument cluster 1400 may display driving information and the like through the display device 2. For example, in some embodiments, the instrument cluster 1400 may be implemented digitally. The instrument cluster 1400 may digitally display vehicle information and driving information as images. For example, the needle and instrument of the tachometer and one or more appropriate warning light icons may be displayed through digital signals.
[0864] See also Figure 6CIn one or more embodiments, 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 some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500.
[0865] Manufacturing method
[0866] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can each be formed in a certain region by using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and laser induced thermal imaging.
[0867] 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., depending on the material to be included in the layer to be formed and the structure of the layer to be formed. -8 About 10 -3 Torr, and at a vacuum of about / second to about The deposition is carried out at a deposition rate in the range of 200 Å / s.
[0868] Definition of terms
[0869] As used herein, the term "C 3 -C 60 "Carbocyclyl" refers to a cyclic group that includes only carbon (e.g., consists of carbon) as a ring-forming atom and has 3 to 60 carbon atoms, and the term "C 1 -C 60 The term "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further having a hetero atom as a ring-forming atom in addition to carbon. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic group may each be: a monocyclic group including one (e.g., exactly one) ring (e.g., consisting of one (e.g., exactly one) ring); or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The number of ring-forming atoms of the heterocyclic group may be 3 to 61.
[0870] As used herein, the term "cyclic group" may include (for example, simultaneously) C 3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups.
[0871] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The term "heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.
[0872] For example,
[0873] C 3 -C 60 The carbocyclic group may be i) a group T1 or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylene group, a peryl group, a pentalenyl group, a heptalenyl group, a tetraphenylene group, a phenanthrenyl group, a hexaphenylene group, a pentacene group, a rubinyl group, a coronet group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthryl group, or an indenoanthryl group),
[0874] C 1 -C 60The heterocyclic group may be i) a group T2, ii) a fused ring group in which at least two of the groups T2 (e.g., at least two of the groups T2) are fused to each other, or iii) a fused ring group in which at least one group T2 and at least one group T1 are fused to each other (e.g., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranoyl group, a benzonaphthothiophenyl group, a benzonaphthothiophenyl group, a benzonaphthothioroloyl group, a benzofuranodiphenyl ... benzofuranyl, benzofurandibenzothienyl, benzothienodibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinolinyl, benzoquinolinyl, benzisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazoline, benzoquinazolinyl, phenanthroline, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl and / or azadibenzofuranyl, etc.),
[0875] Pi-electron-rich C 3 -C 60 The cyclic group may be i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused to each other (e.g., C 3 -C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl and / or benzothiophenylodibenzothiophenyl, etc.),
[0876] π-electron-deficient nitrogen-containing C 1 -C 60 The heterocyclic group may be i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzoimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiophenyl and / or azadibenzofuranyl, etc.),
[0877] The radical T1 can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,
[0878] The radical T2 can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,
[0879] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiolyl or borocyclopentadienyl, and
[0880] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0881] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The "heterocyclic group" may refer to a group fused with any cyclic group (which is fused with another cyclic group (e.g., benzo and / or naphtho, etc.)), a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group and / or a tetravalent group, etc.) according to the structure of the formula using the corresponding term. For example, "phenyl" may be benzo, phenyl and / or phenylene, etc., and those of ordinary skill in the art can easily understand these groups based on the structure of the formula including "phenyl".
[0882] Depending on the context, in the present disclosure, a divalent group may refer to or may be a multivalent group (eg, trivalent, tetravalent, etc., not just divalent), depending on, for example, the structure of a formula associated with the term used.
[0883] Unit Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Non-limiting examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Non-limiting examples of heterocyclic groups are C 3 -C 10 Cycloalkylene, C 1 -C 10Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0884] As used herein, the term "C 1 -C 60 The term “alkyl” refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. As used herein, the term “C 1 -C 60 "Alkylene" refers to C 1 -C 60 The alkyl group has substantially the same structure as a divalent group.
[0885] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end thereof, and non-limiting examples thereof may include vinyl, propenyl and / or butenyl, etc. As used herein, the term “C 2 -C 60 "Alkenylene" refers to C 2 -C 60 The alkenyl group has a divalent group having substantially the same structure.
[0886] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end thereof, and non-limiting examples thereof may include ethynyl and / or propynyl, etc. As used herein, the term “C 2 -C 60 "Alkynylidene" refers to C 2 -C 60 Alkynyl groups have substantially the same structure as a divalent group.
[0887] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60 The monovalent group represented by alkyl) is a monovalent group, and non-limiting examples thereof may include methoxy, ethoxy and / or isopropoxy, and the like.
[0888] 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 non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.
[0889] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent cyclic group of 1 to 10 carbon atoms further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and non-limiting examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl, etc. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.
[0890] 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, at least one carbon-carbon double bond, and no aromaticity in its ring, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group having substantially the same structure.
[0891] As used herein, the term "C 1 -C 10The term "heterocycloalkenyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms which further includes at least one heteroatom as a ring-forming atom and at least one double bond in addition to carbon atoms in its ring structure. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to C 1 -C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.
[0892] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl and / or ovalenyl, etc. When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, these rings may be fused to each other.
[0893] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms which further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms which further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and / or naphthyridinyl, etc. When C 1 -C60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, these rings may be fused to each other.
[0894] The term "monovalent non-aromatic fused polycyclic group" as used in this article refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, only carbon atoms as ring atoms, and no aromaticity in the entire molecular structure when considered as a whole. Non-limiting examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. The term "divalent non-aromatic fused polycyclic group" as used in this article refers to a divalent group having substantially the same structure as the above-mentioned monovalent non-aromatic fused polycyclic group.
[0895] The term "monovalent non-aromatic heterocondensed polycyclic group" as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure when considered as a whole. Non-limiting examples of monovalent non-aromatic heterofused polycyclic groups 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, thiadiazoles, 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.
[0896] As used herein, the term "C 6 -C 60 Aryloxy" indicates -OA 102 (A 102 C 6 -C 60aryl), and as used herein, the term "C 6 -C 60 Arylthio" indicates -SA 103 (A 103 C 6 -C 60 aryl).
[0897] As used herein, the term "C 7 -C 60 "Aralkyl" refers to -A 104 A 105 (A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59 aryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 106 A 107 (A 106 C 1 -C 59 Alkylene, and A 107 C 1 -C 59 heteroaryl).
[0898] As used herein, the term " 10a " can be:
[0899] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0900] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60Heteroaralkyl, -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 (for example, any appropriate) combination thereof;
[0901] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q21 )、-P(=O)(Q 21 )(Q 22 ) or (for example, any appropriate) combination thereof;
[0902] -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 );or
[0903] (e.g., any suitable) combination thereof.
[0904] Q in this disclosure 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any suitable combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0905] As used herein, the term "heteroatom" refers to any atom other than a carbon atom and a hydrogen atom. Non-limiting examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and (e.g., any suitable) combinations thereof.
[0906] The term "transition metal" as used herein may include Hf, Ta, W, Re, Os, Ir, Pt and / or Au, among others.
[0907] As used herein, "Ph" refers to phenyl, as used herein, "Me" refers to methyl, as used herein, "Et" refers to ethyl, as used herein, "tert-Bu" or "Bu" refers to ethyl. t " refers to a tert-butyl group, and "OMe" as used herein refers to a methoxy group.
[0908] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In some embodiments, the "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0909] As used herein, the term "terphenyl" refers to a "phenyl group substituted by a biphenyl group". In some embodiments, the "terphenyl group" may be a phenyl group substituted by a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0910] Unless otherwise specified, *, *' and *" each indicate a binding site to an adjacent atom in the corresponding chemical formula or moiety.
[0911] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in more detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A in the same molar equivalent.
[0912] Example
[0913] Synthesis Example 1: Synthesis of Compound 26
[0914]
[0915]
[0916] Synthesis of Intermediate 26-1
[0917] 6-Bromo-1,1,4,4-tetra(methyl-d 3 )-1,2,3,4-tetrahydronaphthalene-2,2,3,3-d 4 (1.0 eq), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl 2 )(0.05eq), bis(pinacol)diboron (B 2 pin 2) (1.5eq) and potassium acetate (KOAc) (3eq) were mixed with 1,4-dioxane, and then stirred at 100° C. for 24 hours. After the obtained product was cooled to room temperature, the solvent was removed by distillation under a reduced pressure of 8 mbar, and an extraction process was performed three times using dichloromethane (MC) and water to obtain an organic layer. The organic layer thus obtained was dried over magnesium sulfate, concentrated, and then subjected to column chromatography (MC / hexane (Hex) as an eluent) to synthesize intermediate 26-1 (yield 78%).
[0918] Synthesis of Intermediate 26-2
[0919] Intermediate 26-1 (1.0 eq), 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-amine (1.0 eq), chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II) (CX31 Umicore) (0.05 eq) and potassium carbonate (3.0 eq) were mixed with 1,4-dioxane and H in a volume ratio of 3:1. 2 O was mixed, and then stirred at 100° C. for 24 hours. After the obtained product was cooled to room temperature, the solvent was removed by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by subjecting it to three extraction processes using MC and water. The organic layer thus obtained was dried over magnesium sulfate, concentrated, and then subjected to column chromatography (MC / Hex as an eluent) to synthesize intermediate 26-2 (yield 68%).
[0920] Synthesis of intermediate 26-3
[0921] Intermediate 26-2 (1.0 eq), 1-bromo-2-nitrobenzene (2 eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos, 0.10 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq) and sodium tert-butoxide (NaOtBu, 3eq) were mixed with toluene, and then stirred at 110°C for 24 hours to obtain a reaction product. After the reaction product was cooled to room temperature, the solvent was removed by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by subjecting it to three extraction processes using MC and water. The organic layer thus obtained was dried over magnesium sulfate, concentrated, and then subjected to column chromatography (MC / Hex as eluent) to synthesize intermediate 26-3 (yield 83%).
[0922] Synthesis of intermediate 26-4
[0923] Intermediate 26-3 (1.0 eq) and tin (5 eq) were mixed and stirred with ethanol (EtOH), and hydrogen chloride (12 M) was injected therein. The mixed solution was then stirred at 80 ° C for 6 hours. After the product was cooled to room temperature, the solvent was removed by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by subjecting it to three extraction processes using MC and water. The organic layer thus obtained was dried with magnesium sulfate, concentrated, and then subjected to column chromatography (MC / Hex as eluent) to synthesize intermediate 26-4 (yield 85%).
[0924] Synthesis of Intermediate 26-5
[0925] Intermediate 26-4 (1.0 eq), 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 (1.0eq), Pd 2 (dba) 3 (tris(dibenzylideneacetone)dipalladium(0), 0.05eq), Xphos(2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 0.10eq) and sodium tert-butoxide (2.0eq) were dissolved in toluene (0.1M), and then stirred at 110°C for 2 hours. After the resulting product was cooled to room temperature, the solvent was removed by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by subjecting it to three extraction processes using MC and water. The organic layer thus obtained was dried over magnesium sulfate, concentrated, and then subjected to column chromatography (MC:Hex as an eluent) to synthesize intermediate 26-5 (yield 67%).
[0926] Synthesis of Intermediate 26-6
[0927] Intermediate 26-5 (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCl (1.5 eq) was added thereto. The mixed solution was then stirred at 80°C for 24 hours. After the product was cooled to room temperature, the triethyl orthoformate was concentrated and removed. Then, an organic layer was obtained by subjecting it to three extraction processes using MC and water. The organic layer thus obtained was dried with magnesium sulfate, concentrated, and then subjected to column chromatography (MC: methanol as eluent) to synthesize intermediate 26-6 (yield 77%).
[0928] Synthesis of compound 26
[0929] Intermediate 26-6 (1.0 eq), potassium chloride platinum (II) (K 2 PtCl 4) (1.1eq) and 2,6-lutidine (4.0eq) were dissolved in 1,2-dichlorobenzene (o-DCB, 0.05M), and then stirred under nitrogen conditions at 120°C for 18 days. After the resulting product was cooled to room temperature, 1,2-dichlorobenzene was concentrated and removed. Then, an organic layer was obtained by subjecting it to three extraction processes using dichloromethane and water. The organic layer thus obtained was dried over magnesium sulfate, concentrated, and then subjected to column chromatography (MC:Hex as eluent) to synthesize compound 26 (yield 48%).
[0930] ESI-LCMS: [M]+: C 69 H 45 D 25 N 4 OPt, 1189.80
[0931] Synthesis Example 2: Synthesis of Compound 70
[0932]
[0933] Synthesis of Intermediate 70-2
[0934] Intermediate 70-2 was synthesized in substantially the same manner as the synthesis of Intermediate 26-2 in Synthesis Example 1, except that 3-bromo-5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2',2",3",4',4",5",6',6"-d 8 -2-amine replaces 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-Amine.
[0935] Synthesis of Intermediate 70-3
[0936] Intermediate 70-3 was synthesized in substantially the same manner as the synthesis of Intermediate 26-3 in Synthesis Example 1, except that Intermediate 70-2 was used instead of Intermediate 26-2.
[0937] Synthesis of Intermediate 70-4
[0938] Intermediate 70-4 was synthesized in substantially the same manner as the synthesis of Intermediate 26-4 in Synthesis Example 1 (yield 61%), except that Intermediate 70-3 was used instead of Intermediate 26-3.
[0939] Synthesis of Intermediate 70-5
[0940] Intermediate 70-5 was synthesized in substantially the same manner as the synthesis of Intermediate 26-5 in Synthesis Example 1, except that Intermediate 70-4 and 2-(3-bromophenoxy)-9-(4-(methyl-d 3 )pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 Substituting intermediate 26-4 and 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 .
[0941] Synthesis of Intermediate 70-6
[0942] Intermediate 70-6 was synthesized in substantially the same manner as the synthesis of Intermediate 26-6 in Synthesis Example 1, except that Intermediate 70-5 was used instead of Intermediate 26-5.
[0943] Synthesis of compound 70
[0944] Compound 70 was synthesized in substantially the same manner as the synthesis of Compound 26 in Synthesis Example 1 (yield 68%), except that Intermediate 70-6 was used instead of Intermediate 26-6.
[0945] ESI-LCMS: [M]+: C 67 H 27 D 31 N 4 OPt,1159.40
[0946] Synthesis Example 3: Synthesis of Compound 124
[0947]
[0948] Synthesis of Intermediate 124-1
[0949] Intermediate 124-1 was synthesized in substantially the same manner as Intermediate 26-1 in Synthesis Example 1, except that Intermediate 124-0 was used instead of 6-bromo-1,1,4,4-tetra(methyl-d 3 )-1,2,3,4-tetrahydronaphthalene-2,2,3,3-d 4 .
[0950] Synthesis of Intermediate 124-2
[0951] Intermediate 124-2 was synthesized in substantially the same manner as the synthesis of Intermediate 26-2 in Synthesis Example 1, except that Intermediate 124-1 and 3-bromo-5′-phenyl-[1,1′:3′,1″-terphenyl]-2′,2″,3″,4′,4″,5″,6′,6″-d were used respectively. 8-2-amine instead of intermediate 26-1 and 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-Amine.
[0952] Synthesis of Intermediate 124-3
[0953] Intermediate 124-3 was synthesized in substantially the same manner as the synthesis of Intermediate 26-3 in Synthesis Example 1, except that Intermediate 124-2 was used instead of Intermediate 26-2.
[0954] Synthesis of Intermediate 124-4
[0955] Intermediate 124-4 was synthesized in substantially the same manner as the synthesis of Intermediate 26-4 in Synthesis Example 1 (yield 68%), except that Intermediate 124-3 was used instead of Intermediate 26-3.
[0956] Synthesis of Intermediate 124-5
[0957] Intermediate 124-5 was synthesized in substantially the same manner as Intermediate 26-5 in Synthesis Example 1, except that Intermediate 124-4 and 2-(3-bromophenoxy)-9-(4-(2-methylpropyl)-1,1-d 2 )pyridin-2-yl)-9H-carbazole instead of intermediate 26-4 and 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 .
[0958] Synthesis of Intermediate 124-6
[0959] Intermediate 124-6 was synthesized in substantially the same manner as the synthesis of Intermediate 26-6 in Synthesis Example 1, except that Intermediate 124-5 was used instead of Intermediate 26-5.
[0960] Synthesis of compound 124
[0961] Compound 124 was synthesized in substantially the same manner as the synthesis of Compound 26 in Synthesis Example 1 (yield 53%), except that Intermediate 124-6 was used instead of Intermediate 26-6.
[0962] ESI-LCMS: [M]+: C 72 H 47 D 13 N 4 OPt, 1203.30
[0963] Synthesis Example 4: Synthesis of Compound 134
[0964]
[0965] Synthesis of Intermediate 134-2
[0966] Intermediate 134-2 was synthesized in substantially the same manner as Intermediate 26-2 in Synthesis Example 1, except that Intermediate 124-1 and 3-bromo-3′-(tert-butyl)-5′-(2,2-dimethylpropyl)-1,1-diol were used, respectively. 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-amine instead of intermediate 26-1 and 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-Amine.
[0967] Synthesis of Intermediate 134-3
[0968] Intermediate 134-3 was synthesized in substantially the same manner as the synthesis of Intermediate 26-3 in Synthesis Example 1, except that Intermediate 134-2 was used instead of Intermediate 26-2.
[0969] Synthesis of Intermediate 134-4
[0970] Intermediate 134-4 was synthesized in substantially the same manner as the synthesis of Intermediate 26-4 in Synthesis Example 1 (yield 70%), except that Intermediate 134-3 was used instead of Intermediate 26-3.
[0971] Synthesis of Intermediate 134-5
[0972] Intermediate 134-5 was synthesized in substantially the same manner as Intermediate 26-5 in Synthesis Example 1, except that Intermediate 134-4 and 2-(3-bromophenoxy)-9-(4-(2-methylpropyl)-1,1-d 2 )-5-phenylpyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 Substituting intermediate 26-4 and 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 .
[0973] Synthesis of Intermediate 134-6
[0974] Intermediate 134-6 was synthesized in substantially the same manner as the synthesis of Intermediate 26-6 in Synthesis Example 1, except that Intermediate 134-5 was used instead of Intermediate 26-5.
[0975] Synthesis of compound 134
[0976] Compound 134 was synthesized in substantially the same manner as the synthesis of Compound 26 in Synthesis Example 1 (yield 55%), except that Intermediate 134-6 was used instead of Intermediate 26-6.
[0977] ESI-LCMS: [M]+: C 75 H 60 D 14 N 4 OPt,1254.70
[0978] Synthesis Example 5: Synthesis of Compound 185
[0979]
[0980] Synthesis of Intermediate 185-2
[0981] Intermediate 185-2 was synthesized in substantially the same manner as Intermediate 26-2 in Synthesis Example 1, except that 3-bromo-4′-(tert-butyl)-2′-(methyl-d 3 )-[1,1'-biphenyl]-3',5',6'-d 3 -2-amine replaces 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-Amine.
[0982] Synthesis of Intermediate 185-3
[0983] Intermediate 185-3 was synthesized in substantially the same manner as the synthesis of Intermediate 26-3 in Synthesis Example 1, except that Intermediate 185-2 was used instead of Intermediate 26-2.
[0984] Synthesis of Intermediate 185-4
[0985] Intermediate 185-4 was synthesized in substantially the same manner as the synthesis of Intermediate 26-4 in Synthesis Example 1 (yield 62%), except that Intermediate 185-3 was used instead of Intermediate 26-3.
[0986] Synthesis of Intermediate 185-5
[0987] Intermediate 185-5 was synthesized in substantially the same manner as the synthesis of Intermediate 26-5 in Synthesis Example 1, except that Intermediate 185-4 and 2-(3-bromophenoxy)-9-(4-(methyl-d 3 )-5-phenylpyridin-2-yl)-9H-carbazole-5,6,7,8-d 4Substituting intermediate 26-4 and 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 .
[0988] Synthesis of Intermediate 185-6
[0989] Intermediate 185-6 was synthesized in substantially the same manner as the synthesis of Intermediate 26-6 in Synthesis Example 1, except that Intermediate 185-5 was used instead of Intermediate 26-5.
[0990] Synthesis of compound 185
[0991] Compound 185 was synthesized in substantially the same manner as the synthesis of Compound 26 in Synthesis Example 1 (yield 51%), except that Intermediate 185-6 was used instead of Intermediate 26-6.
[0992] ESI-LCMS: [M]+: C 68 H 31 D 29 N 4 OPt, 1171.50
[0993] Synthesis Example 6: Synthesis of Compound 213
[0994]
[0995]
[0996] Synthesis of Intermediate 213-2
[0997] Intermediate 213-2 was synthesized in substantially the same manner as Intermediate 26-2 in Synthesis Example 1, except that 3-bromo-2",4"-di-tert-butyl-[1,1':4',1"-terphenyl]-2',3',5',6'-d 4 -2-amine replaces 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-Amine.
[0998] Synthesis of intermediate 213-3
[0999] Intermediate 213-3 was synthesized in substantially the same manner as the synthesis of Intermediate 26-3 in Synthesis Example 1, except that Intermediate 213-2 was used instead of Intermediate 26-2.
[1000] Synthesis of Intermediate 213-4
[1001] Intermediate 213-4 was synthesized in substantially the same manner as the synthesis of Intermediate 26-4 in Synthesis Example 1 (yield 66%), except that Intermediate 213-3 was used instead of Intermediate 26-3.
[1002] Synthesis of Intermediate 213-5
[1003] Intermediate 213-5 was synthesized in substantially the same manner as Intermediate 26-5 in Synthesis Example 1, except that Intermediate 213-4 and 2-(3-bromophenoxy)-9-(4-(2-methylpropyl)-1,1-d 2 )-5-phenylpyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 Substituting intermediate 26-4 and 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 .
[1004] Synthesis of Intermediate 213-6
[1005] Intermediate 213-6 was synthesized in substantially the same manner as the synthesis of Intermediate 26-6 of Synthesis Example 1, except that Intermediate 213-5 was used instead of Intermediate 26-5.
[1006] Synthesis of compound 213
[1007] Compound 213 was synthesized in substantially the same manner as the synthesis of Compound 26 in Synthesis Example 1 (yield 53%), except that Intermediate 213-6 was used instead of Intermediate 26-6.
[1008] ESI-LCMS: [M]+: C 80 H 47 D 29 N 4 OPt, 1331.60
[1009] Synthesis Example 7: Synthesis of Compound 267
[1010]
[1011]
[1012] Synthesis of Intermediate 267-1
[1013] Intermediate 267-1 was synthesized in substantially the same manner as the synthesis of Intermediate 26-1 in Synthesis Example 1, except that 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene was used instead of 6-bromo-1,1,4,4-tetra(methyl-d 3 )-1,2,3,4-tetrahydronaphthalene-2,2,3,3-d4 .
[1014] Synthesis of Intermediate 267-2
[1015] Intermediate 267-2 was synthesized in substantially the same manner as the synthesis of Intermediate 26-2 in Synthesis Example 1, except that Intermediate 267-1 and 3-bromo-5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2-amine were used instead of Intermediate 26-1 and 3-bromo-3'-(tert-butyl)-5'-(2,2-dimethylpropyl-1,1-d 2 )-[1,1'-biphenyl]-2',4',6'-d 3 -2-Amine.
[1016] Synthesis of Intermediate 267-3
[1017] Intermediate 267-3 was synthesized in substantially the same manner as the synthesis of Intermediate 26-3 in Synthesis Example 1, except that Intermediate 267-2 was used instead of Intermediate 26-2.
[1018] Synthesis of Intermediate 267-4
[1019] Intermediate 267-4 was synthesized in substantially the same manner as the synthesis of Intermediate 26-4 in Synthesis Example 1 (yield 69%), except that Intermediate 267-3 was used instead of Intermediate 26-3.
[1020] Synthesis of Intermediate 267-5
[1021] Intermediate 267-5 was synthesized in substantially the same manner as the synthesis of Intermediate 26-5 in Synthesis Example 1, except that Intermediate 267-4 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole were used instead of Intermediate 26-4 and 2-(3-bromophenoxy)-9-(4-tert-butyl-pyridin-2-yl)-9H-carbazole-5,6,7,8-d, respectively. 4 .
[1022] Synthesis of Intermediate 267-6
[1023] Intermediate 267-6 was synthesized in substantially the same manner as the synthesis of Intermediate 26-6 in Synthesis Example 1, except that Intermediate 267-5 and HCl were used instead of Intermediate 26-5 and DCl, respectively.
[1024] Synthesis of compound 267
[1025] Compound 267 was synthesized in substantially the same manner as the synthesis of Compound 26 in Synthesis Example 1 (yield 55%), except that Intermediate 267-6 was used instead of Intermediate 26-6.
[1026] ESI-LCMS: [M]+: C 70 H 64 N 4 OPt, 1170.50
[1027] For each of the compounds synthesized in Synthesis Examples 1 to 7, high resolution mass spectrometry (HR-MS) was measured, and the results are shown in Table 1. By referring to the synthesis route and raw materials, those skilled in the art can easily identify the synthesis method of compounds other than the compounds synthesized in Synthesis Examples 1 to 7.
[1028] Table 1
[1029]
[1030] Evaluation Example 1
[1031] The HOMO energy level and LUMO energy level of each of Compounds 26, 70, 124, 134, 185, 213, and 267 were evaluated according to the method described in Table 2, and the results are shown in Table 3.
[1032] Table 2
[1033]
[1034] Table 3
[1035] Compound No. HOMO level (eV) LUMO level (eV) 26 -5.27 -1.96 70 -5.26 -1.95 124 -5.25 -1.94 134 -5.27 -1.96 185 -5.25 -1.96 213 -5.24 -2.00 267 -5.26 -1.96
[1036]
[1037]
[1038] Evaluation Example 2
[1039] Compound 26 (2 mg), compound ETH2 (10 mg), compound HTH29 (10 mg) and CH 2 Cl 2 The poly (methyl methacrylate) (PMMA) (wherein the weight of PMMA is 50 mg) in the film was mixed together, and the resulting product was coated on a quartz substrate by using a spin coater. The quartz substrate was heat-treated in an oven at 80° C. and then cooled to room temperature to prepare a film 26 having a thickness of 40 nm. Subsequently, film 70, film 124, film 134, film 185, film 213 and film 267 were each prepared in substantially the same manner as the preparation of film 26, except that compound 70, compound 124, compound 134, compound 185, compound 213 and compound 267 were each used instead of compound 26.
[1040] The emission spectrum of each of the films 26, 70, 124, 134, 185, 213 and 267 was measured by using a Quantaurus-QY absolute PL quantum yield spectrometer manufactured by Hamamatsu Corporation (equipped with a xenon light source, a monochromator, a photon multichannel analyzer and an integrating sphere) and PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, the excitation wavelength was scanned from 320 nm to 380 nm at intervals of 10 nm, and the spectrum measured at an excitation wavelength of 340 nm was taken to obtain the maximum emission wavelength (emission peak wavelength) and the full width at half maximum (FWHM) of the organometallic compound represented by Formula 1 included in each film. The results are summarized in Table 4.
[1041] Next, the PLQY of each of the films 26, 70, 124, 134, 185, 213, and 267 was measured by scanning the excitation wavelength from 320 nm to 380 nm at intervals of 10 nm with a Quantaurus-QY absolute PL quantum yield spectrometer manufactured by Hamamatsu Corporation, and the PLQY measured at an excitation wavelength of 330 nm was taken to obtain the PLQY of the organometallic compound represented by Formula 1 included in each film. The results are summarized in Table 4.
[1042] Table 4
[1043]
[1044]
[1045] Referring to Table 4, it was confirmed that Compound 26, Compound 70, Compound 124, Compound 134, Compound 185, Compound 213, and Compound 267 had excellent or appropriate PLQY, and emitted blue light with a relatively small FWHM.
[1046] Evaluation Example 3
[1047] The PL spectrum of each of the films 26, 70, 124, 134, 185, 213, and 267 was measured at room temperature by using FluoTime 300, which is a time-resolved photoluminescence (TRPL) measurement system of PicoQuant, Inc., and PLS340, which is a pump source (excitation wavelength = 340 nm, spectrum width = 20 nm) of PicoQuant, Inc. Then, the wavelength of the main peak of the PL spectrum was determined, and the number of photons emitted from each of the films at the wavelength of the main peak was measured according to a photon pulse (pulse width = 500 ps) applied to each of the films by PLS340, and the measurement was repeated for several hours based on time-correlated single photon counting (TCSPC) in order to obtain a TRPL curve with a sufficiently good or appropriate fit. The TRPL curve of each of the films 26, 70, 124, 134, 185, 213, and 267 was obtained by fitting one or more exponential decay functions to the obtained results. 衰减 (Ex), that is, decay time, and the results obtained by fitting are shown in Table 5. The function used for fitting is as shown in Equation 20, and T obtained from each exponential decay function used for fitting is obtained. 衰减 The maximum T value 衰减 Value as T 衰减 (Ex). Here, similar measurements are repeated again during the same amount of measurement time as that for obtaining the TRPL curve in the dark state (i.e., the state in which the pump signal incident on the set or predetermined film is blocked) to obtain a baseline or background signal curve, which is used as the baseline for fitting.
[1048] Equation 20
[1049]
[1050] Table 5
[1051]
[1052]
[1053] Referring to Table 5, it was confirmed that Compound 26, Compound 70, Compound 124, Compound 134, Compound 185, Compound 213, and Compound 267 had relatively short luminescence decay times.
[1054] Example 1
[1055] A 15Ω / cm 2 A glass substrate of ITO (product of Corning Incorporated) was cut into a size of 50 mm×50 mm×0.7 mm, cleaned with isopropyl alcohol and then with pure water, each for 5 minutes, by irradiation of ultraviolet rays and exposure to ozone for 30 minutes, and then mounted on a vacuum deposition apparatus.
[1056] 2-TNATA is vacuum deposited on the anode to form (or provide) a thickness of and vacuum depositing N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (hereinafter, referred to as "NPB") on the hole injection layer to form (or provide) a layer with a thickness of hole transport layer.
[1057] The first compound (compound 26), the second compound (compound ETH101), the third compound (compound HTH47) and the fourth compound (compound DFD30) are vacuum deposited on the hole transport layer to form (or provide) a layer with a thickness of Here, the amount of the first compound is 14 wt % of the total weight (100 wt %) of each emission layer, the amount of the fourth compound is 1.3 wt % of the total weight (100 wt %) of each emission layer, and the weight ratio of the second compound to the third compound is adjusted to 3.3:6.7.
[1058] The compound ETH34 is vacuum deposited on the emission layer to form (or provide) a thickness of and vacuum depositing ET46 and Liq on the hole blocking layer at a weight ratio of 4:6 to form (or provide) a hole blocking layer with a thickness of Next, Yb is vacuum deposited on the electron transport layer to form (or provide) a layer with a thickness of and then Mg is vacuum deposited thereon to form (or provide) a layer having a thickness of The cathode of the organic light-emitting device is thus completed.
[1059]
[1060] Examples 2 to 7 and Comparative Examples A to D
[1061] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 6 were used instead of Compound 26 as the first compound forming (or providing) the emission layer. In Table 6, the weight shown in brackets indicates the weight of the corresponding compound per 100 wt % of the emission layer.
[1062] Evaluation Example 4
[1063] The luminance of the organic light-emitting devices of Examples 1 to 7 and Comparative Examples A to D at 1,000 cd / m was measured by using a Keithley SMU 236 meter and a luminance meter PR650. 2 The driving voltage (V), y color coordinate (CIEy), color conversion efficiency (cd / A / y), emission color and lifetime (T 95 ), and the results are shown in Table 7. In Table 7, the lifespan (T 95 ) is the measured value of the time (hr) taken for the brightness to reach 95% of the initial brightness, expressed as the lifetime (T 95 )'s relative value (%).
[1064] Table 6
[1065]
[1066]
[1067]
[1068]
[1069] Table 7
[1070]
[1071]
[1072] Referring to Table 7, it is confirmed that the organic light-emitting devices of Examples 1 to 6 emit blue light and have excellent or appropriate driving voltage, excellent or appropriate color purity, excellent or appropriate color conversion efficiency, and excellent or appropriate life characteristics. It is also confirmed that the organic light-emitting device of Example 7 emits relatively deep blue light and has improved driving voltage, color purity, color conversion efficiency, and life characteristics compared to the organic light-emitting devices of Comparative Examples A to D.
[1073] Examples 11 to 17 and Comparative Examples 1A to 1D
[1074] Organic light-emitting devices were each manufactured in substantially the same manner as in Example 1, except that the amount of the first compound, the fourth compound, and the weight ratio of the second compound to the third compound were changed as shown in Table 8 when forming (or providing) the emission layer. In Table 8, the weight shown in brackets indicates the weight of the corresponding compound per 100 wt % of the emission layer.
[1075] Evaluation Example 5
[1076] The 1,000 cd / m 2 organic light-emitting devices of Examples 11 to 17 and Comparative Examples 1A to 1D were each measured in substantially the same manner as in Evaluation Example 4. 2 The driving voltage V, y color coordinate (CIEy), color conversion efficiency (cd / A / y), emission color and lifetime (T 95 ), and the results are shown in Table 9. In Table 9, the lifespan (T 95 ) is the measured value of the time (hr) taken for the brightness to reach 95% of the initial brightness, expressed as the lifetime (T 95 )'s relative value (%).
[1077] Table 8
[1078]
[1079]
[1080] Table 9
[1081]
[1082]
[1083] Referring to Table 9, it is confirmed that each of the organic light-emitting devices of Examples 11 to 16 emits blue light and has excellent or appropriate driving voltage, excellent or appropriate color purity, excellent or appropriate color conversion efficiency, and excellent or appropriate lifespan characteristics. It is also confirmed that the organic light-emitting device of Example 17 emits relatively deep blue light and has improved driving voltage, color purity, color conversion efficiency, and lifespan characteristics compared to the organic light-emitting devices of Comparative Examples 1A to 1D.
[1084] According to one or more embodiments, the organometallic compound represented by Formula 1 may have excellent or appropriate processability and electrical properties, and thus a light-emitting device including the organometallic compound represented by Formula 1 may have improved color purity, improved luminous efficiency, and / or improved lifespan characteristics.
[1085] In the present disclosure, it will be understood that the terms “comprise(s)”, “include(s)” or “have / has” indicate the presence of stated features, integers, steps, operations, elements and / or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components and / or groups thereof.
[1086] Throughout the present disclosure, when it is mentioned that a component (such as a layer, film, region, or plate) is placed "on" another component (such as a layer, film, region, or plate), it will be understood that it can be directly on the other component (such as a layer, film, region, or plate) or another component (such as a layer, film, region, or plate) can be inserted therebetween. In some embodiments, "directly on..." can refer to the absence of additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and other components. For example, "directly on..." can refer to the provision of two layers or two components without the use of additional components, such as adhesive components therebetween.
[1087] In the present disclosure, although the terms "first", "second", etc. may be used herein to describe one or more elements, components, regions and / or layers, these elements, components, regions and / or layers should not be limited by these terms. These terms are only used to distinguish one component from another component.
[1088] As used herein, the singular forms "a", "an", "one", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of "may" when describing embodiments of the present disclosure refers to "one or more embodiments of the present disclosure."
[1089] As used herein, the terms "substantially," "about," or similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. "About," as used herein, is inclusive of the recited value and means within the range of acceptable deviations for the particular value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" may mean within one or more standard deviations of the recited value, or within ±30%, ±20%, ±10%, or ±5% of the recited value.
[1090] Any numerical range described in this article is intended to include all sub-ranges of the same numerical precision within the range of description. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the minimum value 1.0 described and the maximum value 10.0 described (and including 1.0 and 10.0), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit described in this article is intended to include all lower numerical limits included therein and any minimum numerical limit described in this disclosure is intended to include all higher numerical limits included therein. Accordingly, the applicant reserves the right to modify this disclosure (including claims) to explicitly describe any sub-ranges included within the range explicitly described in this article.
[1091] Light-emitting devices, light-emitting devices, display devices, electronic devices, electronic equipment or any other related devices or components can be implemented using any appropriate hardware, firmware (e.g., dedicated integrated circuits), software or a combination of software, firmware and hardware. For example, the various components of the 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) or a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components to perform the various functions described herein. Computer program instructions are stored in a memory, which can be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). Computer program instructions can also be stored in other non-temporary computer-readable media, such as, for example, a CD ROM or a flash drive, etc. Moreover, those skilled in the art should recognize 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 dedicated computing device can be distributed on one or more other computing devices.
[1092] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more appropriate changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. A composition comprising: An organometallic compound represented by Formula 1; as well as Includes at least one π-electron-deficient nitrogen-containing C1-C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 1 Formula 1A Wherein, Ar1 in Formula 1 is a group represented by Formula 1A, The * in Formula 1A indicates the binding site with the ring CY1 in Formula 1, In Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, X1 to X4 are each independently C or N, i) the bond between X1 and M is a coordinate bond, and ii) one selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and the other two are each covalent bonds, Ring CY1 to Ring CY4 and Ring W4 are each independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Ring W2 is a saturated C3-C8 carbocyclic group, n4 is 0, 1 or 2. When n4 is 0, the formula 1A is The group represented by is a single bond, X 51 is a single bond, *-N(Z 51a )-*', *-B(Z 51a )-*', *-P(Z 51a )-*', *-C(Z 51a )(Z 51b )-*', *-Si(Z 51a )(Z 51b )-*', *-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 51a )=*', *=C(Z 51a )-*', *-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*', X 52 is a single bond, *-N(Z 52a )-*', *-B(Z 52a )-*', *-P(Z 52a )-*', *-C(Z 52a )(Z 52b )-*', *-Si(Z 52a )(Z 52b )-*', *-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 52a )=*', *=C(Z 52a )-*', *-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*', R1 to R4, Z 51a , Z 51b , Z 52a and Z 52b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), T1, T2, T 31 To T 35 and T4 are each independently: Hydrogen, deuterium, -F or cyano; unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; or Each unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl, a1 to a4 are each independently an integer selected from 0 to 10, c1 is an integer selected from 1 to 3, c2 is an integer selected from 1 to 15, c4 is an integer selected from 1 to 10, Formula 1A satisfies at least one selected from Condition A and Condition B: Condition A T 31 and T 35 are different from each other; and Condition B T 32 and T 34 Different from each other, In Formula 1A, The groups represented by The groups represented are different from each other, is selected from ring CY1, ring CY2, ring CY3, ring CY4, R1, R2, R3, R4, Z 51a , Z 51b , Z 52a , Z 52b , T1, T2, T 31 , T 32 , T 33 , T 34 , T 35 and T4 are optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, * indicates the binding site with the neighboring atoms, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; -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 );or Any combination of Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Formula 3 and Among them, in formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 Cyclic group or pyridyl group, X 71 is a single bond, or is a linking group comprising O, S, N, B, C, Si or any combination thereof, and * indicates a bonding site with any atom included in the remaining portion other than the group represented by Formula 3 in the third compound.
2. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emitting layer; as well as An organometallic compound represented by Formula 1: Formula 1 Formula 1A Wherein, Ar1 in Formula 1 is a group represented by Formula 1A, The * in Formula 1A indicates the binding site with the ring CY1 in Formula 1, In Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, X1 to X4 are each independently C or N, i) the bond between X1 and M is a coordinate bond, and ii) one selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and the other two are each covalent bonds, Ring CY1 to Ring CY4 and Ring W4 are each independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Ring W2 is a saturated C3-C8 carbocyclic group, n4 is 0, 1 or 2. When n4 is 0, the formula 1A is The group represented by is a single bond, X 51 is a single bond, *-N(Z 51a )-*', *-B(Z 51a )-*', *-P(Z 51a )-*', *-C(Z 51a )(Z 51b )-*', *-Si(Z 51a )(Z 51b )-*', *-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 51a )=*', *=C(Z 51a )-*', *-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*', X 52 is a single bond, *-N(Z 52a )-*', *-B(Z 52a )-*', *-P(Z 52a )-*', *-C(Z 52a )(Z 52b )-*', *-Si(Z 52a )(Z 52b )-*', *-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 52a )=*', *=C(Z 52a )-*', *-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*', R1 to R4, Z 51a , Z 51b , Z 52a and Z 52b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), T1, T2, T 31 To T 35 and T4 are each independently: Hydrogen, deuterium, -F or cyano; unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; or Each unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl, a1 to a4 are each independently an integer selected from 0 to 10, c1 is an integer selected from 1 to 3, c2 is an integer selected from 1 to 15, c4 is an integer selected from 1 to 10, Formula 1A satisfies at least one selected from Condition A and Condition B: Condition A T 31 and T 35 are different from each other; and Condition B T 32 and T 34 Different from each other, In Formula 1A, The groups represented by The groups represented are different from each other, is selected from ring CY1, ring CY2, ring CY3, ring CY4, R1, R2, R3, R4, Z 51a , Z 51b , Z 52a , Z 52b , T1, T2, T 31 , T 32 , T 33 , T 34 , T 35 and T4 are optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, * indicates the binding site with the neighboring atoms, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; -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 );or any combination thereof, and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.
3. The light emitting device according to claim 2, further comprising: Includes at least one π-electron-deficient nitrogen-containing C1-C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 3 In formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 Cyclic group or pyridyl group, X 71 is a single bond, or is a linking group comprising O, S, N, B, C, Si or any combination thereof, and * indicates a bonding site with any atom included in the remaining portion other than the group represented by Formula 3 in the third compound.
4. The light emitting device according to claim 3, wherein: The second compound comprises a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group or any combination thereof, and The fourth compound is a compound including at least one cyclic group including both 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, The emitting layer is configured to emit blue light.
6. The light emitting device according to claim 3, comprising: The second compound and the third compound, At least one of the second compound and the third compound includes at least one deuterium, at least one silicon, or any combination thereof.
7. An electronic device comprising the light emitting device according to any one of claims 2 to 6.
8. The electronic device according to claim 7, further comprising: Color filters, color conversion layers, touch screen layers, polarizing layers, or any combination thereof.
9. An electronic device comprising the light emitting device according to any one of claims 2 to 6.
10. The electronic device of claim 9, wherein the electronic device is at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a portable phone, a tablet personal computer, a tablet phone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, and a billboard.
11. An organometallic compound represented by Formula 1: Formula 1 Formula 1A in, Ar1 in Formula 1 is a group represented by Formula 1A, The * in Formula 1A indicates the binding site with the ring CY1 in Formula 1, In Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver or copper, X1 to X4 are each independently C or N, i) the bond between X1 and M is a coordinate bond, and ii) one selected from the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M is a coordinate bond, and the other two are each covalent bonds, Ring CY1 to Ring CY4 and Ring W4 are each independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Ring W2 is a saturated C3-C8 carbocyclic group, n4 is 0, 1 or 2. When n4 is 0, the formula 1A is The group represented by is a single bond, X 51 is a single bond, *-N(Z 51a )-*', *-B(Z 51a )-*', *-P(Z 51a )-*', *-C(Z 51a )(Z 51b )-*', *-Si(Z 51a )(Z 51b )-*', *-Ge(Z 51a )(Z 51b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 51a )=*', *=C(Z 51a )-*', *-C(Z 51a )=C(Z 51b )-*', *-C(=S)-*' or *-C≡C-*', X 52 is a single bond, *-N(Z 52a )-*', *-B(Z 52a )-*', *-P(Z 52a )-*', *-C(Z 52a )(Z 52b )-*', *-Si(Z 52a )(Z 52b )-*', *-Ge(Z 52a )(Z 52b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(Z 52a )=*', *=C(Z 52a )-*', *-C(Z 52a )=C(Z 52b )-*', *-C(=S)-*' or *-C≡C-*', R1 to R4, Z 51a , Z 51b , Z 52a and Z 52b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), T1, T2, T 31 To T 35 and T4 are each independently: Hydrogen, deuterium, -F or cyano; unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; or Each unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl, a1 to a4 are each independently an integer selected from 0 to 10, c1 is an integer selected from 1 to 3, c2 is an integer selected from 1 to 15, c4 is an integer selected from 1 to 10, Formula 1A satisfies at least one selected from Condition A and Condition B: Condition A T 31 and T 35 are different from each other; and Condition B T 32 and T 34 Different from each other, In Formula 1A, The groups represented by The groups represented are different from each other, is selected from ring CY1, ring CY2, ring CY3, ring CY4, R1, R2, R3, R4, Z 51a , Z 51b , Z 52a , Z 52b , T1, T2, T 31 , T 32 , T 33 , T 34 , T 35 and T4 are optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, * indicates the binding site with the neighboring atoms, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; -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 );or any combination thereof, and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.
12. The organometallic compound according to claim 11, wherein X1 is C, and Ring CY1 is imidazolyl, triazolyl, benzimidazolyl, naphthoimidazolyl or imidazopyridinyl.
13. The organometallic compound according to claim 11, wherein the ring W2 is a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group.
14. The organometallic compound according to claim 11, wherein R1 to R4, Z 51a , Z 51b , Z 52a and Z 52b Each independently is: Hydrogen, deuterium, -F or cyano; unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; or Each unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 C3-C alkyl) biphenyl or any combination thereof substituted 10 Cycloalkyl, phenyl, naphthyl, dibenzofuranyl or dibenzothienyl.
15. The organometallic compound according to claim 11, wherein Formula 1A satisfies one selected from Condition A-1 to Condition A-3: Condition A-1 T 31 is hydrogen, deuterium or -F, T 35 for: unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; or Each unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl; Condition A-2 T 31 and T 35 are different from each other, and T 31 and T 35 Each is independently unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; and Condition A-3 T 31 is unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl, and T 35 are each unsubstituted or substituted with deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl.
16. The organometallic compound according to claim 11, wherein Formula 1A satisfies one selected from Condition B-1 to Condition B-3: Condition B-1 T 32 is hydrogen, deuterium or -F, T 34 for: unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; or Each unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl) biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl; Condition B-2 T 32 and T 34 are different from each other, and T 32 and T 34 Each is independently unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl; and Condition B-3 T 32 is unsubstituted or substituted with deuterium, -F, cyano, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 Alkyl) biphenyl or any combination thereof substituted C1-C 20 Alkyl, and T 34 are each unsubstituted or substituted with deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl or any combination thereof substituted phenyl, naphthyl, dibenzofuranyl or dibenzothienyl.
17. The organometallic compound according to claim 11, wherein the group represented by Formula 1A is one selected from the groups represented by Formula 1A(1) to Formula 1A(4): Formula 1A (1) Formula 1A (2) Formula 1A (3) Formula 1A (4) In Formula 1A(1) to Formula 1A(4), * indicates the binding site to ring CY1 in formula 1, Ring W2, T1, T2, T 31 To T 35 , c1 and c2 are each independently the same as defined in Formula 1, and T 41 To T 45 Each is independently the same as defined for T4 in Formula 1.
18. The organometallic compound of claim 11, wherein the organometallic compound comprises at least one deuterium.
19. The organometallic compound according to claim 11, wherein the organometallic compound is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 In formula 1-1 and formula 1-2, M, X1 to X4, ring W4, ring W2, n4, X 51 , T1, T2, T 31 To T 35 , T4, c1, c2 and c4 are each independently the same as defined in Formula 1, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, and X 14 C(R 14 ) or N, R 11 To R 14 are each independently the same as defined for R1 in Formula 1, and are selected from R 11 To R 14 Two or more of are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, and X 23 C(R 23 ) or N, R 21 To R 23 Each is independently the same as defined for R2 in Formula 1, and is selected from R 21 To R 23 Two or more of are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, X 31 C(R 31 ) or N, X 32 C(R 32 ) or N, X 33 C(R 33 ) or N, X 34 C(R 34 ) or N, X 35 C(R 35 ) or N, and X 36 C(R 36 ) or N, R 31 To R 36 Each is independently the same as defined for R3 in Formula 1, and is selected from R 31 To R 36 Two or more of are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, X 41 C(R 41 ) or N, X 42 C(R 42 ) or N, X 43 C(R 43 ) or N, and X 44 C(R 44 ) or N, R 41 To R 44 Each is independently the same as defined for R4 in Formula 1, and is selected from R 41 To R 44 Two or more of are optionally bonded together to form an unsubstituted or substituted R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 a heterocyclic group, and Formula 1-1 and Formula 1-2 satisfy at least one selected from Condition A and Condition B: Condition A T 31 and T 35 are different from each other; and Condition B T 32 and T 34 Different from each other, In formula 1-1 and formula 1-2, The groups represented by The groups represented are different from each other, and *Indicates the binding site with the neighboring atoms.
20. The organometallic compound according to claim 19, wherein X 42 C(R 42 ), X 43 C(R 43 ), and R 42 and R 43 At least one of is not hydrogen.
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