Light-emitting device, electronic device, electronic equipment and organometallic compound
By using organometallic compounds as the main components of the emitting layer and the intermediate layer in the light emitting device, the problems of insufficient luminescence efficiency, color purity and service life in the prior art are solved, especially under high temperature conditions, the heat resistance of the material is significantly improved.
Patent Information
- Application Number
- CN202411367436.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-06
- Filing Date
- 2024-09-29
- Publication Date
- 2025-04-08
AI Technical Summary
The existing luminescent devices have shortcomings in color purity, luminous efficiency and service life, especially in high temperature conditions, the materials have poor heat resistance.
A light emitting device structure containing an organometallic compound, wherein the emitting layer and the intermediate layer contain the organometallic compound represented by Formula 1, the luminous efficiency and color purity are improved by optimizing the structure of the electrode and the transport region, and the heat resistance of the material is enhanced by a specific combination of dopants and compounds.
It has achieved improvements in luminous efficiency, improvements in color purity and extended service life, and maintained good heat resistance under high temperature conditions.
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Figure CN119789753A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0133693 filed in the Korean Intellectual Property Office on October 6, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments of the present disclosure are directed to a light-emitting device including an organometallic compound, electronic devices and electronic equipment each including the light-emitting device, and the organometallic 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 arranged on the first electrode in sequence. Holes provided by the first electrode move toward the emission layer through the hole transport region, and electrons provided by the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state and decay to a ground state, thereby generating light. Summary of the invention
[0006] One or more aspects of an embodiment of the present disclosure relate to a light-emitting device including an organometallic compound, electronic devices and electronic equipment each including the light-emitting device, and the organometallic 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 learned by practice of the presented embodiments of the disclosure.
[0008] According to one or more embodiments of the present disclosure, a light emitting device comprises:
[0009] a first electrode;
[0010] a second electrode facing (e.g., opposite to and 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] Formula 1A
[0016]
[0017] Among them, in formula 1,
[0018] 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),
[0019] X 1 Can be N, and X 2 It can be C,
[0020] Cyclo 1 and CY 2 Can be C independently 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,
[0021] L 1 and L 2 can each independently be a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*', and * and *' each represent a binding site with an adjacent atom,
[0022] n1 and n2 can each independently be an integer from 1 to 5,
[0023] R 1 To R 7 , R 1a and R 1b can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0024] a1 and a2 can each independently be an integer from 1 to 20,
[0025] a3, a4, a6 and a7 may each independently be an integer from 1 to 3,
[0026] a5 can be an integer from 1 to 4,
[0027] Ar 1 and Ar 2 may each independently be a group represented by Formula 1A,
[0028] Wherein, in Formula 1A,
[0029] Y 1 To Y 3 , Z 1 and Z 2 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0030] Z 1 and Z 2 At least one of may be unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl groups,
[0031] * indicates the binding site with the adjacent atom in Formula 1,
[0032] Select from a1 R 1 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0033] Select from a2 R 2 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0034] Select from a3 R 3 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0035] Select from a4 R 4 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0036] Select from a5 R 5 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0037] Select from a6 R 6 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0038] Select from a7 R 7 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0039] R 1a and R 1b Optionally combine with each other to form unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0040] Selected from R 1 To R 7 , R 1a , R 1b ,Ar 1 and Ar 2 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0041] R 10a It can be:
[0042] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
[0043] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups;
[0044] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 a heteroarylalkyl group; or
[0045] -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 ),in
[0046] Q 1 To Q 3 , Q11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group or a combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 Heteroarylalkyl groups.
[0047] According to one or more than one embodiments of the present disclosure, an electronic device includes the light emitting device.
[0048] According to one or more embodiments of the present disclosure, electronic equipment includes the light emitting device.
[0049] According to one or more than one embodiments of the present disclosure, the organometallic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0050] 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 serve to explain the principles of the present disclosure. The above and other aspects, features and advantages of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0051] Figure 1 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0052] Figure 2is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0053] Figure 3 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure; and
[0054] Figure 4 , Figure 5 , Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of the structure of an electronic device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0055] Now will be more detailed with reference to embodiment, the example of described embodiment is illustrated in the accompanying drawings, wherein same reference numerals refer to same elements throughout the present disclosure, and for the sake of simplicity, its repeated description may not be provided.In this regard, the embodiment presented may have different forms and should not be construed as being limited to the description set forth herein.Therefore, by referring to the accompanying drawings, only the embodiment of the present disclosure is described, to explain the aspect of the present disclosure.As used herein, the term "and / or" or "or" may include any combination and all combinations of one or more than one of the related listed items.Throughout the present disclosure, the expression such as "at least one (kind) in ... ", "one (kind) in ... " and "selected from " when before a column of elements, modify the elements of the entire column and do not modify the single element of the column. For example, "at least one of a, b, and c", "at least one selected from a, b, and c", "at least one selected from a to c", etc. can mean only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all of a, b, and c, or variations thereof. The " / " used herein can be interpreted as "and" or "or" depending on the circumstances.
[0056] According to one or more embodiments of the present disclosure, a light emitting device may include:
[0057] a first electrode;
[0058] a second electrode facing (e.g., opposite to and facing) the first electrode;
[0059] an intermediate layer between the first electrode and the second electrode and including an emission layer; and
[0060] An organometallic compound represented by Formula 1:
[0061] Formula 1
[0062]
[0063] Details regarding Formula 1 may be the same as described herein.
[0064] In one or more than one embodiments,
[0065] The first electrode of the light emitting device may be an anode,
[0066] The second electrode of the light emitting device may be a cathode,
[0067] The intermediate layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
[0068] 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
[0069] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0070] In one or more than one embodiments, the intermediate layer of the light-emitting device may include the organometallic compound represented by Formula 1 (eg, as a first compound).
[0071] In one or more than one embodiments, the emission layer of the light emitting device may include the organometallic compound represented by Formula 1.
[0072] In one or more than one embodiments, the emission layer of the light emitting device may include a dopant and a host, and the organometallic compound represented by Formula 1 may be included in the dopant. For example, in some embodiments, the organometallic compound may act as a dopant. For example, in some embodiments, the emission layer may be intended to emit blue light. The blue light may have a maximum emission wavelength of, for example, about 430 nm to about 480 nm.
[0073] 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 emissive layer.
[0074] In one or more embodiments, the light emitting device may further include at least one π-electron-deficient nitrogen-containing C 1 -C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
[0075] 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:
[0076] Formula 3
[0077]
[0078] Among them, in formula 3,
[0079] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0080] X 71 can be a single bond or a linking group comprising O, S, N, B, C, Si or any combination thereof, and
[0081] * represents a bonding site with any atom included in the remaining part other than the group represented by Formula 3 in the third compound.
[0082] In one or more than one embodiment, the organometallic compound may comprise at least one deuterium.
[0083] In one or more than one embodiments, the second compound, the third compound, and the fourth compound can each comprise at least one deuterium.
[0084] In one or more embodiments, the second compound may include at least one silicon.
[0085] In one or more than one embodiment, the third compound may include at least one silicon.
[0086] In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the light-emitting device may further include a second compound and a third compound, wherein at least one of the second compound and the third compound may include at least one deuterium, at least one silicon, or any combination thereof.
[0087] 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 include a second compound. At least one of 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 in the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof.
[0088] In one or more than one 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 of 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.
[0089] In one or more than one 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 of the organometallic compound and the fourth compound may include at least one deuterium. The fourth compound can be used to improve the color purity, luminous efficiency and service 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 in the light-emitting device) may further include a second compound, a third compound, or any combination thereof.
[0090] In one or more than one embodiment, 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.
[0091] In one or more embodiments, the emission layer of the light emitting device may include: i) an organometallic compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof, and the emission layer may be designed to emit blue light.
[0092] In one or more embodiments, the maximum emission wavelength of blue light can be 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.
[0093] In one or more than one embodiment, the second compound can include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
[0094] In one or more than one embodiment, the following compounds may be excluded from the third compound:
[0095]
[0096] In one or more embodiments, the difference between the triplet energy level (eV) of the fourth compound and the singlet energy level (eV) of the fourth compound can be about 0 eV or more and about 0.5 eV or less (or about 0 eV or more and about 0.3 eV or less).
[0097] In one or more than one embodiments, the fourth compound may be a compound including at least one cyclic group containing each of boron (B) and nitrogen (N) as a ring-forming atom.
[0098] In one or more than one embodiments, the fourth compound can be a C-containing fused cyclic group comprising at least two fused cyclic groups (eg, one is the first ring and the other is the second ring) sharing a common boron atom (B). 8 -C 60 Polycyclic compounds.
[0099] In one or more than one embodiment, the fourth compound may comprise a fused ring, wherein at least one third ring may be fused to at least one fourth ring, for example to form a fused ring comprising four or more rings,
[0100] The third ring of the fourth compound may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group, and
[0101] The fourth ring of the fourth compound may be a 1,2-azaborinyl group, a 1,3-azaborinyl group, a 1,4-azaborinyl group, a 1,2-dihydro-1,2-azaborinyl group, a 1,4-oxaborinyl group, a 1,4-thiaborinyl group, or a 1,4-dihydroborinyl group.
[0102] In one or more than one embodiments, the third compound may not include (eg, may exclude) (eg, any) compound represented by Formula 3-1 described in the disclosure.
[0103] In one or more than one embodiments, the second compound may include a compound represented by Formula 2:
[0104] Formula 2
[0105]
[0106] In formula 2,
[0107] L 51 To L 53 may be independently a single bond, unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0108] b51 to b53 may each independently be an integer from 1 to 5,
[0109] X 54 Can be N or C (R 54 ), X 55 Can be N or C (R 55 ), X 56 Can be N or C (R 56 ), and selected from X 54 To X 56 At least one of may be N,
[0110] R 51 To R 56 and R 10a Each may be the same as described in the present disclosure, respectively.
[0111] In one or more than one embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0112] Formula 3-1
[0113]
[0114] Formula 3-2
[0115]
[0116] Formula 3-3
[0117]
[0118] Formula 3-4
[0119]
[0120] Formula 3-5
[0121]
[0122] Among them, in Formula 3-1 to Formula 3-5,
[0123] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 a cyclic group or a pyridine group,
[0124] 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 ),
[0125] 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 ),
[0126] X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ), X 85 Can be C or Si,
[0127] L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted divalent π-electron-rich C 3 -C 60 Cyclic groups, either unsubstituted or substituted with at least one R 10a A substituted pyridinylene group wherein Q 4 and Q 5Each can be referred to by referring to the Q 1 The description of * and *' each represents a binding site with an adjacent atom.
[0128] b81 to b85 may each independently be an integer from 1 to 5,
[0129] 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 disclosure,
[0130] a71 to a74 may each independently be an integer from 0 to 20, and
[0131] R 10a Can be the same as described herein.
[0132] In some embodiments, the fourth compound can be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0133] Formula 502
[0134]
[0135] Formula 503
[0136]
[0137] Among them, in equation 502 and equation 503,
[0138] Ring A 501 To Ring A 504 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0139] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0140] Y 506 Can be O, S, N (R 506)、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0141] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0142] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ), Y 51 and Y 52 may be each independently B, P(=O) or S(=O),
[0143] R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b may each be the same as described in the present disclosure, and
[0144] a501 to a504 may each independently be an integer of 0 to 20.
[0145] In one or more than one embodiments, the light emitting device may satisfy at least one selected from Conditions 1 to 4:
[0146] Condition 1
[0147] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound > the LUMO energy level (eV) of the organometallic compound
[0148] Condition 2
[0149] LUMO energy level of the organometallic compound (eV) > LUMO energy level of the second compound (eV)
[0150] Condition 3
[0151] 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.
[0152] Condition 4
[0153] HOMO energy level of the third compound (eV)>HOMO energy level of the second compound (eV)
[0154] Each of the HOMO energy level and the LUMO energy level of each of the organometallic compound, the second compound, and the third compound may be a negative value, and may be measured according to an appropriate method.
[0155] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the second compound may be about 0.1 eV or more and about 1.0 eV or less, the absolute value of the difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the third compound may be about 0.1 eV or more and about 1.0 eV or less, the absolute value of the difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the second compound may be about 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or more), and / or the absolute value of the difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the third compound may be about 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or more).
[0156] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions as described above, a balance between holes and electrons injected into the emission layer can be achieved.
[0157] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0158] First embodiment
[0159] According to a first embodiment, the organometallic compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may further include a host, the organometallic compound may be different from the host, and the emission layer may be intended to emit phosphorescence or fluorescence emitted from the organometallic compound. For example, according to a first embodiment, the organometallic compound may be a dopant or an emitter. In one or more than one embodiments, the organometallic compound may be a phosphorescent dopant or a phosphorescent emitter.
[0160] The phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
[0161] In one or more than one embodiments, the emission layer may further include an auxiliary dopant. The auxiliary dopant may improve the luminous efficiency of the organometallic compound by efficiently transferring energy to the organometallic compound as a dopant or an emitter.
[0162] The auxiliary dopant may be different from the organometallic compound and the host.
[0163] In one or more embodiments, the auxiliary dopant may be a delayed fluorescent compound.
[0164] In some embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0165] Second embodiment
[0166] According to a second embodiment, the organic metal compound may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may further include a host and a dopant, the organic metal compound, the host and the dopant may be different from each other, and the emission layer may be intended to emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
[0167] In one or more than one embodiment, the organometallic compound in the second embodiment may be used not as a dopant but as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0168] In one or more than one embodiment, the organometallic compound of the second embodiment can function as an emitter and also as an auxiliary dopant that transfers energy to the dopant (or emitter).
[0169] For example, in some embodiments, the phosphorescence or fluorescence emitted by the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0170] 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).
[0171] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength of about 390 nanometers (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.
[0172] The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0173] The host in the first and second embodiments may be any host material (eg, a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof).
[0174] In one or more than one embodiments, the host in the first embodiment and the second embodiment can be the second compound, the third compound, or any combination thereof.
[0175] In one or more than one 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).
[0176] In one or more embodiments, the light emitting device may further include at least one of a first covering layer located outside the first electrode (e.g., on the first electrode) and a second covering layer located outside the second electrode (e.g., on the second electrode), and the organic metal compound represented by Formula 1 may be included in at least one of the first covering layer and the second covering layer. The first covering layer and / or the second covering layer may each be the same as described herein.
[0177] In one or more than one embodiments, the light emitting device may further comprise:
[0178] a first covering layer disposed outside the first electrode (eg, on the first electrode) and including an organic metal compound represented by Formula 1;
[0179] a second covering layer disposed outside the second electrode (eg, on the second electrode) and including the organic metal compound represented by Formula 1; or
[0180] A first covering layer and a second covering layer.
[0181] The expression "(the intermediate layer and / or the covering layer) contains at least one organometallic compound represented by Formula 1" as used herein may be interpreted to mean "(the intermediate layer and / or the covering layer) may contain one organometallic compound represented by Formula 1 or two or more different organometallic compounds each represented by Formula 1".
[0182] In one or more embodiments, the intermediate layer and / or the covering layer may contain only compound 1 as an organic metal compound. In this regard, compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the intermediate layer may contain compound 1 and compound 2 as organic metal compounds. In this regard, compound 1 and compound 2 may be present in substantially the same layer (e.g., both compound 1 and compound 2 (e.g., simultaneously) may be present in the emission layer), or may be present in different layers (e.g., compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport region).
[0183] 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.
[0184] According to one or more embodiments of the present disclosure, the electronic device may include a light emitting device. In one or more embodiments, the electronic device may further include a thin film transistor. For example, in some embodiments, the electronic device may further include a thin film transistor, the thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically coupled to the source electrode or the drain electrode. In some embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For more details of the electronic device, reference may be made to the description provided herein.
[0185] According to one or more embodiments of the present disclosure, electronic equipment may include a light emitting device.
[0186] For example, the electronic equipment may include (e.g., may be) at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a signal light, a head-up display, a fully transparent display or a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a portable phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display or an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen or a stadium screen, a light therapy device, and a sign.
[0187] According to one or more than one 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.
[0188] By referring to the synthesis examples and / or embodiments described herein, one of ordinary skill in the art can easily understand methods for synthesizing organometallic compounds.
[0189] Description of Formula 1 and Formula 1A
[0190] Formula 1
[0191]
[0192] In Formula 1, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
[0193] In one or more than one embodiments, M may be platinum (Pt), palladium (Pd), or gold (Au).
[0194] In one or more than one embodiments, M may be Pt.
[0195] Regarding formula 1, X 1 Can be N, and X 2 It can be C.
[0196] Ring CY in Formula 1 1 and CY 2 Can be C independently 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.
[0197] In one or more than one embodiment, CY 1 and CY 2 Can be independently:
[0198] Benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzothioole group, a dibenzothioole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothioole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group The invention also includes but is not limited to: an azole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasilinyl group, a dibenzothiasilinyl group, a dibenzodihydroazasilinyl group, a dibenzodihydrodisilinyl group, a dibenzodihydrosilinyl group, a dibenzodioxinyl group, a dibenzooxathiainyl group, a dibenzoxazine group, a dibenzopyran group, a dibenzodithiainyl group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group or a dibenzodihydropyrazine group.
[0199] In one or more than one embodiment, CY 1 Can be nitrogen-containing C 1 -C 60 Heterocyclic group.
[0200] In one or more than one embodiment, CY 1 It may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a benzopyrazole group, a benzimidazole group or a benzothiazole group.
[0201] In one or more than one embodiment, CY 2 Can be C 2 -C 8 A monocyclic group; or two or three C 2 -C 8 Monocyclic groups fused to each other C 4 -C 20 Polycyclic groups.
[0202] In one or more than one embodiment, CY 2It may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group or an azadibenzosilole group.
[0203] L in Formula 1 1 and L 2 can each independently be a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*'、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*', and * and *' each represent a binding site with an adjacent atom.
[0204] In formula 1, n1 and n2 can represent L 1 The number and L 2 The number of L can be independently an integer from 1 to 5. When n1 is 2 or more, two or more L 1 may be the same as or different from each other, and when n2 is 2 or greater than 2, two or more L 2 May be the same as or different from each other.
[0205] R 1a and R 1b can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -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 ).
[0206] R 10a and Q 1 To Q 3 Can be the same as described herein.
[0207] In one or more than one embodiment, R 1a and R 1b may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups
[0208] R 10a Can be the same as described herein.
[0209] In one or more than one embodiment, R 1a and R 1b Can be independently:
[0210] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0211] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0212] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a an oxazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilyl group; or
[0213] -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 ),
[0214] Where Q 1 To Q 3 and Q 31 To Q 33 may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C 1 -C 60 Alkyl group, C 1 -C 60Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0215] In one or more than one embodiment, L 1 Can be a single bond.
[0216] In one or more than one embodiment, L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0217] In an embodiment, L 1 can be a single bond, and L 2 It may be *-O-*' or *-S-*', and n2 may be 1. * and *' each represent a binding site with an adjacent atom.
[0218] R in Formula 1 1 To R 7 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -C(Q1 )(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 ).
[0219] R 10a and Q 1 To Q 3 Can be the same as described herein.
[0220] a1 to a7 in Formula 1 represent R 1 The number of R 7 , and a1 and a2 may each independently be an integer of 1 to 20, and a3, a4, a6 and a7 may each independently be an integer of 1 to 3, and a5 may be an integer of 1 to 4. When a1 is 2 or more, two or more R 1 may be the same as or different from each other. When a2 is 2 or greater than 2, two or more R 2 may be the same as or different from each other. When a3 is 2 or greater than 2, two or more R 3 may be the same as or different from each other. When a4 is 2 or greater than 2, two or more R 4 may be the same as or different from each other. When a5 is 2 or greater than 2, two or more R 5 may be the same as or different from each other. When a6 is 2 or greater than 2, two or more R 6 may be the same as or different from each other, and when a7 is 2 or greater, two or more R 7 May be the same as or different from each other.
[0221] In one or more than one embodiment, selected from a1 R 1 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0222] In one or more than one embodiment, selected from a2 R 2 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0223] In one or more than one embodiment, selected from a3 R 3 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0224] In one or more than one embodiment, selected from a4 R 4 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0225] In one or more than one embodiment, selected from a5 R 5 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0226] In one or more than one embodiment, selected from a6 R 6 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1 -C 60 Heterocyclic group.
[0227] In one or more than one embodiment, selected from a7 R 7 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0228] R 10a Can be the same as described herein.
[0229] In one or more than one embodiment, R 1 To R 7 Can be independently:
[0230] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0231] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0232] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C 1 -C 10alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a an oxazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilyl group; or
[0233] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0234] Where Q 1 To Q 3 and Q 31 To Q 33 may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy groups; or each unsubstituted or substituted with deuterium, -F, cyano groups, C 1 -C 60Alkyl group, C 1 -C 60 Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0235] In one or more than one embodiment, R 1 To R 7 Can be independently:
[0236] Hydrogen, deuterium, -F, -Cl, -Br, -I or C 1 -C 20 Alkyl groups;
[0237] Unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 an alkyl group; or
[0238] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, pyridyl group, pyrimidinyl group, (C 1 -C 10 alkyl)phenyl group or any combination thereof substituted phenyl group, biphenyl group, terphenyl group, (C 1 -C 10 alkyl)phenyl group or naphthyl group.
[0239] Ar in Formula 1 1 and Ar 2 may each independently be a group represented by Formula 1A:
[0240] Formula 1A
[0241]
[0242] Y in Formula 1A 1 To Y 3 , Z 1 and Z 2 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -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 Can be the same as described herein.
[0243] In one or more than one embodiment, Y 1 To Y 3 , Z 1 and Z 2 Can be independently:
[0244] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0245] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0246] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a an oxazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilyl group; or
[0247] -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 ),
[0248] Where Q 1 To Q 3 and Q 31 To Q 33 can each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group or a combination thereof3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0249] In one or more than one embodiment, Y 1 To Y 3 , Z 1 and Z 2 Can be independently:
[0250] Hydrogen, deuterium, -F, -Cl, -Br, -I or C 1 -C 20 Alkyl groups;
[0251] Unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 an alkyl group; or
[0252] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, pyridyl group, pyrimidinyl group, (C 1 -C 10 alkyl)phenyl group or any combination thereof substituted phenyl group, biphenyl group, terphenyl group, (C 1 -C 10 alkyl)phenyl group or naphthyl group.
[0253] Z in Formula 1A 1 or Z 2At least one of may be unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl group.
[0254] In one or more than one embodiment, Z 1 or Z 2 At least one of can be:
[0255] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group or a tert-pentyl group, each of which is unsubstituted or substituted with at least one deuterium.
[0256] In one or more than one embodiment, Z 1 or Z 2 At least one of the may be a tert-butyl group.
[0257] In one or more than one embodiment, Z 1 and Z 2 (e.g., selected from Z 1 and Z 2 ) one of which may be an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group or a tert-pentyl group, each of which is unsubstituted or substituted with at least one deuterium,
[0258] Z 1 and Z 2 (e.g., selected from Z 1 and Z 2 The other of the two may be neither hydrogen nor deuterium.
[0259] In one or more than one embodiment, Z 1 and Z 2 (e.g., selected from Z 1 and Z 2 ) one of which may be an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group or a tert-pentyl group, each of which is unsubstituted or substituted with at least one deuterium, and
[0260] Z 1 and Z 2 (e.g., selected from Z 1 and Z 2 The other of them may be unsubstituted or substituted with deuterium, C 1 -C 20an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group or a pyrimidyl group substituted with an alkyl group or any combination thereof.
[0261] In one or more than one embodiment, Y 1 To Y 3 may each independently be hydrogen or deuterium.
[0262] The * in Formula 1A represents a binding site with an adjacent atom in Formula 1.
[0263] In one or more than one embodiment, selected from R 1 To R 7 , R 1a , R 1b ,Ar 1 and Ar 2 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group. 10a Can be the same as described herein.
[0264] In one or more than one embodiment, the The group represented by may be a group represented by one selected from CY1(1) to CY1(29):
[0265]
[0266]
[0267]
[0268] Among them, in formula CY1(1) to formula CY1(29),
[0269] R 11 To R 17 can be independently compared with R 1 Same as described,
[0270] * represents the binding site with M in Formula 1, and
[0271] *' represents the L in formula 1 1 binding site.
[0272] In one or more than one embodiment, in Formula 1, The group represented may be a group represented by one selected from the group consisting of formula CY2(1) to formula CY2(25):
[0273]
[0274]
[0275] Among them, in formula CY2(1) to formula CY2(25),
[0276] T 21 It can be B(Y 21 )、C(Y 21 )(Y 22 )、N(Y 21 ), O, S or Si(Y 21 )(Y 22 ),
[0277] T 22 It can be C(Y 21 ), N or Si(Y 21 ),
[0278] R 21 To R 26 , Y 21 and Y 22 can be independently compared with R 2 Same as described,
[0279] * represents the binding site with M in Formula 1,
[0280] *' represents the L in formula 1 1 The binding site
[0281] *" indicates the same as L in Formula 1 2 binding site.
[0282] In one or more than one embodiment, the organometallic compound may be represented by Formula 1-1 or Formula 1-2:
[0283] Formula 1-1
[0284]
[0285] Formula 1-2
[0286]
[0287] Among them, in formula 1-1 and formula 1-2,
[0288] M, Ar 1 and Ar2 may each independently be the same as described herein,
[0289] L 2 It can be *-O-*' or *-S-*', where * and *' each represent the binding site with the adjacent atom.
[0290] X 11 It can be C(R 11 ) or N, X 12 It can be C(R 12 ) or N, X 13 It can be C(R 13 ) or N, and X 14 It can be C(R 14 ) or N,
[0291] X 21 It can be C(R 21 ) or N, X 22 It can be C(R 22 ) or N, X 23 It can be C(R 23 ) or N, X 24 It can be C(R 24 ) or N, X 25 It can be C(R 25 ) or N, X 26 It can be C(R 26 ) or N,
[0292] X 31 It can be C(R 31 ), X 32 It can be C(R 32 ), X 33 It can be C(R 33 ),
[0293] X 41 It can be C(R 41 ), X 42 It can be C(R 42 ), and X 43 It can be C(R 43 ),
[0294] X 51 It can be C(R 51 ), X 52 It can be C(R 52 ), X 53 It can be C(R 53 ), X 54 It can be C(R 54 ),
[0295] X 61It can be C(R 61 ), X 62 It can be C(R 62 ), X 63 It can be C(R 63 ),
[0296] X 71 It can be C(R 71 ), X 72 It can be C(R 72 ), and X 73 It can be C(R 73 ),
[0297] R 11 To R 14 can be independently compared with R 1 Same as described,
[0298] R 21 To R 26 can be independently compared with R 2 Same as described,
[0299] R 31 To R 33 can be independently compared with R 3 Same as described,
[0300] R 41 To R 43 can be independently compared with R 4 Same as described,
[0301] R 51 To R 54 can be independently compared with R 5 Same as described,
[0302] R 61 To R 63 can be independently compared with R 6 Same as described,
[0303] R 71 To R 73 can be independently compared with R 7 Same as described,
[0304] Selected from R 11 To R 14 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1-C 60 Heterocyclic groups,
[0305] Selected from R 21 To R 26 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0306] Selected from R 31 To R 33 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0307] Selected from R 41 To R 43 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0308] Selected from R 51 To R 54 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0309] Selected from R 61 To R 63 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10aSubstituted C 1 -C 60 Heterocyclic groups,
[0310] Selected from R 71 To R 73 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0311] Selected from R 11 To R 14 , R 21 To R 26 , R 31 To R 33 , R 41 To R 43 , R 51 To R 54 , R 61 To R 63 , R 71 To R 73 ,Ar 1 and Ar 2 Two or more adjacent groups in the formula (R) may optionally be combined with each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups, and
[0312] R 10a Same as described in this article.
[0313] In the organometallic compound represented by Formula 1, the terphenyl group is bonded to the benzimidazole group in the ortho-ortho-ortho structure, and each of the substituents Ar represented by Formula 1A 1 and Ar 2 Located on the two benzene rings contained in the terphenyl group. Therefore, when the organometallic compound is used in an electronic device (e.g., an organic light-emitting device, especially an emission layer of an organic light-emitting device), the color purity and luminous efficiency are improved, the service life is increased, and the heat resistance of the material is greatly improved. Therefore, high-quality electronic devices can be manufactured.
[0314] Other descriptions
[0315] Formula 2
[0316]
[0317] L in Formula 2 51 To L 53 may be independently a single bond, unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0318] b51 to b53 in Formula 2 represent L 51 Quantity to L 53 When b51 is 2 or more, two or more L 51 can be the same or different from each other. When b52 is 2 or greater than 2, two or more L 52 may be the same as or different from each other, and when b53 is 2 or greater, two or more L 53 In some embodiments, b51 to b53 may each independently be 1 or 2.
[0319] In one or more than one embodiment, L in Formula 2 51 To L 53 Can be independently:
[0320] a single key; or
[0321] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazine group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzosilyl group, a dimethyldibenzosilyl group, a diphenyldibenzosilyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazolyl group a divalent group selected from the group consisting of a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasilinyl group, a dibenzothiasilinyl group, a dibenzodihydroazasilinyl group, a dibenzodihydrodisilinyl group, a dibenzodioxasilinyl group, a dibenzoxathiasilinyl group, a dibenzoxazine group, a dibenzopyranyl group, a dibenzodithiainyl group, a dibenzothiazine group, a dibenzothiopyranyl group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group or a dibenzodihydropyrazine group,
[0322] Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0323] In one or more than one embodiment, in Formula 2, L 51 With R 51 The key between 52 With R 52 The key between 53 With R 53 The key between the two L51 The key between the two L 52 The key between the two L 53 The bond between 51 With X 54 and X 55 The bonds between the carbons, L in Formula 2 52 With X 54 and X 56 The bonds between the carbons, and L in Formula 2 53 With X 55 and X 56 The bonds between the carbon atoms in the carbon atoms may each be a "carbon-carbon single bond".
[0324] In formula 2, X 54 Can be N or C (R 54 ), X 55 Can be N or C (R 55 ), X 56 Can be N or C (R 56 ), and selected from X 54 To X 56 At least one of may be N. R 54 To R 56 Can be independently the same as described herein. In one or more than one embodiment, selected from X 54 To X 56 Two or three of them can be N.
[0325] R in Formula 2 51 To R 56 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroarylalkyl group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 and R 10a Each may be the same as described herein.
[0326] In one or more than one embodiment, R in Formula 2 51 To R 56 Can be independently:
[0327] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0328] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0329] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, , benzofuranyl group, benzothiophenyl group, benzothiazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazine group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazolyl group, imidazolyl group, imidazolyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q31 )(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 substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilyl group, or a group represented by Formula 91; or
[0330] -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 ),
[0331] Where Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0332] -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
[0333] Each is unsubstituted or substituted with deuterium, C 1 -C 10 An n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, pyridyl group, pyrimidyl group, pyridazinyl group, pyrazinyl group or triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group, or any combination thereof:
[0334] Formula 91
[0335]
[0336] Among them, in formula 91,
[0337] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,
[0338] 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,
[0339] R 10a can be the same as described herein, and
[0340] *Indicates the binding site with the adjacent atom.
[0341] For example, in one or more than one embodiments, in Formula 91,
[0342] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a a substituted phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group or a triazine group,
[0343] R 91 , R 91a and R 91b Can be independently:
[0344] Hydrogen or C 1 -C 10 an alkyl group; or
[0345] Each is unsubstituted or replaced by deuterium, C 1 -C 10 A phenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, or any combination thereof.
[0346] In one or more than one embodiment, the *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented may each be other than a phenyl group.
[0347] In one or more than one embodiment, the *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented may be the same as each other.
[0348] In one or more than one embodiment, the *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented may be different from each other.
[0349] In one or more than one embodiment, b51 and b52 in Formula 2 may be 1, 2 or 3, and L 51 and L 52 may be each independently unsubstituted or substituted with at least one R 10a A divalent group of a substituted phenyl group, pyridine group, pyrimidine group, pyridazine group, pyrazine group or triazine group.
[0350] In one or more than one embodiment, R in Formula 2 51 and R 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),as well as
[0351] Q 1 To Q 3 may be each independently unsubstituted or substituted with deuterium, -F, a cyano group, C 1 -C 60Alkyl group, C 1 -C 60 Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group. 10a Can be the same as described herein.
[0352] In one or more than one embodiments,
[0353] 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
[0354] 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
[0355] In formula 2, *-(L 53 ) b53 -R 53 The group represented by may be a group represented by one selected from the group consisting of Formula CY53-1 to Formula CY53-27, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 )(Q 1 To Q 3 Can be the same as described in this article):
[0356]
[0357]
[0358]
[0359] 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,
[0360] 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 ),
[0361] 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 ),
[0362] 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 ),
[0363] Y in formula CY51-16 and formula CY51-17 63 and Y 64 Each of may not be a single bond at the same time,
[0364] Y in formula CY52-16 and formula CY52-17 67 and Y 68 Each of may not be a single bond at the same time,
[0365] R 51a To R 51e , R 61 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 Each of them may not be hydrogen,
[0366] R 52a To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R68b Each can be referenced by R 52 description to understand, and R 52a To R 52e Each of them may not be hydrogen,
[0367] 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 each be other than hydrogen, and
[0368] *Indicates the binding site with the adjacent atom.
[0369] For example, in one or more than one embodiments,
[0370] In Formula CY51-1 to Formula CY51-26 and Formula CY52-1 to Formula 52-26, R 51a To R 51e and R 52a To R 52e Can be independently:
[0371] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a benzoimidazole group, a benzofuranyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzothiophenyl group, a benzoisobutyl group, a benzo a thiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, or a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilyl group, or a group represented by Formula 91; or
[0372] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ).
[0373] Where Q 1 To Q3 may be each independently unsubstituted or substituted with deuterium, C 1 -C 10 an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group substituted with any combination thereof,
[0374] 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
[0375] 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.
[0376] Formula 3
[0377]
[0378] 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 pyridine group.
[0379] X in Formula 3 71 It can be a single bond or a linking group comprising O, S, N, B, C, Si or any combination thereof.
[0380] * in Formula 3 represents a bonding site with any atom included in the remaining portion other than the group represented by Formula 3 in the third compound.
[0381] Formula 3-1
[0382]
[0383] Formula 3-2
[0384]
[0385] Formula 3-3
[0386]
[0387] Formula 3-4
[0388]
[0389] Formula 3-5
[0390]
[0391] 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 pyridine group.
[0392] 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 ).
[0393] 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 ).
[0394] 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 ).
[0395] X in Formula 3-1 to Formula 3-5 85 It can be C or Si.
[0396] L in Formula 3-1 to Formula 3-5 81 To L85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted divalent π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a Substituted pyridinylene group. * and *' each represent a bonding site to an adjacent atom.
[0397] Q 4 and Q 5 You can each share your experience with Q 1 Same as described.
[0398] b81 to b85 in Formula 3-1 to Formula 3-5 may each independently be an integer of 1 to 5.
[0399] 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.
[0400] a71 to a74 in Formula 3-1 to Formula 3-5 represent R 71 The number of R 74 and may be independently 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 than 2, two or more R 72 can be the same as or different from each other. When a73 is 2 or greater than 2, two or more R 73 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 each independently be an integer from 0 to 8.
[0401] R 10a Can be the same as described herein.
[0402] In one or more than one embodiment, in Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0403] a single key; or
[0404] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*', * and *' each represent a binding site with an adjacent atom; or
[0405] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazine group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzosilyl group, a dimethyldibenzosilyl group, a diphenyldibenzosilyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or a combination thereof substituted with a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, group, cyclopentadiene group, furan group, thiophene group, silole group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzosilole group, dibenzosilole group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, pyridine group, pyrimidine group, pyrazine group a divalent group selected from the group consisting of a benzopyrazole group, a benzoimidazole group, a benzoxazole group, a benzothiazole group, a benzooxadiazole group, or a benzothiadiazole group,
[0406] Where Q 4 , Q 5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0407] In one or more than one embodiment, the 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
[0408] In formula 3-1 and formula 3-3, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-2(1) to Formula CY71-2(8), and / or
[0409] In formula 3-2 and formula 3-4, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-3(1) to Formula CY71-3(32), and / or
[0410] In formula 3-3 to formula 3-5, The group represented by may be a group represented by one selected from the group consisting of Formula CY71-4(1) to Formula CY71-4(32), and / or
[0411] In formula 3-5, The group represented may be a group represented by one selected from the group consisting of formula CY71-5(1) to formula CY71-5(8):
[0412]
[0413]
[0414]
[0415]
[0416] 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),
[0417] X 81 To X 85 , L 81 ,b81,R 81 and R 85 may each be the same as described herein,
[0418] X 86 Can be single bond, O, S, N(R 86 )、B(R 86 )、C(R 86a )(R 86b ) or Si(R 86a )(R 86b ), X 87 Can be single bond, O, S, N(R 87 )、B(R 87 )、C(R 87a )(R 87b ) or Si(R 87a )(R 87b ),
[0419] In Formula CY71-1(1) to Formula CY71-1(8) and Formula CY71-4(1) to Formula CY71-4(32), X 86 and X 87 Each of may not be a single bond at the same time,
[0420] 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(R89 )、B(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0421] In Formulas CY71-2(1) to CY71-2(8), Formulas CY71-3(1) to CY71-3(32), and Formulas CY71-5(1) to CY71-5(8), X 88 and X 89 Each of may not be a single bond at the same time, and
[0422] 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.
[0423] Formula 502
[0424]
[0425] Formula 503
[0426]
[0427] Ring A in Formula 502 and Formula 503 501 To Ring A 504 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0428] 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 ).
[0429] Y in Equation 502 and Equation 503 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R506b ) or Si(R 506a )(R 506b ).
[0430] 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 ).
[0431] 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 ).
[0432] Y in Equation 502 and Equation 503 51 and Y 52 Each may independently be B, P(═O) or S(═O).
[0433] 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 Can be the same as described herein.
[0434] a501 to a504 in Formula 502 and Formula 503 represent R 501 The number of R 504 The number of R and R can be independently an integer from 0 to 20. When a501 is 2 or greater, two or more R 501 can be the same or different from each other. When a502 is 2 or greater than 2, two or more R 502 can be the same or different from each other. When a503 is 2 or greater than 2, two or more R 503 can be the same or different from each other, and when a504 can be 2 or greater than 2, two or more R 504In some embodiments, a501 to a504 may each independently be an integer from 0 to 8.
[0435] 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, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C 7 -C60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroarylalkyl group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 and R 10a Each may be the same as described herein.
[0436] In one or more than one embodiments, i) R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a 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:
[0437] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0438] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0439] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, , benzofuranyl group, benzothiophenyl group, benzothiazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazine group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazolyl group, imidazolyl group, imidazolyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilyl group, or a group represented by Formula 91; or
[0440] -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 ),
[0441] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0442] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0443] Each is unsubstituted or substituted with deuterium, C 1 -C 10 An n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group or a combination thereof.
[0444] In one or more than one embodiment, i) R in Formula 1 1 To R 7 , Y in Formula 1A 1 To Y 3 , Z 1 and Z 2 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:
[0445] Hydrogen, deuterium, -F, cyano group, nitro group, -CH 3 、-CD3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 ;
[0446] A group represented by one selected from Formula 9-1 to Formula 9-19: or
[0447] One selected from Formula 10-1 to Formula 10-246, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -P(=O)(Q 1 )(Q 2 )(Q 1 To Q 3 The groups represented by (may each independently be the same as described herein):
[0448]
[0449]
[0450]
[0451]
[0452]
[0453]
[0454] In Formulae 9-1 to 9-19 and 10-1 to 10-246, * represents a bonding site with an adjacent atom, "Ph" represents a phenyl group, "D" represents deuterium, and "TMS" represents a trimethylsilyl group.
[0455] Examples of Compounds
[0456] In one or more than one embodiments, the organometallic compound represented by Formula 1 may be one selected from Compound BD01 to Compound BD120:
[0457]
[0458]
[0459]
[0460]
[0461]
[0462] Ar in compounds BD01 to BD112 may be a group represented by formula 1B(1), Ar in compounds BD113 and BD114 may be a group represented by formula 1B(2), Ar in compounds BD115 and BD116 may be a group represented by formula 1B(3), Ar in compound BD117 may be a group represented by formula 1B(4), Ar in compound BD118 may be a group represented by formula 1B(5), and Ar in compounds BD119 and BD120 may be a group represented by formula 1B(6),
[0463]
[0464] * in Formula 1B(1) to Formula 1B(6) represents a binding site with an adjacent atom in Formula 1.
[0465] For example, in one or more embodiments, the second compound can be one selected from compound ETH1 to compound ETH100:
[0466]
[0467]
[0468]
[0469]
[0470]
[0471] For example, in one or more than one embodiments, the third compound can be one selected from compound HTH1 to compound HTH46:
[0472]
[0473]
[0474]
[0475] For example, in one or more than one embodiments, the fourth compound can be one selected from compound DFD1 to compound DFD29:
[0476]
[0477]
[0478] In the compounds described above, Ph represents a phenyl group, D 5 means substitution with five deuteriums, and D 4 means substitution with four deuteriums. For example, The group represented by The groups represented are the same.
[0479] Figure 1 Description
[0480] Figure 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments. The light emitting device 10 may include a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .
[0481] In the following, reference will be made to Figure 1 The structure of the light emitting device 10 and the method of manufacturing the light emitting device 10 according to one or more embodiments are described.
[0482] First electrode 110
[0483] exist Figure 1 In one or more embodiments, a substrate may be additionally provided and arranged under the first electrode 110 and / or on the second electrode 150. In one or more embodiments, as the substrate, a glass substrate or a plastic substrate may be used. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0484] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0485] The first electrode 110 may be a reflective electrode, a semi-transmissive reflective 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 than one embodiments, when the first electrode 110 is a semi-transmissive reflective electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0486] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0487] Middle layer 130
[0488] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0489] In one or more embodiments, the intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0490] In one or more embodiments, in addition to one or more suitable organic materials, the intermediate layer 130 may further include metal-containing compounds (e.g., organic metal compounds (e.g., organic metal compounds represented by Formula 1)), inorganic materials (e.g., quantum dots), etc.
[0491] 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 a charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
[0492] Hole transport region in the intermediate layer 130
[0493] The hole transport region may have: i) a single-layer structure including (e.g., consisting of): a single layer containing a single material (e.g., consisting of a single material), ii) a single-layer structure including (e.g., consisting of): a single layer containing a plurality of materials different from each other (e.g., consisting of a plurality of materials different from each other), or iii) a multi-layer structure including a plurality of layers containing a plurality of materials different from each other.
[0494] 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.
[0495] For example, in some embodiments, the hole transport region can have a multi-layer structure, including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the constituent layers of each structure are stacked in sequence from the first electrode 110 in a prescribed order.
[0496] In one or more than one embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0497] Formula 201
[0498]
[0499] Formula 202
[0500]
[0501] In equation 201 and equation 202,
[0502] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0503] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene group, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene group, unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic group, * and *' each represent a binding site with an adjacent atom,
[0504] xa1 to xa4 may each independently be an integer from 0 to 5,
[0505] xa5 can be an integer from 1 to 10,
[0506] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0507] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted 10a Substituted C 8 -C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16),
[0508] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted 10a Substituted C 8 -C 60 Polycyclic groups, and
[0509] na1 can be an integer from 1 to 4. 10a Can be the same as described herein.
[0510] 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:
[0511]
[0512] In formula CY201 to formula CY217, R 10band R 10c can be respectively related to R 10a Same as described, CY 201 To Ring CY 204 Can be C independently 3 -C 20 Carbocyclic group or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R as described herein 10a replace.
[0513] In one or more than one embodiment, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each may independently be a benzene group, a naphthyl group, a phenanthrene group or an anthracene group.
[0514] In one or more than one embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formula CY201 to Formula CY203.
[0515] In one or more than one 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.
[0516] In one or more than one embodiments, in Formula 201, xa1 may be 1, R 201 can be one selected from the groups represented by the formula CY201 to the formula CY203, xa2 can be 0, and R 202 It may be one selected from the groups represented by the formula CY204 to the formula CY207.
[0517] In one or more than one embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any of the groups represented by Formula CY201 to Formula CY203.
[0518] In one or more than one embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) any of the groups represented by Formula CY201 to Formula CY203, and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.
[0519] In one or more than one embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) any of the groups represented by Formula CY201 to Formula CY217. In the present disclosure, "does not include 'component' or any component", "excludes 'component' or any 'component'", "does not contain 'component'", etc. means that the "component" is not added, selected or used as a component in the composition / formulation / structure, but in some embodiments, less than an appropriate amount of the "component" may still be included due to other impurities and / or external factors.
[0520] For example, in one or more embodiments, the hole transport region may include: selected from compound HT1 to compound HT46; 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA); 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA); 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA); N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB(NPD)); β-NPB; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TP D); 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:
[0521]
[0522]
[0523]
[0524]
[0525]
[0526] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about For example, about to about And the thickness of the hole transport layer can be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.
[0527] The emission auxiliary layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0528] p-dopant
[0529] In one or more than one embodiment, in addition to one or more than one of these above-mentioned materials, the hole transport region may further comprise a charge generating material for improving the conductive properties. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer comprising (e.g., consisting of) the charge generating material).
[0530] The charge generating material may be, for example, a p-dopant.
[0531] For example, in one or more embodiments, the p-dopant can have a LUMO level less than or equal to -3.5 eV.
[0532] In one or more than one embodiments, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound containing the element EL1 and the element EL2, or any combination thereof.
[0533] Non-limiting examples of quinone derivatives are tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ), and the like.
[0534] Non-limiting examples of the cyano group-containing compound are dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), the compound represented by Formula 221, and the like:
[0535]
[0536] Formula 221
[0537]
[0538] In formula 221,
[0539] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a can be the same as described herein, and
[0540] Selected from R 221 To R 223 At least one of the following may be independently: each of which is substituted by a cyano group; -F; -Cl; -Br; -I; a C substituted by a cyano group, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 Alkyl group; or any combination thereof substituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0541] 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.
[0542] 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 (Co) (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); late transition metals (for example, zinc (Zn), indium (In), tin (Sn), etc.); lanthanide metals (for example, 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.
[0543] Non-limiting examples of metalloids are silicon (Si), antimony (Sb), tellurium (Te), and the like.
[0544] Non-limiting examples of non-metals are oxygen (O), halogens (eg, F, Cl, Br, I, etc.), and the like.
[0545] 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 a combination of one or more thereof.
[0546] Non-limiting examples of metal oxides are tungsten oxides (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.), rhenium oxides (e.g., ReO 3etc.
[0547] Non-limiting examples of metal halides are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.
[0548] 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, CsI, and the like.
[0549] 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 ,BaI 2 wait.
[0550] 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 、NbCl 3, NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), iron halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 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.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.
[0551] 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.), tin halides (e.g., SnI 2 etc.
[0552] 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 、SmI 3 wait.
[0553] Non-limiting examples of metalloid halides are antimony halides (e.g., SbCl 5 etc.
[0554] Non-limiting examples of metal tellurides are alkali metal tellurides (e.g., Li 2 Te、Na2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.
[0555] Emission layer in the middle layer 130
[0556] 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 a red emission layer, a green emission layer and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).
[0557] In one or more than one 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.
[0558] 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.
[0559] The amount (weight) of the dopant (or emitter) in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0560] The organic metal compound represented by Formula 1 may be included in the emission layer. The amount (weight) of the organic metal compound in the emission layer may be about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight based on 100 parts by weight of the emission layer.
[0561] In one or more embodiments, the emissive layer may comprise quantum dots.
[0562] In one or more than one embodiments, the emissive layer may include a delayed fluorescent material.The delayed fluorescent material may act as a host or a dopant in the emissive layer.
[0563] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within these ranges, excellent or suitable light emitting characteristics may be obtained without a significant increase in driving voltage.
[0564] main body
[0565] The host in the emission layer may include the second compound or the third compound described in the present disclosure, or a combination thereof.
[0566] In one or more than one embodiment, the host may comprise a compound represented by Formula 301:
[0567] Formula 301
[0568] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0569] Wherein, in Formula 301,
[0570] Ar 301 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 301 may be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0571] xb11 can be 1, 2 or 3,
[0572] xb1 can be an integer from 0 to 5.
[0573] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(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 ),
[0574] xb21 can be an integer from 1 to 5, and
[0575] Q 301 To Q 303 You can each share your experience with Q 1 Same as described. 10a Can be the same as described herein.
[0576] 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.
[0577] In one or more than one embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0578] Formula 301-1
[0579]
[0580] Formula 301-2
[0581]
[0582] In Formula 301-1 and Formula 301-2,
[0583] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a can be the same as described in this article,
[0584] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0585] xb22 and xb23 can each independently be 0, 1 or 2,
[0586] L 301 , xb1 and R 301 can be the same as described,
[0587] L 302 To L 304 can be independently related to L 301 Same as described,
[0588] xb2 to xb4 may each independently be the same as described with respect to xb1, and
[0589] R 302 To R 305 and R 311 To R 314 can be respectively compared with this article about R 301 Same as described.
[0590] In one or more embodiments, the host may comprise an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In one or more embodiments, the host may comprise a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0591] In one or more than one embodiments, the host may include: 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-butyl-anthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-di(9H-carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:
[0592]
[0593]
[0594]
[0595]
[0596]
[0597]
[0598]
[0599] In one or more embodiments, the host can include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0600] The subject may have one or more than one suitable modification. For example, the subject may include only one type of compound, or may include two or more than two types of different compounds.
[0601] Phosphorescent dopants
[0602] The emission layer may include the organometallic compound represented by Formula 1 as described in the present disclosure as a phosphorescent dopant.
[0603] In one or more than one embodiments, where the emission layer comprises 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 comprise a phosphorescent dopant.
[0604] The phosphorescent dopant may include at least one transition metal as a central metal.
[0605] 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.
[0606] The phosphorescent dopant may be electrically neutral.
[0607] For example, in some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0608] Formula 401
[0609] M(L 401 ) xc1 (L 402 ) xc2
[0610] Formula 402
[0611]
[0612] In equations 401 and 402,
[0613] 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)),
[0614] 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 L401 can be the same or different from each other,
[0615] 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,
[0616] X 401 and X 402 can each independently be N or C,
[0617] Ring A 401 and Ring A 402 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0618] 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 )-*', * and *' each represent a binding site with an adjacent atom,
[0619] X 403 and X 404 can each independently be a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0620] Q 411 To Q 414 Each and About Q 1 Same as described,
[0621] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C20 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ), R 10a can be the same as described in this article,
[0622] Q 401 To Q 403 Each and About Q 1 Same as described,
[0623] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0624] * and *' in Formula 402 each represent a binding site with M in Formula 401.
[0625] For example, in some embodiments, in Formula 402, i) X 401 can be nitrogen and X 402 It can be carbon, or ii) X 401 and X 402 Each of can be nitrogen.
[0626] In one or more embodiments, when xc1 in Formula 401 is 2 or greater than 2, two or more L 401 The two rings A 401 Optionally, the linkage group may be T 402 connected to each other, and / or two or more L 401 The two rings A 402 Optionally, the linkage group may be T 403 are connected to each other (see Compound PD1 to Compound PD4 and Compound PD7).402 and T 403 can be respectively related to this article about T 401 Same as described.
[0627] 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.
[0628] In one or more than one embodiments, the phosphorescent dopant may include, for example, one selected from Compound PD1 to Compound PD39 and / or any combination thereof:
[0629]
[0630]
[0631]
[0632] Fluorescent dopants
[0633] 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.
[0634] In one or more than one embodiments, where the emission layer comprises 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 comprise an auxiliary dopant.
[0635] 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.
[0636] In one or more than one embodiments, the fluorescent dopant and the auxiliary dopant may each independently comprise a compound represented by Formula 501:
[0637] Formula 501
[0638]
[0639] In formula 501,
[0640] Ar 501 , R 501 and R 502may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 501 To L 503 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic group, R 10a can be the same as described in this article,
[0641] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0642] xd4 can be 1, 2, 3, 4, 5 or 6.
[0643] In one or more than one embodiment, Ar in Formula 501 501 It may be a fused cyclic group in which three or more monocyclic groups are fused together (for example, anthracene groups, group, pyrene group, etc.).
[0644] In some embodiments, xd4 in formula 501 can be 2.
[0645] For example, in one or more than one embodiments, the fluorescent dopant and the auxiliary dopant may each independently include 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:
[0646]
[0647]
[0648]
[0649] Delayed fluorescence material
[0650] In one or more embodiments, the emissive layer may include a delayed fluorescent material.
[0651] In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0652] The delayed fluorescent material may include, for example, the fourth compound described in the present disclosure.
[0653] 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.
[0654] 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 greater than or equal to 0 eV and less than or equal to 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, the 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.
[0655] For example, in one or more embodiments, the delayed fluorescent material may include: i) at least one electron donor (e.g., a π-electron-rich C 3 -C 60 cyclic groups, such as carbazole groups) and at least one electron acceptor (such as sulfoxide groups, cyano groups, π-electron-deficient nitrogen-containing C 1 -C 60 ii) a material comprising at least two cyclic groups fused to each other and sharing boron (B) 8 -C 60 Materials with polycyclic groups, etc.
[0656] Non-limiting examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF14:
[0657]
[0658]
[0659] quantum dots
[0660] In one or more embodiments, the emissive layer may comprise quantum dots.
[0661] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light at one or more than one suitable emission wavelength, depending on the size of the crystal.
[0662] The diameter of the quantum dot can be, for example, from about 1 nm to about 10 nm. In the present disclosure, when the dot or dot particle is spherical, "diameter" means the particle diameter or the average particle diameter, and when the particle is non-spherical, "diameter" means 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, LA-950 laser particle size analyzer can be used. When the size of the particle is measured using a particle size analyzer, the average particle diameter is referred to as D50. D50 refers to the average diameter of the particles whose cumulative volume corresponds to 50% by volume in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in a distribution curve accumulated in the order of the smallest particle size to the largest particle size.
[0663] 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.
[0664] 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).
[0665] 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.
[0666] Non-limiting examples of II-VI semiconductor compounds may be binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZ nSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or a combination of one or more thereof.
[0667] Non-limiting examples of III-V semiconductor compounds may be binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or one or more combinations thereof. In some embodiments, the III-V semiconductor compound may further include a Group II element. Non-limiting examples of the Group III-V semiconductor compound further including a Group II element are InZnP, InGaZnP, InAlZnP, and the like.
[0668] 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 , InTe, etc.; ternary compounds, such as InGaS 3 、InGaSe 3etc.; or a combination of one or more thereof.
[0669] 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 、AgAlO 2 etc.; or a combination of one or more thereof.
[0670] Non-limiting examples of IV-VI semiconductor compounds are: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, etc.; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds, such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or a combination of one or more thereof.
[0671] Non-limiting examples of Group IV elements or compounds are: single elements, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or combinations of one or more thereof.
[0672] Each element contained in the multi-element compound (eg, in the binary compound, the ternary compound, and the quaternary compound) may be present in the particle in a substantially uniform concentration or a substantially non-uniform concentration.
[0673] In one or more than one embodiments, the quantum dot can have a single structure, wherein the concentration of each element in the quantum dot is substantially uniform, or can have a core-shell dual structure. For example, the material contained in the core and the material contained in the shell can be different from each other.
[0674] The shell of a quantum dot can act as a protective layer to prevent or reduce chemical denaturation of the core to maintain semiconductor properties and / or a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layer or multi-layer. The interface between the core and the shell can have a concentration gradient, where the concentration of the element present in the shell decreases toward the center of the core.
[0675] 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 O3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 , NiO, etc.; ternary compounds, such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 、CoMn 2 O 4 etc.; or one or more combinations thereof. Examples of semiconductor compounds are: II-VI semiconductor compounds as described herein; 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 for use 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.
[0676] The quantum dots may have a full width at half maximum (FWHM) of an emission spectrum of no more than about 45 nm, no more than about 40 nm, or, for example, no more than about 30 nm. When the FWHM of the emission spectrum 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.
[0677] 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.
[0678] Because the energy band gap of quantum dots can be adjusted by controlling the size of quantum dots, light with one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths can be realized. In one or more than one embodiments, the size of the quantum dots can be selected so that the quantum dots emit red light, green light, and / or blue light. In some embodiments, quantum dots with suitable sizes can be configured to emit white light by a combination of one or more suitable colors of light.
[0679] Electron transport region in the intermediate layer 130
[0680] The electron transport region may have: i) a single-layer structure including (e.g., consisting of): a single layer containing (e.g., consisting of): a single material, ii) a single-layer structure including (e.g., consisting of): a single layer containing (e.g., consisting of): a plurality of materials different from each other, or iii) a multi-layer structure including a plurality of layers containing (e.g., consisting of): a plurality of materials different from each other.
[0681] 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.
[0682] For example, in one or more than one embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked in sequence from the emission layer in a prescribed order.
[0683] 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 at least one π-electron-deficient nitrogen-containing C 1 -C 60 Metal-free compounds of heterocyclic groups.
[0684] For example, in some embodiments, the electron transport region may include a compound represented by Formula 601:
[0685] Formula 601
[0686] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0687] Wherein, in Formula 601,
[0688] Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0689] xe11 can be 1, 2 or 3,
[0690] xe1 can be 0, 1, 2, 3, 4, or 5,
[0691] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0692] Q 601 To Q 603 You can each share your experience with Q 1 Same as described,
[0693] xe21 can be 1, 2, 3, 4, or 5, and
[0694] At least one of the following conditions may be satisfied: 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group; R 601 may be unsubstituted or substituted with at least one R10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 A cyclic group; and L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group. 10a Can be the same as described herein.
[0695] In one or more than one embodiment, when xe11 in Formula 601 is 2 or greater than 2, two or more Ar 601 can be connected to each other via a single bond.
[0696] In one or more than one embodiment, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracene group. 10a Can be the same as described herein.
[0697] In one or more than one embodiments, the electron transport region may comprise a compound represented by Formula 601-1:
[0698] Formula 601-1
[0699]
[0700] Among them, in formula 601-1,
[0701] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and selected from X 614 To X 616 At least one of may be N,
[0702] L 611 To L 613 Can be respectively with about L 601 Same as described,
[0703] xe611 to xe613 may each be the same as described with respect to xe1,
[0704] R 611 To R 613 can be respectively related to R 601 Same as described, and
[0705] R 614 To R616 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group. 10a Can be the same as described herein.
[0706] For example, in some embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each independently be 0, 1 or 2.
[0707] In one or more than one embodiment, the electron transport region may include: selected from compound ET1 to compound ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); tris(8-hydroxyquinolinato)aluminum (Alq 3 ); bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-ato)aluminum (BAlq); 3-(4-biphenylyl)-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:
[0708]
[0709]
[0710]
[0711] The thickness of the electron transport region may be about to about For example, about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be about to about For example, about to about And the thickness of the electron transport layer can be about to about For example, about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.
[0712] In one or more embodiments, in addition to the one or more materials described above, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material.
[0713] The metal-containing material can include alkali metal complex, alkaline earth metal complex or its any combination. 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 its any combination.
[0714] 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:
[0715]
[0716] In one or more embodiments, the electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0717] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of): a single layer containing a single material (e.g., consisting of a single material), ii) a single-layer structure including (e.g., consisting of): a single layer containing multiple materials different from each other (e.g., consisting of multiple materials different from each other), or iii) a multi-layer structure including multiple layers containing multiple materials different from each other.
[0718] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0719] The alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0720] The compounds containing alkali metals, the compounds containing alkaline earth metals, and the compounds containing rare earth metals may be oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of alkali metals, alkaline earth metals, and rare earth metals, respectively, or any combination thereof.
[0721] The compounds containing alkali metals 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 compounds containing alkaline earth metals 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), Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The compounds containing rare earth metals may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 or any combination thereof. In one or more embodiments, the compounds containing rare earth metals may include lanthanide metal tellurides. Non-limiting examples of lanthanide metal tellurides are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 、Ce 2 Te 3 、Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te3 、Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 、Lu 2 Te 3 wait.
[0722] The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex may respectively contain 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 bound to the metal ion (e.g., the respective metal ion), such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0723] In one or more than one embodiment, the electron injection layer may include (e.g., consisting 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 one or more than one embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0724] In one or more than one embodiments, the electron injection layer may include (e.g., consisting of): i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, in some embodiments, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, etc.
[0725] When the electron injection layer further comprises an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be substantially uniformly or non-uniformly dispersed in the matrix comprising the organic material.
[0726] The thickness of the electron injection layer can be about to about Or for example, about to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.
[0727] The second electrode 150
[0728] The second electrode 150 may be disposed on the intermediate layer 130 having the above structure. The second electrode 150 may be a cathode as an electron injection electrode, and may use metals, alloys, conductive compounds, or any combination thereof each having a low work function as a material for forming the second electrode 150.
[0729] 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 reflective electrode or a reflective electrode.
[0730] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
[0731] Covering
[0732] The first covering layer may be arranged outside the first electrode 110 (e.g., on the first electrode 110) and / or the second covering layer may be arranged 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, and the second electrode 150 are stacked in sequence in a specified order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in sequence in a specified order, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in sequence in a specified order.
[0733] In some embodiments, the light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 can be led outward through the first electrode 110 (which is a semi-transmissive reflective electrode or a transmissive electrode) and the first covering layer. In some embodiments, the light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 can be led outward through the second electrode 150 (which is a semi-transmissive reflective electrode or a transmissive electrode) and the second covering layer.
[0734] The first cover layer and the second cover layer can increase the external emission efficiency according to the principle of constructive interference, thereby increasing the light extraction efficiency of the light emitting device 10, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0735] Each of the first cover layer and the second cover layer may each include a material having a refractive index greater than or equal to 1.6 (eg, at 589 nm).
[0736] The first covering layer and the second covering layer may each independently be an organic covering layer including an organic material, an inorganic covering layer including an inorganic material, or an organic-inorganic composite covering layer including an organic material and an inorganic material.
[0737] 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) contain a carbocyclic compound, a heterocyclic compound, a compound containing an amine group, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the compound containing an amine group may each be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more than one embodiments, at least one 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) contain a compound containing an amine group.
[0738] In one or more than one embodiments, at least one of the first covering layer and the second covering layer may (the first covering layer and the second covering layer may each independently) contain a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0739] In one or more than one embodiment, at least one of the first covering layer and the second covering layer may (the first covering layer and the second covering layer may each independently) contain at least one selected from compounds HT28 to HT33, at least one selected from compounds CP1 to CP6, β-NPB or any combination thereof:
[0740]
[0741] membrane
[0742] The organometallic compound represented by Formula 1 may be included in one or more than one suitable film. 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 extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, a layer containing quantum dots, etc.), a light blocking member (e.g., a light reflecting layer, a light absorbing layer, etc.), and / or a protective member (e.g., an insulating layer, a dielectric layer, etc.).
[0743] Electronic devices
[0744] The light emitting device 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, a verification device, etc.
[0745] 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.
[0746] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the sub-pixel regions.
[0747] A pixel defining layer may be disposed between the sub-pixel regions to define each of the sub-pixel regions.
[0748] The color filter may further include a plurality of color filter regions and a light shielding pattern disposed between the color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern disposed between the color conversion regions.
[0749] 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 one or more quantum dots. In some embodiments, the first region may include red quantum dots that emit red light, the second region may include green quantum dots that emit green light, and the third region may not include (e.g., may exclude) any quantum dots. For details about 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.
[0750] For example, in one or more embodiments, the light emitting device may be intended to emit a first light, the first region may be intended to absorb the first light to emit a first-first color light, the second region may be intended to absorb the first light to emit a second-first color light, and the third region may be intended 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.
[0751] In one or more embodiments, in addition to the light-emitting device as 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.
[0752] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0753] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0754] In one or more than one 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 led out to the outside, and in parallel (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one layer of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0755] In one or more than one embodiments, in addition to the color filter and / or color conversion layer, various suitable functional layers can be additionally arranged on the sealing portion, depending on the purpose of the electronic device. Non-limiting examples of the functional layer can include a touch screen layer, a polarization layer, etc. The touch screen layer can be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
[0756] The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living being, such as a fingertip, a pupil, etc. In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.
[0757] The electronic device can be applied to one or more displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), projectors, etc.
[0758] Electronic equipment
[0759] The light emitting device may be included in one or more than one suitable electronic equipment.
[0760] For example, electronic equipment incorporating a light emitting device may include (e.g., may be) at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a lamp and / or a signal lamp for indoor or outdoor lighting, a head-up display, a fully transparent or partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall comprising multiple displays stitched together, a theater or stadium screen, a light therapy device, and a sign.
[0761] Since the light emitting device has excellent or suitable effects in terms of light emitting efficiency and long lifespan, electronic equipment including the light emitting device may have desired characteristics of high brightness, high resolution, and low power consumption.
[0762] Figure 2 and Figure 3 Description
[0763] Figure 2 is a cross-sectional view showing a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0764] Figure 2 The light emitting apparatus may include a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation part 300 that seals the light emitting device.
[0765] 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.
[0766] 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.
[0767] The active layer 220 may include an inorganic semiconductor (eg, silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0768] 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 .
[0769] 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 each other.
[0770] Source electrode 260 and drain electrode 270 may be on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may be arranged to contact exposed portions of the source and drain regions of active layer 220, respectively.
[0771] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0772] 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.
[0773] A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a certain area of the first electrode 110, and the intermediate layer 130 may be formed in the exposed area of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic acid-based 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 so as to be arranged in the form of a common layer.
[0774] The second electrode 150 may be on the intermediate layer 130, and a second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0775] 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; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic-based resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0776] Figure 3 is a cross-sectional view of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0777] Figure 3 Light emitting devices and Figure 2 The light emitting device of the embodiment of the present invention is substantially the same, but the light shielding pattern 500 and the functional area 400 are additionally arranged on the encapsulation part 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, including Figure 3 The light emitting devices in the light emitting apparatus may be series light emitting devices.
[0778] Figure 4 Description
[0779] Figure 4 1 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. The electronic device 1 may be a portable electronic device as a device for displaying moving images or still images, such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic diary, 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, a monitor, a billboard, or an Internet of Things (IoT) device. The electronic device 1 may be such a product or a component thereof. In some embodiments, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type or quasi-display or a head-mounted display (HMD), or a component 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 center panel of a vehicle, a central information display arranged on the dashboard of a vehicle, an interior mirror display of a vehicle instead of a side mirror, an entertainment display for a rear seat of a vehicle, or a display arranged on the back of a front seat, or a head-up display (HUD) mounted in front of the vehicle or projected on the front windshield, and / or a computer-generated holographic augmented reality head-up display (CGHAR HUD). For ease of explanation, Figure 4An embodiment is illustrated in which the electronic equipment 1 is a smartphone.
[0780] 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.
[0781] The non-display area NDA is an area where no image is displayed, and may completely surround the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to a display device arranged on the display area DA may be arranged. In the non-display area NDA, a pad may be arranged, which is an area to which an electronic component or a printed circuit board may be electrically connected.
[0782] In the electronic device 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 , the length in the x-axis direction may be shorter than the length (e.g., width) in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be substantially the same as the length (e.g., width) in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length (e.g., width) in the y-axis direction.
[0783] Figure 5 and FIG. 6A to FIG. 6C Description
[0784] Figure 5 is a schematic diagram of an exterior of a vehicle 1000 as an electronic device including a lighting device according to one or more embodiments. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.
[0785] 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 sea or a river, and an airplane flying in the air using the action of air.
[0786] In one or more than one 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 can 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.
[0787] The vehicle 1000 may include a main body having an interior and an exterior, and a chassis in which mechanical equipment necessary for driving is installed as the remaining components other than the main body. The exterior of the main body may include a front plate, a bonnet, a top plate, a rear plate, a luggage compartment, and pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear wheels, left and right wheels, etc.
[0788] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster piece 1400 , a center panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0789] 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 .
[0790] The side window glass 1100 may be mounted on the side of the vehicle 1000. In some embodiments, the side window glass 1100 may be mounted on the door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In some embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In some embodiments, the first side window glass 1110 may be arranged adjacent to the cluster piece 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0791] In one or more embodiments, the side window glass 1100 may be spaced apart from each other in the x direction or the -x direction (the direction opposite to the x direction). For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or in the -x direction. In other words, the virtual straight line L connecting the side window glass 1100 may extend in the x direction or in the -x direction. For example, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x direction or in the -x direction.
[0792] 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.
[0793] The side view mirror 1300 can provide a rear view of the vehicle 1000. The side view mirror 1300 can be installed on the outside of the vehicle body. In one embodiment, a plurality of side view mirrors 1300 can be provided. Any one of the plurality of side view mirrors 1300 can be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 can be arranged outside the second side window glass 1120.
[0794] Cluster piece 1400 may be arranged in front of the steering wheel. Cluster piece 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a trip meter, an automatic transmission selector lever indicator, a door open warning light, an oil warning light, and / or a low fuel warning light.
[0795] The center panel 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and / or a seat heater are provided. The center panel 1500 may be disposed on one side of the cluster piece 1400 .
[0796] The passenger seat instrument panel 1600 may be spaced apart from the cluster piece 1400 with the center panel 1500 disposed therebetween. In some embodiments, the cluster piece 1400 may be disposed to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be disposed to correspond to the passenger seat. In some embodiments, the cluster piece 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0797] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In some embodiments, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster member 1400, the center panel 1500, and the passenger seat instrument panel 1600.
[0798] The display device 2 may include an organic light-emitting display device, an inorganic EL display device, a quantum dot display device, etc. Hereinafter, as a display device 2 according to one or more embodiments, an organic light-emitting display device including 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 as described above may be used in the embodiments of the present disclosure.
[0799] refer to Fig. 6AIn one or more embodiments, the display device 2 can be arranged on the central panel 1500. In some embodiments, the display device 2 can display navigation information. In some embodiments, the display device 2 can display audio, video or information about vehicle settings.
[0800] refer to Figure 6B In one or more embodiments, the display device 2 may be disposed on the clusterware 1400. When the display device 2 is disposed on the clusterware 1400, the clusterware 1400 may display driving information and the like through the display device 2. For example, the clusterware 1400 may be implemented digitally. The clusterware 1400 may digitally display vehicle information and driving information as images. For example, the needle and gauge of a tachometer and one or more suitable warning light icons may be displayed through digital signals.
[0801] refer to Figure 6C In one or more embodiments, the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In some embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 1500.
[0802] Manufacturing method
[0803] 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 using one or more suitable methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging, etc.).
[0804] 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 about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and approx. / second to about Deposition was carried out at a deposition rate of / s.
[0805] Definition of terms
[0806] As used herein, the term "C 3 -C 60 A "carbocyclic group" refers to a cyclic group that contains (e.g., consists of) only carbon as ring atoms and has from one to sixty carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms), and as used herein, the term "C 1 -C 60 The term "heterocyclic group" refers to a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and further having a heteroatom other than carbon as a ring-forming atom. 3 -C 60 Carbocyclic groups and C 1 -C 60 The heterocyclic groups may each be a monocyclic group comprising (eg, consisting of) one (eg, exactly one) ring or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The number of ring-forming atoms of the heterocyclic group may be 3 to 61 (eg, 3 to 30, 3 to 20, 3 to 15, or 3 to 10).
[0807] As used herein, the term "cyclic group" may include C 3 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups both (eg, simultaneously).
[0808] As used herein, the term "π-electron-rich C 3 -C 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms) and not containing *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The term "heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms (eg, 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and containing *-N=*' as a ring-forming portion.
[0809] For example,
[0810] C 3 -C 60The carbocyclic group may be i) a group T1 (e.g., one or more than one group in the group T1) or ii) a fused cyclic group in which two or more groups T1 (e.g., two or more than two groups in the group T1) are fused to each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthyl group, an azulene group, an indacene group, an acenaphthylene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a benzophenone group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),
[0811] C 1 -C 60 The heterocyclic group may be i) a group T2, ii) a fused cyclic group in which two or more groups T2 are fused to each other, or iii) a fused cyclic group in which at least one group T2 (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 pyrrole group, a thiophene group, a furan group, an indole group, a benzindole group, a naphthoindole group, an isoindole group, benzoisoindole group, naphthoisoindole group, benzosilole group, benzothiophene group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolecarbazole group, benzofuranocarbazole group, benzothiophenocarbazole group, benzosiloleocarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzo furanodibenzofuran group, benzofuranodibenzothiophene group, benzothienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),
[0812] 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 a carbocyclic group, a 1H-pyrrole group, a thiol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiol group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiol group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothioylcarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiol group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophenodibenzothiophene group, and the like),
[0813] π-electron-deficient nitrogen-containing C 1 -C 60 The cyclic group may be i) a group T4, ii) a fused cyclic group in which two or more groups T4 are fused to each other, iii) a fused cyclic group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused cyclic group in which at least one group T4 and at least one group T3 are fused to each other, 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., a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a azole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),
[0814] The group T1 can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,
[0815] The group T2 can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borocyclopentadiene group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,
[0816] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group or a borole group, and
[0817] The group T4 can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
[0818] As used herein, the term "cyclic group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic groups, π-electron-rich C 3 -C 60 Cyclic groups or nitrogen-containing C with π-electron deficiency 1 -C 60 The “heterocyclic group” may refer to a group condensed with 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 using the corresponding term. For example, a “phenyl group” may be a benzo group, a phenyl group, a phenylene group, etc., which may be easily understood by a person of ordinary skill in the art based on the structure of the formula including the “phenyl group”.
[0819] Unit Price C3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Non-limiting examples of heterocyclic groups are C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Non-limiting examples of heterocyclic groups are C 3 -C 10 Cycloalkylene group, C 1 -C 10 Heterocycloalkylene group, C 3 -C 10 Cycloalkenylene group, C 1 -C 10 Heterocycloalkenylene group, C 6 -C 60 Arylene group, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0820] As used herein, the term "C 1 -C 60 The term “alkyl group” refers to a straight or branched aliphatic hydrocarbon monovalent group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms), and non-limiting examples thereof are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. As used herein, the term “C1 -C 60 "Alkylene group" refers to a group having 1 -C 60 Alkyl groups are divalent groups of substantially the same structure.
[0821] As used herein, the term "C 2 -C 60 "Alkenyl group" means a 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof are a vinyl group, a propenyl group, a butenyl group, and the like. 2 -C 60 "Alkenylene group" refers to a 2 -C 60 Alkenyl groups are divalent radicals of substantially the same structure.
[0822] As used herein, the term "C 2 -C 60 "Alkynyl group" means a 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof are an ethynyl group, a propynyl group, and the like. 2 -C 60 "Alkyne group" refers to a 2 -C 60 Alkynyl groups are divalent radicals of substantially the same structure.
[0823] As used herein, the term "C 1 -C 60 "Alkoxy group" refers to a group consisting of -OA 101 (A 101 It is C 1 -C 60 The term "alkyl group" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof are a methoxy group, an ethoxy group, an isopropoxy group, and the like.
[0824] As used herein, the term "C 3 -C 10 The term "cycloalkyl group" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and the like. As used herein, the term "C3 -C 10 "Cycloalkylene group" refers to a group having a 3 -C 10 Cycloalkyl groups are divalent groups of substantially the same structure.
[0825] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl group" refers to a monovalent cyclic group of 1 to 10 carbon atoms further containing at least one heteroatom other than carbon atoms as a ring-forming atom, and non-limiting examples thereof are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, and the like. As used herein, the term "C 1 -C 10 The term "heterocycloalkylene group" refers to a 1 -C 10 Heterocycloalkyl groups are divalent radicals of substantially the same structure.
[0826] As used herein, the term "C 3 -C 10 The term "cycloalkenyl group" as used herein refers to a monovalent cyclic group having three to ten carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof are a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. 3 -C 10 "Cycloalkenylene group" refers to a group having a 3 -C 10 Cycloalkenyl groups are divalent radicals of substantially the same structure.
[0827] 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 further contains at least one heteroatom other than carbon atoms as a ring-forming atom in its cyclic structure and has at least one double bond. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups are 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, 2,3-dihydrothienyl groups, and the like. 1 -C 10 The term "heterocycloalkenylene group" refers to a 1 -C 10 Heterocycloalkenyl groups are divalent radicals of substantially the same structure.
[0828] As used herein, the term "C 6 -C 60"Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms), and the term "C 6 -C 60 The term "arylene group" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms). 6 -C 60 Non-limiting examples of aryl groups are phenyl groups, pentalenyl groups, naphthyl groups, azulenyl groups, indacenyl groups, acenaphthenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, The phenyl group includes a phenyl group, a peryl group, a pentaphenyl group, a heptaphenyl group, a tetraphenyl group, a peryl group, a hexaphenyl group, a pentacene group, a rubidinyl group, a coronet group, an ovaphenyl group, and the like. 6 -C 60 Aryl groups and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.
[0829] As used herein, the term "C 1 -C 60 The term "heteroaryl group" refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) further containing at least one heteroatom other than carbon atoms as a ring-forming atom. As used herein, the term "C 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) further including at least one heteroatom other than carbon atoms as a ring-forming atom. 1 -C 60 Non-limiting examples of heteroaryl groups are pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, benzoquinolyl groups, isoquinolyl groups, benzoisoquinolyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinnolinyl groups, phenanthrolinyl groups, phthalazinyl groups and naphthyridinyl groups. 1 -C 60 Heteroaryl groups and C 1 -C 60When the heteroarylene groups each include two or more rings, the rings may be fused to each other.
[0830] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms, e.g., 8 to 30, 8 to 20, 8 to 15, or 8 to 10 carbon atoms) having two or more rings fused to each other, only carbon atoms as ring atoms, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of monovalent non-aromatic fused polycyclic groups are indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenophenanthryl groups, indenoanthryl groups, etc. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as the monovalent non-aromatic fused polycyclic group described above.
[0831] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms, e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) having two or more rings fused to each other, further containing at least one heteroatom other than a carbon atom as a ring-forming atom and having no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thienyl group, a furanyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothiorolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, an imidazotriazine group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolecarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzothiorrolocarbazolyl group, a benzoindolecarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothienyl group, a benzonaphthothiorryl group, a benzofuranodibenzofuranyl group, a benzofuranodibenzothienyl group and a benzothienodibenzothienyl group. 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.
[0832] As used herein, the term "C 6 -C 60 "Aryloxy group" means -OA 102 (A 102 It is C 6 -C 60 aryl group), and as used herein, the term "C 6 -C 60 "Arylthio group" means -SA 103 (A 103 It is C 6 -C 60 aryl group).
[0833] As used herein, the term "C7 -C 60 "Arylalkyl group" refers to -A 104 A 105 (A 104 It is C 1 -C 54 An alkylene group, and A 105 It is C 6 -C 59 aryl group), and as used herein, the term "C 2 -C 60 A "heteroarylalkyl group" refers to an -A 106 A 107 (A 106 It is C 1 -C 59 An alkylene group, and A 107 It is C 1 -C 59 heteroaryl group).
[0834] As used herein, the term "R 10a " can be:
[0835] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
[0836] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted C 1 -C 60Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups;
[0837] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group or C 2 -C 60 a heteroarylalkyl group; or
[0838] -Si(Q31 )(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 ).
[0839] The Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy groups; each unsubstituted or deuterated, -F, cyano groups, C 1 -C 60 Alkyl group, C 1 -C 60 Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl group or C 2 -C 60 Heteroarylalkyl groups.
[0840] The term "heteroatom" as used herein refers to any atom other than a carbon atom and a hydrogen atom, and the number of the heteroatom may be 1 to 10, for example 1, 2, 3, 4 or 5. Non-limiting examples of heteroatoms are O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0841] The term "transition metal" as used herein includes Hf, Ta, W, Re, Os, Ir, Pt, Au, and the like.
[0842] As used herein, "Ph" refers to a phenyl group, as used herein, "Me" refers to a methyl group, as used herein, "Et" refers to an ethyl group, as used herein, "tert-Bu" or "Bu" refers to an ethyl group. t " refers to a tert-butyl group, and "OMe" as used herein refers to a methoxy group.
[0843] As used herein, the term "biphenyl group" refers to a "phenyl group substituted by a phenyl group". In some embodiments, the "biphenyl group" may be a C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0844] As used herein, the term "terphenyl group" refers to a "phenyl group substituted by a biphenyl group". In some embodiments, the "terphenyl group" is a phenyl group substituted by a C 6 -C 60 Aryl-substituted C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0845] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0846] In the present disclosure, the x-axis, y-axis, and z-axis are not limited to the three axes in the orthogonal coordinate system, and can be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis can refer to those that are orthogonal to each other, or can refer to those in different directions that are not orthogonal to each other.
[0847] Hereinafter, an organometallic compound according to one or more embodiments and a light-emitting device according to one or more embodiments will be described in more detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used to describe a synthesis example means using an equimolar equivalent of B instead of A.
[0848] Example
[0849] Synthesis Example 1: Synthesis of Intermediate IM-1a
[0850] 3,8-Dichloro-10-nitro-9H-tetrabenzo[b,d,f,h]azoline (12.0 g, 27.6 mmol), 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.1 g, 41.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3) (2.6 g, 2.8 mmol), (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)SPhos (1.7 g, 4.1 mmol) and NaO t Bu (10.6 g, 110.4 mmol) was placed in a reaction vessel and suspended in toluene (250 mL) under nitrogen, then heated and stirred at 120 ° C for 12 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and 150 mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The result thus obtained was subjected to column chromatography to obtain an intermediate IM-1a (17.8 g, 24.0 mmol) with a yield of 87%.
[0851] Synthesis Example 2: Synthesis of Intermediate IM-1b
[0852] Intermediate IM-1b (17.6 g, 23.5 mmol) was obtained in 85% yield in substantially the same manner as in Synthesis Example 1, except that 2-(3,5-di-tert-butylphenyl-2,4,6-d 3 )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
[0853] Synthesis Example 3: Synthesis of Intermediate IM-1c
[0854] Intermediate IM-1c (17.9 g, 23.5 mmol) was obtained in 85% yield in substantially the same manner as in Synthesis Example 1, except that 3,8-dichloro-10-nitro-9H-tetrabenzo[b,d,f,h]azoline-1,2,4,5,6,7,11,12,13,14,15,16,17-d was used in the synthesis of intermediate IM-1c. 13 Replace 3,8-dichloro-10-nitro-9H-tetrabenzo[b,d,f,h]azoline.
[0855] Synthesis Example 4: Synthesis of Intermediate IM-1d
[0856] Intermediate IM-1d (18.0 g, 22.6 mmol) was obtained in 82% yield in substantially the same manner as in Synthesis Example 3, except that 2-(3,5-bis(methyl-d 3 )propan-2-yl-1,1,1,3,3,3-d 6 )phenyl-2,4,6-d 3)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
[0857] Synthesis Example 5: Synthesis of Intermediate IM-1e
[0858] Intermediate IM-1e (18.0 g, 22.1 mmol) was obtained in 80% yield in substantially the same manner as in Synthesis Example 1, except that 2-(5-(tert-butyl)-[1,1′-biphenyl]-3-yl-2,2′,3′,4,4′,5′,6,6′-d 8 )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
[0859] Synthesis Example 6: Synthesis of Intermediate IM-1f
[0860] Intermediate IM-1f (20.1 g, 21.8 mmol) was obtained in a yield of 79% in substantially the same manner as in Synthesis Example 5, except that 2-(4',5-di-tert-butyl-[1,1'-biphenyl]-3-yl-2,2',3',4,5',6,6'-d 7 )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2-(5-(tert-butyl)-[1,1'-biphenyl]-3-yl-2,2',3',4,4',5',6,6'-d 8 )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
[0861] Synthesis Example 7: Synthesis of Intermediate IM-1g
[0862] Intermediate IM-1g (21.0 g, 22.4 mmol) was obtained in a yield of 81% in substantially the same manner as in Synthesis Example 6, except that 2-(3′-(tert-butyl)-5-(2-(methyl-d 3 )propan-2-yl-1,1,1,3,3,3-d 6 )-[1,1'-biphenyl]-3-yl-2,2',4,4',5',6,6'-d 7 )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2-(4',5-di-tert-butyl-[1,1'-biphenyl]-3-yl-2,2',3',4,5',6,6'-d 7)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
[0863] Synthesis Example 8: Synthesis of Intermediate IM-2a
[0864] A mixture comprising intermediate IM-1a (17.8 g, 24.0 mmol) and tin (8.5 g, 72 mmol) was placed in a reaction vessel, suspended in a mixed solution comprising ethanol (EtOH) (240 mL) and 37% HCl (10.8 mL), and then heated to 80 ° C, and stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction solution was cooled at room temperature, and 150 mL of distilled water was added thereto and then neutralized, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried with sodium sulfate. The result thus obtained was subjected to column chromatography to obtain intermediate IM-2a (15.0 g, 21.1 mmol) with a yield of 88%.
[0865] Synthesis Example 9: Synthesis of Intermediate IM-2b
[0866] Intermediate IM-2b (15.5 g, 21.6 mmol) was obtained in a yield of 90% in substantially the same manner as in Synthesis Example 8, except that Intermediate IM-1b was used instead of Intermediate IM-1a in the synthesis of Intermediate IM-2b.
[0867] Synthesis Example 10: Synthesis of Intermediate IM-2c
[0868] Intermediate IM-2c (15.8 g, 21.6 mmol) was obtained in a yield of 90% in substantially the same manner as in Synthesis Example 8, except that Intermediate IM-1c was used instead of Intermediate IM-1a in the synthesis of Intermediate IM-2c.
[0869] Synthesis Example 11: Synthesis of Intermediate IM-2d
[0870] Intermediate IM-2d (16.0 g, 20.9 mmol) was obtained in a yield of 87% in substantially the same manner as in Synthesis Example 8, except that Intermediate IM-1d was used instead of Intermediate IM-1a in the synthesis of Intermediate IM-2d.
[0871] Synthesis Example 12: Synthesis of Intermediate IM-2e
[0872] Intermediate IM-2e (15.8 g, 20.6 mmol) was obtained in a yield of 86% in substantially the same manner as in Synthesis Example 8, except that Intermediate IM-1e was used instead of Intermediate IM-1a in the synthesis of Intermediate IM-2e.
[0873] Synthesis Example 13: Synthesis of Intermediate IM-2f
[0874] Intermediate IM-2f (18.3 g, 20.6 mmol) was obtained at a yield of 86% in substantially the same manner as in Synthesis Example 8, except that Intermediate IM-1f was used instead of Intermediate IM-1a in the synthesis of Intermediate IM-2f.
[0875] Synthesis Example 14: Synthesis of Intermediate IM-2g
[0876] Intermediate IM-2g (19.0 g, 20.9 mmol) was obtained at a yield of 87% in substantially the same manner as in Synthesis Example 8, except that Intermediate IM-1g was used instead of Intermediate IM-1a in the synthesis of Intermediate IM-2g.
[0877] Synthesis Example 15: Synthesis of Intermediate IM-3a
[0878] Intermediate IM-2a (8.1 g, 11.4 mmol), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (5.4 g, 11.4 mmol), Pd 2 (dba) 3 (0.2 g, 0.2 mmol), SPhos (1.9 g, 4.6 mmol) and NaO t Bu (1.7g, 18.2mmol) is placed in a reaction vessel and suspended in 114mL toluene, then heated and stirred at 110°C for 4 hours. After the reaction is complete, the reaction solution is cooled at room temperature, and 300mL of distilled water is added thereto, and the organic layer is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The result thus obtained is subjected to column chromatography to obtain intermediate IM-3a (8.2g, 7.4mmol) with a yield of 65%.
[0879] Synthesis Example 16: Synthesis of Intermediate IM-3b
[0880] Intermediate IM-3b (8.6 g, 7.8 mmol) was obtained in a yield of 68% in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 Instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole.
[0881] Synthesis Example 17: Synthesis of Intermediate IM-3c
[0882] Intermediate IM-3c (8.9 g, 8.0 mmol) was obtained in 70% yield in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2b was used instead of Intermediate IM-2a.
[0883] Synthesis Example 18: Synthesis of Intermediate IM-3d
[0884] Intermediate IM-3d (9.0 g, 7.8 mmol) was obtained in a yield of 68% in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d was used in the synthesis of intermediate IM-3d. 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2e was used instead of Intermediate IM-2a.
[0885] Synthesis Example 19: Synthesis of Intermediate IM-3e
[0886] Intermediate IM-3e (9.0 g, 8.0 mmol) was obtained in a yield of 70% in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2c was used instead of Intermediate IM-2a.
[0887] Synthesis Example 20: Synthesis of Intermediate IM-3f
[0888] Intermediate IM-3f (9.5 g, 8.2 mmol) was obtained in a yield of 72% in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d was used in the synthesis of intermediate IM-3f. 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2d was used instead of Intermediate IM-2a.
[0889] Synthesis Example 21: Synthesis of Intermediate IM-3g
[0890] Intermediate IM-3g (9.4 g, 7.3 mmol) was obtained in a yield of 64% in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2f was used instead of Intermediate IM-2a.
[0891] Synthesis Example 22: Synthesis of Intermediate IM-3h
[0892] Intermediate IM-3h (10.1 g, 7.8 mmol) was obtained in a yield of 68% in substantially the same manner as in Synthesis Example 15, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2g was used instead of Intermediate IM-2a.
[0893] Synthesis Example 23: Synthesis of Intermediate IM-3i
[0894] Intermediate IM-3i (9.1 g, 7.4 mmol) was obtained in 65% yield in substantially the same manner as in Synthesis Example 15, except that 2-((5-bromo-2-(methyl-d 3 )-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 )oxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 4 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2c was used instead of Intermediate IM-2a.
[0895] Synthesis Example 24: Synthesis of Intermediate IM-3j
[0896] Intermediate IM-3j (10.0 g, 7.2 mmol) was obtained in 63% yield in substantially the same manner as in Synthesis Example 15, except that 2-((5-bromo-2-(methyl-d 3 )-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 )oxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d 42-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole was substituted and Intermediate IM-2g was used instead of Intermediate IM-2a.
[0897] Synthesis Example 25: Synthesis of Compound BD01
[0898] Intermediate IM-3a (8.2g, 7.4mmol), triethyl orthoformate (74mL, 443mmol) and HCl (37%) were placed in a reaction vessel and heated and stirred at 80°C for 12 hours. After the reaction was completed, the reaction solution was cooled at room temperature, and the obtained solid was filtered and washed with ether, and the washed solid was dried to obtain intermediate IM-4a (8.0g, 7.0mmol) with a yield of 95%. Subsequently, intermediate IM-4a (8.0g, 7.0mmol), dichloro (1,5-cyclooctadiene) platinum (2.8g, 7.6mmol) and NaOAc (1.7g, 20.7mmol) were suspended in 150mL of 1,4-dioxane, and then heated and stirred at 120°C for 72 hours. After the reaction was completed, the reaction solution was cooled at room temperature, and 150mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous NaCl solution and MgSO 4 The resultant was dried and subjected to column chromatography to obtain compound BD01 (2.7 g, 2.1 mmol) in a yield of 30%.
[0899] Synthesis Example 26: Synthesis of Compound BD02
[0900] Intermediate IM-4b (8.1 g, 7.0 mmol) was obtained in a yield of 95%, and compound BD02 (2.9 g, 2.2 mmol) was obtained from intermediate IM-4b in a yield of 32% in substantially the same manner as in Synthesis Example 25, but in the synthesis of compound BD02, intermediate IM-3b was used instead of intermediate IM-3a.
[0901] Synthesis Example 27: Synthesis of Compound BD113
[0902] Intermediate IM-4c (8.1 g, 7.0 mmol) was obtained in a yield of 95%, and compound BD113 (2.8 g, 2.1 mmol) was obtained from intermediate IM-4c in a yield of 32% in substantially the same manner as in Synthesis Example 25, but in the synthesis of compound BD113, intermediate IM-3c was used instead of intermediate IM-3a.
[0903] Synthesis Example 28: Synthesis of Compound BD114
[0904] Intermediate IM-4e (8.3 g, 7.0 mmol) was obtained in a yield of 95%, and compound BD114 (2.8 g, 2.1 mmol) was obtained from intermediate IM-4e in a yield of 31% in substantially the same manner as in Synthesis Example 25, but in the synthesis of compound BD114, intermediate IM-3e was used instead of intermediate IM-3a.
[0905] Synthesis Example 29: Synthesis of Compound BD117
[0906] Intermediate IM-4d (8.4 g, 7.0 mmol) was obtained in a yield of 95%, and compound BD117 (3.0 g, 2.2 mmol) was obtained from intermediate IM-4d in a yield of 31% in substantially the same manner as in Synthesis Example 25, but in the synthesis of compound BD117, intermediate IM-3d was used instead of intermediate IM-3a.
[0907] Synthesis Example 30: Synthesis of Compound BD115
[0908] Intermediate IM-4f (8.4 g, 7.0 mmol) was obtained in a yield of 95% in substantially the same manner as in Synthesis Example 25, and compound BD115 (3.0 g, 2.2 mmol) was obtained from intermediate IM-4f in a yield of 32%, but when synthesizing compound BD115, intermediate IM-3f was used instead of intermediate IM-3a.
[0909] Synthesis Example 31: Synthesis of Compound BD118
[0910] Intermediate IM-4g (9.3 g, 7.0 mmol) was obtained in a yield of 95%, and compound BD118 (2.9 g, 2.0 mmol) was obtained from intermediate IM-4g in a yield of 31% in substantially the same manner as in Synthesis Example 25, but in the synthesis of compound BD118, intermediate IM-3g was used instead of intermediate IM-3a.
[0911] Synthesis Example 32: Synthesis of Compound BD119
[0912] Intermediate IM-4h (9.4 g, 7.0 mmol) was obtained in a yield of 95% in substantially the same manner as in Synthesis Example 25, and compound BD119 (2.7 g, 1.8 mmol) was obtained from intermediate IM-4h in a yield of 31%, but when synthesizing compound BD119, intermediate IM-3h was used instead of intermediate IM-3a.
[0913] Synthesis Example 33: Synthesis of Compound BD116
[0914] Intermediate IM-4i (8.9 g, 7.0 mmol) was obtained in a yield of 95% in substantially the same manner as in Synthesis Example 25, and compound BD116 (3.3 g, 2.2 mmol) was obtained from intermediate IM-4i in a yield of 32%, but when synthesizing compound BD116, intermediate IM-3i was used instead of intermediate IM-3a.
[0915] Synthesis Example 34: Synthesis of Compound BD120
[0916] Intermediate IM-4j (10.0 g, 7.0 mmol) was obtained in a yield of 95% in substantially the same manner as in Synthesis Example 25, and compound BD120 (2.8 g, 1.8 mmol) was obtained from intermediate IM-4j in a yield of 25%, but when synthesizing compound BD120, intermediate IM-3j was used instead of intermediate IM-3a.
[0917] The compounds synthesized according to the synthesis examples 1 H nuclear magnetic resonance spectrum (NMR) and mass spectrum / fast atom bombardment (MS / FAB) are shown in Table 1. Those skilled in the art can easily recognize the synthesis methods of compounds other than those synthesized in the above synthesis examples by referring to the synthesis routes and starting materials.
[0918] Table 1
[0919]
[0920]
[0921]
[0922] Evaluation Example 1
[0923] The HOMO energy level and the LUMO energy level of each of Compound BD01, Compound BD02, Compound BD113 to Compound BD120, and Compound A and Compound B were evaluated according to the method in Table 2, and the results thereof are shown in Table 3.
[0924] Table 2
[0925]
[0926] Table 3
[0927]
[0928]
[0929]
[0930] Evaluation Example 2
[0931] Polymethyl methacrylate (PMMA) was prepared in CH 2 Cl 2 The solution in was mixed with compound BD01 (4 wt % compared to PMMA), and the resultant was applied to a quartz substrate using a spin coater, heat treated in an oven at 80° C., and then cooled to room temperature, thereby producing film BD01 having a thickness of 40 nm. Films BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, film A, and film B were each prepared in substantially the same manner as for preparing film BD01, except that compound BD02, compound BD113, compound BD114, compound BD115, compound BD116, compound BD117, compound BD118, compound BD119, compound BD120, compound A, and compound B were used, respectively, instead of compound BD01.
[0932] The emission spectrum of each of the films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A and B was measured using a Hamamatsu Quantaurus-QY absolute PL quantum yield spectrometer (xenon light source) equipped with a monochromator, a photon multichannel analyzer and an integrating sphere and using the photoluminescence quantum yield (PLQY) measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, the excitation wavelength was scanned from 320 nm to 380 nm at intervals of 10 nm, and the emission spectrum measured at an excitation wavelength of 340 nm was taken to obtain the maximum emission wavelength (emission peak wavelength) and FWHM of the organic metal compound contained in each film, which are shown in Table 4.
[0933] Subsequently, using Hamamatsu's Quantaurus-QY absolute PL quantum yield spectrometer, the luminescence quantum efficiency of each of film BD01, film BD02, film BD113, film BD114, film BD115, film BD116, film BD117, film BD118, film BD119, film BD120, film A and film B was measured by scanning at 10 nm intervals from 300 nm to 380 nm, and the PLQY measured at an excitation wavelength of 330 nm was taken, and thus, the luminescence quantum efficiency of the organometallic compound contained in each film was calculated and summarized in Table 4.
[0934] Table 4
[0935]
[0936]
[0937] From Table 4, it is confirmed that compound BD01, compound BD02, compound BD113, compound BD114, compound BD115, compound BD116, compound BD117, compound BD118, compound BD119 and compound BD120 each emit blue light while having equal or better PLQY and relatively equal or smaller FWHM than compound A and compound B.
[0938] Evaluation Example 3
[0939] The PL spectrum of each of the films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A and B was evaluated at room temperature by using FluoTime 300 (which is a time-resolved photoluminescence (TRPL) measurement system of PicoQuant) and PLS340 ((excitation wavelength = 340 nm, spectrum width = 20 nm), which is a pump source of PicoQuant), and then, the wavelength of the main peak of the spectrum was determined, and the number of photons emitted by each film at the wavelength of the main peak by the photon pulse (pulse width = 500 picoseconds) applied to each film by PLS340 was repeatedly measured over time based on time-correlated single photon counting (TCSPC) to obtain a TRPL curve that can be fully fitted. The results thus obtained were fitted with one or more exponential decay functions to obtain T 衰减 (Ex), i.e., the decay time (decay) of each of the films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, film A, and film B. The results are shown in Table 5. The function used for fitting is shown in Equation 20, and T obtained from each exponential decay function used for fitting 衰减 value, obtained as T 衰减 (Ex) Maximum T 衰减 In this regard, similar measurements were performed during the same amount of measurement time as that used to obtain the TRPL curve in the dark state (where the pump signal entering the membrane was blocked) to obtain a baseline or background signal curve, which was used as the baseline for the fitting.
[0940] Equation 20
[0941]
[0942] Table 5
[0943] Film No. Film composition (4wt% in PMMA) <![CDATA[T 衰减 (Ex)(μs)]]> BD01 BD01 2.31 BD02 BD02 2.32 BD113 BD113 2.35 BD114 BD114 2.36 BD115 BD115 2.35 BD116 BD116 2.36 BD117 BD117 2.34 BD118 BD118 2.32 BD119 BD119 2.34 BD120 BD120 2.36 A A 2.25 B B 2.12
[0944] Table 5 confirms that compound BD01, compound BD02, compound BD113, compound BD114, compound BD115, compound BD116, compound BD117, compound BD118, compound BD119 and compound BD120 each have a luminescence decay time equal to or longer than compound A and compound B (i.e., a lower luminescence conversion rate (Kr)).
[0945] Evaluation Example 4
[0946] For each of Compound A, Compound B, Compound BD01, Compound BD113, Compound BD115, and Compound BD116, thermogravimetric analysis (TGA) was performed under vacuum (temperature range: 0°C to 600°C (10°C / min), pan type or kind: Pt pan in disposable Al pan) to evaluate the temperature at which 10 wt% weight loss occurred (V-TGA_10 wt% loss, °C) and the temperature at which 50 wt% weight loss occurred (V-TGA_50wt% loss, °C) for each compound. The results are shown in Table 6.
[0947] Table 6
[0948]
[0949] As can be seen from Table 6, each of Compound BD01, Compound BD113, Compound BD115, and Compound BD116 has excellent or suitable heat resistance, because the V-TGA_10 wt% loss and the V-TGA_50 wt% loss of each of Compound BD01, Compound BD113, Compound BD115, and Compound BD116 occur at a higher temperature than that of Compound A.
[0950] Evaluation Example 5
[0951] The phase transition of each of Compound A, Compound B, Compound BD01, Compound BD113, Compound BD115, and Compound BD116 was evaluated using a SETSYS Evolution TG-DTA instrument from Setaram, and thus, the phase transition of each of Compound A, Compound B, Compound BD01, Compound BD113, Compound BD115, and Compound BD116 at an evaporation pressure (6.4×10 -4 The temperatures were calculated using the flow rate data of the reactor and are summarized in Table 7.
[0952] Table 7
[0953]
[0954]
[0955] As can be seen from Table 7, each of Compound BD01, Compound BD113, Compound BD115, and Compound BD116 has a lower phase transition temperature than Compound A and Compound B, and thus has excellent or suitable heat resistance.
[0956] Evaluation Example 6
[0957] The purity of each of Compound A, Compound B, Compound BD01, Compound BD113, Compound BD115, and Compound BD116 was measured using high performance liquid chromatography (HPLC) to evaluate P(0Hr)(%) of each compound. P(0Hr)(%) is the purity of the compound before heat treatment.
[0958] Subsequently, each of Compound A, Compound B, Compound BD01, Compound BD113, Compound BD115, and Compound BD116 was heat-treated for 360 hours in a chamber where the internal temperature was maintained at an evaporation pressure (6.4×10 -4 The precipitate was collected and then subjected to HPLC again to obtain the P(360Hr)(%) of each compound. P(360Hr)(%) is the purity of the compound after heat treatment for 360 hours.
[0959] Therefore, the purity change (%) P(360Hr)-P(0Hr) (%) after heat treatment of each compound was evaluated, and the results are shown in Table 8.
[0960] Table 8
[0961]
[0962]
[0963] As can be seen from Table 8, each of Compound BD01, Compound BD113, Compound BD115, and Compound BD116 has excellent or suitable heat resistance because the absolute value of the purity change after heat treatment is small compared with Compound A and Compound B.
[0964] Example 1
[0965] As an anode, it will have a 15Ω / cm 2 A glass substrate (product of Corning Inc.) on which ITO was formed was cut into a size of 50 mm x 50 mm x 0.7 mm, ultrasonicated with isopropyl alcohol and (then) pure water for 5 minutes each, cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes, and then fixed on a vacuum deposition apparatus.
[0966] 2-TNATA was vacuum deposited on the anode to form a A hole injection layer having a thickness of 1000 Å was formed, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as “NPB”) was vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .
[0967] On the hole transport layer, compound BD01 (organometallic compound represented by Formula 1), compound ETH2 (second compound) and compound HTH29 (third compound) were vacuum deposited on the hole transport layer to form a Herein, the amount of the compound BD01 was adjusted to about 13 wt% / total weight of the emission layer (100 wt%), and the weight ratio of the compound ETH2 to the compound HTH29 was adjusted to 3.5:6.5.
[0968] The compound ETH34 is vacuum deposited on the emission layer to form a A hole blocking layer with a thickness of , and ET46 and Liq were vacuum deposited on the hole blocking layer at a weight ratio of 4:6 to form a Next, Yb is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and then Mg is vacuum deposited thereon to form A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0969]
[0970]
[0971] Examples 2 to 14 and Comparative Examples A and B
[0972] Each organic light-emitting device was manufactured in substantially the same manner as in Example 1, but when forming the emission layer, the organometallic compound represented by Formula 1, the second compound, the third compound and / or the fourth compound and the amount thereof shown in Table 9 were used. The weight in brackets in Table 9 represents the weight of the compound based on 100% by weight of the emission layer.
[0973] Table 9
[0974]
[0975]
[0976]
[0977]
[0978] Evaluation Example 7
[0979] The brightness of each of the organic light-emitting devices manufactured in Examples 1 to 14 and Comparative Examples A and B at 1000 cd / m 2 The driving voltage (V), color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and service life (T 95 The results are shown in Table 10. The service life (T 95 ) represents the time (hours) taken to reach 95% brightness compared to the initial brightness.
[0980] Table 10
[0981]
[0982]
[0983] It can be confirmed from Table 10 that, compared with the organic light-emitting devices of Comparative Example A and Comparative Example B, the organic light-emitting devices of Examples 1 to 14 each emit deep blue light, and have excellent or suitable driving voltage, excellent or suitable color purity, excellent or suitable luminous efficiency, and excellent or suitable color conversion efficiency and excellent or suitable service life characteristics.
[0984] Comparative Example A-heat, Comparative Example B-heat and Example 1-heat, Example 3-heat, Example 5-heat and Example 6-heat
[0985] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that when forming the emission layer, the organometallic compound was changed as shown in Table 11. The "heat-treated compound" in Table 11 refers to a compound collected after heat treatment for 360 hours in a room as in Evaluation Example 6, wherein the internal temperature was maintained at an evaporation pressure (6.4×10 -4 (Trust).
[0986] Evaluation Example 9
[0987] The luminous efficiency (cd / A) of each of the organic light-emitting devices manufactured in Comparative Example A-Heat, Comparative Example B-Heat, and Example 1-Heat, Example 3-Heat, Example 5-Heat, and Example 6-Heat was each measured in substantially the same manner as in Evaluation Example 7. 2 and service life (T 95 The results are shown in Table 11. The service life (T 95 ) represents the time (hours) taken to reach 95% brightness compared to the initial brightness.
[0988] Then, "(Comparative Example A-heat luminous efficiency-luminous efficiency of Comparative Example A) / luminous efficiency of Comparative Example A×100" (%) and "(Comparative Example A-heat service life-service life of Comparative Example A) / service life of Comparative Example A×100" (%) were evaluated. The results are shown in Table 11. This evaluation was performed on each organic light-emitting device using compound BD01, compound BD113, compound BD115, and compound BD116, and the results are shown in Table 11.
[0989] Table 11
[0990]
[0991]
[0992] It can be seen from Table 11 that after the heat treatment of the organic light-emitting device using each of Compound BD01, Compound BD113, Compound BD115, and Compound BD116, the absolute values of the luminous efficiency change rate and the service life change rate are smaller than those of the organic light-emitting device using Compound A and Compound B. Therefore, it can be seen that the organic light-emitting device manufactured using the organometallic compound represented by Formula 1 (for example, manufactured by a deposition process) can have excellent or suitable luminous efficiency and service life characteristics at the same time.
[0993] By using the organometallic compound of the present disclosure, a light-emitting device having reduced driving voltage, improved color purity and luminous efficiency, and increased lifetime and a high-quality electronic device including the light-emitting device may be manufactured.
[0994] In the present disclosure, it should be understood that the terms “comprise(s)”, “include(s)” or “have / has” indicate the presence of specified features, integers, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components and / or groups thereof.
[0995] Throughout the present disclosure, when it is mentioned that a component such as a layer, film, region, or plate is "placed" on another component, it should be understood that it can be placed directly on the other component, or another component can be interposed therebetween. In some embodiments, "directly on..." can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and other parts. For example, "directly on..." can mean that two layers or two components are disposed without using additional components, such as adhesive components, therebetween.
[0996] In the present disclosure, although the terms "first", "second", etc. may be used herein to describe one or more than one element, component, region and / or layer, 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.
[0997] As used herein, the singular forms "a", "an", "one", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. In addition, the use of "may" when describing embodiments of the present disclosure means "one or more than one embodiment of the present disclosure."
[0998] As used herein, the terms "substantially," "about," or similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. "About," as used herein, includes the specified value and means within an acceptable range of deviations of the specified value as determined by one of ordinary skill in the art taking into account the relevant measurements and the errors associated with the measurement of the particular quantity (i.e., the limits of the measurement system). For example, "about" can mean within one or more than one standard deviation, or within ±30%, ±20%, ±10%, ±5% of the specified value.
[0999] Any numerical range listed herein is intended to include all sub-ranges of the same numerical precision included in the listed range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including end 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 value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in the present disclosure is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify the present disclosure (including claims) to clearly list any sub-ranges included in the scope clearly listed herein.
[1000] Any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware, and hardware may be used to implement the light emitting device, light emitting device, display device, electronic device, electronic device, or any other related device or component according to the embodiments of the present disclosure described herein. For example, the various components of the device may be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device may be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components for performing the various functions described herein. The computer program instructions are stored in a memory, which may be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions may also be stored in other non-temporary computer-readable media, such as a CD-ROM, a flash drive, etc. as an example. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or that the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[1001] It should be understood that the embodiments described herein should be considered in a descriptive sense only, and not for limiting purposes. The description of the features or aspects in each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more than one embodiment has been described with reference to the accompanying drawings, it should be understood by those of ordinary skill in the art that one or more than one suitable changes in form and detail may be made herein without departing from the subject and scope defined by the appended claims and their equivalents.
Claims
1. A light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; as well as An organometallic compound represented by Formula 1: Formula 1 Formula 1A Among them, in formula 1, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 is N, and X2 is C, Ring CY1 and ring CY2 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, L1 and L2 are each independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', * and *' each represent a binding site with an adjacent atom, n1 and n2 are each independently an integer from 1 to 5, R1 to R7, R 1a and R 1b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), a1 and a2 are each independently an integer from 1 to 20, a3, a4, a6 and a7 are each independently an integer from 1 to 3, a5 is an integer from 1 to 4, Ar1 and Ar2 are each independently a group represented by formula 1A, Wherein, in Formula 1A, Y1 to Y3, Z1 and Z2 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), At least one of Z1 and Z2 is unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, * indicates the binding site with the adjacent atom in Formula 1, Two or more adjacent groups selected from a1 R1 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a2 R2 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a3 R3 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a4 R4 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a5 R5 are optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a6 R6 are optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a7 R7 are optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, R 1a and R 1b Optionally combine with each other to form unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R1, R2, R3, R4, R5, R6, R7, R 1a , R 1b Two or more adjacent groups among Ar1 and Ar2 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, and Where R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted with C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, or C2-C 60 a heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C4 substituted with an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group, or C2-C 60 Heteroarylalkyl groups.
2. The light emitting device according to claim 1, wherein The emission layer comprises a host and a dopant, and The dopant includes the organometallic compound.
3. The light emitting device according to claim 1, further comprising: Contains at least one nitrogen-containing C1-C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, The organometallic compound, the second compound, the third compound and the fourth compound are different from each other: Formula 3 In formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 a cyclic group or a pyridine group, X 71 is a single bond; or a linking group comprising O, S, N, B, C, Si or any combination thereof, and * represents a bonding site with any atom included in the remaining part except 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 pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or any combination thereof, and The fourth compound is a compound including at least one cyclic group containing 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 comprising the light emitting device according to any one of claims 1 to 5.
7. The electronic device as claimed in claim 6, further comprising Thin film transistors, where 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 as claimed in claim 6, further comprising Color filters, color conversion layers, touch screen layers, polarizing layers, or any combination thereof.
9. Electronic equipment comprising the light emitting device according to any one of claims 1 to 5.
10. The electronic device of 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 light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a portable phone, a tablet personal computer, a tablet phone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device and a sign.
11. An organometallic compound represented by Formula 1: Formula 1 Formula 1A in, In formula 1, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 is N, and X2 is C, Ring CY1 and ring CY2 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, L1 and L2 are each independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', * and *' each represent a binding site with an adjacent atom, n1 and n2 are each independently an integer from 1 to 5, R1 to R7, R 1a and R 1b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), a1 and a2 are each independently an integer from 1 to 20, a3, a4, a6 and a7 are each independently an integer from 1 to 3, a5 is an integer from 1 to 4, Ar1 and Ar2 are each independently a group represented by formula 1A, Wherein, in Formula 1A, Y1 to Y3, Z1 and Z2 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 an arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), At least one of Z1 and Z2 is unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl groups, * indicates the binding site with the adjacent atom in Formula 1, Two or more adjacent groups selected from a1 R1 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a2 R2 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a3 R3 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a4 R4 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a5 R5 are optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a6 R6 are optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Two or more adjacent groups selected from a7 R7 are optionally combined with each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, R 1a and R 1b Optionally combine with each other to form unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R1, R2, R3, R4, R5, R6, R7, R 1a , R 1b Two or more adjacent groups among Ar1 and Ar2 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, and Where R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted with C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, or C2-C 60 a heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C4 substituted with an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group, or C2-C 60 Heteroarylalkyl groups.
12. The organometallic compound according to claim 11, wherein Ring CY1 and ring CY2 are each independently Benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzothioole group, a dibenzothioole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothioole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group The invention also includes but is not limited to: an azole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasilinyl group, a dibenzothiasilinyl group, a dibenzodihydroazasilinyl group, a dibenzodihydrodisilinyl group, a dibenzodihydrosilinyl group, a dibenzodioxinyl group, a dibenzooxathiainyl group, a dibenzoxazine group, a dibenzopyran group, a dibenzodithiainyl group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group or a dibenzodihydropyrazine group.
13. The organometallic compound according to claim 11, wherein L1 is a single bond, L2 is *-O-*' or *-S-*', and n1 is 1, * and *' each represent a binding site with an adjacent atom.
14. The organometallic compound according to claim 11, wherein R1 to R7 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 Alkoxy groups; Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a (C1-C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C1-C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a an oxazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilyl group; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Q1 to Q3 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C4 substituted with an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group.
15. The organometallic compound according to claim 11, wherein Y1 to Y3, Z1 and Z2 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 Alkoxy groups; Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a (C1-C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted by a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, (C1-C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a an oxazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilyl group; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Q1 to Q3 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C4 substituted with an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group.
16. The organometallic compound according to claim 11, wherein one selected from Z1 and Z2 is an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group or a tert-pentyl group, each of which is unsubstituted or substituted with at least one deuterium, and The other selected from Z1 and Z2 is neither hydrogen nor deuterium.
17. The organometallic compound according to claim 11, wherein one selected from Z1 and Z2 is an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group or a tert-pentyl group, each of which is unsubstituted or substituted with at least one deuterium, and The other one selected from Z1 and Z2 is each unsubstituted or substituted with deuterium, C1-C 20 an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group or a pyrimidyl group substituted with an alkyl group or any combination thereof.
18. The organometallic compound according to claim 11, wherein Y1 to Y3 are each independently hydrogen or deuterium.
19. The organometallic compound according to claim 11, wherein In formula 1, Depend on The group represented by is represented by one selected from the group consisting of Formula CY1(1) to Formula CY1(29), and Depend on The group represented by is represented by one selected from the formula CY2(1) to the formula CY2(25): In Formulas CY1(1) to CY1(29) and CY2(1) to CY2(25), R 11 To R 17 are each independently the same as defined for R1 in Formula 1, T 21 is B(Y 21 ), C(Y 21 )(Y 22 ), N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 is C(Y 21 ), N or Si(Y 21 ), R 21 To R 26 , Y 21 and Y 22 Each is independently the same as defined for R2 in Formula 1, * represents the binding site with M in Formula 1, *' represents the binding site with L1 in Formula 1, and *" indicates the binding site with L2 in Formula 1.
20. The organometallic compound according to claim 11, wherein the organometallic compound is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 In formula 1-1 and formula 1-2, M, Ar1 and Ar2 are each the same as defined in Formula 1, L2 is *-O-*' or *-S-*', * and *' each represent the binding site with the adjacent atom, X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, X 24 is C(R 24 ) or N, X 25 is C(R 25 ) or N, X 26 is C(R 26 ) or N, X 31 is C(R 31 ), X 32 is C(R 32 ), X 33 is C(R 33 ), X 41 is C(R 41 ), X 42 is C(R 42 ), X 43 is C(R 43 ), X 51 is C(R 51 ), X 52 is C(R 52 ), X 53 is C(R 53 ), X 54 is C(R 54 ), X 61 is C(R 61 ), X 62 is C(R 62 ), X 63 is C(R 63 ), X 71 is C(R 71 ), X 72 is C(R 72 ), X 73 is C(R 73 ), R 11 To R 14 are each independently the same as defined for R1 in Formula 1, R 21 To R 26 are each independently the same as defined for R2 in Formula 1, R 31 To R 33 are each independently the same as defined for R3 in Formula 1, R 41 To R 43 are each independently the same as defined for R4 in Formula 1, R 51 To R 54 are each independently the same as defined for R5 in Formula 1, R 61 To R 63 are each independently the same as defined for R6 in Formula 1, R 71 To R 73 are each independently the same as defined for R7 in Formula 1, Selected from R 11 To R 14 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 21 To R 26 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 31 To R 33 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 41 To R 43 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 51 To R 54 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 61 To R 63 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 71 To R 73 Two or more adjacent groups in the formula (R) are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, Selected from R 11 To R 14 , R 21 To R 26 , R 31 To R 33 , R 41 To R 43 , R 51 To R 54 , R 61 To R 63 , R 71 To R 73 Two or more adjacent groups among Ar1 and Ar2 are optionally combined with each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, and R 10a Same as defined in Formula 1.
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