Light-emitting device, electronic device, electronic equipment, and organometallic compound
By using specific organometallic compounds in the light emitting device, optimizing their energy level differences to achieve balanced hole and electron injection, the problems of insufficient color purity, luminous efficiency and lifetime in the prior art are solved, and optical performance is improved.
Patent Information
- Application Number
- CN202410392871.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-07-10
- Filing Date
- 2024-04-02
- Publication Date
- 2025-01-10
AI Technical Summary
The existing light emitting devices have shortcomings in color purity, luminous efficiency and lifetime, and it is difficult to achieve excellent performance when using organometallic compounds.
Using specific organometallic compounds (such as compounds composed of metal groups such as platinum, palladium, copper, and heterocyclic groups with carbon or nitrogen content) as materials for the emission layer and electron transport region, adjust the structure and composition of the compound. Its energy levels differ to achieve equilibrium hole and electron injection.
The chromatic purity, luminous efficiency and life of the light emitting device are improved, and better optical performance is achieved.
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Figure CN119285678A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0089048 filed in the Korean Intellectual Property Office on July 10, 2023, the disclosure of which is incorporated herein in its entirety by reference. Technical Field
[0003] One or more embodiments of the present disclosure relate to a light-emitting device including an organic metal compound, an electronic device including the light-emitting device, an electronic equipment including the light-emitting device, and the organic metal compound. Background Art
[0004] Among light-emitting devices, self-emitting devices (eg, organic light-emitting devices) have relatively wide viewing angles, relatively high contrast ratios, relatively short response times, and excellent or suitable characteristics in terms of brightness, driving voltage, and response speed.
[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. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. Excitons can transition from an excited state and decay 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 a light-emitting device including an organic metal compound, an electronic device including the light-emitting device, an electronic equipment including the light-emitting device, and the organic metal compound.
[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 taught by practice of the presented embodiments of the disclosure.
[0008] According to one or more embodiments of the present disclosure, a light emitting device includes:
[0009] a first electrode;
[0010] a second electrode, facing the first electrode;
[0011] an intermediate layer between the first electrode and the second electrode and including an emission layer, and
[0012] An organometallic compound represented by Formula 1:
[0013]
[0014] Among them, in formula 1,
[0015] M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm),
[0016] X 11 , X 12 and X 2 To X 4 can be independently C or N,
[0017] Cyclo 1 To Ring CY 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0018] L 1 To L 3 can be independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*', wherein * and *' each indicate a binding site with an adjacent atom,
[0019] n1 to n3 can each independently be an integer from 1 to 5,
[0020] R 1 To R 4 , R 1a and R 1bcan be each 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 1 -C 60 Alkylthio, 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 )、-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 ),
[0021] a1 to a4 can each independently be an integer from 1 to 20,
[0022] Ar 1 It may be a group represented by Formula 2-1 or Formula 2-2,
[0023] When a1 is 2 or more, the number of R1 Two or more of may be optionally bonded to each other (ie, may be bonded to each other or may not be bonded to each other) to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0024] When a2 is 2 or more, the number of R 2 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0025] When a3 is 2 or more, the number of R 3 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0026] When a4 is 2 or more, the number of R 4 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0027] R 1a and R 1b may be optionally bonded to each other to form an unsubstituted or substituted group with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0028] Selected from R 1 To R4 , R 1a , R 1b and Ar 1 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0029] In formula 2-1 and formula 2-2,
[0030] Y 1 and Y 2 can be independently B or N, wherein Y 1 and Y 2 can be different from each other,
[0031] Z 1 To Z 7 can be each 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 1 -C 60 Alkylthio, 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 )(Q2 )(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 ),
[0032] *Indicates the same as X in Formula 1 12 The binding site
[0033] Selected from Z 1 To Z 7 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0034] R 10a Can be:
[0035] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0036] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q11 )(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;
[0037] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q21 )(Q 22 ) or any combination thereof; or
[0038] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0039] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0040] According to one or more embodiments of the present disclosure, an electronic device includes the light emitting device.
[0041] According to one or more embodiments of the present disclosure, electronic equipment includes the light emitting device.
[0042] According to one or more embodiments of the present disclosure, an organic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0043] 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 accompanying drawings illustrate embodiments of the present disclosure and together with the specification are used to illustrate the principles of the present disclosure. The above and other aspects, features and advantages of specific embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings, in which:
[0044] Figure 1 is a schematic cross-sectional view of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0045] Figure 2 is a schematic cross-sectional view showing a structure of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure;
[0046] Figure 3 is a schematic cross-sectional view of a structure of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure; and
[0047] Figure 4 , Figure 5 , Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of a structure of electronic equipment according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0048] Now will be more detailed with reference to embodiment, its example shows the example of embodiment in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the disclosure, and for the sake of brevity, its repeated description may not be provided.In this respect, the embodiment of the present disclosure may have different forms, and should not be interpreted as being limited to the description set forth in this article.Therefore, the embodiment of the present disclosure is described only by reference to the accompanying drawings, to illustrate the various aspects of the present disclosure.The term "and / or" or "or" may include any and all combinations of one or more associated listed items.Throughout the present disclosure, such as "at least one (kind / person) in ... ", "one (kind / person) in ... " and "selected from ... " before or after a column of elements, what is modified is the whole column of elements, and the individual elements in the column are not modified. For example, "at least one of a, b, and c", "at least one selected from a, b, and c", "at least one selected from a to c" may indicate only a, only b, only c, both a and b (e.g., a and b simultaneously), both a and c (e.g., a and c simultaneously), both b and c (e.g., b and c simultaneously), all a, b, and c, or variations thereof. As used herein, " / " may be interpreted as "and" or "or", depending on the circumstances.
[0049] According to one or more embodiments of the present disclosure, a light emitting device may include:
[0050] a first electrode;
[0051] a second electrode facing the first electrode;
[0052] an intermediate layer between the first electrode and the second electrode and including an emission layer; and
[0053] An organometallic compound represented by Formula 1:
[0054] Formula 1
[0055]
[0056] Wherein, the description of Formula 1 provided elsewhere herein is incorporated herein by reference (eg, provided in greater detail elsewhere herein).
[0057] In one or more embodiments,
[0058] The first electrode of the light emitting device may be an anode,
[0059] The second electrode of the light emitting device may be a cathode, and
[0060] The intermediate layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
[0061] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0062] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0063] In one or more embodiments, the intermediate layer of the light emitting device may include the organic metal compound represented by Formula 1.
[0064] In one or more embodiments, an emission layer of a light emitting device may include the organometallic compound represented by Formula 1 (eg, as a first compound).
[0065] In one or more embodiments, the emission layer of the light emitting device may include a dopant and a host, and the dopant may include an organic metal compound represented by Formula 1. For example, in some embodiments, the organic metal compound may act as a dopant. For example, in some embodiments, the emission layer may emit blue light. The blue light may have a maximum emission wavelength in the range of, for example, about 430 nm to about 480 nm.
[0066] In one or more embodiments, the electron transport region of the light emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In one or more embodiments, the hole blocking layer may directly contact the emission layer.
[0067] In one or more embodiments, the light emitting device may further include: a nitrogen-containing C having at least one π-electron-deficient 1 -C 60 a second compound comprising a heterocyclic group; a third compound comprising a group represented by Formula 3; a fourth compound capable of emitting delayed fluorescence; or any combination thereof,
[0068] Wherein, the organometallic compound (for example, as the first compound), the second compound, the third compound, and the fourth compound in the light-emitting device may be different from each other:
[0069] Formula 3
[0070]
[0071] Among them, in formula 3,
[0072] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group, or pyridyl group,
[0073] X 71 may be a single bond, or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and
[0074] * indicates a bonding site with any atom included in the remaining part other than the group represented by Formula 3 in the third compound.
[0075] In one or more embodiments, the organometallic compound may include at least one deuterium.
[0076] In one or more embodiments, the second compound, the third compound, and the fourth compound may each include at least one deuterium.
[0077] In one or more embodiments, the second compound may include at least one silicon.
[0078] In one or more embodiments, the third compound may include at least one silicon.
[0079] In one or more embodiments, in addition to the organic metal compound represented by Formula 1, the light-emitting device (e.g., an emission layer in a light-emitting device) may also include a second compound and a third compound, wherein at least one selected from the second compound and the third compound may include at least one deuterium, at least one silicon, or a combination thereof.
[0080] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound. At least one selected from the organometallic compound and the second compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound and the second compound, 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.
[0081] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound. At least one selected from the organometallic compound and the third compound may include at least one deuterium. In one or more embodiments, in addition to the organometallic compound and the third compound, 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.
[0082] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., an emission layer in a light-emitting device) may further include a fourth compound. At least one of the organometallic compound and the fourth compound may include at least one deuterium. The fourth compound may have the effect of improving the color purity, luminous efficiency, and life characteristics of the light-emitting device. In one or more embodiments, in addition to the organometallic compound and the fourth compound, the light-emitting device (e.g., an emission layer in a light-emitting device) may further include a second compound, a third compound, or any combination thereof.
[0083] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound and a third compound. The second compound and the third compound may form an exciplex. At least one of the organometallic compound, the second compound, and the third compound may include at least one deuterium.
[0084] In one or more embodiments, the emission layer in the light emitting device may include: i) an organic metal compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, and the emission layer may emit blue light.
[0085] In one or more embodiments, the blue light may have a maximum emission wavelength in a range of about 430nm to about 480nm, about 430nm to about 475nm, about 440nm to about 475nm, about 450nm to about 475nm, about 430nm to about 470nm, about 440nm to about 470nm, about 450nm to about 470nm, about 430nm to about 465nm, about 440nm to about 465nm, about 450nm to about 465nm, about 430nm to about 460nm, about 440nm to about 460nm, or about 450nm to about 460nm.
[0086] In one or more embodiments, the second compound may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0087] In one or more embodiments, the following compounds may be excluded from the third compound:
[0088]
[0089] In one or more embodiments, the difference between the triplet energy level (eV) of the fourth compound and the singlet energy level (eV) of the fourth compound may be about 0 eV or higher and about 0.5 eV or lower (or about 0 eV or higher and about 0.3 eV or lower).
[0090] In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including each of boron (B) and nitrogen (N) as a ring-constituting atom.
[0091] In one or more embodiments, the fourth compound may be a compound comprising C 8 -C 60 A polycyclic compound comprising C 8 -C 60 The polycyclic compound includes two or more cyclic groups (eg, one is a first ring and the other is a second ring) that are fused and simultaneously share boron (B).
[0092] 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 (eg, to form a fused ring including four or more rings),
[0093] wherein the third ring can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and
[0094] The fourth ring can be a 1,2-azaborinine group, a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group or a 1,4-dihydroborinine group.
[0095] In one or more embodiments, the third compound may not include (e.g., may exclude) (e.g., any) compound represented by Formula 3-1 described in the present disclosure. In the present disclosure, "not including "component" or any "component", "excluding "component" or any "component"" and / or "not containing "component"" etc. means that the "component" is not added, selected or used as a component in the composition / element, but in some embodiments, due to other impurities and / or external factors, less than an appropriate amount of "component" may still be included.
[0096] In one or more embodiments, the second compound may include a compound represented by Formula 2:
[0097] Formula 2
[0098]
[0099] Among them, in formula 2,
[0100] 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 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0101] b51 to b53 may each independently be an integer from 1 to 5,
[0102] 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 (R56 ), and selected from X 54 To X 56 At least one of them may be N, and
[0103] R 51 To R 56 and R 10a Each may be the same as described in the present disclosure.
[0104] In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0105] Formula 3-1
[0106]
[0107] Formula 3-2
[0108]
[0109] Formula 3-3
[0110]
[0111] Formula 3-4
[0112]
[0113] Formula 3-5
[0114]
[0115] Among them, in Formula 3-1 to Formula 3-5,
[0116] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 Cyclic group, or pyridyl group,
[0117] 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 ),
[0118] 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 ),
[0119] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0120] X 85 Can be C or Si,
[0121] 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 Cyclic group, either unsubstituted or substituted with at least one R 10a Substituted pyridyl, wherein Q 4 and Q 5 You can each share your experience with Q 1 Same as described,
[0122] b81 to b85 may each independently be an integer from 1 to 5,
[0123] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may each be the same as described in the present disclosure,
[0124] a71 to a74 may each independently be an integer from 0 to 20, and
[0125] R 10a May be the same as described herein.
[0126] In one or more embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0127] Formula 502
[0128]
[0129] Formula 503
[0130]
[0131] Among them, in equation 502 and equation 503,
[0132] Ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0133] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0134] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0135] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0136] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0137] Y51 and Y 52 may be each independently B, P(=O) or S(=O),
[0138] 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 in the present disclosure, and
[0139] a501 to a504 may each independently be an integer of 0 to 20.
[0140] In one or more embodiments, the light emitting device may satisfy at least one condition selected from conditions 1 to 4:
[0141] Condition 1
[0142] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound is greater than the LUMO energy level (eV) of the organometallic compound;
[0143] Condition 2
[0144] The LUMO energy level (eV) of the organometallic compound> the LUMO energy level (eV) of the second compound;
[0145] Condition 3
[0146] The highest occupied molecular orbital (HOMO) energy level (eV) of the organometallic compound is greater than the HOMO energy level (eV) of the third compound; and
[0147] Condition 4
[0148] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.
[0149] Each of the HOMO energy level and the LUMO energy level of each of the organometallic compound, the second compound, and the third compound may be a negative value, and may be measured according to an appropriate method.
[0150] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the organic metal compound and the LUMO energy level of the second compound can be about 0.1 eV or higher and about 1.0 eV or lower, the absolute value of the difference between the LUMO energy level of the organic metal compound and the LUMO energy level of the third compound can be about 0.1 eV or higher and about 1.0 eV or lower, the absolute value of the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the second compound can be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher), and the absolute value of the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the third compound can be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher).
[0151] When the relationship between the LUMO energy level and the HOMO energy level satisfies the above conditions, a balance between holes and electrons injected into the emission layer can be achieved.
[0152] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0153] First embodiment
[0154] According to a first embodiment, an organic metal compound may be included in an emission layer of an intermediate layer in a light-emitting device, wherein the emission layer may also include a host, the organic metal compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence emitted from the organic metal compound. For example, according to the first embodiment, the organic metal compound may be a dopant or an emitter. In one or more embodiments, the organic metal compound may be a phosphorescent dopant or a phosphorescent emitter.
[0155] The phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
[0156] 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 used as a dopant or emitter, and in this regard, the auxiliary dopant may be used to improve the light emitting efficiency of the organic metal compound.
[0157] The auxiliary dopant may be different from each of the organometallic compound and the host.
[0158] In one or more embodiments, the auxiliary dopant may be a compound capable of emitting delayed fluorescence.
[0159] In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including each of B and N as a ring-forming atom.
[0160] Second embodiment
[0161] According to a second embodiment, an organic metal compound may be included in an emission layer of an intermediate layer in a light-emitting device, wherein the emission layer may also include a host and a dopant, the organic metal compound, the host and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
[0162] In one or more embodiments, the organometallic compound of the second embodiment may be used as an auxiliary dopant that transfers energy to a dopant (or emitter) rather than as a dopant.
[0163] In one or more embodiments, the organometallic compound in the second embodiment may be used as an emitter, and may also be used as an auxiliary dopant that transfers energy to a dopant (or emitter).
[0164] For example, phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0165] The dopant (or emitter) in the second embodiment can be a phosphorescent dopant material (e.g., an organic metal compound represented by Formula 1, an organic metal compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof).
[0166] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength in the range of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
[0167] The auxiliary dopant in the first embodiment may include, for example, a compound represented by Formula 502 or Formula 503 as the fourth compound.
[0168] 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 any combination thereof).
[0169] In one or more embodiments, the subject in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
[0170] In one or more embodiments, the light emitting device may further include a covering layer located outside the first electrode (eg, on the first electrode) and / or outside the second electrode (eg, on the second electrode).
[0171] In one or more embodiments, the light emitting device may further include at least one of a first covering layer located outside the first electrode (e.g., on the first electrode) and a second covering layer located outside the second electrode (e.g., on the second electrode), and at least one of the first covering layer and the second covering layer may (e.g., the first covering layer and the second covering layer may each independently) include an organic metal compound represented by Formula 1. A more detailed description of the first covering layer and / or the second covering layer may be referenced by the description provided elsewhere herein.
[0172] In one or more embodiments, the light emitting device may include:
[0173] a first capping layer located outside the first electrode (eg, on the first electrode) and including an organic metal compound represented by Formula 1;
[0174] a second covering layer located outside the second electrode (eg, on the second electrode) and including an organic metal compound represented by Formula 1; or
[0175] Both the first cover layer and the second cover layer (eg, the first cover layer and the second cover layer simultaneously).
[0176] The phrase “(the intermediate layer and / or the covering layer) includes the organic metal compound represented by Formula 1” as used herein may be understood as “(the intermediate layer and / or the covering layer) may include one type of organic metal compound represented by Formula 1 or two different types of organic metal compounds each represented by Formula 1”.
[0177] In one or more embodiments, the intermediate layer and / or the covering layer may include only compound 1 as an organic metal compound. Here, compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the intermediate layer may include compound 1 and compound 2 as organic metal compounds. In this regard, compound 1 and compound 2 may be present in substantially the same layer (e.g., both compound 1 and compound 2 (e.g., compound 1 and compound 2 at the same time) 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).
[0178] The term "intermediate layer" as used herein refers to a single layer and / or all of a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0179] 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, the thin film transistor including a source electrode and a drain electrode, and the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode of the thin film transistor. In one or more embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. A more detailed description of the electronic device may be referenced by the description provided elsewhere in this document.
[0180] According to one or more embodiments of the present disclosure, electronic equipment may include a light emitting device.
[0181] For example, the electronic equipment can be at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a signal light, a head-up display, a fully or partially transparent display, a flexible display (such as a rollable display, a foldable display, a stretchable display), a laser printer, a phone (cellular phone, tablet phone), a tablet personal computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater or stadium screen, a light therapy device, and a billboard.
[0182] According to one or more embodiments of the present disclosure, there is provided an organometallic compound represented by Formula 1. The description of Formula 1 may be the same as described herein.
[0183] By referring to the synthetic examples and / or examples provided herein, one of ordinary skill in the art can recognize methods for synthesizing organometallic compounds.
[0184] Description of Formula 1, Formula 2-1 and Formula 2-2
[0185] Formula 1
[0186]
[0187] In Formula 1, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
[0188] In one or more embodiments, M may be Pt, Pd, or Au.
[0189] In one or more embodiments, M may be Pt.
[0190] In formula 1, X 11 , X 12 and X 2 To X 4 They may each independently be C or N.
[0191] In one or more embodiments, X 11 It can be C.
[0192] In one or more embodiments, X 11 Can be C, and X 11 The bond between M and N may be a coordination bond.
[0193] In one or more embodiments, X 11 It may be C of a carbene moiety.
[0194] In one or more embodiments, X 2 and X 3 can each be C, and X 4 Can be N.
[0195] In one or more embodiments, i) X 11 The bond between M and X may be a coordination bond, and ii) is selected from X 2 The key between M and X 3 The bond between M and X 4 One of the bonds to M may be a coordinate bond, and the other two bonds may each be a covalent bond.
[0196] In one or more embodiments, X 11 The bond between M and X 4 The bonds between X and M can each be coordination bonds, and 2 The bond between M and X 3 The bonds with M may each be covalent bonds.
[0197] In one or more embodiments, X 11 , X 2 and X 3 can each be C, and X 4 It can be N,
[0198] X 11 The bond between M and X 4 The bonds between M and each other can be coordination bonds, and
[0199] X 2 The bond between M and X 3 The bonds to M may each be covalent bonds.
[0200] In one or more embodiments, X 12 Can be N.
[0201] In Formula 1, ring CY 1 To Ring CY 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group.
[0202] In one or more embodiments, CY 1 To Ring CY 4 Can be independently:
[0203] Phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, yl, cyclopentadienyl, furanyl, thienyl, thirolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirolyl, dibenzothirolyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl , pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxacillinyl, dibenzothiacillinyl, dibenzodihydroazacillinyl, dibenzodihydrodicillinyl, dibenzodihydrocillinyl, dibenzodioxanyl, dibenzoxathine group, dibenzoxazinyl, dibenzopyranyl, dibenzodithiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl.
[0204] In one or more embodiments, CY 1 It can be C containing nitrogen 1 -C 60 Heterocyclic group.
[0205] In one or more embodiments, CY 1 It may be an imidazolyl group, a triazolyl group, a benzimidazolyl group, a naphthoimidazolyl group or an imidazopyridyl group.
[0206] In one or more embodiments, X 11 can be C, and
[0207] Cyclo 1It may be an imidazolyl group, a triazolyl group, a benzimidazolyl group, a naphthoimidazolyl group or an imidazopyridyl group.
[0208] In one or more embodiments, X 11 may be C of the carbene portion, and
[0209] Cyclo 1 It may be an imidazolyl group, a triazolyl group, a benzimidazolyl group, a naphthoimidazolyl group or an imidazopyridyl group.
[0210] In one or more embodiments, CY 2 It may be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzocarbazolyl, benzofluorenyl, naphthobenzosilyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzocarbazolyl, dibenzofluorenyl, dinaphthosilyl, azadibenzofuranyl, dinaphthothiophenyl, The invention also includes an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group, an oxazolidinyl group
[0211] In one or more embodiments, CY 2 It may be a phenyl group, a pyridyl group, a pyrimidyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group or a dibenzosilyl group.
[0212] In one or more embodiments, CY 3 Can be: C 2 -C 8 Monocyclic group; or C 4 -C 20 Polycyclic groups, 2 or 3 of which are C 2 -C 8 The monocyclic groups are fused to each other.
[0213] In one or more embodiments, CY 3 It may be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilyl, azadibenzofuranyl, azadibenzothiophenyl, azacarbazolyl, azafluorenyl or azadibenzosilyl.
[0214] In one or more embodiments, CY 4 It can be C containing nitrogen 1 -C 60 Heterocyclic group.
[0215] In one or more embodiments, CY4 It may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, benzopyrazolyl, benzimidazolyl or benzothiazolyl.
[0216] In formula 1, L 1 To L 3 can be independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*', wherein * and *' each indicate a binding site with an adjacent atom,
[0217] In Formula 1, n1 to n3 represent L 1 Quantity to L 3 The number of L1 and L2 can be an integer from 1 to 5. When n1 is 2 or more, two or more L 1 can be the same as or different from each other. When n2 is 2 or greater, two or more L 2 may be the same as or different from each other, and when n3 is 2 or greater, two or more L 3 May be the same as or different from each other.
[0218] In one or more embodiments, R 1a and R 1b Can be independently:
[0219] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0220] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof;
[0221] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl 1-(4-(4-benzo-1-oxo-1-yl)-2-nitro-1-yl)-2-nitro-1-nitro-2-nitro-1-yl, 1-(4-(4-benzo-1-oxo-1-yl)-2-nitro-1-nitro-2-nitro ... 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 -C10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0222] -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
[0223] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1-C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0224] In one or more embodiments, L 1 and L 3 Each may be a single bond.
[0225] In one or more embodiments, L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0226] In one or more embodiments, L 1 and L 3 can each be a single bond, and
[0227] L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0228] In formula 1, R 1 To R 4 , R 1a and R 1b can be each 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 1 -C 60Alkylthio, 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 )、-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 ).
[0229] R 10a and Q 1 To Q 3 Each may be the same as described herein.
[0230] In Formula 1, a1 to a4 may each independently be an integer of 1 to 20.
[0231] In one or more embodiments, R 1 To R 4 Can be independently:
[0232] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0233] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof;
[0234] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl 1-(4-(4-benzo-1-oxo-1-yl)-2-nitro-1-yl)-2-nitro-1-nitro-2-nitro-1-yl, 1-(4-(4-benzo-1-oxo-1-yl)-2-nitro-1-nitro-2-nitro ... 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, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0235] -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
[0236] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0237] In one or more embodiments, R 1 To R 4 Can be independently:
[0238] Hydrogen, deuterium, -F, -Cl, -Br, -I or C 1 -C 20 alkyl;
[0239] Deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 C substituted with alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof 1 -C 20 Alkyl; or
[0240] Phenyl, biphenyl, terphenyl, (C 1 -C 10 alkyl)phenyl or naphthyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, (C 1 -C 10 alkyl)phenyl or any combination thereof.
[0241] In formula 1, Ar 1 It may be a group represented by Formula 2-1 or Formula 2-2.
[0242] In one or more embodiments, when a1 is 2 or greater, the number of R 1 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0243] In one or more embodiments, when a2 is 2 or greater, the number of R 2 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0244] In one or more embodiments, when a3 is 2 or greater, the number of R 3 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0245] In one or more embodiments, when a4 is 2 or greater, the number of R 4 Two or more of the R may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0246] In one or more embodiments, R 1a and R 1b may be optionally bonded to each other to form an unsubstituted or substituted group with at least one R 10aSubstituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0247] In one or more embodiments, selected from R 1 To R 4 , R 1a , R 1b and Ar 1 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0248] In one or more embodiments, the formula 1 is The group represented by may be a group represented by one selected from the group consisting of formula CY1(1) to formula CY1(11):
[0249]
[0250]
[0251] Among them, in formula CY1(1) to formula CY1(11),
[0252] Ar 1 can be the same as described in this article,
[0253] R 11 To R 18 can be respectively related to R 1 Same as described,
[0254] * indicates the binding site with M in Formula 1, and
[0255] *' indicates the same as L in formula 1 1 binding site.
[0256] In one or more embodiments, the formula 1 is The group represented by may be a group represented by one selected from the group consisting of formula CY2(1) to formula CY2(13):
[0257]
[0258] Among them, in formula CY2(1) to formula CY2(13),
[0259] T 21 It can be B(Y 21 )、C(Y 21 )(Y 22 )、N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 It can be C(Y 21 ), N or Si(Y 21 ),
[0260] R 21 To R 26 , Y 21 and Y 22 can be respectively related to R 2 Same as described,
[0261] * indicates the binding site with M in Formula 1,
[0262] *' indicates the same as L in formula 1 1 binding site, and
[0263] *" indicates the same as L in Formula 1 2 binding site.
[0264] In one or more embodiments, the formula 1 is The group represented by may be a group represented by one selected from the group consisting of formula CY3(1) to formula CY3(25):
[0265]
[0266]
[0267]
[0268] Among them, in formula CY3(1) to formula CY3(25),
[0269] T 31 It can be B(Y 31 )、C(Y 31 )(Y 32 )、N(Y 31 ), O, S or Si(Y 31 )(Y 32 ),
[0270] T 32 It can be C(Y 31 ), N or Si(Y 31 ),
[0271] R 31 To R36 , Y 31 and Y 32 can be respectively related to R 3 Same as described,
[0272] * indicates the binding site with M in Formula 1,
[0273] *" indicates the same as L in Formula 1 2 binding site, and
[0274] *"' indicates the same as L in Formula 1 3 binding site.
[0275] In one or more embodiments, the formula 1 is The group represented by may be a group represented by one selected from the group consisting of formula CY4(1) to formula CY4(29):
[0276]
[0277]
[0278] Among them, in formula CY4(1) to formula CY4(29),
[0279] R 41 To R 47 can be respectively related to R 4 Same as described,
[0280] * indicates the binding site with M in Formula 1, and
[0281] *"' indicates the same as L in Formula 1 3 binding site.
[0282]
[0283]
[0284] In formula 2-1 and formula 2-2, Y 1 and Y 2 can be independently B or N, wherein Y 1 and Y 2 Can be different from each other.
[0285] In one or more embodiments, i) Y 1 can be B, and Y 2 Can be N, or ii) Y 1 Can be N, and Y 2 It can be B.
[0286] In one or more embodiments, Y 1 Can be N, and Y2 It can be B.
[0287] In one or more embodiments, Y 1 can be B, and Y 2 Can be N.
[0288] In formula 2-1 and formula 2-2, Z 1 To Z 7 can be each 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 1 -C 60 Alkylthio, 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 )、-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).
[0289] R 10a and Q 1 To Q 3 Each may be the same as described herein.
[0290] In one or more embodiments, Z 1 To Z 7 Can be independently:
[0291] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0292] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof;
[0293] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl 1-(4-(4-benzo-1-oxo-1-yl)-2-nitro-1-yl)-2-nitro-1-nitro-2-nitro-1-yl, 1-(4-(4-benzo-1-oxo-1-yl)-2-nitro-1-nitro-2-nitro ... 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, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31)、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0294] -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
[0295] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0296] In one or more embodiments, Z 1 To Z 7 Can be independently:
[0297] Hydrogen, deuterium, -F, -Cl, -Br, -I or C 1 -C 20 alkyl;
[0298] Deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, C 1 -C 10 C substituted with alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof 1 -C 20 Alkyl; or
[0299] Phenyl, biphenyl, terphenyl, (C 1 -C 10 alkyl)phenyl or naphthyl, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, (C 1 -C 10 alkyl)phenyl or any combination thereof.
[0300] In one or more embodiments, selected from Z 1 To Z 7 At least one of them may not be hydrogen.
[0301] In one or more embodiments, selected from Z 1 To Z 7 At least two of them may not be hydrogen.
[0302] In one or more embodiments, Z in Formula 2-1 1 and Z 2 may not be hydrogen, and Z in Formula 2-2 1 and Z 6 It may not be hydrogen.
[0303] In one or more embodiments, selected from Z 1 To Z 7 At least one of them may include deuterium.
[0304] In Formula 2-1 and Formula 2-2, * indicates the same as X in Formula 1.12 binding site.
[0305] In one or more embodiments, selected from Z 1 To Z 7 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0306] In one or more embodiments, the organometallic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:
[0307] Formula 1-1
[0308]
[0309] Formula 1-2
[0310]
[0311] Among them, in formula 1-1 and formula 1-2,
[0312] M.Y 1 , Y 2 and Z 1 To Z 7 may each be the same as described herein,
[0313] L 2 Can be *-O-*' or *-S-*',
[0314] X 13 It can be C(R 13 ) or N, X 14 It can be C(R 14 ) or N, X 15 It can be C(R 15 ) or N, and X 16 It can be C(R 16 ) or N,
[0315] X 21 It can be C(R 21 ) or N, X 22 It can be C(R 22 ) or N, and X 23 It can be C(R 23 ) or N,
[0316] X 31 It can be C(R31 ) or N, X 32 It can be C(R 32 ) or N, X 33 It can be C(R 33 ) or N, X 34 It can be C(R 34 ) or N, X 35 It can be C(R 35 ) or N, and X 36 It can be C(R 36 ) or N,
[0317] X 41 It can be C(R 41 ) or N, X 42 It can be C(R 42 ) or N, X 43 It can be C(R 43 ) or N, and X 44 It can be C(R 44 ) or N,
[0318] R 13 To R 16 can be respectively related to R 1 Same as described,
[0319] R 21 To R 23 can be respectively related to R 2 Same as described,
[0320] R 31 To R 36 can be respectively related to R 3 Same as described,
[0321] R 41 To R 44 can be respectively related to R 4 Same as described,
[0322] Selected from R 13 To R 16 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0323] Selected from R 21 To R 23 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group.10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0324] Selected from R 31 To R 36 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0325] Selected from R 41 To R 44 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0326] Selected from R 13 To R 16 , R 21 To R 23 , R 31 To R 36 , R 41 To R 44 and Z 1 To Z 7 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0327] Selected from Z 1 To Z 7 Two or more of them may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1 -C 60 a heterocyclic group, and
[0328] R 10a May be the same as described herein.
[0329] Unless otherwise defined herein, for example, in one or more embodiments, R in Formula 1, Formula 2-1, and Formula 2-2 10a Can be:
[0330] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0331] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0332] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0333] -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 ).
[0334] Unless otherwise defined herein, for example, Q in Formula 1, Formula 2-1, and Formula 2-2 is 1 To Q 3 , Q11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0335] When Ar in the organometallic compound represented by Formula 1 1 When the group is represented by Formula 2-1 or Formula 2-2, a blue shift of the maximum emission wavelength may occur, the Huang-Rhys factor (HRF) may decrease, and the triplet metal and ligand charge transfer state ( 3 The presence ratio of MLCT) may increase. Since the maximum emission wavelength is blue-shifted, the color coordinates of the organic metal compound represented by Formula 1 can be improved. In addition, since HRF is reduced and 3 The existence ratio of MLCT increases, so non-luminescent transitions can be suppressed or reduced and quantum efficiency can be improved, thereby improving luminous efficiency. Therefore, when the organometallic compound represented by Formula 1 is used in an electronic device (e.g., an organic light-emitting device, and, for example, in an emission layer of an organic light-emitting device), color purity and efficiency can be improved, and lifespan can be increased.
[0336] Description of other chemical formulas
[0337] Formula 2
[0338]
[0339] In formula 2, L 51 To L 53may be independently a single bond, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0340] In Formula 2, b51 to b53 respectively indicate L 51 The number of L 53 When b51 is 2 or more, two or more L 51 can be the same or different from each other. When b52 is 2 or greater, 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 some embodiments, b51 to b53 may be 1 or 2, respectively.
[0341] In one or more embodiments, in Formula 2, L 51 To L 53 Can be independently:
[0342] a single key; or
[0343] Phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, yl, cyclopentadienyl, furanyl, thienyl, thiolsyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothiolsyl, dibenzothiolsyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiolsyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl , quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzoxasiline dibenzothiasiline group, dibenzodihydroazasiline group, dibenzodihydrodisiline group, dibenzodihydrosiline group, dibenzodioxanyl group, dibenzothiophene group, dibenzoxazinyl group, dibenzopyranyl group, dibenzodithiine group, dibenzothiazinyl group, dibenzothiopyranyl group, dibenzocyclohexadienyl group, dibenzodihydropyridinyl group or dibenzodihydropyrazinyl group, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32) or any combination thereof, and
[0344] 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.
[0345] In one or more embodiments, in Formula 2, L 51 With R 51 The key between 52 With R 52 The key between 53 With R 53 The key between the two L 51 The key between the two L 52 The key between two L53, L 51 With X in Eq. 2 54 and X 55 The bonds between carbons, L 52 With X in Eq. 2 54 and X 56 The bonds between the carbons and L 53 With X in Eq. 2 55 and X 56 The bonds between the carbon atoms in the carbon atoms may each be a "carbon-carbon single bond".
[0346] In formula 2, X 54 Can be N or C (R 54 ), X 55 Can be N or C (R 55 ), X 56 Can be N or C (R 56 ), and selected from X 54 To X 56 At least one of may be N. 54 To R 56 Can be the same as described above. In one or more embodiments, selected from X 54 To X 56 Two or three of them can be N respectively.
[0347] In formula 2, R 51 To R 56 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ), and Q 1 To Q 3 Each may be the same as described herein.
[0348] In one or more embodiments, in Formula 2, R 51 To R 56 Can be independently:
[0349] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0350] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof;
[0351] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azabenzothiorolyl or a group represented by formula 91, each of which is unsubstituted or substituted by 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 -C20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0352] -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 ),
[0353] Among them, Q 1 To Q 3and Q 31 To Q 33 Can be independently:
[0354] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0355] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each of which is unsubstituted or substituted with deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof:
[0356] Formula 91
[0357]
[0358] Among them, in formula 91,
[0359] Cyclo 91 and CY 92 may be independently unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group,
[0360] X 91 Can be single bond, O, S, N(R 91 )、B(R 91 )、C(R91a )(R 91b ) or Si(R 91a )(R 91b ),
[0361] R 91 , R 91a and R 91b can be respectively related to R 82 , R 82a and R 82b Same as described,
[0362] R 10a may be the same as described herein, and
[0363] *Indicates the binding site with the neighboring atoms.
[0364] For example, in some embodiments, in Formula 91,
[0365] Cyclo 91 and CY 92 can be each independently unsubstituted or substituted with at least one R 10a substituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, and
[0366] R 91 , R 91a and R 91b Can be independently:
[0367] Hydrogen or C 1 -C 10 Alkyl; or
[0368] Phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, each of which is unsubstituted or substituted with deuterium, C 1 -C 10 The alkyl group may be substituted with phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0369] In one or more embodiments, in Formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented by each may not be phenyl.
[0370] 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.
[0371] 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.
[0372] In one or more embodiments, in Formula 2, b51 and b52 may each be 1, 2, or 3; and L 51 and L 52 can be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0373] In one or more embodiments, R in Formula 2 51 and R 52 may be 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
[0374] Q 1 To Q 3 may be independently unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0375] In one or more embodiments,
[0376] In formula 2, *-(L 51 ) b51 -R 51 The group represented by may be a group represented by one of formula CY51-1 to formula CY51-26, and / or
[0377] In formula 2, *-(L 52 ) b52 -R 52 The group represented by may be a group represented by one of formula CY52-1 to formula CY52-26, and / or
[0378] In formula 2, *-(L 53 ) b53 -R 53 The group represented by may be 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 ) represents a group:
[0379]
[0380]
[0381]
[0382]
[0383] 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,
[0384] 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 ),
[0385] 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 ),
[0386] Y 67 Can be single bond, O, S, N(R 67 )、B(R 67 )、C(R 67a )(R 67b ) or Si(R 67a )(R 67b ), Y 68 Can be single bond, O, S, N(R 68 )、B(R 68 )、C(R 68a )(R 68b ) or Si(R 68a )(R 68b ),
[0387] Y in formula CY51-16 and formula CY51-17 63 and Y 64 It can be a single key at different times.
[0388] Y in formula CY52-16 and formula CY52-17 67 and Y 68 It can be a single key at different times.
[0389] R 51a To R 51e , R 61 To R 64 , R 63a , R 63b , R 64a and R 64b can be respectively related to R 51 Same as described, where R 51a To R 51e Each of them may not be hydrogen,
[0390] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b can be respectively related to R 52 Same as described, where R 52a To R 52e Each of them may not be hydrogen,
[0391] R 53a To R 53e , R 69a and R 69b can be respectively related to R 53Same as described, where R 53a To R 53e each may not be hydrogen, and
[0392] *Indicates the binding site with the neighboring atoms.
[0393] For example, in one or more embodiments,
[0394] 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:
[0395] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azabenzothiorolyl or a group represented by formula 91, each of which is unsubstituted or substituted by 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, triphenylenyl, pyrenyl, substituted with 1,2-diphenyl-2-yl, ...
[0396] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0397] Q 1 To Q 3 can be independently unsubstituted or substituted with deuterium, C 1 -C 10 phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl substituted with alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, or any combination thereof,
[0398] In formula CY51-16 and formula CY51-17, i) Y 63 Can be O or S, and Y 64 It can be Si(R 64a )(R 64b ), or ii) Y 63 It can be Si(R 63a )(R 63b ), and Y 64 can be O or S, and
[0399] In formula CY52-16 and formula CY52-17, i) Y 67 Can be O or S, and Y 68 It can be Si(R 68a )(R 68b ), or ii) Y 67 It can be Si(R 67a )(R 67b ), and Y 68 Can be O or S.
[0400] Formula 3
[0401]
[0402] In Formula 3, ring CY 71 and CY 72 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridyl group.
[0403] In formula 3, X 71 It can be: a single bond; or a linking group including O, S, N, B, C, Si or any combination thereof.
[0404] In Formula 3, * indicates a bonding site with any atom included in the remaining part other than the group represented by Formula 3 in the third compound.
[0405] Formula 3-1
[0406]
[0407] Formula 3-2
[0408]
[0409] Formula 3-3
[0410]
[0411] Formula 3-4
[0412]
[0413] Formula 3-5
[0414]
[0415] In Formula 3-1 to Formula 3-5, ring CY 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridyl group.
[0416] In Formula 3-1 to Formula 3-5, X 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a )(R 82b ).
[0417] In Formula 3-1 to Formula 3-5, 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 ).
[0418] In Formula 3-1 to Formula 3-5, X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ).
[0419] In Formula 3-1 to Formula 3-5, X 85 It can be C or Si.
[0420] In Formula 3-1 to Formula 3-5, L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted π-electron-rich C 3 -C 60 Cyclic group, either unsubstituted or substituted with at least one R 10a Substituted pyridinyl.
[0421] Q 4 and Q 5 You can each share your experience with Q 1 Same as described.
[0422] In Formulae 3-1 to 3-5, b81 to b85 may each independently be an integer of 1 to 5.
[0423] In Formula 3-1 to Formula 3-5, R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b Each may be the same as described herein.
[0424] In Formula 3-1 to Formula 3-5, a71 to a74 respectively indicate R 71 The number of R74 and may each independently be an integer from 0 to 20. When a71 is 2 or greater, two or more R 71 can be the same as or different from each other. When a72 is 2 or greater, two or more R 72 can be the same as or different from each other. When a73 is 2 or greater, two or more R 73 may be the same as or different from each other, and when a74 is 2 or greater, two or more R 74 In some embodiments, a71 to a74 may be an integer from 0 to 8 independently of one another.
[0425] R 10a May be the same as described herein.
[0426] In Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0427] a single key; or
[0428] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*';or
[0429] Phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, yl, cyclopentadienyl, furanyl, thienyl, thiolsyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothiolsyl, dibenzothiolsyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiolsyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isocyanate ... quinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl or benzothiadiazolyl, each of which is unsubstituted or substituted with 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, -O(Q 31 )、-S(Q31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, and
[0430] 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.
[0431] 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
[0432] 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
[0433] 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),
[0434] 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
[0435] 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):
[0436]
[0437]
[0438]
[0439]
[0440] 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),
[0441] X 81 To X 85 , L 81 ,b81,R 81 and R 85 may each be the same as described herein,
[0442] 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 ),
[0443] 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 ),
[0444] In Formula CY71-1(1) to Formula CY71-1(8) and Formula CY71-4(1) to Formula CY71-4(32), X 86 and X 87 Each may not be a single bond at the same time (for example, they may not all be single bonds at the same time),
[0445] 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 ),
[0446] X89 Can be single bond, O, S, N(R 89 )、B(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0447] In Formulas CY71-2(1) to CY71-2(8), Formulas CY71-3(1) to CY71-3(32), and Formulas CY71-5(1) to CY71-5(8), X 88 and X 89 Each may not be a single bond at the same time (for example, they may not all be single bonds at the same time), and
[0448] R 86 To R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b can be respectively related to R 81 Same as described.
[0449] Formula 502
[0450]
[0451] Formula 503
[0452]
[0453] In Formula 502 and Formula 503, ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0454] In equations 502 and 503, Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ).
[0455] In equations 502 and 503, Y 506 Can be O, S, N (R 506)、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ).
[0456] In equations 502 and 503, Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ).
[0457] In equations 502 and 503, Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ).
[0458] In equations 502 and 503, Y 51 and Y 52 Each may independently be B, P(═O) or S(═O).
[0459] In equations 502 and 503, R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b Each may be the same as described herein.
[0460] In equations 502 and 503, a501 to a504 respectively indicate R 501 The number of R 504 and may be independently an integer from 0 to 20. When a501 is 2 or more, two or more R 501 can be the same as or different from each other. When a502 is 2 or greater, two or more R 502 can 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 504In some embodiments, a501 to a504 may be an integer from 0 to 8 independently of one another.
[0461] 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 , R 507a , R 507b , R 508a and R 508b can be each 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 60Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each may be the same as described herein.
[0462] In one or more embodiments, i) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b , and ii) R 10a , can be independently:
[0463] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0464] C 1 -C20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof;
[0465] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl , benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azabenzothiorolyl or a group represented by formula 91, each of which is unsubstituted or substituted by 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, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0466] -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
[0467] Among them, Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0468] -CH 3 、-CD 3、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0469] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each of which is unsubstituted or substituted with deuterium, C 1 -C 10 The alkyl group may be substituted with phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0470] In one or more embodiments, i) R in Formula 1 1 To R 4 And Z in Formula 2-1 and Formula 2-2 1 To Z 7 ii) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502 and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R508a and R 508b , and iii) R 10a , can be independently:
[0471] Hydrogen, deuterium, -F, cyano, nitro, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H or -CFH 2 ;
[0472] A group represented by one selected from Formula 9-1 to Formula 9-19; or
[0473] 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 Q 1 To Q 3 may each be the same as described herein):
[0474]
[0475]
[0476]
[0477]
[0478]
[0479]
[0480] 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.
[0481] Examples of Compounds
[0482] In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from Compound A-1 to Compound A-21, Compound A-1-D to Compound A-21-D, Compound B-1 to Compound B-21, Compound B-1-D to Compound B-21-D, Compound C-1 to Compound C-21, Compound C-1-D to Compound C-21-D, Compound D-1 to Compound D-21, and Compound D-1-D to Compound D-21-D:
[0483]
[0484]
[0485]
[0486]
[0487]
[0488]
[0489]
[0490]
[0491]
[0492]
[0493]
[0494]
[0495] For example, in one or more embodiments, the second compound may be at least one selected from compounds ETH1 to ETH100:
[0496]
[0497]
[0498]
[0499]
[0500]
[0501] For example, in one or more embodiments, the third compound may be at least one selected from compound HTH1 to compound HTH40:
[0502]
[0503]
[0504] For example, in one or more embodiments, the fourth compound may be at least one selected from compound DFD1 to compound DFD29:
[0505]
[0506]
[0507] In the above compounds, Ph represents phenyl, D 5 indicates that it is replaced by five deuteriums, and D 4 means replaced by four deuterium. The group represented by The groups represented are the same.
[0508] Figure 1 Description
[0509] Figure 1 1 is a schematic cross-sectional view of a structure of a light emitting device 10 according to one or more embodiments of the present disclosure. The light emitting device 10 may include a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .
[0510] 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.
[0511] First electrode 110
[0512] exist Figure 1 In one or more embodiments, a substrate may be additionally provided and arranged below the first electrode 110 and / or on the second electrode 150. In one or more embodiments, as the substrate, a glass substrate or a plastic substrate may be utilized. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0513] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0514] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0515] 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 three-layer structure of ITO / Ag / ITO.
[0516] Middle layer 130
[0517] The intermediate layer 130 may be on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0518] In one or more embodiments, the intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0519] In one or more embodiments, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds and / or inorganic materials such as quantum dots, in addition to one or more suitable organic materials.
[0520] In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer between the two or more emission units. When the intermediate layer 130 includes two or more emission units and the charge generation layer, the light emitting device 10 may be a tandem light emitting device.
[0521] Hole transport region in the intermediate layer 130
[0522] 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 multi-layer structure including a plurality of layers including materials different from each other.
[0523] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0524] For example, in one or more embodiments, the hole transport region may have a multi-layer structure, which includes 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 sequentially from the first electrode 110 in the order stated respectively.
[0525] In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0526] Formula 201
[0527]
[0528] Formula 202
[0529]
[0530] Among them, in equation 201 and equation 202,
[0531] L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0532] 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 C2-C20 alkenylene, unsubstituted or replaced by at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0533] xa1 to xa4 can each independently be an integer from 0 to 5,
[0534] xa5 can be an integer from 1 to 10,
[0535] R 201 To R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0536] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene, either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (eg, carbazole groups, etc.) (eg, see compound HT16),
[0537] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 Alkylene, either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups, and
[0538] na1 can be an integer from 1 to 4.
[0539] 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:
[0540]
[0541] Among them, in the formula CY 201To CY 217 In, R 10b and R 10c can be respectively related to R 10a 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.
[0542] 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.
[0543] 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.
[0544] In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulas CY201 to CY203 and at least one selected from the groups represented by Formulas CY204 to CY217.
[0545] In one or more embodiments, in formula 201, xa1 may be 1, R 201 can be one selected from the groups represented by the formula CY201 to the formula CY203, xa2 can be 0, and R 202 It may be one selected from the groups represented by the formulae CY204 to CY207.
[0546] 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.
[0547] In one or more embodiments, each of Formulae 201 and 202 may not include (eg, may exclude) any group represented by Formulae CY201 to CY203, and may include at least one selected from among the groups represented by Formulae CY204 to CY217.
[0548] 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 CY217.
[0549] For example, in one or more embodiments, the hole transport region may include: at least one selected from compounds HT1 to 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(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB(NPD)); β-NPB; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diphenylamine; amine (TPD); spiro-TPD; spiro-NPB; methylated NPB; 4,4'-cyclohexylenebis[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 any combination thereof:
[0550]
[0551]
[0552]
[0553]
[0554]
[0555] The thickness of the hole transport region can be approximately To about In the range of, for example, about To about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about To about In the range of, for example, about To about and the thickness of the hole transport layer can be in the range of about To about In the range of, 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.
[0556] The light-emitting auxiliary layer can improve the light-emitting efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0557] p-dopant
[0558] In one or more embodiments, in addition to the aforementioned materials, the hole transport region may further include a charge generating material for improving the conductive properties. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer including (e.g., consisting of) the charge generating material).
[0559] The charge generating material may be, for example, a p-dopant.
[0560] For example, in some embodiments, the p-dopant can have a LUMO level less than or equal to -3.5 eV.
[0561] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0562] Non-limiting examples of quinone derivatives may include tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), etc.:
[0563]
[0564] 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, etc.:
[0565]
[0566] Formula 221
[0567]
[0568] Among them, in formula 221,
[0569] R 221 To R 223may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and
[0570] Selected from R 221 To R 223 At least one of them can be independently: C 3 -C 60 Carbocyclic or C 1 -C 60 heterocyclic group, each of which is substituted by the following groups: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0571] In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0572] Non-limiting examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc. (e.g., tantalum (tm), ytterbium (Yb), lutetium (Lu), thulium (Tm), ytterbium (Yb), lutetium (Lu), 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), lutetium (Lu), etc.); and the like.
[0573] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te), among others.
[0574] Non-limiting examples of non-metals may include oxygen (O) and / or halogens (eg, F, Cl, Br, I, etc.), and the like.
[0575] For example, in one or more embodiments, the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
[0576] Non-limiting examples of metal oxides may include tungsten oxide (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and / or rhenium oxide (e.g., ReO 3 etc.
[0577] 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, and the like.
[0578] 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.
[0579] 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 , CaBr2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 wait.
[0580] Non-limiting examples of transition metal halides may include titanium halides (e.g., TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2, TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), iron halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.
[0581] Non-limiting examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 etc.
[0582] 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.
[0583] Non-limiting examples of metalloid halides may include antimony halides (e.g., SbCl 5 etc.
[0584] Non-limiting examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.
[0585] Emission layer in the middle layer 130
[0586] When the light-emitting device 10 is a full-color light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers 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).
[0587] In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In one or more embodiments, in addition to the host and the dopant (or emitter), the emission layer may also include an auxiliary dopant that promotes energy transfer to the dopant (or emitter). When the emission layer includes a dopant (or emitter) and an auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
[0588] 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.
[0589] 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.
[0590] 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 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.
[0591] In one or more embodiments, the emission layer may include quantum dots.
[0592] In one or more embodiments, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emission layer.
[0593] The thickness of the emitter layer can be approximately To about within the range of, for example, about To about When the thickness of the emission layer is within these ranges, excellent or suitable light emitting characteristics may be obtained without significantly increasing the driving voltage.
[0594] main body
[0595] In one or more embodiments, the host in the emission layer may include the second compound, the third compound, or any combination thereof described in the present disclosure.
[0596] In one or more embodiments, the host may include a compound represented by Formula 301:
[0597] Formula 301
[0598] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0599] Wherein, in Formula 301,
[0600] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0601] xb11 can be 1, 2 or 3,
[0602] xb1 can be an integer from 0 to 5.
[0603] R 301 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted 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 R10a 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 ),
[0604] xb21 can be an integer from 1 to 5, and
[0605] Q 301 To Q 303 You can each share your experience with Q 1 Same as described.
[0606] 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.
[0607] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0608] Formula 301-1
[0609]
[0610] Formula 301-2
[0611]
[0612] Among them, in Formula 301-1 and Formula 301-2,
[0613] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0614] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0615] xb22 and xb23 can each independently be 0, 1 or 2,
[0616] L 301 , xb1 and R 301 may each be the same as described herein,
[0617] L 302 To L 304 can be independently related to L 301 Same as described,
[0618] xb2 to xb4 may each independently be the same as described with respect to xb1, and
[0619] R 302 To R3 05 and R 311 To R 314 can be compared with the 301 Same as described.
[0620] In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0621] In one or more embodiments, the host may include: at least one selected from Compound H1 to Compound H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-tert-butylanthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-di(carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:
[0622]
[0623]
[0624]
[0625]
[0626]
[0627]
[0628]
[0629] In one or more embodiments, the body may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0630] The host may have one or more suitable modifications. For example, the host may include only one compound, or may include two or more different compounds.
[0631] Phosphorescent dopants
[0632] The emission layer may include the organometallic compound represented by Formula 1 as described in the present disclosure as a phosphorescent dopant.
[0633] In one or more embodiments, when the emission layer includes the organic metal compound represented by Formula 1 and the organic metal compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0634] The phosphorescent dopant may include at least one transition metal as a central metal.
[0635] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0636] The phosphorescent dopant may be electrically neutral.
[0637] For example, in some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0638] Formula 401
[0639] M(L 401 ) xc1 (L 402 ) xc2
[0640] Formula 402
[0641]
[0642] Among them, in equation 401 and equation 402,
[0643] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0644] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 can be the same or different from each other,
[0645] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, and when xc2 is 2 or greater, two or more L 402 can be the same or different from each other,
[0646] X 401 and X 402 can be independently N or C,
[0647] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0648] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C(Q 411 )-*',
[0649] X 403 and X 404 can be each 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 ),
[0650] Q 411 To Q414 You can each share your experience with Q 1 Same as described,
[0651] R 401 and R 402 can be each 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 ),
[0652] Q 401 To Q 403 You can each share your experience with Q 1 Same as described,
[0653] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0654] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0655] For example, in some embodiments, in equation 402, i)X 401 can be nitrogen and X 402 may be carbon, or ii) X 401 and X 402 Each of can be nitrogen.
[0656] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two rings A 401It can be optionally connected via T as a linker 402 connected to each other, and / or two or more L 401 The two rings A 402 It can be optionally connected via T as a linker 403 are connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be respectively with about T 401 Same as described.
[0657] 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, a phosphite group, etc.), or any combination thereof.
[0658] In one or more embodiments, the phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD39 or any combination thereof:
[0659]
[0660]
[0661]
[0662] Fluorescent dopants
[0663] In one or more embodiments, when the emission layer includes the organic metal compound represented by Formula 1 and the organic metal compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0664] In one or more embodiments, when the emission layer includes the organic metal compound represented by Formula 1 and the organic metal compound represented by Formula 1 is used as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0665] The fluorescent dopant and the auxiliary dopant may each independently include an aromatic amine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0666] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
[0667] Formula 501
[0668]
[0669] Wherein, in Formula 501,
[0670] Ar 501 , L 501 To L 503 , R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0671] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0672] xd4 can be 1, 2, 3, 4, 5 or 6.
[0673] For example, in some embodiments, Ar in Formula 501 501 It may be a fused cyclic group in which three or more monocyclic groups are fused together (e.g., anthracenyl, yl, pyrene, etc.).
[0674] For example, in some embodiments, xd4 in equation 501 may be 2.
[0675] For example, in one or more embodiments, the fluorescent dopant and the auxiliary dopant may each include at least one selected from the group consisting of Compound FD1 to Compound FD37, 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi), 4,4'-bis[4-(N,N-diphenylamino)phenylvinyl]biphenyl (DPAVBi), or any combination thereof:
[0676]
[0677]
[0678]
[0679] Delayed fluorescence material
[0680] In one or more embodiments, the emission layer may include a delayed fluorescent material.
[0681] In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0682] The delayed fluorescent material may include, for example, the fourth compound described herein.
[0683] The delayed fluorescent material included in the emission layer may act as a host or a dopant according to the types or kinds of other materials included in the emission layer.
[0684] In one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be about 0 eV or more and about 0.5 eV or less. When the difference between the triplet energy level of the delayed fluorescent material and the singlet energy level of the delayed fluorescent material satisfies the above range, up-conversion from the triplet state of the delayed fluorescent material to the singlet state may effectively occur, and therefore, the luminous efficiency of the light-emitting device 10 may be improved, etc.
[0685] For example, in one or more embodiments, the delayed fluorescent material may include: i) at least one electron donor (eg, π-electron-rich C 3 -C 60 a cyclic group such as a carbazolyl group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π-electron-deficient nitrogen-containing C 1 -C 60 and / or ii) including C wherein two or more cyclic groups are fused together and share boron (B) 8 -C 60 Polycyclic materials.
[0686] Non-limiting examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF14:
[0687]
[0688]
[0689] quantum dots
[0690] In one or more embodiments, the emissive layer may include one or more quantum dots.
[0691] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light at one or more suitable emission wavelengths depending on the size of the crystal.
[0692] The diameter of the quantum dot can be, for example, in the range of about 1 nm to about 10 nm. In the present disclosure, when a point, a plurality of points or a point particle is spherical, "diameter" indicates the particle diameter or the average particle diameter, and when the particle is non-spherical, "diameter" indicates the major axis length or the average major axis length. The diameter of the particle can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, HORIBA's LA-950 laser particle size analyzer can be used. When the size of the particle is measured using a particle size analyzer, the average particle diameter is referred to as D50. D50 refers to the average diameter of the particles whose cumulative volume corresponds to 50% by volume in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% starting from the smallest particle when the total number of particles is 100% in a distribution curve accumulated in the order of the smallest particle size to the largest particle size.
[0693] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0694] The wet chemical process is a method that includes mixing the precursor material of the quantum dot with an organic solvent and then growing the quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal, so that the growth of the quantum dot particles can be controlled or selected by a process that is less expensive and easier than vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0695] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.
[0696] Non-limiting examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, C dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.
[0697] Non-limiting examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. In some embodiments, the III-V semiconductor compounds may also include Group II elements. Non-limiting examples of Group III-V semiconductor compounds further including Group II elements may include InZnP, InGaZnP, InAlZnP, and the like.
[0698] Non-limiting examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 , InTe, etc.; ternary compounds such as InGaS 3 、InGaSe 3 etc.; or any combination thereof.
[0699] Non-limiting examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 etc.; or any combination thereof.
[0700] Non-limiting examples of IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.
[0701] The Group IV elements or compounds may include: single elements, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or any combination thereof.
[0702] Each element included in the multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present in the particle at a substantially uniform concentration or a non-uniform concentration.
[0703] In some embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or a core-shell dual structure. For example, in some embodiments, the material included in the core and the material included in the shell may be different from each other.
[0704] The shell of the quantum dot (e.g., the shell of each quantum dot (e.g., the shell surrounding the core of each quantum dot)) can act as a protective layer to prevent chemical degradation of the core to maintain semiconductor properties, and / or act as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or a multilayer. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.
[0705] Non-limiting examples of the shell of a quantum dot may include: oxides of metals, metalloids, or non-metals, semiconductor compounds; or any combination thereof. Non-limiting examples of oxides of metals, metalloids, or non-metals may include: binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 , NiO, etc.; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 、CoMn 2 O 4 etc.; and any combination thereof. As described above, non-limiting examples of semiconductor compounds may include: II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; or any combination thereof. Non-limiting examples of semiconductor compounds suitable as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0706] The full width at half maximum (FWHM) of the emission spectrum of the quantum dot can be about 45nm or less, such as about 40nm or less, or, for example, about 30nm or less, and within these ranges, the color purity or color reproducibility of the quantum dot can be improved. In some embodiments, because the light emitted by the quantum dot is emitted in all directions, the wide viewing angle can be improved.
[0707] In some embodiments, quantum dots may be in the form of spherical particles, pyramidal particles, multi-arm particles, cubic nanoparticles, nanotube particles, nanowire particles, nanofiber particles, and / or nanoplate particles, among others.
[0708] Because the band gap of quantum dots can be adjusted by controlling the size of quantum dots, light having one or more suitable wavelength bands can be obtained from an emission layer containing quantum dots. Therefore, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths can be realized. In one or more embodiments, the size of the quantum dots can be selected so that the quantum dots can emit red light, green light, and / or blue light. In some embodiments, quantum dots of suitable size can be configured to emit white light through a combination of one or more suitable colors of light.
[0709] Electron transport region in the intermediate layer 130
[0710] 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.
[0711] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0712] 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 and / or a buffer layer / electron transport layer / electron injection layer structure, etc., wherein the constituent layers of each structure are stacked sequentially from the emission layer 130 in the order stated respectively.
[0713] 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.
[0714] For example, in one or more embodiments, the electron transport region may include a compound represented by Formula 601:
[0715] Formula 601
[0716] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0717] Wherein, in Formula 601,
[0718] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0719] xe11 can be 1, 2 or 3,
[0720] xe1 can be 0, 1, 2, 3, 4, or 5,
[0721] 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 ),
[0722] Q 601 To Q 603 You can each share your experience with Q 1 Same as described,
[0723] xe21 can be 1, 2, 3, 4, or 5, and
[0724] 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 -C 60 Heterocyclic group.
[0725] 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.
[0726] In one or more embodiments, Ar in Formula 601 601 It may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0727] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
[0728] Formula 601-1
[0729]
[0730] Among them, in formula 601-1,
[0731] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and selected from X 614 To X 616 At least one of them can be N,
[0732] L 611 To L 613 Can be respectively with about L 601 Same as described,
[0733] xe611 to xe613 may each be the same as described with respect to xe1,
[0734] R 611 To R 613 can be respectively related to R 601 Same as described, and
[0735] 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 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0736] 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.
[0737] In one or more embodiments, the electron transport region may include: at least one selected from the group consisting of Compound ET1 to Compound ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); 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 any combination thereof:
[0738]
[0739]
[0740]
[0741] The thickness of the electron transport region can be approximately To about within the range of, for example, about To about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about To about within the range of, for example, about To about and the thickness of the electron transport layer can be in the range of about To about within the range of, 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.
[0742] In one or more embodiments, in addition to the aforementioned materials, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material.
[0743] The metal-containing material can include alkali metal complex, alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex can be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of the alkaline earth metal complex can be Be ion, Mg ion, Ca ion, Sr ion or Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0744] 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:
[0745]
[0746] 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.
[0747] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including a single material (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 (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 injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0749] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0750] The alkali metal-containing compound, the alkaline earth metal-containing compound and the rare earth metal-containing compound can be one or more oxides, one or more halides (e.g., fluorides, chlorides, bromides and / or iodides) and / or one or more tellurides of the alkali metal, alkaline earth metal and rare earth metal, respectively, or any combination thereof.
[0751] The compounds containing alkali metals may include: alkali metal oxides such as Li 2 O, Cs 2 O, K2O, etc.; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc.; or any combination thereof. The compounds containing alkaline earth metals may include alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying the condition 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying the condition 0 < x < 1), etc. The compounds containing rare earth metals may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 、 or any combination thereof. In one or more embodiments, the compounds containing rare earth metals 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 、Gd2Te 3 、Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 、Er 2 Te 3 、Tm 2 Te3 , Yb 2 Te 3 and / or Lu 2 Te 3 wait.
[0752] The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex may respectively 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, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0753] In one or more embodiments, the electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).
[0754] In one or more embodiments, the electron injection layer may include (e.g., consist 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 any combination thereof. 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.
[0755] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof can be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.
[0756] The thickness of the electron injection layer can be about To about within the range of, 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.
[0757] The second electrode 150
[0758] The second electrode 150 may be disposed on the intermediate layer 130 having the aforementioned structure. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for forming the second electrode 150, metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used.
[0759] The second electrode 150 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, Yb, Ag-Yb, ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0760] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
[0761] Covering
[0762] The first cover layer may be disposed outside the first electrode 110 (e.g., disposed on the first electrode 110), and / or the second cover layer may be disposed outside the second electrode 150 (e.g., disposed on the second electrode 150). In one or more embodiments, the light emitting device 10 may have a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150 are sequentially stacked in the order stated, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the order stated, or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the order stated.
[0763] In some embodiments, light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be emitted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first covering layer. In some embodiments, light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be emitted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second covering layer.
[0764] According to the principle of constructive interference, the first cover layer and the second cover layer can improve the external emission efficiency, thereby improving the light emission efficiency of the light emitting device 10 and thus improving the light emitting efficiency of the light emitting device 10.
[0765] Each of the first cover layer and the second cover layer may include a material having a refractive index of 1.6 or greater (eg, at 589 nm).
[0766] The first cover layer and the second cover layer may each independently be an organic cover layer including an organic material, an inorganic cover layer including an inorganic material, or an organic-inorganic composite cover layer including an organic material and an inorganic material.
[0767] At least one of the first covering layer or the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be optionally substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first covering layer or the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include an amine-containing compound.
[0768] In one or more embodiments, at least one of the first covering layer or the second covering layer may (eg, the first covering layer and the second covering layer may each independently) include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0769] In one or more embodiments, at least one of the first cover layer or the second cover layer may (for example, the first cover layer and the second cover layer may each independently) include at least one selected from compounds HT28 to HT33, at least one selected from compounds CP1 to CP6, β-NPB, or any combination thereof:
[0770]
[0771]
[0772] membrane
[0773] The organometallic compound represented by Formula 1 may be included in one or more suitable films. Therefore, one or more embodiments of the present disclosure provide a film including an organometallic compound represented by Formula 1. The film may be, for example, an optical member (or light control element) (e.g., a color filter, a color conversion member, a cover layer, a light exit efficiency enhancement layer, a selective light absorption layer, a polarization layer, or a layer containing quantum dots, etc.), a light blocking member (e.g., a light reflecting layer and / or a light absorbing layer, etc.), and / or a protective member (e.g., an insulating layer and / or a dielectric layer, etc.).
[0774] Electronic devices
[0775] Light emitting device (e.g. Figure 1The light emitting device 10 in the embodiment may be included in one or more suitable electronic devices. For example, in one or more embodiments, the electronic device including the light emitting device may be a light emitting device and / or an authentication device, etc.
[0776] 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). The description of the light emitting device may be the same as described herein. In some embodiments, the color conversion layer may include quantum dots.
[0777] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the sub-pixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the sub-pixel areas.
[0778] A pixel defining film may be disposed between the sub-pixel regions to define each sub-pixel region.
[0779] The color filter may further include a plurality of color filter regions and a light shielding pattern thereon, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern thereon.
[0780] 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, and the second region may include green quantum dots to emit green light, while the third region may not include (e.g., may exclude any) quantum dots. The detailed description of the quantum dots may be the same as described herein. The first region, the second region, and / or the third region may also each include a scatterer.
[0781] For example, in one or more embodiments, the light emitting device may emit 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. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths 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.
[0782] 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, wherein one selected from the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the light emitting device.
[0783] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.
[0784] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.
[0785] 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 may allow light from the light emitting device to be emitted to the outside, and prevent ambient air and moisture from penetrating into the light emitting device (for example, at the same time). 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.
[0786] Depending on the purpose of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may be further arranged on the sealing portion. Non-limiting examples of the functional layer may include a touch screen layer and / or a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
[0787] The authentication device may be, for example, a biometric authentication device that authenticates an individual by utilizing biometric information of a living body (eg, fingertip, pupil, etc.) In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.
[0788] The electronic device can be applied to one or more of a display, a light source, a lighting equipment, a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic organizer, an electronic dictionary, an electronic game console, a medical instrument (e.g., an electronic thermometer, a blood pressure meter, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram display, an ultrasound diagnostic device, or an endoscope display), a fish finder, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), and / or a projector, etc.
[0789] Electronic equipment
[0790] The light emitting device may be included in one or more suitable electronic equipment.
[0791] For example, an electronic device including a light emitting device can be at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a signal light, a head-up display, a fully or partially transparent display, a flexible display (such as a rollable display, a foldable display, a stretchable display), a laser printer, a phone (such as a mobile phone, a tablet phone), a tablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays stitched together, a theater or stadium screen, a light therapy device, and a billboard.
[0792] The light emitting device may have excellent or appropriate light emitting efficiency and a long lifespan, and thus electronic equipment including the light emitting device may have desired characteristics such as high brightness, high resolution, and low power consumption.
[0793] Figure 2 and Figure 3 Description
[0794] Figure 2 is a schematic cross-sectional view illustrating a structure of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0795] Figure 2 The light emitting device may include a substrate 100, a thin film transistor (TFT), a light emitting device (eg, Figure 1 The light emitting device 10) and the packaging part 300 that seals the light emitting device.
[0796] 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 (eg, disposed on the substrate 100). The buffer layer 210 may prevent or reduce impurities from penetrating the substrate 100 and provide a flat surface on the substrate 100.
[0797] The TFT may be on (eg, disposed on) the buffer layer 210 . The TFT may include an active layer 220 , a gate electrode 240 , a source electrode 260 , and a drain electrode 270 .
[0798] 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.
[0799] The gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on (eg, disposed on) the active layer 220 , and the gate electrode 240 may be on (eg, disposed on) the gate insulating film 230 .
[0800] The interlayer insulating film 250 may be on (eg, disposed on) the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate these electrodes from each other.
[0801] The source electrode 260 and the drain electrode 270 may be on (e.g., disposed on) the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0802] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device may be disposed on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0803] The first electrode 110 may be on (eg, disposed on) the passivation layer 280 . The passivation layer 280 may be disposed to expose a portion of the drain electrode 270 without completely covering the drain electrode 270 , and the first electrode 110 may be disposed to be connected to the exposed portion of the drain electrode 270 .
[0804] The pixel defining layer 290 including an insulating material may be on the first electrode 110 (e.g., arranged on the first electrode 110). The pixel defining layer 290 may expose a specific region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic organic film. In some embodiments, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290, thereby being arranged in the form of a common layer.
[0805] The second electrode 150 may be on (eg, disposed on) the intermediate layer 130, and a second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0806] The encapsulation part 300 may be on the second cover layer 170 (eg, disposed on the second cover layer 170). The encapsulation part 300 may be disposed on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic films and organic films.
[0807] Figure 3 is a schematic cross-sectional view of a structure of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0808] In addition to the light shielding pattern 500 and the functional region 400 being additionally arranged on the encapsulation portion 300, Figure 3 Light emitting devices and Figure 2 The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, the functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. Figure 3 The light emitting devices in the light emitting apparatus may be series light emitting devices.
[0809] Figure 4 Description
[0810] Figure 41 is a schematic perspective view of an electronic device 1 including a light emitting device according to one or more embodiments. As a device for displaying moving images or still images, the electronic device 1 may be a portable electronic device such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigation or ultra-mobile PC (UMPC), and one or more suitable products such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device. The electronic device 1 may be such a product or a part thereof. In some embodiments, the electronic device 1 may be a wearable device such as a smart watch, a watch phone, a display of a glasses type or kind, or a head-mounted display (HMD), or a part of a wearable device. However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the electronic equipment 1 may include a dashboard of a vehicle, a central information display on a central control panel or dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, an entertainment display arranged for a rear seat of a vehicle or arranged behind a front seat thereof, a head-up display (HUD) mounted at the front of the vehicle or projected on a front windshield, and / or a computer-generated hologram augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 An embodiment is shown in which the electronic equipment 1 is a smartphone.
[0811] 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 an array of a plurality of pixels two-dimensionally arranged in the display area DA.
[0812] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. On the non-display area NDA, a driver for providing an electrical signal or power to a display device arranged on the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic component or a printed circuit board may be electrically connected, may be arranged.
[0813] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. In one or more embodiments, Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be substantially the same as the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0814] Figure 5 and FIG. 6A to FIG. 6C Description
[0815] Figure 5is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to one or more embodiments. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.
[0816] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable devices for moving a transported object such as a person, object, or animal from a departure 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 sky using the action of air.
[0817] In one or more embodiments, the vehicle 1000 can travel on a road or track. The vehicle 1000 can move in a set or predetermined direction according to the rotation of at least one of its wheels. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, or a train running on a track.
[0818] The vehicle 1000 may include a body having an interior and an exterior and a chassis in which mechanical equipment required for driving is installed as other components in addition to the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or a column provided at a boundary between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, and / or front and rear wheels, left and right wheels, etc.
[0819] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster 1400 , a central instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0820] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0821] The side window glass 1100 may be mounted on a 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 the plurality of side window glasses 1100 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 cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0822] 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-direction). For example, in some embodiments, 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 may extend in the x-axis direction or the -x-axis direction.
[0823] The front window glass 1200 may be mounted on the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0824] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In one or more embodiments, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be disposed outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be disposed outside the second side window glass 1120.
[0825] Cluster 1400 may be arranged in front of the steering wheel. Cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge turn indicator, a high beam indicator, warning lights, a seat belt warning light, an odometer, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0826] The center instrument panel 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and / or a heater of a seat are disposed. The center instrument panel 1500 may be disposed at one side of the cluster 1400 .
[0827] The passenger seat instrument panel 1600 may be spaced apart from the cluster 1400, with the center console instrument panel 1500 disposed therebetween. In some embodiments, the cluster 1400 may be disposed to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be disposed to correspond to the passenger seat. In some embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0828] 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 the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the central control instrument panel 1500, or the passenger seat instrument panel 1600.
[0829] 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. In the following, 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 suitable types (kinds) of the aforementioned display devices may be used in the embodiments.
[0830] Reference Fig. 6A In one or more embodiments, the display device 2 may be arranged on the central control instrument panel 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.
[0831] refer to Figure 6B In one or more embodiments, the display device 2 may be arranged on the cluster 1400. When the display device 2 is arranged on the cluster 1400, the cluster 1400 may display driving information and the like through the display device 2. For example, the cluster 1400 may be implemented digitally. The digital cluster 1400 may display vehicle information and driving information as images. For example, the needle and instrument of the tachometer and one or more suitable warning light icons may be displayed through digital signals.
[0832] refer to Figure 6C In 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 cluster 1400 and / or the information displayed on the central control instrument panel 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster 1400 and / or the information displayed on the central control instrument panel 1500.
[0833] Manufacturing method
[0834] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can each be formed in a specific region by utilizing one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and / or laser induced thermal imaging.
[0835] 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. ... -8 Up to about 10 -3 Torr range and under vacuum at about To about The deposition is performed at a deposition rate within a range of .
[0836] Definition of terms
[0837] As used herein, the term "C 3 -C 60 "Carbocyclyl" refers to a cyclic group that includes (e.g., consists of) only 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 having a hetero atom as a ring-forming atom in addition to carbon. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups may each be: a monocyclic group including one (eg, only one) ring (eg, consisting of one (eg, only 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.
[0838] As used herein, the term "cyclic group" may include C 3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups (for example, both C 3 -C 60 Carbocyclic and C 1 -C 60 heterocyclic group).
[0839] As used herein, the term "π-electron-rich C 3 -C 60The 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.
[0840] For example,
[0841] C 3 -C 60 The carbocyclic group may be i) a group T1 or ii) a fused cyclic group in which two or more groups T1 are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthrenyl or indenoanthryl),
[0842] C 1 -C 60 The heterocyclic group may be i) a group T2, ii) a fused cyclic group in which two or more groups T2 are fused to each other, or iii) a fused cyclic group in which at least one group T2 and at least one group T1 are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthosilolyl, benzofuranodibenzofuranyl, benzo benzothiophene, benzofuranodibenzothiophene, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl , benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0843] Pi-electron-rich C 3 -C 60 The cyclic group may be i) a group T1, ii) a fused cyclic group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused cyclic group in which two or more groups T3 are fused to each other, or v) a fused cyclic group in which at least one group T3 and at least one group T1 are fused to each other (e.g., C 3 -C 60 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.),
[0844] π-electron-deficient nitrogen-containing C 1 -C 60 The heterocyclic group may be i) a group T4, ii) a fused cyclic group in which two or more groups T4 are fused to each other, iii) a fused cyclic group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused cyclic group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused cyclic 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, oxazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, 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, azadibenzofuranyl, etc.),
[0845] 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) radical, norbornenyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,
[0846] 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,
[0847] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiole or borocyclopentadienyl, and
[0848] 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.
[0849] 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 to any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula in which the corresponding term is used. For example, "phenyl" may be benzo, phenyl and / or phenylene, etc., which may be easily understood by a person of ordinary skill in the art based on the structure of the formula including "phenyl".
[0850] Depending on the context, in the present disclosure, a divalent group may refer to or be a multivalent group (eg, trivalent, tetravalent, etc., not just divalent), according to, for example, the structure of a formula associated with a term.
[0851] One Price C3 -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 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0852] 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 a group having a C 1 -C 60 Alkyl groups are divalent groups of substantially the same structure.
[0853] As used herein, the term "C 2 -C60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof may include vinyl, propenyl and / or butenyl, etc. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of substantially the same structure.
[0854] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof may include ethynyl and / or propynyl, etc. 2 -C 60 "Alkynylidene" refers to a 2 -C 60 Alkynyl is a divalent group of substantially the same structure.
[0855] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 A univalent group represented by 101 It is C 1 -C 60 alkyl), and non-limiting examples thereof may include methoxy, ethoxy and / or isopropoxy, and the like.
[0856] As used herein, the term "C 3 -C 10 The term "cycloalkyl" as used herein refers to a monovalent saturated hydrocarbon cyclic 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 cyclic 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 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of substantially the same structure.
[0857] As used herein, the term "C 1 -C 10"Heterocycloalkyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms and 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. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a 1 -C 10 Heterocycloalkyl is a divalent group of substantially the same structure.
[0858] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of substantially the same structure.
[0859] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms and has at least one double bond 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 a 1 -C 10 Heterocycloalkenyl is a divalent group of substantially the same structure.
[0860] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, corynyl and / or ovaphenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, these rings may be fused to each other.
[0861] 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 includes at least one heteroatom as a ring 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 and containing at least one heteroatom as a ring 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 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, these rings may be fused to each other.
[0862] 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 generally no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. The term "divalent non-aromatic fused polycyclic group" as used in this article refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group described above.
[0863] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings fused to each other which includes at least one heteroatom as a ring-constituting atom in addition to carbon atoms and has no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic radical are pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazoles, The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0864] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 It is C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 It is C 6 -C 60 aryl).
[0865] As used herein, the term "C 7 -C 60 "Arylalkyl" refers to -A 104 A 105 (A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59aryl), 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).
[0866] As used herein, the term " 10a " can be:
[0867] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0868] C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0869] C 3 -C 60 Carbocyclic group, C 1 -C 60Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0870] -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 ).
[0871] 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; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof; C 7 -C 60 Aralkyl; or C 2 -C 60 Heteroaralkyl.
[0872] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Non-limiting examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0873] The term "third row transition metal" as used herein includes Hf, Ta, W, Re, Os, Ir, Pt and / or Au, among others.
[0874] 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 tert-butyl, and "OMe" as used herein refers to methoxy.
[0875] 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 substituted phenyl group having an aryl group as a substituent.
[0876] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In some embodiments, the "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl substituted C 6 -C 60 A substituted phenyl group having an aryl group as a substituent.
[0877] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0878] In the present disclosure, the x-axis direction, the y-axis direction, and the z-axis direction are not limited to the three axes in the orthogonal coordinate system, and can be interpreted in a broad sense including these axes. For example, the x-axis direction, the y-axis direction, and the z-axis direction can refer to those axes that are orthogonal to each other, or can refer to those axes in different directions that are not orthogonal to each other.
[0879] Hereinafter, compounds according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A in the same molar equivalent.
[0880] Example
[0881] Synthesis Example 1: Synthesis of Compound A-1
[0882]
[0883] (1) Synthesis of intermediate IM-1-1
[0884] 2,4-Dibromo-[1,2]azaborin[1,2-a][1,2]azaborin-3-amine (1 equivalent), Pd(PPh 3 ) 4 (0.02 equivalent), K 2 CO 3 (3 equivalents) and phenylboronic acid (2 equivalents) were suspended in a mixed solution containing toluene and distilled water (volume ratio of 3:1, 0.125 M), and the resulting solution was heated and stirred at 100° C. under nitrogen for 6 hours. After cooling to room temperature, distilled water was added thereto, and an extraction process with ethyl acetate was performed to extract an organic layer, and the extracted organic layer was washed with a saturated NaCl aqueous solution and MgSO 4 The obtained product was subjected to column chromatography (100% (volume ratio) hexane to 1% (volume ratio) dichloromethane (MC) / hexane as eluent) to obtain Intermediate IM-1-1 (yield: 75%).
[0885] (2) Synthesis of intermediate IM-2-1
[0886] Intermediate IM-1-1 (1 equivalent), 1-iodo-2-nitrobenzene (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (0.02 equivalent), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos) (0.04 equivalent) and NaOtBu (1.6 equivalent) were suspended in a toluene solvent, and the resulting solution was heated at 120° C. for 12 hours in a nitrogen atmosphere. After cooling to room temperature, distilled water was added thereto, and an extraction process using ethyl acetate was performed to extract an organic layer, and the extracted organic layer was washed with a saturated NaCl aqueous solution and MgSO 4 The obtained product was subjected to column chromatography (5% (volume ratio) ethyl acetate (EA) / hexane as an eluent) to obtain Intermediate IM-2-1 (yield: 78%).
[0887] (3) Synthesis of intermediate IM-3-1
[0888] The intermediate IM-2-1 (1 equivalent) was dissolved in ethanol (0.1 M) and added dropwise to 37% HCl (1% by volume). After Sn (1 equivalent) was added to the reaction mixture and the temperature was raised, the resulting reaction mixture was stirred at 80°C for 10 hours. After the reaction was completed, the reaction product was cooled to room temperature and neutralized with 1N NaOH aqueous solution. It was subjected to an extraction process using MC and distilled water, and then MgSO 4 The dried compound was used in the next reaction without further purification.
[0889] (4) Synthesis of intermediate IM-4-1
[0890] Intermediate IM-4-1 was synthesized in essentially the same manner as intermediate IM-2-1, except that intermediate IM-3-1 was used instead of intermediate IM-1-1 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was used instead of 1-iodo-2-nitrobenzene (yield: 71%).
[0891] (5) Synthesis of intermediate IM-5-1
[0892] Intermediate IM-4-1 (1 equivalent) was dissolved in triethyl orthoformate (50 equivalents) and added dropwise to 12N HCl (1.2 equivalents). The temperature was raised to 80°C and the reaction mixture was stirred for 12 hours. After the reaction was complete, the solvent was removed under reduced pressure and the reaction product was subjected to an extraction process using ethyl acetate and distilled water. The reaction mixture was concentrated to 4% MgSO 4After drying, the obtained solid was purified by column chromatography (5% (volume ratio) MeOH / MC as eluent) to obtain Intermediate IM-5-1 (yield: 82%).
[0893] (6) Synthesis of intermediate IM-6-1
[0894] Intermediate IM-5-1 (1 equivalent) and NH 4 PF 6 (3 equivalents) was dissolved in methanol (0.2M), and the mixed solution was stirred at room temperature for 24 hours. After the reaction was completed, the solid was filtered and washed several times with ether. After drying at room temperature, intermediate IM-6-1 was obtained (yield: 80%).
[0895] (7) Synthesis of Compound A-1
[0896] Intermediate IM-6-1 (1 equivalent), (1,5-cyclooctadiene) platinum (II) dichloride (Pt(COD)Cl 2 ) (1.2 eq.) and NaOAc (3 eq.) were mixed with 1,4-dioxane (0.05 M). The reaction mixture was stirred at 110° C. for 72 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the reaction product was subjected to an extraction process using ethyl acetate and NaCl solution. 4 After drying, the obtained solid was purified by column chromatography (5% (volume ratio) MeOH / MC as an eluent) to obtain Compound A-1 (yield: 78%).
[0897] Synthesis Example 2: Synthesis of Compound B-1
[0898]
[0899] (1) Synthesis of intermediate IM-1-2
[0900] Intermediate IM-1-2 was obtained in substantially the same manner as the synthesis of intermediate IM-1-1, except that 1,3-dibromo-[1,2]azaborin-2-amine was used instead of 2,4-dibromo-[1,2]azaborin-3-amine (yield: 77%).
[0901] (2) Synthesis of intermediate IM-2-2
[0902] Intermediate IM-2-2 was obtained in substantially the same manner as in the synthesis of Intermediate IM-2-1, except that Intermediate IM-1-2 was used instead of Intermediate IM-1-1 (yield: 81%).
[0903] (3) Synthesis of intermediate IM-3-2
[0904] Intermediate IM-3-2 was obtained in substantially the same manner as in the synthesis of Intermediate IM-3-1, except that Intermediate IM-2-2 was used instead of Intermediate IM-2-1.
[0905] (4) Synthesis of intermediate IM-4-2
[0906] Intermediate IM-4-2 was obtained in substantially the same manner as in the synthesis of Intermediate IM-4-1, except that Intermediate IM-3-2 was used instead of Intermediate IM-3-1 (yield: 72%).
[0907] (5) Synthesis of intermediate IM-5-2
[0908] Intermediate IM-5-2 was obtained in substantially the same manner as in the synthesis of Intermediate IM-5-1, except that Intermediate IM-4-2 was used instead of Intermediate IM-4-1 (yield: 74%).
[0909] (6) Synthesis of intermediate IM-6-2
[0910] Intermediate IM-6-2 was obtained in substantially the same manner as in the synthesis of Intermediate IM-6-1, except that Intermediate IM-5-2 was used instead of Intermediate IM-5-1 (yield: 79%).
[0911] (7) Synthesis of Compound B-1
[0912] Compound B-1 was obtained in substantially the same manner as in the synthesis of Compound A-1, except that Intermediate IM-6-2 was used instead of Intermediate IM-6-1 (yield: 70%).
[0913] Synthesis Example 3: Synthesis of Compound C-1
[0914]
[0915] (1) Synthesis of intermediate IM-1-3
[0916] Intermediate IM-1-3 was obtained in substantially the same manner as the synthesis of intermediate IM-1-1, except that 3,7-dibromo-[1,2]azaborin-4-amine was used instead of 2,4-dibromo-[1,2]azaborin-3-amine (yield: 70%).
[0917] (2) Synthesis of intermediate IM-2-3
[0918] Intermediate IM-2-3 was obtained in substantially the same manner as in the synthesis of Intermediate IM-2-1, except that Intermediate IM-1-3 was used instead of Intermediate IM-1-1 (yield: 68%).
[0919] (3) Synthesis of intermediate IM-3-3
[0920] Intermediate IM-3-3 was obtained in substantially the same manner as in the synthesis of Intermediate IM-3-1, except that Intermediate IM-2-3 was used instead of Intermediate IM-2-1.
[0921] (4) Synthesis of intermediate IM-4-3
[0922] Intermediate IM-4-3 was obtained in substantially the same manner as in the synthesis of Intermediate IM-4-1, except that Intermediate IM-3-3 was used instead of Intermediate IM-3-1 (yield: 62%).
[0923] (5) Synthesis of intermediate IM-5-3
[0924] Intermediate IM-5-3 was obtained in substantially the same manner as in the synthesis of Intermediate IM-5-1, except that Intermediate IM-4-3 was used instead of Intermediate IM-4-1 (yield: 76%).
[0925] (6) Synthesis of intermediate IM-6-3
[0926] Intermediate IM-6-3 was obtained in substantially the same manner as in the synthesis of Intermediate IM-6-1, except that Intermediate IM-5-3 was used instead of Intermediate IM-5-1 (yield: 78%).
[0927] (7) Synthesis of Compound C-1
[0928] Compound C-1 was obtained in substantially the same manner as in the synthesis of Compound A-1, except that Intermediate IM-6-3 was used instead of Intermediate IM-6-1 (yield: 80%).
[0929] Synthesis Example 4: Synthesis of Compound D-1
[0930]
[0931] (1) Synthesis of intermediate IM-1-4
[0932] Intermediate IM-1-4 was obtained in substantially the same manner as the synthesis of intermediate IM-1-1, except that 2,8-dibromo-[1,2]azaborin-1-amine was used instead of 2,4-dibromo-[1,2]azaborin-3-amine (yield: 81%).
[0933] (2) Synthesis of intermediate IM-2-4
[0934] Intermediate IM-2-4 was obtained in substantially the same manner as in the synthesis of Intermediate IM-2-1, except that Intermediate IM-1-4 was used instead of Intermediate IM-1-1 (yield: 85%).
[0935] (3) Synthesis of intermediate IM-3-4
[0936] Intermediate IM-3-4 was obtained in substantially the same manner as in the synthesis of Intermediate IM-3-1, except that Intermediate IM-2-4 was used instead of Intermediate IM-2-1.
[0937] (4) Synthesis of intermediate IM-4-4
[0938] Intermediate IM-4-4 was obtained in substantially the same manner as in the synthesis of Intermediate IM-4-1, except that Intermediate IM-3-4 was used instead of Intermediate IM-3-1 (yield: 79%).
[0939] (5) Synthesis of intermediate IM-5-4
[0940] Intermediate IM-5-4 was obtained in substantially the same manner as in the synthesis of Intermediate IM-5-1, except that Intermediate IM-4-4 was used instead of Intermediate IM-4-1 (yield: 83%).
[0941] (6) Synthesis of intermediate IM-6-4
[0942] Intermediate IM-6-4 was obtained in substantially the same manner as in the synthesis of Intermediate IM-6-1, except that Intermediate IM-5-4 was used instead of Intermediate IM-5-1 (yield: 80%).
[0943] (7) Synthesis of Compound D-1
[0944] Compound D-1 was obtained in substantially the same manner as in the synthesis of Compound A-1, except that Intermediate IM-6-4 was used instead of Intermediate IM-6-1 (yield: 78%).
[0945] Compounds synthesized according to the synthesis examples 1H nuclear magnetic resonance spectroscopy (NMR) and mass spectroscopy / fast atom bombardment (MS / FAB) are shown in Table 1. By referring to the synthesis routes and source materials, one of ordinary skill in the art can easily recognize methods for synthesizing compounds other than those synthesized in the above synthesis examples.
[0946] Table 1
[0947]
[0948] Evaluation Example 1
[0949] For the above-described compounds A-1, B-1, C-1, and D-1 and the following compound CE2, the HOMO level (eV), LUMO level (eV), T1 level (nm), Huang-Rhys factor (HRF) (cm -1 ), dipole moment (Debye), and triplet metal-ligand charge transfer state ( 3 The results are shown in Table 2.
[0950] Table 2
[0951]
[0952]
[0953] Example 1
[0954] As the anode, Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was mounted on a vacuum deposition device.
[0955] 2-TNATA was vacuum deposited on an ITO glass substrate to form A hole injection layer having a thickness of 1000 Å was formed, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) was vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .
[0956] Compound HTH29 and compound ETH100 as hosts and compound A-1 as a dopant were co-deposited on the hole transport layer at a weight ratio of 60:30:10 (HTH29:ETH100:A-1) to form a The thickness of the emission layer.
[0957] Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was vacuum deposited on the emission layer to form a A hole blocking layer of a thickness of 1000 nm is formed, and then Alq is deposited on the hole blocking layer. 3 To form a An electron transport layer having a thickness of . Alkali metal halide LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form a A LiF / Al cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.
[0958]
[0959] Examples 2 to 4 and Comparative Examples 1 to 3
[0960] Light-emitting devices were each manufactured in substantially the same manner as in Example 1, except that a compound shown in Table 3 was each used as a dopant instead of Compound A-1 in forming an emission layer.
[0961] Evaluation Example 2
[0962] The brightness of the light emitting devices of Examples 1 to 4 and Comparative Examples 1 to 3 at 1,000 cd / m 2 The driving voltage (V), efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and device life (h) at a brightness of 1.5 Å were measured, and the results are shown in Table 3. In Table 3, the life ratio (T95, reference ratio) refers to the time (h) required for the brightness to reach 95% of the initial brightness of each of the light-emitting devices of the above examples and comparative examples, expressed as a percentage (%) relative to the life of the light-emitting device of Comparative Example 1 set to 100.
[0963] Table 3
[0964]
[0965]
[0966] Referring to Table 3, it is confirmed that the light emitting devices according to Examples 1 to 4 each have excellent or appropriate driving voltage, light emitting efficiency, and lifespan characteristics compared to the light emitting devices according to Comparative Examples 1 to 3.
[0967] According to one or more embodiments, a light-emitting device having reduced driving voltage, improved color purity and efficiency, and long lifetime, and a high-quality electronic device including the light-emitting device may be manufactured using the organometallic compound of the present disclosure.
[0968] In the present disclosure, it will be understood that the terms “includes,” “comprising,” or “having” specify 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.
[0969] Throughout this disclosure, when it is mentioned that a component such as a layer, film, region, or plate is "on" another component, it will be understood that it can be directly on the other component, or other components can be interposed between them. In some embodiments, "directly on..." can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and the other component. For example, "directly on..." can mean that two layers or two components are arranged without using additional components such as bonding components between them.
[0970] 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.
[0971] As used herein, the singular forms “a”, “an”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. In addition, when describing embodiments of the present disclosure, the use of “may” refers to “one or more embodiments of the present disclosure”.
[0972] As used herein, the terms "substantially," "approximately," or similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent deviations in measured or calculated values that one of ordinary skill in the art would recognize. Taking into account the measurement in question and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system), "approximately" as used herein includes the stated value and means within an acceptable range of deviations of the particular value determined by one of ordinary skill in the art. For example, "approximately" can mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.
[0973] Any numerical range described in this article is intended to include all sub-ranges of the same numerical precision contained in the described range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the described minimum value 1.0 and the described maximum value 10.0 (and including the endpoint values), 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 2.4 to 7.6. Any maximum numerical limit described in this article is intended to include all numerical lower limits included therein, and any minimum numerical limit described in this specification is intended to include all numerical upper limits included therein. Therefore, the applicant reserves the right to modify this specification (including the claims) to explicitly describe any sub-ranges included in the range explicitly described in this article.
[0974] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for the purpose of limitation. The description of features or aspects within each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. A light emitting device, wherein: The light emitting device comprises: a first electrode; a second electrode, facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and An organometallic compound represented by Formula 1: Formula 1 Among them, in formula 1, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X 11 , X 12 and X2 to X4 are each independently C or N, Ring CY1 to Ring CY4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1 to L3 are each independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', * and *' each indicate a binding site with an adjacent atom, n1 to n3 are each independently an integer from 1 to 5, R1 to R4, R 1a and R 1b 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 C1-C 60 Alkylthio, 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), a1 to a4 are each independently an integer from 1 to 20, Ar1 is a group represented by Formula 2-1 or Formula 2-2, and when a1 is 2 or more, two or more of the R1s in the number a1 are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, When a2 is 2 or more, two or more of the R2 in the number a2 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, When a3 is 2 or more, two or more of the R3 in the number a3 may be optionally bonded to each other to form an unsubstituted or substituted R3. 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, When a4 is 2 or more, two or more of the R4 in number a4 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, R 1a and R 1b are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Selected from R1 to R4, R 1a , R 1b and Ar1 are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, In formula 2-1 and formula 2-2, Y1 and Y2 are each independently B or N, Y1 and Y2 are different from each other, Z1 to Z7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio, 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, -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), *Indicates the same as X in Formula 1 12 The binding site Two or more selected from Z1 to Z7 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, R 10a yes: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ), -C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
2. The light emitting device according to claim 1, wherein: The emission layer includes a host and a dopant, and The dopant includes the organometallic compound.
3. The light emitting device according to claim 1, wherein: The light emitting device further comprises: Contains at least one nitrogen-containing C1-C 60 a second compound comprising a heterocyclic group; a third compound comprising 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 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 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 part 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 each of boron and nitrogen as a ring-constituting atom.
5. The light emitting device according to claim 3, wherein: The transmitting layer comprises: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound or any combination thereof, and Wherein, the emission layer emits blue light.
6. An electronic device, wherein: The electronic device comprises the light emitting device according to any one of claims 1 to 5.
7. The electronic device according to claim 6, wherein: The electronic device further comprises: A thin film transistor, wherein The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode of the thin film transistor.
8. The electronic device according to claim 6, wherein: The electronic device also includes a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
9. An electronic device, wherein: The electronic equipment comprises the light emitting device according to any one of claims 1 to 5.
10. The electronic equipment according to claim 9, wherein: The electronic equipment is at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable 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 or augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater or stadium screen, a light therapy device, and a billboard.
11. An organometallic compound represented by Formula 1, wherein Formula 1 Among them, in formula 1, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X 11 , X 12 and X2 to X4 are each independently C or N, Ring CY1 to Ring CY4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1 to L3 are each independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', * and *' each indicate a binding site with an adjacent atom, n1 to n3 are each independently an integer from 1 to 5, R1 to R4, R 1a and R 1b 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 C1-C 60 Alkylthio, 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), a1 to a4 are each independently an integer from 1 to 20, Ar1 is a group represented by Formula 2-1 or Formula 2-2, When a1 is 2 or more, two or more of the R1 in the number a1 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, When a2 is 2 or more, two or more of the R2 in the number a2 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, When a3 is 2 or more, two or more of the R3 in the number a3 may be optionally bonded to each other to form an unsubstituted or substituted R3. 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, When a4 is 2 or more, two or more of the R4 in number a4 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, R 1a and R 1b are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Selected from R1 to R4, R 1a , R 1b and Ar1 are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, In formula 2-1 and formula 2-2, Y1 and Y2 are each independently B or N, Y1 and Y2 are different from each other, Z1 to Z7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio, 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, -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), *Indicates the same as X in Formula 1 12 The binding site Two or more selected from Z1 to Z7 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, R 10a yes: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
12. The organometallic compound according to claim 11, wherein M is Pt, Pd or Au.
13. The organometallic compound according to claim 11, wherein X 11 , X2 and X3 are each C, and X4 is N, X 11 The bond between X4 and M and the bond between X4 and M are each coordination bonds, and The bond between X2 and M and the bond between X3 and M are each a covalent bond.
14. The organometallic compound according to claim 11, wherein X 12 is N.
15. The organometallic compound according to claim 11, wherein Ring CY1 to Ring CY4 are each independently: Phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, yl, cyclopentadienyl, furanyl, thienyl, thirolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirolyl, dibenzothirolyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl , isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzoxacillinyl, dibenzothiacillinyl, dibenzodihydroazacillinyl, dibenzodihydrodicillinyl, dibenzodihydrocillinyl, dibenzodioxanyl, dibenzooxathiacyclohexadienyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiadienyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl.
16. The organometallic compound according to claim 11, wherein L1 and L3 are each a single bond, and L2 is *-O-*' or *-S-*', and n2 is 1.
17. The organometallic compound according to claim 11, wherein R1 to R4 and Z1 to Z7 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 Alkoxy; C1-C 20 Alkyl or C1-C 20 Alkoxy, each deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl or any combination thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl , triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azabenzothiorol, each of which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or -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), and Q1 to Q3 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or C3-C 60 Carbocyclic or C1-C 60 Heterocyclic groups, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
18. The organometallic compound according to claim 11, wherein At least two selected from Z1 to Z7 are each not hydrogen.
19. The organometallic compound according to claim 11, wherein In formula 1, Depend on The group represented by is a group represented by one of the formulas CY1(1) to CY1(11), Depend on The group represented by is a group represented by one of the formulas CY2(1) to CY2(13), Depend on The group represented by is a group represented by one of the formulas CY3(1) to CY3(25), and Depend on The group represented is a group represented by one of the formulas CY4(1) to CY4(29): And wherein, in Formulas CY1(1) to CY1(11), Formulas CY2(1) to CY2(13), Formulas CY3(1) to CY3(25) and Formulas CY4(1) to CY4(29), Ar1 is the same as defined in Formula 1, T 21 is B(Y 21 ), C(Y 21 )(Y 22 ), N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 is C(Y 21 ), N or Si(Y 21 ), T 31 is B(Y 31 ), C(Y 31 )(Y 32 ), N(Y 31 ), O, S or Si(Y 31 )(Y 32 ), T 32 is C(Y 31 ), N or Si(Y 31 ), R 11 To R 18 Each is the same as defined with respect to R1 in Formula 1, R 21 To R 26 , Y 21 and Y 22 Each is the same as defined with respect to R2 in Formula 1, R 31 To R 36 , Y 31 and Y 32 Each is the same as defined with respect to R3 in Formula 1, R 41 To R 47 Each is the same as defined with respect to R4 in Formula 1, * indicates the binding site with M in Formula 1, *' represents the binding site with L1 in Formula 1, *" indicates the binding site with L2 in Formula 1, and *"' indicates the binding site with L3 in Formula 1.
20. The organometallic compound according to claim 11, wherein The organometallic compound is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 And wherein, in Formula 1-1 and Formula 1-2, M, Y1, Y2 and Z1 to Z7 are each the same as defined in Formula 1, Formula 2-1 and Formula 2-2, L2 is *-O-*' or *-S-*', X 13 C(R 13 ) or N, X 14 C(R 14 ) or N, X 15 C(R 15 ) or N, and X 16 C(R 16 ) or N, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, and X 23 C(R 23 ) or N, 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, 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 13 To R 16 Each is the same as defined with respect to R1 in Formula 1, R 21 To R 23 Each is the same as defined with respect to R2 in Formula 1, R 31 To R 36 Each is the same as defined with respect to R3 in Formula 1, R 41 To R 44 Each is the same as defined with respect to R4 in Formula 1, Selected from R 13 To R 16 Two or more of them are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Selected from R 21 To R 23 Two or more of them are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Selected from R 31 To R 36 Two or more of them are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Selected from R 41 To R 44 Two or more of them are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Selected from R 13 To R 16 , R 21 To R 23 , R 31 To R 36 , R 41 To R 44 and two or more of Z1 to Z7 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Two or more selected from Z1 to Z7 are optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 a heterocyclic group, and R 10a Same as defined in Formula 1.
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