Light-emitting device, electronic device, electronic equipment, and organometallic compound
By using the organometallic compounds represented by Formula 1 in the light emitting device, the structure and energy level relationship of the emission layer is optimized, and the shortcomings of the existing light emitting devices in terms of color purity, luminous efficiency and lifetime are solved, and a high-performance luminous effect is achieved.
Patent Information
- Application Number
- CN202411299414.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-09-19
- Filing Date
- 2024-09-18
- Publication Date
- 2025-03-21
AI Technical Summary
The existing light emitting devices have shortcomings in color purity, luminous efficiency and life, and it is difficult to meet the needs of high-performance electronic devices.
The organometallic compound represented by Formula 1 is used as the main component in the emission layer, and the second compound, the third compound and the fourth compound are combined to improve the performance of the light emitting device by optimizing the molecular structure and energy level relationship.
The color purity improvement, luminous efficiency improvement and life extension of the light emitting device are achieved, and the requirements of high-performance electronic devices are met.
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Figure CN119661598A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0124995 filed in the Korean Intellectual Property Office on September 19, 2023, the entire contents of which are incorporated herein 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 and 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. These excitons 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 and 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] Formula 1
[0014]
[0015] Among them, in formula 1,
[0016] 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),
[0017] X 1 To X 4 can be independently C or N,
[0018] Cyclo 1 CY 2 CY 31 To Ring CY 33 and CY 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0019] L 1 , L 2 , L 31 and L 32 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 -*'、*-Ge(R 1a )(R 1b )-*', unsubstituted or replaced by at least one R 10a Substituted C 5 -C 30 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1 -C 30 heterocyclic group, and * and *' each indicate a binding site to an adjacent atom,
[0020] n1, n2, n31 and n32 may each independently be an integer from 1 to 10,
[0021] R 1 , R 2 , R 31 To R 33 , R 4 , R 1a and R 1b can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 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)(Q1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0022] a1, a2, a31 to a33 and a4 may each independently be an integer from 1 to 20,
[0023] Select from a1 R 1 、a2R 2 、a31R 31 、a32 R 32 、a33 R 33 、a4R 4 , R 1a and R 1b Two or more adjacent groups may be optionally combined with each other (ie, may be combined with each other or may not be combined with 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,
[0024] R 10a Can be:
[0025] hydrogen, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0026] 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, -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;
[0027] C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 Arylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0028] -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 ),
[0029] Among them, 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 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.
[0030] According to one or more embodiments of the present disclosure, an electronic device includes the light emitting device.
[0031] According to one or more embodiments of the present disclosure, an electronic equipment includes the light emitting device.
[0032] According to one or more embodiments of the present disclosure, an organometallic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0033] 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 description 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:
[0034] 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;
[0035] Figure 2is 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;
[0036] 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
[0037] Figure 4 , Figure 5 , Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of the structure of electronic equipment according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0038] Now will be more detailed with reference to embodiment, the example of embodiment is shown in the accompanying drawings, wherein, the same reference numerals refer to the same elements throughout the disclosure, and for the sake of simplicity, its repeated description may not be provided. In this respect, the embodiment of the present disclosure can 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 this description. As used in this article, the term "and / or" or "or" can include any combination 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 selected from a, b, and c", "at least one selected from a to c", etc. 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.
[0039] According to one or more embodiments of the present disclosure, a light emitting device may include:
[0040] a first electrode;
[0041] a second electrode, facing the first electrode;
[0042] an intermediate layer between the first electrode and the second electrode and including an emission layer; and
[0043] An organometallic compound represented by Formula 1:
[0044] Formula 1
[0045]
[0046] Details regarding Formula 1 may be the same as described herein.
[0047] In one or more embodiments,
[0048] The first electrode of the light emitting device may be an anode,
[0049] The second electrode of the light emitting device may be a cathode,
[0050] The intermediate layer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode.
[0051] 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
[0052] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0053] In one or more embodiments, the intermediate layer of the light emitting device may include the organic metal compound represented by Formula 1.
[0054] 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).
[0055] In one or more embodiments, the emission layer of the light emitting device may include a dopant and a host, and the organic metal compound represented by Formula 1 may be included in the dopant. For example, in some embodiments, the organic metal compound may act as a dopant. For example, in some embodiments, the emission layer may be used to emit blue light. The blue light may have a maximum emission wavelength in the range of, for example, about 430 nm to about 480 nm.
[0056] 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.
[0057] In one or more embodiments, the light emitting device may further include a nitrogen-containing C 1 -C 60 a second compound including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
[0058] 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.
[0059] Formula 3
[0060]
[0061] Among them, in formula 3,
[0062] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group, or pyridyl group,
[0063] X 71 It may be a single bond, or a linking group including O, S, N, B, C, Si, or any combination thereof, and
[0064] * indicates a bonding site with any atom included in the remaining part other than the group represented by Formula 3 in the third compound.
[0065] In one or more embodiments, the organometallic compound may include at least one deuterium.
[0066] In one or more embodiments, the second compound, the third compound, and the fourth compound may each include at least one deuterium.
[0067] In one or more embodiments, the second compound may include at least one silicon.
[0068] In one or more embodiments, the third compound may include at least one silicon.
[0069] In one or more embodiments, in addition to the organic metal compound represented by Formula 1, the light emitting device may further 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 any combination thereof.
[0070] According to one or more embodiments, in addition to the organometallic compound, the light-emitting device (e.g., the emission layer of 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. For example, in some embodiments, in addition to the organometallic compound and the second compound, the light-emitting device (e.g., the emission layer of the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof.
[0071] In one or more embodiments, in addition to the organometallic compound, the light emitting device (e.g., the emission layer of 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. For example, in some embodiments, in addition to the organometallic compound and the third compound, the light emitting device (e.g., the emission layer of the light emitting device) may further include a second compound, a fourth compound, or any combination thereof.
[0072] In one or more embodiments, in addition to the organometallic compound, the light-emitting device (e.g., the emission layer of the light-emitting device) may further include a fourth compound. At least one selected from the organometallic compound and the fourth compound may include at least one deuterium. The fourth compound may improve the color purity, luminous efficiency, and life characteristics of the light-emitting device. For example, in some embodiments, in addition to the organometallic compound and the fourth compound, the light-emitting device (e.g., the emission layer of the light-emitting device) may further include a second compound, a third compound, or any combination thereof.
[0073] In one or more embodiments, in addition to the organometallic compound, the light-emitting device (e.g., the emission layer of 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 selected from the organometallic compound, the second compound, and the third compound may include at least one deuterium.
[0074] In one or more embodiments, the emission layer of the light emitting device may include: i) an organic metal compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, and the emission layer may be used to emit blue light.
[0075] In one or more embodiments, the maximum emission wavelength of blue light can be in the range of about 430nm to about 480nm, about 430nm to about 475nm, about 440nm to about 475nm, about 450nm to about 475nm, about 430nm to about 470nm, about 440nm to about 470nm, about 450nm to about 470nm, about 430nm to about 465nm, about 440nm to about 465nm, about 450nm to about 465nm, about 430nm to about 460nm, about 440nm to about 460nm, or about 450nm to about 460nm.
[0076] 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.
[0077] In one or more embodiments, the following compounds may be excluded from the third compound:
[0078]
[0079] 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).
[0080] 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 ring-forming atoms.
[0081] In one or more embodiments, the fourth compound may be a C-containing 8 -C 60 A polycyclic compound includes at least two fused cyclic groups (eg, one is a first ring and the other is a second ring) that share a boron atom (B).
[0082] In one or more embodiments, the fourth compound may include a fused ring, wherein at least one third ring may be fused with at least one fourth ring, for example to form a fused ring including four or more rings,
[0083] The third ring of the fourth compound can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and
[0084] The fourth ring of the fourth compound 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.
[0085] In one or more embodiments, the third compound may not include (eg, may exclude) (eg, any) compound represented by Formula 3-1 described in the present disclosure.
[0086] In one or more embodiments, the second compound may include a compound represented by Formula 2:
[0087] Formula 2
[0088]
[0089] In formula 2,
[0090] L 51 To L 53 may be independently a single bond, 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,
[0091] b51 to b53 may each independently be an integer from 1 to 5,
[0092] 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 them can be N,
[0093] R 51 To R 56 and R 10a Each may be the same as described in the present disclosure.
[0094] 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:
[0095] Formula 3-1
[0096]
[0097] Formula 3-2
[0098]
[0099] Formula 3-3
[0100]
[0101] Formula 3-4
[0102]
[0103] Formula 3-5
[0104]
[0105] Among them, in Formula 3-1 to Formula 3-5,
[0106] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 Cyclic group, or pyridyl group,
[0107] 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 ),
[0108] 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 ),
[0109] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0110] X 85 Can be C or Si,
[0111] 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, or unsubstituted or substituted with at least one R 10a Substituted pyridyl, wherein Q 4 and Q 5 Each can be referred to in the Q 1 To understand the description,
[0112] b81 to b85 may each independently be an integer from 1 to 5,
[0113] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may be the same as described in the present disclosure,
[0114] a71 to a74 may each independently be an integer from 0 to 20, and
[0115] R 10a May be the same as described herein.
[0116] 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:
[0117] Formula 502
[0118]
[0119] Formula 503
[0120]
[0121] Among them, in equation 502 and equation 503,
[0122] Ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0123] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0124] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a)(R 506b ),
[0125] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0126] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0127] Y 51 and Y 52 may be each independently B, P(=O) or S(=O),
[0128] R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b may be each the same as described in the present disclosure, and
[0129] a501 to a504 may each independently be an integer of 0 to 20.
[0130] In one or more embodiments, the light emitting device may satisfy at least one selected from Condition 1 to Condition 4:
[0131] Condition 1
[0132] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound > the LUMO energy level (eV) of the organometallic compound
[0133] Condition 2
[0134] LUMO energy level of the organometallic compound (eV) > LUMO energy level of the second compound (eV)
[0135] Condition 3
[0136] 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.
[0137] Condition 4
[0138] HOMO energy level of the third compound (eV)>HOMO energy level of the second compound (eV)
[0139] Each of the HOMO energy level and the LUMO energy level 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.
[0140] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the organic metal compound and the LUMO energy level of the second compound may be approximately 0.1 eV or higher and approximately 1.0 eV or lower, and / or the absolute value of the difference between the LUMO energy level of the organic metal compound and the LUMO energy level of the third compound may be approximately 0.1 eV or higher and approximately 1.0 eV or lower, and the absolute value of the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the second compound may be approximately 1.25 eV or lower (e.g., approximately 1.25 eV or lower and approximately 0.2 eV or higher), and / or the absolute value of the difference between the HOMO energy level of the organic metal compound and the HOMO energy level of the third compound may be approximately 1.25 eV or lower (e.g., approximately 1.25 eV or lower and approximately 0.2 eV or higher).
[0141] 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.
[0142] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0143] First embodiment
[0144] According to a first embodiment, an organic metal compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may also include a host, the organic metal compound may be different from the host, and the emission layer may be used to emit phosphorescence or fluorescence emitted from the organic metal compound. For example, according to the first embodiment, the organic metal compound may be a dopant or an emitter. In one or more embodiments, the organic metal compound may be a phosphorescent dopant or a phosphorescent emitter.
[0145] The phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
[0146] In one or more embodiments, the emission layer may further include an auxiliary dopant. The auxiliary dopant may improve the light emitting efficiency of the organic metal compound by efficiently transferring energy to the organic metal compound as a dopant or an emitter.
[0147] The auxiliary dopant may be different from the organometallic compound and the host.
[0148] In one or more embodiments, the auxiliary dopant may be a delayed fluorescence emission compound.
[0149] In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0150] Second embodiment
[0151] According to a second embodiment, an organic metal compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may also include a host and a dopant, the organic metal compound, the host and the dopant may be different from each other, and the emission layer may be used to emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
[0152] In one or more embodiments, the organometallic compound in the second embodiment may not be used as a dopant, but as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0153] 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).
[0154] For example, in some embodiments, the phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0155] 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).
[0156] 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.
[0157] The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0158] The host in the first and second embodiments may be any host material (eg, the compound represented by Formula 301, the compound represented by Formula 301-1, the compound represented by Formula 301-2, or any combination thereof).
[0159] 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.
[0160] In one or more embodiments, the light emitting device may further include a covering layer arranged outside the first electrode (eg, on the first electrode) and / or outside the second electrode (eg, on the second electrode).
[0161] 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., located on the first electrode) and a second covering layer located outside the second electrode (e.g., located on the first electrode), and at least one of the first covering layer and the second covering layer may include an organic metal compound represented by Formula 1. The first covering layer and / or the second covering layer may each be the same as described herein.
[0162] In one or more embodiments, the light emitting device may further include:
[0163] a first covering layer disposed outside the first electrode (eg, on the first electrode) and including an organic metal compound represented by Formula 1;
[0164] a second covering layer disposed outside the second electrode (eg, on the second electrode) and including an organic metal compound represented by Formula 1; or
[0165] A first covering layer and a second covering layer.
[0166] The expression "(the intermediate layer and / or the covering layer) includes at least one organic metal compound represented by Formula 1" as used herein may be interpreted to mean "(the intermediate layer and / or the covering layer) may include one organic metal compound represented by Formula 1 or two or more different organic metal compounds each represented by Formula 1".
[0167] In one or more embodiments, the intermediate layer and / or the covering layer may include only compound 1 as an organic metal compound. In this regard, compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the intermediate layer may include compound 1 and compound 2 as organic metal compounds. In this regard, compound 1 and compound 2 may be present in substantially the same layer (e.g., both compound 1 and compound 2 (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).
[0168] The term "intermediate layer" as used herein refers to a single layer and / or a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0169] According to one or more embodiments of the present disclosure, an 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, wherein 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 some embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. For more details of the electronic device, reference may be made to the description provided herein.
[0170] According to one or more embodiments of the present disclosure, electronic equipment may include a light emitting device.
[0171] For example, the electronic device 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, a signal light, a head-up display, a fully or partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a portable phone or a 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.
[0172] According to one or more embodiments of the present disclosure, there is provided an organometallic compound represented by Formula 1. Details regarding Formula 1 may be the same as described herein.
[0173] Those of ordinary skill in the art can readily understand methods of synthesizing organometallic compounds by referring to the synthesis examples and / or examples described herein.
[0174] Description of Formula 1
[0175] Formula 1
[0176]
[0177] M in Formula 1 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).
[0178] In one or more embodiments, M may be platinum (Pt), palladium (Pd), or gold (Au).
[0179] In one or more embodiments, M may be Pt.
[0180] X in Formula 1 1 To X 4 They may each independently be C or N.
[0181] In one or more embodiments, X 1 It can be C.
[0182] In one or more embodiments, X 1 Can be C, and X 1 The bond between M and M may be a coordinate bond.
[0183] In one or more embodiments, X 1 It may be carbon (C) of a carbene moiety.
[0184] In one or more embodiments, X 2 and X 3 can each be C, and X 4 Can be N.
[0185] In one or more embodiments, i) X 1 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 may each be a covalent bond.
[0186] In one or more embodiments, X 1 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.
[0187] In one or more embodiments, X 1 , X 2 and X 3 Can be C, X 4 Can be N, X 1 The bond between M and X 4 The bonds between X and M can each be coordination bonds, and 2 The bond between M and X 3 The bonds with M may each be covalent bonds.
[0188] Ring CY in Formula 1 1 CY 2 CY 31 To Ring CY 33 and CY 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group.
[0189] In one or more embodiments, CY 1 CY 2 CY 31 To Ring CY 33 and CY 4 Can be independently:
[0190] 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.
[0191] In one or more embodiments, CY 1It can be C containing nitrogen 1 -C 60 Heterocyclic group.
[0192] 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.
[0193] In one or more embodiments, X 1 Can be C, and the ring CY 1 It may be an imidazolyl group, a triazolyl group, a benzimidazolyl group, a naphthoimidazolyl group or an imidazopyridyl group.
[0194] In one or more embodiments, X 1 It can be a carbon (C) of a carbene part, and the ring CY 1 It may be an imidazolyl group, a triazolyl group, a benzimidazolyl group, a naphthoimidazolyl group or an imidazopyridyl group.
[0195] 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
[0196] 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.
[0197] In one or more embodiments, CY 31 To Ring CY 33 Each of them independently 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.
[0198] In one or more embodiments, CY 4 It can be C containing nitrogen 1 -C 60 Heterocyclic group.
[0199] In one or more embodiments, CY 4It may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, benzopyrazolyl, benzimidazolyl or benzothiazolyl.
[0200] L in Formula 1 1 , L 2 , L 31 and L 32 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 -*'、*-Ge(R 1a )(R 1b )-*', unsubstituted or replaced by 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, and * and *' each indicate a binding site to an adjacent atom.
[0201] R 10a May be the same as described herein.
[0202] In formula 1, n1, n2, n31 and n32 represent L 1 The number of L 2 The number of L 31 The number and L 32 The number of L1 and L2 may be independently an integer from 1 to 10. 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 2may be the same as or different from each other. When n31 is 2 or greater, two or more L 31 may be the same as or different from each other, and when n32 is 2 or greater, two or more L 32 May be the same as or different from each other.
[0203] R in Formula 1 1a and R 1b can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 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 )(Q2 ).
[0204] R 10a and Q 1 To Q 3 Each may be the same as described herein.
[0205] In one or more embodiments, R 1a and R 1b may be optionally linked to form an 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.
[0206] In one or more embodiments, L 1 and L 31 Each may be a single bond.
[0207] In one or more embodiments, L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0208] In one or more embodiments, L 1 and L 31 Each of them can be a single bond, L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0209] In one or more embodiments, *-(L 32 ) n32 -*' can form a ring having 8 or more ring atoms (for example, *-(L in Formula 1) 32 ) n32 -*'、*-(L 31 ) n31 -*'、Cy 4 CY 32 and two nitrogen atoms can form a ring having 8 or more ring atoms).
[0210] In one or more embodiments, L 32 Can be: 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 )-*';
[0211] Phenylene, naphthylene, fluorenylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, pyrenylene ylene, pyrrolylene, thienylene, furanylene, imidazolylene, pyridylene, pyrazinylene, pyrimidylene, pyridazinylene, indolylene, quinolylene, isoquinolylene, benzoquinolylene, phenanthridylene, acridinylene, phenanthrolinylene, benzofuranylene, benzothiophenylene, triazolylene, tetrazolylene, triazinylene, dibenzofuranylene, or dibenzothiophenylene; or
[0212] Phenylene, naphthylene, fluorenylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, pyrenylene substituted with -1, -2, -1, -2, -1, -2, -1, -2, -1, -2, -1, -2, -2, -1, -2, -2, -1, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2, -2 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, The invention may be substituted with at least one of 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine, 1,2-diphenylamine,
[0213] In one or more embodiments, L 32 Can be a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*' or *-Si(R 1a )(R 1b )-*',or
[0214] Phenylene or naphthylene, each unsubstituted or substituted with deuterium, C 1 -C 20 Alkyl, C 1 -C 20 The present invention is substituted by at least one of alkoxy, phenyl or naphthyl.
[0215] In one or more embodiments, n32 may be an integer from 1 to 5.
[0216] In one or more embodiments, L 32 It can be selected from formula L(1) to formula L(13):
[0217]
[0218] Wherein, in formulas L(1) to L(13),
[0219] R 1a and R 1b each being the same as described herein,
[0220] R L1 To R L6 can be respectively related to R 10a Same as described, and
[0221] * and *' each indicate a binding site with an adjacent atom.
[0222] In one or more embodiments, R1a and R 1b Can be independently:
[0223] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0224] 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;
[0225] 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, -CFH2 , 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, 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
[0226] -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 ),in,
[0227] 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.
[0228] R in Formula 1 1 , R 2 , R 31 To R 33 and R 4 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 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 60Heterocyclic 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] a1, a2, a31 to a33 and a4 in Formula 1 represent R 1 The number of R 2 The number of R 31 To R 33 The number and R 4 and may each independently be an integer from 1 to 20. When a1 is 2 or greater, 2 or more R 1 may be the same or different from each other. When a2 is 2 or greater, 2 or more R 2 may be the same as or different from each other, and when a31 is 2 or greater, 2 or more R 31 can be the same or different from each other. When a32 is 2 or greater, 2 or more R 32 may be the same or different from each other. When a33 is 2 or greater, 2 or more R 33 may be the same as or different from each other, and when a4 is 2 or more, 2 or more R 4 May be the same as or different from each other.
[0231] In one or more embodiments, R 1 , R 2 , R 31 To R 33 and R 4Can 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.-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;
[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, C1 -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, 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
[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 ),
[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; 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.
[0237] In one or more embodiments, R 1 , R 2 , R 31 To R 33 and R 4 Can be independently:
[0238] Hydrogen, deuterium, -F, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0239] C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy, each deuterated, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl or any combination thereof;
[0240] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl, each of which is unsubstituted or substituted with deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof; or
[0241] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -N(Q 1 )(Q 2 ),
[0242] Among them, Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C1 -C 60 Alkoxy; or C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic groups, each of which is unsubstituted or substituted with deuterium, -F, C 1 -C 60 Alkyl, C 1 -C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
[0243] In one or more embodiments, R 1 , R 2 , R 31 To R 33 and R 4 Can be independently:
[0244] Hydrogen, deuterium or C 1 -C 20 alkyl;
[0245] C 1 -C 20 Alkyl, deuterated, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl or any combination thereof;
[0246] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 alkyl)phenyl or naphthyl, each of which is unsubstituted or substituted with deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C 1 -C 10 Alkyl)phenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 ) or any combination thereof, or
[0247] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q2 )(Q 3 ),
[0248] Among them, Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; or C 3 -C 60 Carbocyclic, unsubstituted or substituted with deuterium, C 1 -C 60 The present invention is substituted with alkyl, phenyl, biphenyl or any combination thereof.
[0249] In one or more embodiments, selected from a1 R 1 、a2R 2 、a31R 31 、a32 R 32 、a33 R 33 、a4R 4 , R 1a and R 1b Two or more adjacent groups may be optionally combined with each other to form a group which is 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.
[0250] R 10a May be the same as described herein.
[0251] In one or more embodiments, at least one R 1 It may be a group represented by formula S1:
[0252]
[0253] Wherein, in Formula S1,
[0254] R 111 To R 113 can be respectively related to R in this disclosure 1 Same as described,
[0255] a111 can be an integer from 1 to 5,
[0256] a112 can be an integer from 1 to 3,
[0257] a113 can be an integer from 1 to 5, and
[0258] * is the binding site with the adjacent atom.
[0259] In one or more embodiments, selected from a111 R 111 、a112 R 112 and a113 R 113 Two or more adjacent groups may optionally combine to form a group which is 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.
[0260] R 10a May be the same as described herein.
[0261] In one or more embodiments, the formula (1) The group represented by may be a group represented by one selected from CY1(1) to CY1(11):
[0262]
[0263]
[0264] Among them, in formula CY1(1) to formula CY1(11),
[0265] R 11 To R 17 can be respectively related to R 1 Same as described,
[0266] * indicates the binding site with M in Formula 1, and
[0267] *' indicates the same as L in formula 1 1 binding site.
[0268] In one or more embodiments, the The group may be a group represented by one selected from the group consisting of formula CY2(1) to formula CY2(13):
[0269]
[0270] Among them, in formula CY2(1) to formula CY2(13),
[0271] T21 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 ),
[0272] R 21 To R 26 , Y 21 and Y 22 can be respectively related to R 2 Same as described,
[0273] * indicates the binding site with M in Formula 1,
[0274] *' indicates the same as L in formula 1 1 The binding site
[0275] *" indicates the same as L in Formula 1 2 binding site.
[0276] In one or more embodiments, the formula (1) The group represented by may be a group represented by one selected from the group consisting of formula CY3(1) to formula CY3(16):
[0277]
[0278]
[0279]
[0280] Among them, in formula CY3(1) to formula CY3(16),
[0281] R 311 To R 314 can be respectively related to R 31 Same as described,
[0282] R 321 To R 324 can be respectively related to R 32 Same as described,
[0283] R 331 To R 336 can be respectively related to R 33 Same as described,
[0284] * indicates the binding site with M in Formula 1,
[0285] *" indicates the same as L in Formula 1 2 The binding site
[0286] *"' indicates the same as L in Formula 1 31 binding site, and
[0287] *"" indicates the same as L in Formula 1 32 binding site.
[0288] In one or more embodiments, the formula (1) The group represented by may be a group represented by one selected from the group consisting of formula CY4(1) to formula CY4(18):
[0289]
[0290] Among them, in formula CY4(1) to formula CY4(18),
[0291] R 41 To R 47 can be respectively related to R 4 Same as described,
[0292] * indicates the binding site with M in Formula 1,
[0293] *"' indicates the same as L in Formula 1 31 binding site, and
[0294] *"" indicates the same as L in Formula 1 32 binding site.
[0295] In one or more embodiments, the organometallic compound represented by Formula 1 may be an organometallic compound represented by Formula 1A(1) or Formula 1A(2):
[0296] Formula 1A (1)
[0297]
[0298] Formula 1A (2)
[0299]
[0300] Wherein, in Formula 1A(1) and Formula 1A(2),
[0301] M, X 1 To X 4 CY 1 CY 2 CY 31 To CY 33 CY 4 , L 1 , L 2, L 31 、n1、n2、n31、R 1 , R 2 , R 31 To R 33 , R 4 , a1, a2, a31 to a33 and a4 may each independently be the same as described herein,
[0302] T 31 To T 33 Can be respectively with about L 32 Same as described,
[0303] b31 to b33 may each independently be an integer from 0 to 3,
[0304] Cyclo 34 and CY 35 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 a heterocyclic group, and
[0305] R 34 and R 35 can be respectively related to R 10a a34 and a35 may each independently be an integer of 1 to 20.
[0306] In one or more embodiments, the organometallic compound represented by Formula 1 may be an organometallic compound represented by Formula 1B(1) or Formula 1B(2):
[0307] Formula 1B (1)
[0308]
[0309] Formula 1B (2)
[0310]
[0311] Wherein, in Formula 1B(1) and Formula 1B(2),
[0312] M and L 2 each being the same as described herein, and
[0313] T 31 To T 33 Can be respectively with about L 32 Same as described,
[0314] X 11 It can be C(R 11 ) or N, X 12 It can be C(R12 ) or N, X 13 It can be C(R 13 ) or N, and X 14 It can be C(R 14 ) 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 311 It can be C(R 311 ) or N, X 312 It can be C(R 312 ) or N, X 321 It can be C(R 321 ) or N, X 322 It can be C(R 322 ) or N, X 331 It can be C(R 331 ) or N, X 332 It can be C(R 332 ) or N, X 333 It can be C(R 333 ) or N, X 334 It can be C(R 334 ) or N, X 341 It can be C(R 341 ) or N, X 342 It can be C(R 342 ) or N, X 343 It can be C(R 343 ) or N, X 344 It can be C(R 344 ) or N, X 351 It can be C(R 351 ) or N, X 352 It can be C(R 352 ) or N, X 353 It can be C(R 353 ) or N, and X 354 It can be C(R 354 ) or N,
[0317] X 41 It can be C(R 41 ) or N, X 42 It can be C(R 42 ) or N, and X 43 It can be C(R 43 ) or N,
[0318] R 11 To R 15 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 311 and R 312 can be respectively related to R 31 Same as described,
[0321] R 321 and R 322 can be respectively related to R 32 Same as described,
[0322] R 331 To R 334 can be respectively related to R 33 Same as described,
[0323] R 341 To R 344 and R 351 To R 354 can be respectively related to R 10a Same as described,
[0324] R 41 To R 43 can be respectively related to R 4 Same as described, and
[0325] Selected from R 11 To R 15 , R 21 To R 23 , R 311 , R 312 , R 321 , R 322 , R 331 To R 334 , R 341 To R 344 , R 351 To R 354 , R 41 To R 43 , R 1a and R 1b Two or more adjacent groups may be optionally linked to each other to form a group which is 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 10aSubstituted C 1 -C 60 Heterocyclic group.
[0326] The organometallic compound represented by Formula 1 includes a ring CY 31 To Ring CY 33 Thus, the intramolecular charge transfer can be facilitated, and thus when the organometallic compound is used in a light-emitting device, the driving voltage of the light-emitting device can be reduced. In one or more embodiments, in the organometallic compound represented by Formula 1, the ring CY 31 To Ring CY 33 The indolecarbazolyl moiety formed can be connected by a linker L 31 and a linker L 32 With ring CY 4 Together they form a ring, thereby increasing molecular rigidity and reducing molecular vibration, which increases the molecular emission energy level (e.g., T 1 energy level) and molecular quenching energy level (e.g. 3 As a result, the photoluminescence quantum yield (PLQY) and molecular stability of the organometallic compound are increased. Therefore, by using the organometallic compound represented by Formula 1, an electronic device (e.g., an organic light-emitting device) with reduced driving voltage, improved color purity and efficiency, and extended life can be achieved.
[0327] Other descriptions
[0328] Formula 2
[0329]
[0330] L in Formula 2 51 To L 53 may be independently a single bond, 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.
[0331] b51 to b53 in Formula 2 represent L 51 The number of L 53 When b51 is 2 or more, 2 or more L 51 can be the same or different from each other. When b52 is 2 or greater, 2 or more L 52 can be the same or different from each other. When b53 is 2 or greater, 2 or more L 53In some embodiments, b51 to b53 may be 1 or 2, respectively.
[0332] In one or more embodiments, L in Formula 2 51 To L 53 Can be independently:
[0333] a single key; or
[0334] 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, dibenzodithiin 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(Q31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof,
[0335] Among them, 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.
[0336] 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 the two L 53 The key between 51 With X in Eq. 2 54 and X 55 The bonds between carbons, L 52 With X in Eq. 2 54 and X 56 The bonds between the carbons and L 53 With X in Eq. 2 55 and X 56 The bonds between the carbon atoms in the carbon atoms may each be a "carbon-carbon single bond".
[0337] 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 them can be N. 54 To R 56Can be independently the same as described herein. In one or more embodiments, selected from X 54 To X 56 Two or three of them can be N.
[0338] R in Formula 2 51 To R 56 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each may be the same as described herein.
[0339] In one or more embodiments, R in Formula 2 51 To R 56 Can be independently:
[0340] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0341] 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;
[0342] 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, azadibenzothiorolyl 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, 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)(Q31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0343] -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 ),
[0344] Among them, Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0345] -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
[0346] 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;
[0347] Formula 91
[0348]
[0349] Among them, in formula 91,
[0350] Cyclo 91 and CY 92 may be each 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,
[0351] X 91 Can be single bond, O, S, N(R 91 )、B(R 91 )、C(R 91a )(R 91b ) or Si(R 91a )(R 91b ), R 91 , R 91a and R 91b can be respectively related to R 82 , R 82a and R 82b Same as described,
[0352] R 10a may be the same as described herein, and
[0353] *Indicates the binding site with the neighboring atoms.
[0354] For example, in one or more embodiments, in Formula 91,
[0355] 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,
[0356] R 91 , R91a and R 91b Can be independently:
[0357] Hydrogen or C 1 -C 10 Alkyl; or
[0358] 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.
[0359] 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 by each may not be phenyl.
[0360] 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.
[0361] 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.
[0362] In one or more embodiments, b51 and b52 in Formula 2 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.
[0363] In one or more embodiments, R in Formula 2 51 and R 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10aSubstituted 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
[0364] Q 1 To Q 3 Can be independently: 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.
[0365] In one or more embodiments,
[0366] In formula 2, *-(L 51 ) b51 -R 51 The group represented by may be a group represented by one selected from the group consisting of Formula CY51-1 to Formula CY51-26, and / or
[0367] In formula 2, *-(L 52 ) b52 -R 52 The group represented by may be a group represented by one selected from the group consisting of Formula CY52-1 to Formula CY52-26, and / or
[0368] In formula 2, *-(L 53 ) b53 -R 53 The group represented by may be selected from the group consisting of formula CY53-1 to formula CY53-27, -C(Q 1 )(Q 2 )(Q 3 ) and -Si(Q 1 )(Q 2 )(Q 3 ) is a group represented by one of the following.
[0369]
[0370]
[0371]
[0372] 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,
[0373] 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 ),
[0374] 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 ),
[0375] 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 ),
[0376] Y in formula CY51-16 and formula CY51-17 63 and Y 64 It can be a single key at different times.
[0377] Y in formula CY52-16 and formula CY52-17 67 and Y 68 It can be a single key at different times.
[0378] R 51a To R 51e , R61 To R 64 , R 63a , R 63b , R 64a and R 64b Each can be referenced by R 51 description to understand, and R 51a To R 51e It may not all be hydrogen.
[0379] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b Each can be referenced by R 52 description to understand, and R 52a To R 52e It may not all be hydrogen.
[0380] R 53a To R 53e , R 69a and R 69b Each can be referenced by R 53 description to understand, and R 53a To R 53e may not all be hydrogen, and
[0381] *Indicates the binding site with the neighboring atoms.
[0382] For example, in one or more embodiments,
[0383] 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:
[0384] 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, azadibenzothiorolyl 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, ...
[0385] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),
[0386] Among them, Q 1 To Q 3can 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,
[0387] 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
[0388] 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.
[0389] Formula 3
[0390]
[0391] Among them, the ring CY in formula 3 71 and CY 72 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridyl group.
[0392] X in Formula 3 71 It may be a single bond, or a linking group including O, S, N, B, C, Si, or any combination thereof.
[0393] * 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.
[0394] Formula 3-1
[0395]
[0396] Formula 3-2
[0397]
[0398] Formula 3-3
[0399]
[0400] Formula 3-4
[0401]
[0402] Formula 3-5
[0403]
[0404] Ring CY in Formula 3-1 to Formula 3-5 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridyl group.
[0405] X in Formula 3-1 to Formula 3-5 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a )(R 82b ).
[0406] X in Formula 3-1 to Formula 3-5 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ).
[0407] X in Formula 3-1 to Formula 3-5 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ).
[0408] X in Formula 3-1 to Formula 3-5 85 It can be C or Si.
[0409] L in Formula 3-1 to Formula 3-5 81 To L 85 can be independently a single bond, *-C(Q4 )(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, or unsubstituted or substituted with at least one R 10a Substituted pyridinyl.
[0410] Q 4 and Q 5 You can each share your experience with Q 1 Same as described.
[0411] b81 to b85 in Formula 3-1 to Formula 3-5 may each independently be an integer of 1 to 5.
[0412] 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.
[0413] a71 to a74 in Formula 3-1 to Formula 3-5 represent R 71 The number of R 74 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.
[0414] R 10a May be the same as described herein.
[0415] In one or more embodiments, in Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0416] a single key; or
[0417] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*';or
[0418] 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(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,
[0419] Among them, Q 4 , Q 5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0420] 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
[0421] From 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
[0422] From formula 3-2 and formula 3-4 The group represented by may be a group represented by one selected from the group consisting of Formula CY71-3(1) to Formula CY71-3(32), and / or
[0423] From 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
[0424] From 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):
[0425]
[0426]
[0427]
[0428]
[0429] 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),
[0430] X 81 To X 85 , L 81 ,b81,R 81 and R 85 may each be the same as described herein,
[0431] X86 Can be single bond, O, S, N(R 86 )、B(R 86 )、C(R 86a )(R 86b ) or Si(R 86a )(R 86b ), X 87 Can be single bond, O, S, N(R 87 )、B(R 87 )、C(R 87a )(R 87b ) or Si(R 87a )(R 87b ),
[0432] 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,
[0433] X 88 Can be single bond, O, S, N(R 88 )、B(R 88 )、C(R 88a )(R 88b ) or Si(R 88a )(R 88b ), X 89 Can be single bond, O, S, N(R 89 )、B(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0434] X in formula CY71-2(1) to formula CY71-2(8), formula CY71-3(1) to formula CY71-3(32) and formula CY71-5(1) to formula CY71-5(8) 88 and X 89 Each may not be a single bond at the same time, and
[0435] 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.
[0436] Formula 502
[0437]
[0438] Formula 503
[0439]
[0440] Ring A in Formula 502 and Formula 503 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0441] Y in Equation 502 and Equation 503 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ).
[0442] Y in Equation 502 and Equation 503 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ).
[0443] Y in Formula 503 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ).
[0444] Y in Formula 503 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ).
[0445] Y in Equation 502 and Equation 503 51 and Y 52 Each may independently be B, P(═O) or S(═O).
[0446] R in Equation 502 and Equation 503 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b May be the same as described herein.
[0447] a501 to a504 in equation 502 and equation 503 respectively indicate R 501 The number of R 504 When a501 may be 2 or more, two or more R 501 can be the same or different from each other. When a502 can be 2 or greater, two or more R 502 can be the same or different from each other. When a503 can be 2 or greater, two or more R 503 may be the same as or different from each other, and when a504 is 2 or greater, two or more R 504 In some embodiments, a501 to a504 may be an integer from 0 to 8 independently of one another.
[0448] 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 with at least one R 10a Substituted C1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each may be the same as described herein.
[0449] 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 R74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b , and ii) R 10a , can be independently:
[0450] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0451] 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;
[0452] 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, azadibenzothiorolyl 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, 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)(Q31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0453] -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 ),
[0454] Among them, Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0455] -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
[0456] 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.
[0457] In one or more embodiments, i) R in Formula 1 1 , R 2 , R 31 To R 33 and R 4 ii) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502 and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b , and iii) R 10a , can be independently:
[0458] Hydrogen, deuterium, -F, cyano, nitro, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H or -CFH 2 ;
[0459] A group represented by one selected from Formula 9-1 to Formula 9-19; and a group represented by one selected from Formula 9-1 to Formula 9-19; and
[0460] Selected from Formula 10-1 to Formula 10-246, -C(Q 1 )(Q 2 )(Q3 )、-Si(Q 1 )(Q 2 )(Q 3 ) and -P(=O)(Q 1 )(Q 2 ) represents a group (Q 1 To Q 3 may each independently be the same as described herein):
[0461]
[0462]
[0463]
[0464]
[0465]
[0466]
[0467]
[0468] In Formulae 9-1 to 9-19 and 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.
[0469] Examples of Compounds
[0470] In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from Compound 1 to Compound 120:
[0471]
[0472]
[0473]
[0474]
[0475]
[0476] For example, in one or more embodiments, the second compound may be at least one selected from compounds ETH1 to ETH32:
[0477]
[0478]
[0479] For example, in one or more embodiments, the third compound may be at least one selected from compound HTH1 to compound HTH40:
[0480]
[0481]
[0482] For example, in one or more embodiments, the fourth compound may be at least one selected from compound DFD1 to compound DFD29:
[0483]
[0484]
[0485] In the above compounds, Ph represents phenyl, D 5 Denotes substitution by 5 deuteriums, D 4 means replaced by 4 deuterium. The group represented by The groups represented are the same.
[0486] Figure 1 Description
[0487] 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 .
[0488] In the following, reference will be made to Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described in more detail.
[0489] First electrode 110
[0490] exist Figure 1 In one or more embodiments, a substrate may be provided in addition and 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.
[0491] 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 injection of holes.
[0492] 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.
[0493] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.
[0494] Middle layer 130
[0495] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0496] In one or more embodiments, the intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 150 .
[0497] In one or more embodiments, in addition to one or more suitable organic materials, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds (eg, organometallic compounds represented by formula), and / or inorganic materials such as quantum dots.
[0498] 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.
[0499] Hole transport region in the intermediate layer 130
[0500] 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.
[0501] 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.
[0502] For example, in some embodiments, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the constituent layers of each structure are stacked sequentially from the first electrode 110 in the order stated.
[0503] 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:
[0504] Formula 201
[0505]
[0506] Formula 202
[0507]
[0508] In equation 201 and equation 202,
[0509] L 201 To L 204 may be each 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,
[0510] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C20 Alkenylene, 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,
[0511] xa1 to xa4 can each independently be an integer from 0 to 5,
[0512] xa5 can be an integer from 1 to 10,
[0513] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0514] 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),
[0515] 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
[0516] na1 can be an integer from 1 to 4.
[0517] 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:
[0518]
[0519] In formula CY201 to formula CY217, 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.
[0520] 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.
[0521] 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.
[0522] In one or more embodiments, Formula 201 may include at least one selected from the group represented by Formulas CY201 to CY203 and at least one selected from the group represented by Formulas CY204 to CY217.
[0523] In one or more embodiments, in formula 201, xa1 may be 1, R 201 may be one selected from the group represented by the formula CY201 to the formula CY203, xa2 may be 0, and R 202 It may be one selected from the groups represented by the formulae CY204 to CY207.
[0524] 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.
[0525] In an embodiment, each of Formula 201 and Formula 202 may not include (eg, may exclude) any group represented by Formula CY201 to Formula CY203, and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.
[0526] In an embodiment, each of Formula 201 and Formula 202 may not include (e.g., may exclude) any group represented by Formula CY201 to Formula CY217. In the present disclosure, "does not include 'component' or any 'component'", "excludes 'component' or any 'component'" and / or "does not contain 'component'", etc., means that the "component" is not added, selected or used as a component in the composition / formula / structure, but in some embodiments, due to other impurities and / or external factors, less than an appropriate amount of the "component" may still be included.
[0527] 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:
[0528]
[0529]
[0530]
[0531]
[0532]
[0533] 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.
[0534] The emission auxiliary layer can improve the luminous 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.
[0535] p-dopant
[0536] In one or more embodiments, in addition to one or more of 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 monolayer consisting of the charge generating material).
[0537] The charge generating material may be, for example, a p-dopant.
[0538] For example, in one or more embodiments, the p-dopant may have a LUMO level less than or equal to -3.5 eV.
[0539] 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.
[0540] Non-limiting examples of quinone derivatives are tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), etc.:
[0541]
[0542] Non-limiting examples of the cyano group-containing compound include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or a compound represented by Formula 221, and the like:
[0543]
[0544] Formula 221
[0545]
[0546] In formula 221,
[0547] R 221 To R 223 may be each 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
[0548] 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 substituted by: cyano; -F; -Cl; Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0549] 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.
[0550] Non-limiting examples of metals are: 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 (Cs), etc.); o), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and / or lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); etc.
[0551] Non-limiting examples of metalloids are silicon (Si), antimony (Sb), and / or tellurium (Te), among others.
[0552] Non-limiting examples of non-metals are oxygen (O) and / or halogens (eg, F, Cl, Br, I, etc.), and the like.
[0553] Non-limiting examples of compounds containing element EL1 and element EL2 are metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or one or more combinations thereof.
[0554] Non-limiting examples of metal oxides are tungsten oxide (e.g., 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., ReO3 etc.
[0555] Non-limiting examples of metal halides are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides, and the like.
[0556] Non-limiting examples of alkali metal halides are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI and / or CsI, etc.
[0557] A non-limiting example of an alkaline earth metal halide is BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 wait.
[0558] Non-limiting examples of transition metal halides are 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 、NbCl3 , 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 2etc.), 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.
[0559] Non-limiting examples of late transition metal halides are 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.
[0560] Non-limiting examples of lanthanide metal halides are YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and / or SmI 3 wait.
[0561] Non-limiting examples of metalloid halides are antimony halides (e.g., SbCl 5 etc.
[0562] Non-limiting examples of metal tellurides are alkali metal tellurides (e.g., Li 2 Te、Na 2Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.
[0563] Emission layer in the middle layer 130
[0564] 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 emission material, the green emission material and the blue emission 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).
[0565] In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In some embodiments, in addition to the host and the dopant (or emitter), the emission layer may further include an auxiliary dopant that facilitates 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.
[0566] 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.
[0567] 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.
[0568] The emission layer may include an organic metal compound represented by Formula 1. The amount (weight) of the organic metal compound in the emission layer may be about 0.01 to about 30 parts by weight, about 0.1 to about 20 parts by weight, or about 0.1 to about 15 parts by weight based on 100 parts by weight of the emission layer.
[0569] In one or more embodiments, the emission layer may include quantum dots.
[0570] 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.
[0571] The thickness of the emitter layer can be approximately To about In 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.
[0572] main body
[0573] The host in the emission layer may include the second compound or the third compound described in the present disclosure, or a combination thereof.
[0574] In one or more embodiments, the host may include a compound represented by Formula 301:
[0575] Formula 301
[0576] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0577] Wherein, in Formula 301,
[0578] Ar 301 and L 301 may be each 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,
[0579] xb11 can be 1, 2 or 3,
[0580] xb1 can be an integer from 0 to 5.
[0581] R 301 It 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 R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0582] xb21 can be an integer from 1 to 5, and
[0583] Q 301 To Q 303 You can each share your experience with Q 1 Same as described.
[0584] 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.
[0585] 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:
[0586] Formula 301-1
[0587]
[0588] Formula 301-2
[0589]
[0590] In Formula 301-1 and Formula 301-2,
[0591] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0592] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0593] xb22 and xb23 can each independently be 0, 1 or 2,
[0594] L 301 , xb1 and R 301 may each be the same as described herein,
[0595] L 302 To L 304 can be independently related to L 301 Same as described,
[0596] xb2 to xb4 may each independently be the same as described with respect to xb1, and
[0597] R 302 To R 305 and R 311 To R 314 can be respectively related to R 301 Same as described.
[0598] In one or more embodiments, the host can include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In some embodiments, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0599] 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(9H-carbazolyl)benzene (mCP); 1,3,5-tri(9-carbazolyl)benzene (TCP); or any combination thereof:
[0600]
[0601]
[0602]
[0603]
[0604]
[0605]
[0606]
[0607] In one or more embodiments, the body may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0608] The body may have one or more suitable modifications. For example, the body may include only one type of compound, or may include two or more types of different compounds.
[0609] Phosphorescent dopants
[0610] The emission layer may include the organometallic compound represented by Formula 1 as described in the present disclosure as a phosphorescent dopant.
[0611] In one or more embodiments, where the emission layer includes an organic metal compound represented by Formula 1 as described herein and the organic metal compound represented by Formula 1 as described herein acts as an auxiliary dopant (eg, embodiments), the emission layer may further include a phosphorescent dopant.
[0612] The phosphorescent dopant may include at least one transition metal as a central metal.
[0613] 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.
[0614] The phosphorescent dopant may be electrically neutral.
[0615] For example, in some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0616] Formula 401
[0617] M(L 401 ) xc1 (L 402 ) xc2
[0618] Formula 402
[0619]
[0620] In equations 401 and 402,
[0621] 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)),
[0622] 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,
[0623] 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,
[0624] X 401 and X 402can be independently N or C,
[0625] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0626] 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 )-*',
[0627] 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 ),
[0628] Q 411 To Q 414 Each and About Q 1 Same as described,
[0629] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with 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 ),
[0630] Q 401 To Q 403 Each and About Q 1 Same as described,
[0631] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0632] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0633] 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.
[0634] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two rings A 401 It 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.
[0635] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include halogen, diketone group (e.g., acetylacetonate group), carboxylic acid group (e.g., picolinate group), -C(=O), isonitrile group, -CN, phosphorus-containing group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.
[0636] In one or more embodiments, the phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD39 or any combination thereof:
[0637]
[0638]
[0639]
[0640] Fluorescent dopants
[0641] In the case where the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein serves as an auxiliary dopant (eg, embodiments), the emission layer may further include a fluorescent dopant.
[0642] In one or more embodiments, where the emission layer includes an organic metal compound represented by Formula 1 as described herein and the organic metal compound represented by Formula 1 as described herein acts as a phosphorescent dopant (eg, embodiments), the emission layer may further include an auxiliary dopant.
[0643] The fluorescent dopant and the auxiliary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0644] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
[0645] Formula 501
[0646]
[0647] In formula 501,
[0648] Ar 501 , L 501 To L 503 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0649] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0650] xd4 can be 1, 2, 3, 4, 5 or 6.
[0651] In one or more 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.).
[0652] In one or more embodiments, xd4 in equation 501 may be 2.
[0653] For example, in one or more embodiments, the fluorescent dopant and the auxiliary dopant may each include: at least one selected from 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:
[0654]
[0655]
[0656]
[0657] Delayed fluorescence material
[0658] In one or more embodiments, the emission layer may include a delayed fluorescent material.
[0659] In the present disclosure, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0660] The delayed fluorescent material may include, for example, the fourth compound described in the present disclosure.
[0661] 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.
[0662] 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 at least about 0 eV and not greater than about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus, the light emitting device 10 may have improved luminous efficiency.
[0663] 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 (for example, a sulfoxide group, a cyano group and / or a π-electron-deficient nitrogen-containing C 1 -C 60 heterocyclic group, etc.); and / or ii) including C 8 -C 60 Polycyclic materials, the C 8 -C 60 The polycyclic group includes at least two cyclic groups fused to each other while sharing boron (B); and the like.
[0664] Non-limiting examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF14:
[0665]
[0666]
[0667] quantum dots
[0668] In one or more embodiments, the emission layer may include quantum dots.
[0669] 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.
[0670] 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 vol% in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
[0671] 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.
[0672] 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).
[0673] 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.
[0674] Non-limiting examples of II-VI semiconductor compounds are binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS e, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe, etc.; or one or more combinations thereof.
[0675] Non-limiting examples of III-V semiconductor compounds are: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs and / or InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs and / or InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and / or InAlPSb, etc.; or one or more combinations thereof. In one or more embodiments, the III-V semiconductor compounds may also include Group II elements. Non-limiting examples of Group III-V semiconductor compounds that also include Group II elements are InZnP, InGaZnP, and / or InAlZnP, and the like.
[0676] Non-limiting examples of III-VI semiconductor compounds are: binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and / or InTe, etc.; ternary compounds such as InGaS 3 and / or InGaSe 3 etc.; or one or more combinations thereof.
[0677] Non-limiting examples of Group I-III-VI semiconductor compounds are: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and / or AgAlO 2 etc.; or one or more combinations thereof.
[0678] Non-limiting examples of IV-VI semiconductor compounds are: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe and / or SnPbSTe; or one or more combinations thereof.
[0679] Non-limiting examples of Group IV elements or compounds are: single elements, such as Si and / or Ge, etc.; binary compounds, such as SiC and / or SiGe, etc.; or one or more combinations thereof.
[0680] 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.
[0681] In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or may have a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
[0682] The shell of a quantum dot can act as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or act as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be monolayer or 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.
[0683] Examples of quantum dot shells are oxides of metals, metalloids or non-metals, semiconductor compounds or any combination thereof. Non-limiting examples of oxides of metals, metalloids or non-metals are: binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and / or NiO, etc.; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4、NiFe 2 O 4 and / or CoMn 2 O 4 etc.; or one or more combinations thereof. As described herein, examples of semiconductor compounds are: II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; or one or more combinations thereof. Non-limiting examples of semiconductor compounds suitable as shells are CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0684] The quantum dots may have a full width at half maximum (FWHM) of the emission spectrum of less than or equal to about 45 nm, less than or equal to about 40 nm, or, for example, less than or equal to about 30 nm. When the FWHM of the quantum dots is within these ranges, the quantum dots may have improved color purity or improved color reproducibility. In some embodiments, because the light emitted by the quantum dots is emitted in all directions, the wide viewing angle may be improved.
[0685] In one or more embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles or cubic nanoparticles, nanotubes, nanowires, nanofibers or nanoplates.
[0686] Because the energy 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 the quantum dot emission layer. 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 having a suitable size can be configured to emit white light through a combination of one or more suitable colors of light.
[0687] Electron transport region in the intermediate layer 130
[0688] The electron transport region 140 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.
[0689] 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.
[0690] For example, in one or more embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked sequentially from the emission layer in the order stated.
[0691] In one or more embodiments, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group.
[0692] For example, in some embodiments, the electron transport region may include a compound represented by Formula 601:
[0693] Formula 601
[0694] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0695] Wherein, in Formula 601,
[0696] Ar 601 and L 601 may be each 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,
[0697] xe11 can be 1, 2 or 3,
[0698] xe1 can be 0, 1, 2, 3, 4, or 5,
[0699] 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 R10a 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 ),
[0700] Q 601 To Q 603 You can each share your experience with Q 1 Same as described,
[0701] xe21 can be 1, 2, 3, 4, or 5, and
[0702] Selected from Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group.
[0703] In one or more 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.
[0704] In one or more embodiments, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0705] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
[0706] Formula 601-1
[0707]
[0708] Among them, in formula 601-1,
[0709] 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 616At least one of them can be N,
[0710] L 611 To L 613 Can be respectively with about L 601 Same as described,
[0711] xe611 to xe613 may each be the same as described with respect to xe1,
[0712] R 611 To R 613 can be respectively related to R 601 Same as described, and
[0713] 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.
[0714] 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.
[0715] 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:
[0716]
[0717]
[0718]
[0719] The thickness of the electron transport region can be approximately To about In 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 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.
[0720] In one or more embodiments, in addition to one or more of the above materials, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material.
[0721] 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.
[0722] 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:
[0723]
[0724] 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.
[0725] The electron injection layer may have: i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material); ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a plurality of different materials (e.g., consisting of a plurality of different materials); or iii) a multi-layer structure including a plurality of layers that includes a plurality of different materials.
[0726] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0727] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0728] The compound containing an alkali metal, the compound containing an alkaline earth metal, and the compound containing a rare earth metal may be oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, or any combination thereof.
[0729] The compound containing an alkali metal may include: alkali metal oxides such as Li 2 O, Cs 2 O, K 2 O, etc.; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc.; or any combination thereof. The compound containing an alkaline earth metal may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The compound containing a rare earth metal may include YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3Or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, LaTe, 2 Te 3 、Ce 2 Te 3 , Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 、Gd2Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 and / or Lu 2 Te 3 wait.
[0730] 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 (e.g., the corresponding metal ion), such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0731] In one or more embodiments, the electron injection layer may include (e.g., be composed of): an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In some embodiments, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).
[0732] 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.
[0733] When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof can be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.
[0734] The thickness of the electron injection layer can be about To about in the range of, or for example, in the range of 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.
[0735] The second electrode 150
[0736] 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.
[0737] 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.
[0738] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
[0739] Covering
[0740] The first covering layer may be disposed outside the first electrode 110 (e.g., on the first electrode 110), and / or the second covering layer may be disposed outside the second electrode 150 (e.g., on the second electrode 150). In one or more embodiments, the light emitting device 10 may have a structure in which the first covering 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 covering layer are sequentially stacked in the order stated, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are sequentially stacked in the order stated.
[0741] In some embodiments, light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be emitted to the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first cover layer. In some embodiments, light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be emitted to the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second cover layer.
[0742] The first cover layer and the second cover layer can increase the external emission efficiency according to the principle of constructive interference, thereby increasing the light emission efficiency of the light emitting device 10 and improving the light emitting efficiency of the light emitting device 10.
[0743] Each of the first cover layer and the second cover layer may include a material having a refractive index greater than or equal to 1.6 (eg, at 589 nm).
[0744] 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.
[0745] 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 porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first covering layer and the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include an amine-containing compound.
[0746] In one or more embodiments, at least one of the first covering layer and the second covering layer may (eg, the first covering layer and the second covering layer may each independently) include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0747] In one or more embodiments, at least one of the first cover layer and 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:
[0748]
[0749]
[0750] membrane
[0751] The organometallic compound represented by Formula 1 may be included in one or more suitable films. Therefore, one or more aspects of the embodiments of the present disclosure relate to a film comprising 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.).
[0752] Electronic devices
[0753] Light emitting device (e.g. Figure 1 The 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.
[0754] 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 of travel of the light emitted from the light emitting device. For example, in some embodiments, the light emitted from the light emitting device may be blue light, green light, or white light (e.g., combined white light). For details about the light emitting device, reference may be made to the description provided herein. In some embodiments, the color conversion layer may include quantum dots.
[0755] 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 plurality of sub-pixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the plurality of sub-pixel areas.
[0756] A pixel defining film may be disposed between the plurality of sub-pixel regions to define each sub-pixel region.
[0757] The color filter may further include a plurality of color filter areas and a light shielding pattern disposed between the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and a light shielding pattern disposed between the color conversion areas.
[0758] A plurality of color filter regions (or a 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, a plurality of color filter regions (or a plurality of color conversion regions) may include quantum dots. In some embodiments, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) any quantum dots. For details on quantum dots, reference may be made to the description provided herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0759] For example, in one or more embodiments, the light emitting device may be used to emit a first light, the first region may be used to absorb the first light to emit a first-first color light, the second region may be used to absorb the first light to emit a second-first color light, and the third region may be used to absorb the first light to emit a third-first color light. Here, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. 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.
[0760] In one or more embodiments, in addition to the light emitting device described above, 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.
[0761] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.
[0762] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.
[0763] In one or more embodiments, the electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be emitted to the outside, and at the same time (for example, compromisingly) prevents ambient air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one layer of an organic layer and / or an inorganic layer. When the encapsulation portion is a thin film encapsulation layer, the electronic device may be flexible.
[0764] 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.
[0765] The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information of a living body (eg, fingertips, pupils, etc.) In addition to the light emitting device described above, the authentication device may also include a biometric information collector.
[0766] The electronic device can be applied to one or more of a display, a light source, a lighting device, 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.
[0767] Electronic equipment
[0768] The light emitting device may be included in one or more suitable electronic equipment.
[0769] For example, the electronic equipment including the 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, a signal light, a head-up display, a fully or partially transparent display, a flexible display (such as a rollable display, a foldable display, or a stretchable display), a laser printer, a phone (such as a mobile phone or a tablet phone), a tablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 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.
[0770] Since the light emitting device has excellent or appropriate effects in terms of light emitting efficiency and long life, electronic equipment including the light emitting device may have characteristics of high brightness, high resolution, and low power consumption.
[0771] Figure 2 and Figure 3 Description
[0772] 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.
[0773] 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 encapsulates the light emitting device.
[0774] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce impurities from penetrating through the substrate 100, and may provide a flat surface on the substrate 100.
[0775] The TFT may be on the buffer layer 210 . The TFT may include an active layer 220 , a gate electrode 240 , a source electrode 260 , and a drain electrode 270 .
[0776] 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.
[0777] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220 , and the gate electrode 240 may be on the gate insulating film 230 .
[0778] An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 and the drain electrode 270 from each other.
[0779] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be arranged to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0780] 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 layer, an organic insulating layer, or a 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.
[0781] The first electrode 110 may be on the passivation layer 280 . The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without completely covering the drain electrode 270 , and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270 .
[0782] A pixel defining layer 290 including an insulating material may be 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.
[0783] The second electrode 150 may be on the intermediate layer 130, and the second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0784] The encapsulation part 300 may be on the second cover layer 170. The encapsulation part 300 may be arranged on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl 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.
[0785] 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.
[0786] 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.
[0787] Figure 4 Description
[0788] Figure 4 , Figure 5 , Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of the structure of electronic equipment according to one or more embodiments of the present disclosure. Figure 41 is a schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments of the present disclosure. As a device for displaying moving images or still images, the electronic device 1 may be a portable electronic device such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an e-book, a portable multimedia player (PMP), a navigation or ultra-mobile PC (UMPC), and one or more suitable products such as a television, a laptop computer, a monitor, a billboard, and 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, the electronic equipment 1 may include a dashboard of a vehicle, a central control panel of a vehicle, a central information display arranged on the dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle or a display arranged behind its front seat, or a head-up display (HUD) and / or a computer-generated holographic augmented reality head-up display (CGH AR HUD) installed at the front of the vehicle or projected on the front windshield. For ease of explanation, Figure 4 An embodiment is shown in which the electronic equipment 1 is a smartphone.
[0789] 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.
[0790] The non-display area NDA is an area where an image is not displayed, and may be around the display area DA (e.g., may completely surround the display area DA). In the non-display area NDA, a driver for providing an electrical signal or power to a display device arranged in the display area DA may be arranged. In the non-display area NDA, a pad as an area to which an electronic component or a printed circuit board can be electrically connected may be arranged.
[0791] In the electronic equipment 1, the length in the x-axis direction and the length (eg, width) in the y-axis direction may be different from each other. Figure 4 As shown in , the length in the x-axis direction may be shorter than the length (e.g., width) in the y-axis direction. In some embodiments, the length in the x-axis direction may be substantially the same as the length (e.g., width) in the y-axis direction. In some embodiments, the length in the x-axis direction may be longer than the length (width) in the y-axis direction.
[0792] Figure 5 and 6A to Figure 6C Description
[0793] Figure 5 According to one or more embodiments, the light emitting device 10 (see Figure 1 ) is a schematic diagram of the appearance of a vehicle 1000 with an electronic device. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.
[0794] 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, an object, or an animal from a starting point to a destination point. The vehicle 1000 may include a vehicle traveling on roads or tracks, a ship moving on the ocean or a river, and / or an airplane flying in the sky using the action of air.
[0795] 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 traveling on a track.
[0796] 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 of the vehicle 1000 may include a front panel, a hood, a roof panel, a rear panel, a luggage compartment, and / or a column disposed 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 and left and right wheels, etc.
[0797] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , an instrument cluster 1400 , a central control instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0798] 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 .
[0799] The side window glass 1100 may be installed on a side of the vehicle 1000. In some embodiments, the side window glass 1100 may be installed 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 instrument cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0800] In one or more embodiments, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). For example, 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.
[0801] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0802] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the outside of the body of the vehicle 1000. In some 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.
[0803] Instrument cluster 1400 may be arranged in front of the steering wheel. Instrument cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a trip meter, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0804] The central 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 central instrument panel 1500 may be disposed at one side of the instrument cluster 1400 .
[0805] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, with the center console instrument panel 1500 disposed therebetween. In some embodiments, the instrument 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 instrument cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0806] 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 instrument cluster 1400, the central control instrument panel 1500, or the passenger seat instrument panel 1600.
[0807] The display device 2 may include an organic light-emitting display device, an inorganic EL display device, and / or a quantum dot display device, etc. In the following, as the display device 2 according to one or more embodiments of the present disclosure, an organic light-emitting display device including a light-emitting device according to the present disclosure will be described as an example, but one or more suitable types (kinds) of display devices described above may be used in the embodiments of the present disclosure.
[0808] refer to 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.
[0809] refer to Figure 6B In one or more embodiments, the display device 2 may be arranged on the instrument cluster 1400. When the display device 2 is arranged on the instrument cluster 1400, the instrument cluster 1400 may display driving information and the like through the display device 2. For example, the instrument cluster 1400 may be implemented digitally. The digital instrument cluster 1400 may display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and one or more suitable warning light icons may be displayed through digital signals.
[0810] refer to Figure 6CIn one or more embodiments, the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument cluster 1400 and / or the information displayed on the central control instrument panel 1500. In some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the central control instrument panel 1500.
[0811] Manufacturing method
[0812] 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.
[0813] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are each formed by vacuum deposition, the deposition temperature may be within a range of about 100° C. to about 500° C., the deposition temperature may be ... -8 Up to about 10 -3 Torr range and under vacuum at about / second to approximately The deposition is performed at a deposition rate in the range of 200 Å / s.
[0814] Definition of terms
[0815] 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 60The number of ring-forming atoms of the heterocyclic group may be 3 to 61.
[0816] As used herein, the term "cyclic group" may include C 3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups.
[0817] As used herein, the term "π-electron-rich C 3 -C 60 The term "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The term "heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.
[0818] For example,
[0819] C 3 -C 60 The carbocyclic group may be i) a group T1 (e.g., one or more groups in group T1) or ii) a fused cyclic group in which two or more groups T1 (e.g., two or more groups in group T1) are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthrenyl or indenoanthryl),
[0820] C 1 -C 60The 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 (e.g., at least one group in the group T2) and at least one group T1 (e.g., at least one group in the group T1) are fused to each other (e.g., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothirolyl group, a benzothienyl group, a benzofuranyl group, a carbazolyl group, a dibenzothirolyl group, a dibenzothienyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzothiorrolocarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothienyl group, a benzonaphthothienyl group, a benzonaphtho thiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothienyl, benzothienodibenzothienyl, 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, quinazoline, benzoquinazoline, phenanthroline, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0821] 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.),
[0822] 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, benzo[1-,2-,3-,4-diazole). pyrazolyl, 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.),
[0823] 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, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,
[0824] 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,
[0825] The group T3 may be furyl, thienyl, 1H-pyrrolyl, thiolsyl or borocyclopentadienyl, and
[0826] The group T4 can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0827] 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".
[0828] One Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Non-limiting examples of heterocyclic groups are 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.
[0829] 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 are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. As used herein, the term “C 1 -C 60 "Alkylene" refers to 1 -C 60 The alkyl group has substantially the same structure as a divalent group.
[0830] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof are vinyl, propenyl and / or butenyl, etc. 2 -C 60 "Alkenylene" refers to 2 -C 60 The alkenyl group has a divalent group having substantially the same structure.
[0831] 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 are ethynyl and / or propynyl, etc. 2 -C 60 "Alkynylidene" refers to 2 -C 60 Alkynyl groups have substantially the same structure as a divalent group.
[0832] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 A univalent group represented by 101 It is C 1 -C60 alkyl), and non-limiting examples thereof are methoxy, ethoxy and / or isopropoxy, and the like.
[0833] 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 are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl. 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.
[0834] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, and non-limiting examples thereof are 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl, etc. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.
[0835] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof are cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group having substantially the same structure.
[0836] 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 10Non-limiting examples of heterocycloalkenyl are 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to 1 -C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.
[0837] 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 are 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.
[0838] 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 are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 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.
[0839] The term "monovalent non-aromatic fused polycyclic group" as used herein 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-forming atoms, and generally having no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups are indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group described above.
[0840] 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 include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothioyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazoles, The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
[0841] 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).
[0842] As used herein, the term "C 7 -C 60 "Aralkyl" refers to -A 104 A 105 (A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59 aryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 106 A 107 (A 106 C 1 -C 59 Alkylene, and A 107 C 1 -C 59 heteroaryl).
[0843] As used herein, the term " 10a " can be:
[0844] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0845] 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;
[0846] 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)(Q 21 )(Q 22 ) or any combination thereof; or
[0847] -Si(Q 31 )(Q32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0848] As used in this article, 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; 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.
[0849] As used herein, the term "heteroatom" refers to any atom other than carbon and hydrogen atoms. Non-limiting examples of heteroatoms are O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0850] The term "third row transition metal" as used herein includes Hf, Ta, W, Re, Os, Ir, Pt and / or Au, among others.
[0851] 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.
[0852] 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.
[0853] 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.
[0854] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0855] In the present disclosure, the x-axis (x-axis direction), the y-axis (y-axis direction), and the z-axis (z-axis direction) are not limited to the three axes (directions) in the orthogonal coordinate system, and can be interpreted in a broad sense including these axes (directions). For example, the x-axis (x-axis direction), the y-axis (y-axis direction), and the z-axis (z-axis direction) may refer to axes (directions) that are orthogonal to each other, or may refer to axes (directions) that are in different directions that are not orthogonal to each other.
[0856] 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.
[0857] Example
[0858] Synthesis Example 1: Synthesis of Compound 10
[0859]
[0860] 1) Synthesis of intermediate [10-A]
[0861] 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (7.0mmol, 2.1g), 1-chloro-2-fluorobenzene (10.5mmol, 1.4g) and tripotassium phosphate (21.0mmol, 4.5g) were placed in a reaction vessel and suspended in 70mL dimethylformamide (DMF). The reaction mixture was heated at 160°C and stirred for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and an extraction process was performed using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 2.3g (5.7mmol) of the target compound.
[0862] 2) Synthesis of intermediate [10-B]
[0863] Intermediate [10-A] (5.7mmol, 2.3g), 1-bromo-4-methoxy-2-nitrobenzene (6.8mmol, 1.6g), tetrakis(triphenylphosphine)palladium (0.3mmol, 0.3g) and potassium carbonate (11.4mmol, 1.6g) were placed in a reaction vessel and suspended in a mixture of 60mL of tetrahydrofuran and water in a volume ratio of 3:1. The reaction mixture was heated and stirred at reflux for 24 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and an extraction process was performed using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried using sodium sulfate. The residue from which the solvent had been removed was separated by column chromatography to obtain 2.0g (4.6mmol) of the target compound.
[0864] 3) Synthesis of intermediate [10-C]
[0865] Intermediate [10-B] (4.6mmol, 2.0g) and triphenylphosphine (9.2mmol, 2.4g) are put into a reaction vessel, and suspended in 45mL 1,2-dichlorobenzene (o-DCB). The reaction mixture is heated and stirred at 160°C for 24 hours. After the reaction is complete, the reaction mixture is cooled to room temperature, and ethyl acetate is used to carry out the extraction process. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and by using sodium sulfate drying. Separate by column chromatography by removing the residue of the solvent therefrom, thereby obtaining 1.1g (2.8mmol) of the target compound.
[0866] 4) Synthesis of intermediate [10-D]
[0867] Intermediate [10-C] (2.8mmol, 1.1g), 2-fluoro-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (3.4mmol, 1.0g), tetrakis(triphenylphosphine)palladium (0.14mmol, 160mg), potassium carbonate (5.6mmol, 770mg) were added to a reaction vessel and suspended in a mixture of 30mL of tetrahydrofuran and water in a volume ratio of 3:1. The reaction mixture was heated and stirred at reflux for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and an extraction process was performed using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 1.1g (2.0mmol) of the target compound.
[0868] 5) Synthesis of intermediate [10-E]
[0869] Intermediate [10-D] (2.0mol, 1.1g) and potassium phosphate (6.0mol, 1.3g) are added in the reaction vessel, and are suspended in 20mL DMF. The reaction mixture is heated to 160 ℃ and stirred for 24 hours. After the reaction is complete, the reaction mixture is cooled to room temperature, and ethyl acetate is utilized to carry out the extraction process. The organic layer extracted therefrom is washed with saturated sodium chloride aqueous solution, and by utilizing dried over sodium sulfate. Separate by column chromatography by removing the resistates of solvent therefrom, thereby obtain 820mg (1.6mmol) of target compound.
[0870] 6) Synthesis of intermediate [10-F]
[0871] Intermediate [10-E] (1.6mmol, 820mg) is suspended in 15mL dichloromethane, and the reaction temperature is reduced to 0 ℃. 1.9mL boron tribromide 1.0M dichloromethane (DCM) is slowly dripped, and the reaction temperature is raised to room temperature and stirred for 24 hours. After the reaction is complete, the reaction mixture is neutralized and ethyl acetate is used to extract. The organic layer extracted therefrom is washed with saturated sodium chloride aqueous solution, and dried over sodium sulfate. Separate by column chromatography by removing the residue from which the solvent is removed, thereby obtaining 550mg (1.1mmol) of the target compound.
[0872] 7) Synthesis of intermediate [10-G]
[0873] Intermediate [10-F] (1.1mmol, 550mg), 1-(3-bromophenyl)-1H-benzo[d]imidazole (1.3mmol, 360mg), potassium phosphate (2.2mmol, 470mg), copper (I) iodide (0.11mmol, 20mg) and 1,10-phenanthroline (0.11mmol, 20mg) were placed in a reaction vessel and suspended in 10mL dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 12 hours. After the reaction was completed, the reaction product was cooled to room temperature, 20mL of distilled water was added thereto, and an extraction process was performed by using ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 550mg (0.8mmol) of the target compound.
[0874] 8) Synthesis of intermediate [10-H]
[0875] Intermediate [10-G] (0.8mmol, 550mg) and iodomethane (1.6mmol, 230mg) were added to the reaction vessel and suspended in 10mL toluene. The reaction mixture was heated to a temperature of 110°C and stirred for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, a portion of the solvent was removed, distilled water was added thereto, and the resulting solid was obtained by filtration. The solid after the filtration was purified using a recrystallization method to obtain 470mg (0.56mmol) of the target compound.
[0876] 9) Synthesis of intermediate [10-I]
[0877] Intermediate [10-H] (0.56mmol, 470mg) and ammonium hexafluorophosphate (1.1mmol, 180mg) were added to the reaction vessel and suspended in a solution of methanol and water in a ratio of 2:1. The reaction mixture was stirred at room temperature for 12 hours. The resulting solid was obtained by filtration and purified using a recrystallization method to obtain 450mg (0.53mmol) of the target compound.
[0878] 10) Synthesis of Compound 10
[0879] Intermediate [10-I] (0.53mmol, 450mg), dichloro (1,5-cyclooctadiene) platinum (0.58mmol, 220mg) and sodium acetate (1.6mmol, 130mg) are suspended in 20mL 1,4-dioxane. The reaction mixture is heated and stirred at 110°C for 24 hours. After the reaction is complete, the reaction product is cooled to room temperature, 20mL distilled water is added thereto, and an extraction process is performed on it by utilizing ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by utilizing sodium sulfate. The residue having the solvent removed therefrom is separated by column chromatography, thereby obtaining 100mg (0.11mmol) of the target compound.
[0880] Synthesis Example 2: Synthesis of Compound 21
[0881]
[0882] In addition to using 2-fluoro-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-3,4,5,6- 4 100 mg (0.11 mmol) of Compound 21 was obtained in substantially the same manner as in Synthesis Example 1, except that 2-fluoro-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine was used instead of 2-fluoro-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine.
[0883] Synthesis Example 3: Synthesis of Compound 36
[0884]
[0885] 1) Synthesis of intermediate [36-A]
[0886] Intermediate [10-F] (1.6mmol, 800mg), 1-bromo-3-fluorobenzene (3.2mmol, 560mg) and potassium phosphate (4.8mmol, 1.0g) are added in the reaction vessel and are suspended in 20mL DMF. The reaction mixture is heated to 160 ℃ and stirred for 24 hours. After the reaction is complete, the reaction mixture is cooled to room temperature, and ethyl acetate is utilized to carry out the extraction process. The organic layer extracted therefrom is washed with saturated sodium chloride aqueous solution, and by utilizing dried over sodium sulfate. Separate by column chromatography by removing the resistates of solvent therefrom, thereby obtain 720mg (1.1mmol) of target compound.
[0887] 2) Synthesis of intermediate [36-B]
[0888] In a reaction vessel, intermediate [36-A] (1.1 mmol, 720 mg), N1-([1,1':3',1"-terphenyl]-2'-yl-2,2",3,3",4,4",5,5",6,6"-D 10 )benzene-1,2-diamine (1.3mmol, 450mg), tri(dibenzylideneacetone)dipalladium (0.06mmol, 55mg), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (0.11mmol, 45mg), sodium tert-butoxide (3.3mmol, 320mg) were suspended in 10mL toluene. The reaction temperature was raised to 110°C, and the reaction mixture was stirred for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried with sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 820mg (0.85mmol) of the target compound.
[0889] 3) Synthesis of intermediate [36-C]
[0890] Intermediate [36-B] (0.85 mmol, 820 mg), triethyl orthoformate (46.8 mmol, 6.9 g) and 35 wt% HCl solution (4.7 mmol, 0.39 mL) were added to a reaction vessel, heated and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the residue from which the solvent was removed was separated by column chromatography to obtain 640 mg (0.64 mmol) of the target compound.
[0891] 4) Synthesis of Compound 36
[0892] Intermediate [36-C] (0.64mmol, 640mg), dichloro (1,5-cyclooctadiene) platinum (0.70mmol, 260mg) and sodium acetate (1.9mmol, 160mg) were suspended in 25mL 1,4-dioxane. The reaction mixture was heated and stirred at 110°C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried with sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 120mg (0.11mmol) of the target compound.
[0893] Synthesis Example 4: Synthesis of Compound 48
[0894]
[0895] In addition to using N1-(2-(5,5,8,8-tetra(methyl-D 3 )-5,6,7,8-tetrahydronaphthalen-2-yl-1,3,4,6,6,7,7-D 7 )-6-(5,5,8,8-tetra(methyl-D 3 )-5,6,7,8-tetrahydronaphthalen-2-yl-1,3,4,6,6,7,7-D 7 )phenyl-3,4,5-D 3 )benzene-1,2-diamine instead of N1-([1,1':3',1"-terphenyl]-2'-yl-2,2",3,3",4,4",5,5",6,6"-D 10 160 mg (0.11 mmol) of Compound 48 was obtained in substantially the same manner as in Synthesis Example 3 except for 1,2-benzene-1,2-diamine.
[0896] Table 1 shows the properties of the compounds synthesized according to the synthesis examples. 1 H nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry / fast atom bombardment (MS / FAB).Through reference to the synthesis routes and source materials, those skilled in the art can easily recognize the synthesis methods of compounds other than those synthesized in the above synthesis examples.
[0897] Table 1
[0898]
[0899]
[0900] [Evaluation Example 1]
[0901] The HOMO energy level and LUMO energy level of each of Compound 10, Compound 21, Compound 36, Compound 48, and Compound CE were evaluated according to the method shown in Table 2, and the results thereof are shown in Table 3.
[0902] Table 2
[0903]
[0904] Table 3
[0905]
[0906]
[0907]
[0908] [Evaluation Example 2]
[0909] The CH2 Cl 2 The solution and compound 10 (4 wt % relative to PMMA) were mixed with each other, and the resulting product was then applied to a quartz substrate by using a spin coater. It was then heat-treated at 80° C. in an oven and then cooled at room temperature to prepare a film 1 having a thickness of 40 nm. Subsequently, films 2 to 5 were respectively manufactured in substantially the same manner as for the manufacture of film 1, except that compound 21, compound 36, compound 48, and compound CE were used instead of compound 10, respectively.
[0910] For each of Films 1 to 5, the emission spectrum was measured by using a Quantaurus-QY absolute PL quantum yield spectrometer manufactured by Hamamatsu (using a xenon light source, and equipped with a monochromator, a photon multi-channel analyzer and an integrating sphere, and using PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, the excitation wavelength was scanned from 320 nm to 380 nm at intervals of 10 nm, and a spectrum measured at an excitation wavelength of 340 nm was obtained, thereby obtaining the maximum emission wavelength (emission peak wavelength) and FWHM of the organic metal compound included in each film, which are shown in Table 4.
[0911] The luminescence quantum efficiency of each of Films 1 to 5 was measured by scanning the excitation wavelength from 300 nm to 380 nm at intervals of 10 nm using Hamamatsu's Quantaurus-QY absolute PL quantum yield spectrometer, and the luminescence quantum efficiency (PLQY) measured at an excitation wavelength of 330 nm was obtained, thereby obtaining the luminescence quantum efficiency of the organic metal compound included in each film and summarizing it in Table 4.
[0912] Table 4
[0913]
[0914]
[0915] As can be seen from Table 4, compared with Compound CE, Compound 10, Compound 21, Compound 36, and Compound 48 emit blue light with excellent or suitable PLQY and narrow FWHM.
[0916] Example 1
[0917] As the anode, a 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and (then) pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes.The ITO glass substrate was provided to a vacuum deposition apparatus.
[0918] 2-TNATA was vacuum deposited on an ITO substrate to form A hole injection layer having a thickness of 1000 Å was formed, and then 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) as a hole transport compound was vacuum deposited thereon to form a The hole transport layer has a thickness of .
[0919] Compound 10 in a blue fluorescent emission layer is simultaneously (e.g., concurrently) deposited on the hole transport layer at a ratio of 13 wt % together with a ETH2:HTH29 mixed host (weight ratio 3.5:6.5) to form a blue fluorescent emission layer having The thickness of the emission layer.
[0920] Then, the compound HBL-1 is vacuum deposited on the emission layer to form a Then, a mixed layer of CNNPTRZ:Liq with a weight ratio of 4.0:6.0 is deposited on the hole blocking layer to form a An electron transport layer having a thickness of , and Yb is deposited on the electron transport layer to form An electron injection layer with a thickness of 1000 mm was formed, and Mg was vacuum deposited to form a An electrode (cathode) with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0921]
[0922] Examples 2 to 6 and Comparative Example A
[0923] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compound was changed as shown in Table 5 when the emission layer was formed.
[0924] Table 5
[0925]
[0926]
[0927] [Evaluation Example 1]
[0928] The brightness of each light emitting device manufactured according to Examples 1 to 6 and Comparative Example A at 1,000 cd / m was measured by using a Keithley MU236 and a luminance meter PR650. 2The driving voltage (V), color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and lifetime (T 95 ), and the results are shown in Table 6. In this regard, the lifespan (T 95 ) is a measure of the time (hours) taken until the brightness drops to 95% of the initial brightness. In Table 6, the color conversion efficiency ratio indicates the ratio (%) of the color conversion efficiency of each example when the color conversion efficiency of Comparative Example A is set to 100, and the lifespan ratio indicates the lifespan (T) of each example when the lifespan of Comparative Example A is set to 100. 95 ) ratio (%).
[0929] Table 6
[0930]
[0931]
[0932] It can be confirmed from Table 6 that, compared with the organic light-emitting device according to Comparative Example A, the organic light-emitting devices according to Examples 1 to 6 each have a lower driving voltage, a higher color conversion efficiency, and a longer device lifespan.
[0933] By utilizing the organometallic compound of the present disclosure, a light-emitting device having a reduced driving voltage, improved color purity and / or efficiency, and / or extended lifetime and a high-quality electronic device including the light-emitting device may be manufactured.
[0934] In the present disclosure, it will be understood that the terms “include,” “comprises,” or “has” 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.
[0935] Throughout this disclosure, when it is mentioned that a component such as a layer, film, region, or plate is located "on" another component, it will be understood that the component 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 component such as a layer, film, region, plate, etc. and another 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.
[0936] 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.
[0937] Unless the context clearly indicates otherwise, as used herein, the singular forms "a", "an", "an", and "the" are intended to include the plural forms as well. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."
[0938] 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. "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 taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "approximately" may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.
[0939] Any numerical range described in this article is intended to include all sub-ranges of the same numerical precision contained in the range described. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the minimum value 1.0 described and the maximum value 10.0 described (and including 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 disclosure is intended to include all numerical upper limits included therein. Therefore, the applicant reserves the right to modify this disclosure (including claims) to explicitly describe any sub-ranges included in the range explicitly described in this article.
[0940] According to the embodiments of the present disclosure described herein, the light-emitting device, light-emitting equipment, display device, electronic device, electronic device or any other related device or component can be implemented using any suitable hardware, firmware (e.g., a dedicated integrated circuit), software or a combination of software, firmware and hardware. For example, the various components of the device can be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device can be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be processes or threads that run on one or more processors, in one or more computing devices, execute computer program instructions and interact with other system components to perform the various functions described herein. The computer program instructions are stored in a memory, which can be implemented in a computing device using a standard storage device (e.g., a random access memory (RAM)). The computer program instructions can also be stored in other non-temporary computer-readable media (e.g., a compact disc read-only memory (CD-ROM) or a flash drive, etc.). In addition, those skilled in the art should recognize that without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices can be combined or integrated into a single computing device, or the functions of a specific computing device can be distributed on one or more other computing devices.
[0941] 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, X1 to X4 are each independently C or N, CycloCY1, CycloCY2, CycloCY 31 To Ring CY 33 and ring CY4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1, L2, L 31 and L 32 Each is 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-*', *-Ge(R 1a )(R 1b )-*', unsubstituted or replaced by at least one R 10a Substituted C5-C 30 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group, * and *' each indicate a binding site to an adjacent atom, n1, n2, n31 and n32 are each independently an integer from 1 to 10, R1, R2, R 31 To R 33 , R4, R 1a and R 1b Each is 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), a1, a2, a31 to a33 and a4 are each independently an integer from 1 to 20, Selected from a1 R1, a2 R2, a31 R 31 、a32 R 32 、a33 R 33 、a4R4、R 1a and R 1b Two or more adjacent groups may be optionally combined with each other to form a group which is unsubstituted or substituted with at least one 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: hydrogen, -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, -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 or C6-C 60 Arylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; 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 Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently: 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.
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 including a heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, wherein the organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 3 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 ring-constituting atoms.
5. The light emitting device according to claim 3, wherein: The transmitting layer comprises: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound or any combination thereof, and The emitting layer is configured to emit blue light.
6. An electronic device, wherein: The electronic device includes 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.
8. The electronic device according to claim 6, wherein: The electronic device further comprises: Color filters, color conversion layers, touch screen layers, polarizing layers, or any combination thereof.
9. An electronic device, wherein: The electronic equipment includes 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, 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, wherein The organometallic compound is 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, X1 to X4 are each independently C or N, CycloCY1, CycloCY2, CycloCY 31 To Ring CY 33 and ring CY4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1, L2, L 31 and L 32 Each is 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-*', *-Ge(R 1a )(R 1b )-*', unsubstituted or replaced by at least one R 10a Substituted C5-C 30 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group, * and *' each indicate a binding site to an adjacent atom, n1, n2, n31 and n32 are each independently an integer from 1 to 10, R1, R2, R 31 To R 33 , R4, R 1a and R 1b Each is 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), a1, a2, a31 to a33 and a4 are each independently an integer from 1 to 20, Selected from a1 R1, a2 R2, a31 R 31 、a32 R 32 、a33 R 33 、a4R4、R 1a and R 1b Two or more adjacent groups may be optionally combined with each other to form a group which is unsubstituted or substituted with at least one 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: hydrogen, -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, -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 or C6-C 60 Arylthio, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; 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 Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently: 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.
12. The organometallic compound according to claim 11, wherein X1, X2 and X3 are each C, and X4 is N, The bond between X1 and M and the bond between X4 and M are each a coordination bond, and The bond between X2 and M and the bond between X3 and M are each a covalent bond.
13. The organometallic compound according to claim 11, wherein CycloCY1, CycloCY2, CycloCY 31 To Ring CY 33 and 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.
14. The organometallic compound according to claim 11, wherein In formula 1, *-(L 32 ) n32 -*'、*-(L 31 ) n31 -*', CY4, CY 32 Together with two nitrogen atoms, it forms a ring having eight or more ring atoms.
15. The organometallic compound according to claim 11, wherein L1 and L 31 Each is a single bond, L2 is *-O-*' or *-S-*', and n2 is 1, L 32 For: single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=C(R 1b )-*' or *-Si(R 1a )(R 1b )-*'; or phenylene or naphthylene, each unsubstituted or substituted by a substituted aryl group selected from deuterium, C1-C 20 Alkyl, C1-C 20 At least one of alkoxy, phenyl and naphthyl is substituted, R 1a and R 1b are each the same as defined in Formula 1, and R 1a and R 1b are optionally linked 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.
16. The organometallic compound according to claim 11, wherein R1, R2, R 31 To R 33 and R4 are each independently: Hydrogen, Deuterium, -F, C1-C 20 Alkyl or C1-C 20 Alkoxy; C1-C 20 Alkyl or C1-C 20 Alkoxy, each deuterated, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl or any combination thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl) phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl, each of which is unsubstituted or substituted with deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2), and Among them, Q1 to Q3 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; 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, C1-C 60 Alkyl, C1-C 60 The present invention is substituted with alkoxy, phenyl, biphenyl or any combination thereof.
17. The organometallic compound according to claim 11, wherein In formula 1, The group represented is a group represented by one selected from the group consisting of formula CY3(1) to formula CY3(16): And wherein, in Formula CY3(1) to Formula CY3(16), R 311 To R 314 Each of them is related to R in Formula 1 31 The same as defined, R 321 To R 324 Each of them is related to R in Formula 1 32 The same as defined, R 331 To R 336 Each of them is related to R in Formula 1 33 The same as defined, * indicates the binding site with M in Formula 1, *" indicates the binding site with L2 in Formula 1, *"' indicates the same as L in Formula 1 31 binding site, and *"" indicates the same as L in Formula 1 32 binding site.
18. The organometallic compound according to claim 11, wherein in, In formula 1, Depend on The group represented by is a group represented by one selected from the group consisting of formula CY1(1) to formula CY1(11), Depend on The group represented by is a group represented by one selected from the group consisting of formula CY2(1) to formula CY2(13), and Depend on The group represented is a group represented by one selected from the group consisting of formula CY4(1) to formula CY4(18): And wherein, in Formulas CY1(1) to CY1(11), Formulas CY2(1) to CY2(13) and Formulas CY4(1) to CY4(18), T 21 for B(Y 21 ), C(Y 21 )(Y 22 ), N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 is C(Y 21 ), N or Si(Y 21 ), R 11 To R 17 Each is the same as defined with respect to R1 in Formula 1, R 21 To R 26 , Y 21 and Y 22 Same as defined for R2 in Formula 1, R 41 To R 47 Each is the same as defined for R4 in Formula 1, * indicates the binding site with M in Formula 1, *' indicates the binding site with L1 in Formula 1, *" indicates the binding site with L2 in Formula 1, *"' indicates the same as L in Formula 1 31 binding site, and *"" indicates the same as L in Formula 1 32 binding site.
19. The organometallic compound according to claim 11, wherein The organometallic compound represented by Formula 1 is an organometallic compound represented by Formula 1A(1) or Formula 1A(2): Formula 1A (1) Formula 1A (2) And among them, In Formula 1A(1) and Formula 1A(2), M, X1 to X4, CY1, CY2, CY 31 To CY 33 ,CY4,L1,L2,L 31 ,n1,n2,n31,R1,R2,R 31 To R 33 , R4, a1, a2, a31 to a33 and a4 are the same as defined in Formula 1, T 31 To T 33 Each of them is related to L in formula 1 32 The same as defined, b31 to b33 are each independently an integer from 0 to 3, Cyclo 34 and CY 35 Each independently is C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, R 34 and R 35 Each of them is related to R in Formula 1 10a are defined the same as a34 and a35 are each independently an integer of 1 to 20.
20. The organometallic compound according to claim 11, wherein The organic metal compound represented by Formula 1 may be an organic metal compound represented by Formula 1B(1) or Formula 1B(2): Formula 1B (1) Formula 1B (2) And among them, In Formula 1B(1) and Formula 1B(2), M and L2 are each the same as defined in Formula 1, T 31 To T 33 Each of them is related to L in formula 1 32 The same as defined, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, and X 14 C(R 14 ) or N, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, and X 23 C(R 23 ) or N, X 311 C(R 311 ) or N, X 312 C(R 312 ) or N, X 321 C(R 321 ) or N, X 322 C(R 322 ) or N, X 331 C(R 331 ) or N, X 332 C(R 332 ) or N, X 333 C(R 333 ) or N, X 334 C(R 334 ) or N, X 341 C(R 341 ) or N, X 342 C(R 342 ) or N, X 343 C(R 343 ) or N, X 344 C(R 344 ) or N, X 351 C(R 351 ) or N, X 352 C(R 352 ) or N, X 353 C(R 353 ) or N, and X 354 C(R 354 ) or N, X 41 C(R 41 ) or N, X 42 C(R 42 ) or N, and X 43 C(R 43 ) or N, R 11 To R 15 Each is the same as defined with respect to R1 in Formula 1, R 21 To R 23 Each is the same as defined for R2 in Formula 1, R 311 and R 312 Each of them is related to R in Formula 1 31 The same as defined, R 321 and R 322 Each of them is related to R in Formula 1 32 The same as defined, R 331 To R 334 Each of them is related to R in Formula 1 33 The same as defined, R 341 To R 344 and R 351 To R 354 With respect to R in Formula 1 10a The same as defined, R 41 To R 43 are each the same as defined with respect to R4 in Formula 1, and Selected from R 11 To R 15 , R 21 To R 23 , R 311 , R 312 , R 321 , R 322 , R 331 To R 334 , R 341 To R 344 , R 351 To R 354 , R 41 To R 43 , R 1a and R 1b Two or more adjacent groups are optionally linked to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group.
Citation Information
Patent Citations
Sialyltransferase for the production of 6'-sialyllactose
KR1020230124995A