Organic light emitting device and organometallic compound
By using organometallic compounds with specific structures in organic light-emitting devices, particularly the first compound represented by Formula 1 and optional compounds represented by Formulas 2 and 3, the luminous efficiency and lifetime are improved, solving the problems of insufficient efficiency and lifetime in the prior art.
Patent Information
- Application Number
- CN202010473842.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-06-14
- Filing Date
- 2020-05-29
- Publication Date
- 2025-12-09
- Estimated Expiration
- 2040-05-29
AI Technical Summary
Existing organic light-emitting devices are insufficient in terms of luminous efficiency and lifespan, making it difficult to meet high-performance requirements.
Compounds that use organometallic compounds with specific structures as emission layers, including a first compound represented by Formula 1 and optional second and third compounds represented by Formula 2 and Formula 3, constitute an organic layer to improve luminescence efficiency and lifetime.
This improves the luminous efficiency and extends the lifespan of organic light-emitting devices, meeting the demands of high-performance applications.
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Figure CN112086566B_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0071060, filed on June 14, 2019, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments relate to organic light-emitting devices and organometallic compounds. Background Technology
[0004] Organic light-emitting devices are self-emitting devices, and compared with other devices in the field, they have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] An example of such an organic light-emitting device may include a first electrode on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied by the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied by the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) recombine in the emitter layer to generate excitons. These excitons transition from excited states (e.g., transition or relaxation) to the ground state, thereby generating light. Summary of the Invention
[0006] One or more embodiments include organic light-emitting devices with high luminous efficiency and long lifespan, as well as organometallic compounds.
[0007] Other aspects of the implementation 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 proposed implementation.
[0008] Embodiments of this disclosure provide an organic light-emitting device, including:
[0009] First electrode;
[0010] The second electrode facing the first electrode; and
[0011] An organic layer between the first and second electrodes, including an emission layer.
[0012] The organic layer includes a first compound represented by Formula 1:
[0013] Formula 1
[0014]
[0015] In Equation 1,
[0016] M can be a transition metal, but can not be iridium, and
[0017] L2may be a monodentate ligand represented by Formula 2-1 or Formula 2-2, but can not be any one of -F, -Cl, -Br, and -I:
[0018]
[0019] In Formula 1, Formula 2-1, and Formula 2-2,
[0020] X1to X4may be each independently N or C, wherein at least one of X1to X3may be a carbon atom (C) of the carbene moiety,
[0021] T 11 to T 14 may be each independently a bond, *-O-*', *-S-*', *-B(R')-*', *-N(R')-*', *-P(R')-*', *-C(R')(R")-*', *-Si(R')(R")-*', *-Ge(R')(R")-*', *-C(=O)-*', or *-C(=S)-*,
[0022] T 15 may be a bond, *-O-*', *-S-*', *-B(R')-*', *-N(R')-*', *-P(R')-*', *-C(R')(R")-*', *-Si(R')(R")-*', *-Ge(R')(R")-*', *-C(=O)-*', *-C(=S)-*', *-O-C(=O)-*', *-S-C(=O)-*', *-O-C(=S)-*', *-S-C(=S)-*', *-C(R')=C(R")-*', *-C≡C-*', *-C≡C-C(=O)-*', or *-C≡C-C(=S)-*,
[0023] when T 11 is a bond, X1and M can be directly connected to each other, when T 12 is a bond, X2and M can be directly connected to each other, when T 13 is a bond, X3and M can be directly connected to each other, and when T 14 or T 15 is a bond, X4or R5and M can be directly connected to each other,
[0024] selected from i) a bond between X1or T 11 and M, ii) a bond between X2or T 12 and M, iii) a bond between X3or T 13a bond between M and X4, and iv) a bond between M and T 14 , R5or T 15 two of the bonds between M and X4, and between M and T can each be a coordinate bond, and the other two bonds can each be a covalent bond,
[0025] T1may be a single bond, a double bond, *-N(R6)-*, *-B(R6)-*, *-P(R6)-*, *-C(R 6a )(R 6b )-*, *-Si(R 6a )(R 6b )-*, *-Ge(R 6a )(R 6b )-*, *-S-*, *-Se-*, *-O-*, *-C(=O)-*, *-S(=O)-*, *-S(=O)2-*, *-C(R6)=*, * = C(R6)-*, *-C(R 6a ) = C(R 6b )-*, *-C(=S)-*, or *-C=C-*,
[0026] T2may be a single bond, a double bond, *-N(R7)-*, *-B(R7)-*, *-P(R7)-*, *-C(R 7a )(R 7b )-*, *-Si(R 7a )(R 7b )-*, *-Ge(R 7a )(R 7b )-*, *-S-*, *-Se-*, *-O-*, *-C(=O)-*, *-S(=O)-*, *-S(=O)2-*, *-C(R7)=*, * = C(R7)-*, *-C(R 7a ) = C(R 7b )-*, *-C(=S)-*, or *-C=C-*,
[0027] rings CY1to CY4may each independently be a C5-C 30 carbocyclyl or a C1-C 30 heterocyclyl,
[0028] R1to R4, R6, R 6a , R 6b , R7, R 7a , R 7b , R' and R" can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, substituted or unsubstituted C1-C 60alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic 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),
[0029] R5may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, -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), wherein, when T 15 may not be any one of -F, -Cl, -Br, and -I,
[0030] a1to a4may each independently be one of integers from 0 to 20,
[0031] two or more of the plurality of R1(e.g., a number a1 of R1) can optionally be connected to each other to form an unsubstituted or substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl,
[0032] two or more of the plurality of R1(e.g., a number a1 of R1) can optionally be connected to each other to form an unsubstituted or substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl,
[0033] two or more of the plurality of R1(e.g., a number a1 of R1) can optionally be connected to each other to form an unsubstituted or substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl,
[0034] two or more of the plurality of R1(e.g., a number a1 of R1) can optionally be connected to each other to form an unsubstituted or substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl,
[0035] two or more of the plurality of R1(e.g., a number a1 of R1) can optionally be connected to each other to form an unsubstituted or substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 10a substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 30 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl,
[0036] R 10a may be the same as defined in connection with R1, and R 10a is not hydrogen,
[0037] * and *' each indicate a point of attachment to an adjacent atom,
[0038] substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 60 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 60 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 60 substituted C5-C10carbocyclyl, or an unsubstituted or substituted 3- to 10-membered heterocyclyl, 60alkyl, C2-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 aralkylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic radical and monovalent non-aromatic fused heteropolycyclic radical can be:
[0039] deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy;
[0040] C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 aralkylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic radical and monovalent non-aromatic fused heteropolycyclic radical, -O(Q 11 ), -S(Q 11 ), -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -P(Q 11 )(Q12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof;
[0041] Each of the following C3-Cs that are not substituted or are substituted by: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -O(Q 21 -S(Q) 21 ), -Si(Q 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21)(Q 22 ) or any combination thereof;
[0042] -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 ), or -P(=O)(Q 31 )(Q 32 ); or
[0043] any combination thereof, and
[0044] Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazino; hydrazono; C1-C 60 alkyl unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; C3-C 10 cycloalkyl; C1-C 10 heterocycloalkyl; C3-C 10 cycloalkenyl; C1-C 10 heterocycloalkenyl; C6-C 60 aryl unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C6-C 60 aryloxy; C6-C 60 arylthio; C1-C 60 heteroaryl unsubstituted or substituted with deuterium, -F, cyano, C1-C 60alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.
[0045] In one or more embodiments, the organic layer can further include a second compound represented by Formula 2, a third compound including a group represented by Formula 3, or any combination thereof, and
[0046] The second compound is different from the third compound:
[0047] Formula 2
[0048]
[0049] Formula 3
[0050]
[0051] wherein, in Formula 2 and Formula 3,
[0052] Ring CY 71 and Ring CY 72 may each independently be a C5-C 30 carbocyclic group, or a C1-C 30 heterocyclic group,
[0053] L 51 to L 53 may each independently be unsubstituted or substituted with at least one R 10a substituted C5-C 30 carbocyclic group, or unsubstituted or substituted with at least one R 10a substituted C1-C 30 heterocyclic group,
[0054] b51 to b53 can each independently be one of an integer of 0 to 5, wherein, when b51 is 0, *-(L 51 ) b51 *-' is a single bond, when b52 is 0, *-(L 52 ) b52 *-' is a single bond, and when b53 is 0, *-(L 53 ) b53 *-' is a single bond,
[0055] when b51 is 2 or more, two or more L 51 may be the same as or different from each other; when b52 is 2 or more, two or more L 52 may be the same as or different from each other, and when b53 is 2 or more, two or more L 53 may be the same as or different from each other,
[0056] X54 may be N or C(R 54 ), X 55 may be N or C(R 55 ), X 56 may be N or C(R 56 ), and X 54 may be N, 56
[0057] X 81 may be a single bond, O, S, N(R 81 ), B(R 81 ), C(R 81a )(R 81b ), or Si(R 81a )(R 81b ),
[0058] R 51 to R 56 , R 71 , R 72 , R 81 , R 81a , and R 81b may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -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),
[0059] R 10a It can be the same as the one defined above, and R 10a Not hydrogen,
[0060] a71 and a72 can each be an integer from 0 to 20 independently.
[0061] When a71 is 2 or greater, two or more R 71 They can be the same or different from each other; and when a72 is 2 or greater, two or more R... 72 They can be the same or different from each other.
[0062] * and *' can each indicate a binding site with an adjacent atom.
[0063] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 The substituents of alkyl heteroaryl groups, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heterocyclic groups can be:
[0064] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy;
[0065] Each of the following C1-C is replaced60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic, fused polycyclic group, monovalent non-aromatic, fused heteropolycyclic group, -O(Q 11 ), -S(Q 11 ), -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -P(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0066] each unsubstituted or each substituted C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic, fused polycyclic group or monovalent non-aromatic, fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -O(Q 21 -S(Q) 21 ), -Si(Q 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof;
[0067] -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 ) or -P(=O)(Q 31 (Q) 32 );or
[0068] Its arbitrary combination, and
[0069] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q31 to Q 33 may each independently be hydrogen; deuterium; -F; -CI; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazino; hydrazone; C1-C 60 alkyl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; C3-C 10 cycloalkyl; C1-C 10 heterocycloalkyl; C3-C 10 cycloalkenyl; C1-C 10 heterocycloalkenyl; C6-C 60 aryl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C6-C 60 aryloxy; C6-C 60 arylthio; C1-C 60 heteroaryl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.
[0070] Another aspect of the embodiments of the present disclosure provides an organic metal compound represented by Formula 1. BRIEF DESCRIPTION OF DRAWINGS
[0071] These and / or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings in which:
[0072] Figure 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment;
[0073] Figure 2 is a wavelength-emission intensity graph of the organic light emitting devices manufactured according to Example 5 and Comparative Examples 1 and 2;
[0074] Figure 3 is a luminance-luminous efficiency graph of the organic light emitting devices manufactured according to Example 5 and Comparative Examples 1 and 2;
[0075] Figure 4 is a wavelength-emission intensity graph of the organic light emitting devices manufactured according to Example 5 and Comparative Examples 1 and 2; is a wavelength-emission intensity graph of the organic light emitting devices manufactured according to Example 5 and Comparative Examples 1 and 2;
[0076] Figure 5 Wavelength-emission intensity graphs for organic light emitting devices manufactured according to Examples 16 to 18;
[0077] Figure 6 Luminance-luminous efficiency graphs for organic light emitting devices manufactured according to Examples 5 and 12 to 18;
[0078] Figure 7 Time-luminance graphs for organic light emitting devices manufactured according to Examples 12 to 18; and
[0079] Figure 8 Time-resolved electroluminescence (TREL) spectra for organic light emitting devices manufactured according to Examples 14 and 17. DETAILED DESCRIPTION
[0080] Reference will now be made in detail to implementations, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present implementations can have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the implementations are described below, by reference to the drawings, to explain aspects of the present description. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
[0081] Aspects of implementations of the present disclosure provide an organic light emitting device, including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes a first compound represented by the following Formula 1:
[0082] Formula 1
[0083]
[0084] Formula 1 can be the same as described herein above.
[0085] In addition to the first compound represented by Formula 1, the organic layer can further include a second compound represented by Formula 2, a third compound including a group represented by Formula 3, or any combination thereof:
[0086] Formula 2
[0087]
[0088] Formula 3
[0089]
[0090] Formula 2 and Formula 3 can each independently be the same as described herein above.
[0091] The second compound and the third compound can be different from each other.
[0092] In one embodiment, the organic layer can include the second compound and the third compound.
[0093] In one or more embodiments, the organic layer can include the first compound, the second compound, and the third compound, and the first compound, the second compound, and the third compound can all be included in the emission layer.
[0094] M in Formula 1 can be a transition metal, but can not be iridium.
[0095] For example, M can be titanium (Ti), cobalt (Co), copper (Cu), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), gold (Au), osmium (Os), or rhenium (Re).
[0096] In one embodiment, M in Formula 1 can be Pt, Pd, or Au.
[0097] L2 in Formula 1 can be a monodentate ligand represented by Formula 2-1 or Formula 2-2, but can not be any one of -F, -Cl, -Br, and -I:
[0098]
[0099] Formula 2-1 and Formula 2-2 can each independently be the same as described herein.
[0100] X1 to X4 in Formula 1 and Formula 2-1 can each independently be N or C, wherein at least one of X1 to X3 can be a carbon atom (C) of a carbene moiety.
[0101] For example, X1 and X3 in Formula 1 can each be a carbon atom (C) of a carbene moiety.
[0102] T in Formula 1 and Formula 2-1 11 to T 14 may each independently be a bond (e.g., a single bond), *-O-*', *-S-*', *-B(R')-*', *-N(R')-*', *-P(R')-*', *-C(R')(R")-*', *-Si(R')(R")-*', *-Ge(R')(R")-*', *-C(=O)-*', or *-C(=S)-*', and T 15may be a chemical bond (e.g., a single bond), *-O-*', *-S-*', *-B(R')-*', *-N(R')-*', *-P(R')-*', *-C(R')(R")-*', *-Si(R')(R")-*', *-Ge(R')(R")-*', *-C(=O)-*', *-C(=S)-*', *-O-C(=O)-*', *-S-C(=O)-*', *-O-C(=S)-*', *-S-C(=S)-*', *-C(R')=C(R")-*', *-C≡C-*', *-C≡C-C(=O)-*', or *-C≡C-C(=S)-*.
[0103] In Formula 1, Formula 2-1, and Formula 2-2, when T 11 is a chemical bond (e.g., a single bond), X1and M can be directly connected to each other, when T 12 is a chemical bond (e.g., a single bond), X2and M can be directly connected to each other, when T 13 is a chemical bond (e.g., a single bond), X3and M can be directly connected to each other, and when T 14 or T 15 is a chemical bond (e.g., a single bond), X4or R5, respectively, and M can be directly connected to each other.
[0104] For example, in Formula 1, Formula 2-1, and Formula 2-2, T 11 to T 13 may each independently be a chemical bond (e.g., a single bond), and T 14 and T 15 may be a chemical bond (e.g., a single bond), O, or S, but embodiments of the present disclosure are not limited thereto.
[0105] In Formula 1, Formula 2-1, and Formula 2-2, two bonds selected from i) a bond between X1or T 11 and M, ii) a bond between X2or T 12 and M, iii) a bond between X3or T 13 and M, and iv) a bond between X4, T 14 , R5, or T 15 and M can each be a coordinate bond (which can also be referred to as a dative covalent bond or a dative bond), and the other two bonds can each be a covalent bond. Thus, the first compound represented by Formula 1 can be electrically neutral (e.g., the first compound represented by Formula 1 can have no charge or substantially no charge).
[0106] In one embodiment, in Formula 1, T 11 to T 13Each bond can be a chemical bond (e.g., a single bond). The bonds between X1 and M, and between X3 and M, can each be coordinate bonds (also called coordinate covalent bonds or coordinate bonds). The bond between X2 and M can be a covalent bond, and X4, T... 14 R5 or T 15 The bond between M and M can be a covalent bond, but the embodiments of this disclosure are not limited thereto.
[0107] In Equation 1, T1 can be a single bond, a double bond, *-N(R6)-*', *-B(R6)-*', *-P(R6)-*', or *-C(R6)-*'. 6a (R) 6b )-*'、*-Si(R 6a (R) 6b )-*'、*-Ge(R 6a (R) 6b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R6)=*', *=C(R6)-*', *-C(R 6a )=C(R 6b )-*', *-C(=S)-*' or *-C≡C-*', and T2 can be a single bond, a double bond, *-N(R7)-*', *-B(R7)-*', *-P(R7)-*', *-C(R7)-*', or *-C(R7)-*'. 7a (R) 7b )-*'、*-Si(R 7a (R) 7b )-*'、*-Ge(R 7a (R) 7b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R7)=*', *=C(R7)-*', *-C(R 7a )=C(R 7b )-*'、*-C(=S)-*' or*-C≡C-*'.
[0108] For example, T1 and T2 in Equation 1 can be single bonds.
[0109] In Equations 1, 2-1, and 3, rings CY1 to CY4, and ring CY 71 and CY 72 Each can be independently designated as C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group.
[0110] In one embodiment, in Formula 1, Formula 2-1, and Formula 3, ring CY1to ring CY4, ring CY 71 and ring CY 72 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused (e.g., joined together) to one another, iv) a fused ring in which two or more second rings are fused (e.g., joined together) to one another, or v) a fused ring in which one or more first rings are fused (e.g., joined together) to one or more second rings.
[0111] The first ring can be a cyclopentyl, cyclopentadienyl, furanyl, thienyl, pyrrolyl, thiopyrrolyl, oxazolyl, isoxazolyl, oxadiazolyl, isoxadiazolyl, oxatriazolyl, isoxatriazolyl, thiazolyl, isothiazolyl, thiadiazolyl, isothiadiazolyl, thiatricazolyl, isothiatricazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, azathiopyrrolyl, diazathiopyrrolyl, or trizathiopyrrolyl.
[0112] The second ring can be an adamantyl, norbornyl, norbornenyl, cyclohexyl, cyclohexenyl, phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, oxasilacyclohexadienyl, thiasilacyclohexadiene, dihydroazasilacyclohexadienyl, dihydrosilacyclohexadienyl, dihydrosilacyclohexadienyl, dioxinyl, oxathianyl, oxazinyl, pyryl, dithianyl, thiazinyl, thiopyryl, cyclohexadienyl, dihydropyridyl, or dihydropyrazinyl.
[0113] In one or more embodiments, in Formula 1, ring CY1and ring CY3may each independently be i) a first ring, iii) a fused ring in which two or more first rings are fused (e.g., joined together) to one another, or v) a fused ring in which one or more first rings are fused (e.g., joined together) to one or more second rings, and ring CY2may be ii) a second ring, iv) a fused ring in which two or more second rings are fused (e.g., joined together) to one another, or v) a fused ring in which one or more first rings are fused (e.g., joined together) to one or more second rings.
[0114] In one or more embodiments, in Formula 1, Formula 2-1, and Formula 3, ring CY1to ring CY4, ring CY 71 and ring CY 72may each independently be phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, chrysenyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzothiazolyl, benzogermanolyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzothiazolyl, dibenzogermanolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzothiazolyl, azabenzogermanolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzothiazolyl, azadibenzogermanolyl, azadibenzoborolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene 5-oxide, azido-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, phenothiazine 5,5-dioxide, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolyl, or 5,6,7,8-tetrahydroquinolyl.
[0115] In one or more embodiments, in Formula 1 and Formula 2-1,
[0116] Ring CY1 and Ring CY3 may each independently be imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, azabenzimidazolyl, azabenzoxazolyl, azabenzothiazolyl, azabenzoxadiazolyl, or azabenzothiadiazolyl,
[0117] Ring CY2may be phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, chrysenyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, 5,6,7,8-tetrahydroisoquinolyl, or 5,6,7,8-tetrahydroquinolyl, and
[0118] The ring CY4may be phenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, pyrenyl, perylenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, indolyl, benzoborolyl, benzo phospholyl, indenyl, benzothiazolyl, benzo germyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzothiazolyl, dibenzogermolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzothiazolyl, azabenzogermolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzothiazolyl, azadibenzogermolyl, azadibenzoborolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene 5-oxide, azido-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, phenothiazine 5,5-dioxide, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolyl, or 5,6,7,8-tetrahydroquinolyl.
[0119] In Formula 2, L 51 to L 53 may each independently be unsubstituted or substituted with at least one R 10a substituted C5-C 30 carbocyclyl, or unsubstituted or substituted with at least one R 10a substituted C1-C 30 heterocyclyl.
[0120] For example, in Formula 2, L 51 to L 53may each independently be phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, chrysenyl, cyclopentadienyl, furanyl, thiophenyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzosilolyl, dibenzosilolyl, azaf luorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, or benzothiadiazolyl, each unsubstituted or substituted with: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilolyl, dimethyldibenzosilolyl, diphenyldibenzosilolyl, -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(=0)(Q 31 ), -S(=0)2(Q 31 ), -P(=0)(Q 31 )(Q 32 ), or any combination thereof, and
[0121] Q 31 through Q 33 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
[0122] In one embodiment, in Formula 2, the bond between L 51 and R 51 , the bond between L 52 and R 52 , the bond between L 53 and R53 The key between two or more L 51 The key between two or more L 52 The key between two or more L 53 The key between them, L in Formula 2 51 With X 54 and X 55 The bonds between carbon atoms, L in Formula 2 52 With X 54 and X 56 The bonds between carbon atoms, and L in Equation 2 53 With X 55 and X 56 The bonds between carbon atoms can each be "carbon-carbon single bonds", but the embodiments of this disclosure are not limited thereto.
[0123] In Equation 2, b51 to b53 each indicate L. 51 To L 53 The quantity, and can be an integer from 0 to 5, where, when b51 is 0, *-(L 51 ) b51 -*' can be a single key; when b52 is 0, *-(L 52 ) b52 -*' can be a single key, and when b53 is 0, *-(L 53 ) b53 -*' can be a single key; when b51 is 2 or greater, it can be two or more L's. 51 They can be the same or different from each other; when b52 is 2 or greater, two or more Ls 52 They can be the same or different from each other, and when b53 is 2 or greater, two or more Ls 53 They can be the same or different from each other. For example, b51 to b53 can each be 0, 1 or 2 independently.
[0124] In Equation 2, X 54 It can be N or C(R) 54 ), X 55 It can be N or C(R) 55 ), X 56 It can be N or C(R) 56 ), and X 54 To X 56 At least one of them can be N. R 54 To R 56 Each can be independently identical to the one described above. For example, X 54 To X 56 Two or three of them can be N independently.
[0125] In Equation 3, X81 may be a single bond, O, S, N(R 81 ), B(R 81 ), C(R 81a )(R 81b ), or Si(R 81a )(R 81b ). R 81 , R 81a , and R 81b may each independently be the same as described herein above.
[0126] R1to R4, R6, R 6a , R 6b , R7, R 7a , R 7b , R', R", R 51 to R 56 , R 71 , R 72 , R 81 , R 81a , and R 81b may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic 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), wherein Q1to Q3may be understood by reference to the corresponding description provided herein.
[0127] R 10a may be the same as defined in connection with R1, and R 10a is not hydrogen.
[0128] For example, R1to R4, R6, R 6a , R 6b , R7, R 7a , R 7b , R', R", R 51 to R 56 , R 71 , R 72 , R 81 , R 81a and R 81b may each independently be:
[0129] hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl or C1-C 20 alkoxy;
[0130] C1-C 20 alkyl or C1-C 20 alkoxy each substituted with deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, or any combination thereof;
[0131] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10alkyl, C1-C 20 alkyl, C1-C 20 alkyl, C1-C 10 alkyl, C1-C 31 alkyl, C1-C 31 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C 33 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C 31 alkyl, C1-C 31 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C
[0132] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0133] Q1to Q3and Q 31 to Q 33 may each independently be:
[0134] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0135] each unsubstituted or substituted with deuterium, C1-C6alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof, 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof,
[0136] However, embodiments of the present disclosure are not limited thereto:
[0137] Formula 91
[0138]
[0139] In Formula 91,
[0140] Ring CY 91 and Ring CY 92 may each independently be unsubstituted or substituted with at least one R 10a substituted C5-C 30 carbocyclyl, or unsubstituted or substituted with at least one R 10a substituted C1-C 30 heterocyclyl,
[0141] X 91 may be a single bond, O, S, N(R 91 ), B(R 91 ), C(R 91a )(R 91b ), or Si(R 91a )(R 91b ),
[0142] R 91 , R91a and R 91b Each can independently combine with R 81 R 81a and R 81b The same as the specified ones,
[0143] R 10a It can be the same as that defined by R1, and R 10a Not hydrogen, and
[0144] * Indicates the binding site with adjacent atoms.
[0145] For example, in Equation 91,
[0146] CY 91 and CY 92 Each can be independently of its own unsubstituted or each can be controlled by at least one R. 10a Substituted phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, or triazinyl,
[0147] R 91 R 91a and R 91b They can be independently:
[0148] Hydrogen or C1-C 10 Alkyl; or
[0149] Each of the following unsubstituted or substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl groups: deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, or any combination thereof.
[0150] However, the embodiments disclosed herein are not limited thereto.
[0151] In formula 2-2, R5 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, or a substituted or unsubstituted C1-C group. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10heterocycloalkenyl, -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), wherein, when T in Formula 2-2 is a chemical bond (e.g., a single bond), R5may not be any one of -F, -Cl, -Br, and -I. 15 When T in Formula 2-2 is a chemical bond (e.g., a single bond), R5may not be any one of -F, -Cl, -Br, and -I.
[0152] For example, R5may be:
[0153] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, or C1-C 20 alkoxy;
[0154] each C1-C 20 alkyl or C1-C 20 alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, or any combination thereof; or
[0155] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0156] Q1to Q3are the same as described herein above.
[0157] In one or more embodiments, R1to R4, R6, R 6a , R 6b , R7, R 7a , R 7b , R', R", R 51 to R 56 , R 71 , R 72 , R 81 , R 81a , and R 81beach independently hydrogen, deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of formulae 9-1 to 9-19, a group represented by one of formulae 10-1 to 10-243, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), or -P(=O)(Q1)(Q2), and R5may be deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of formulae 9-1 to 9-19, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), or -P(=O)(Q1)(Q2) (wherein Q1to Q3are the same as described herein above), but embodiments of the present disclosure are not limited thereto:
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165] In formulae 9-1 to 9-19 and formulae 10-1 to 10-243, * indicates a bonding site with an adjacent atom, Ph indicates a phenyl group, and TMS indicates a trimethylsilyl group.
[0166] R 10a may be the same as defined in connection with R1, and R 10a is not hydrogen. In one embodiment, at least one of R2in formula 1 (e.g., R2in the number of a2) can each independently be a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C 10 cycloalkenyl, a substituted or unsubstituted C1-C 10 heterocycloalkenyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C7-C 60 alkylaryl, a substituted or unsubstituted C6-C 60 aryloxy, a substituted or unsubstituted C6-C60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.
[0167] For example, at least one of R2in Formula 1 (e.g., the R2of quantity a2) can each independently be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azaf luorenyl, azadibenzosilolyl, or a group represented by Formula 91: 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 ), -S(Q 31), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 (or any combination thereof).
[0168] In one or more embodiments, at least one of R4 in Equation 2-1 (e.g., R4 in quantity a4) can be:
[0169] Cyano; or
[0170] Unsubstituted or substituted C1-C groups with -F, cyano, or any combination thereof (e.g., -CF3, etc.) 20 alkyl,
[0171] However, the embodiments disclosed herein are not limited thereto.
[0172] In Equations 1, 2-1, and 3, a1 to a4, a71, and a72 each indicate R1 to R4, R... 71 and R 72 The number of R1s can be an integer from 0 to 20 (e.g., an integer from 0 to 5). When a1 is 2 or greater, two or more R1s can be the same or different from each other, and this can be equally applied to a2 to a4, a71 and a72, and R2 to R4, R... 71 and R 72 .
[0173] In Formula 1, i) two or more of the plurality of R1s (e.g., R1s in number a1) may optionally (e.g., via single bonds, double bonds or a first linking group) be linked together to form an unsubstituted or at least one R1 10a Replacement C5-C 30 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 30 (ii) Two or more of a plurality of R2 groups (e.g., R2 in a number of a2) may optionally (e.g., via a single bond, double bond, or first linking group) be linked together to form an unsubstituted or at least one R2 group. 10a Replacement C5-C 30 Carbocyclic group, or unsubstituted or with at least one R 10asubstituted C1-C 30 two or more of the plurality of R3(e.g., a number a3 of R3) are optionally (e.g., via a single bond, a double bond, or a first linking group) connected to one another to form an unsubstituted or substituted C5-C 10a substituted C5-C 30 carbon ring group, or an unsubstituted or substituted C1-C 10a substituted C1-C 30 hetero ring group, and iv) two or more of the plurality of R4(e.g., a number a4 of R4) can be optionally (e.g., via a single bond, a double bond, or a first linking group) connected to one another to form an unsubstituted or substituted C5-C 10a substituted C5-C 30 carbon ring group, or an unsubstituted or substituted C1-C 10a substituted C1-C 30 hetero ring group. R 10a may be the same as defined in connection with R1, and R 10a is not hydrogen. The first linking group can be selected from the group consisting of *-N(R 95 )-*’, *-B(R 95 )-*’, *-P(R 95 )-*’, *-C(R 95a )(R 95b )-*’, *-Si(R 95a )(R 95b )-*’, *-Ge(R 95a )(R 95b )-*’, *-S-*’, *-Se-*’, *-O-*’, *-C(=O)-*’, *-S(=O)-*’, *-S(=O)2-*’, *-C(R 95 )=*’, *=C(R 95 )-*’, *-C(R 95a )=C(R 95b )-*’, *-C(=S)-*’, and *-C≡C-*’, and R 95 , R 95a , and R 95b may each independently be the same as defined in connection with R1. As described herein, “C5-C 30 carbon ring group” and “C1-C 30 hetero ring group” can be understood by reference to the description provided herein in connection with ring CY1.
[0174] In one embodiment, the group represented by in Formula 1 can be a group represented by one of Formula A1-1(1) to Formula A1-1(55):
[0175]
[0176]
[0177] In Formulae A1-1(1) to A1-1(55),
[0178] X1and R1may each independently be the same as described herein,
[0179] X 11 may be O, S, C(R 11 )(R 12 ), Si(R 11 )(R 12 ), or N(R 12 ),
[0180] X 12 may be O, S, or N(R 12 ),
[0181] R 11 to R 18 may each independently be the same as defined in connection with R1,
[0182] a16may be one of an integer from 0 to 6,
[0183] a15may be one of an integer from 0 to 5,
[0184] a14may be one of an integer from 0 to 4,
[0185] a13may be one of an integer from 0 to 3,
[0186] a12may be one of an integer from 0 to 2,
[0187] * indicates a binding site to T 11 or M in Formula 1, and
[0188] * indicates a binding site to T1in Formula 1.
[0189] In one or more embodiments, the group represented by in Formula 1 can be a group represented by the formula
[0190]
[0191] In Formulae A2-1(1) to A2-1(15),
[0192] X2and R2may each independently be the same as described herein,
[0193] R 21 to R 28each independently the same as defined in connection with R2,
[0194] a25may be one of an integer from 0 to 5,
[0195] a24may be one of an integer from 0 to 4,
[0196] a23may be one of an integer from 0 to 3,
[0197] a22may be one of an integer from 0 to 2,
[0198] * indicates a binding site to T 12 or M in Formula 1,
[0199] * indicates a binding site to T1in Formula 1, and
[0200] * indicates a binding site to T2in Formula 1.
[0201] In one or more embodiments, the group represented by in Formula 1 can be a group represented by Formula CY2-1 :
[0202]
[0203] In Formula CY2-1,
[0204] X2may be the same as described herein above,
[0205] X 21 may be N or C(R 21 ), and X 23 may be N or C(R 23 ),
[0206] R 21 and R 23 may each independently be the same as defined in connection with R2,
[0207] R 22 may be substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
[0208] * indicates the binding site to T 12 or M in Formula 1,
[0209] * indicates the binding site to T1in Formula 1, and
[0210] * indicates the binding site to T2in Formula 1.
[0211] In one or more embodiments, the group represented by in Formula 1 can be a group represented by one of Formula A3-1(1) to Formula A3-1(55):
[0212]
[0213]
[0214] In Formula A3-1(1) to Formula A3-1(55),
[0215] X3and R3may each independently be the same as described herein,
[0216] X 31 may be O, S, C(R 31 )(R 32 ), Si(R 31 )(R 32 ), or N(R 32 ),
[0217] X 32 may be O, S, or N(R 32 ),
[0218] R 31 to R 38 may each independently be the same as defined in connection with R3,
[0219] a36may be one of an integer from 0 to 6,
[0220] a35may be one of an integer from 0 to 5,
[0221] a34may be one of an integer from 0 to 4,
[0222] a33may be one of an integer from 0 to 3,
[0223] a32may be one of an integer from 0 to 2,
[0224] indicates the binding site to T2in Formula 1. 13 or M, and
[0225] *"indicates the binding site to T2in Formula 1.
[0226] In one embodiment, i) in Formula 1, X1may be C, and the group represented by may be a group represented by one of Formula A1-1(44) to Formula A1-1(55), and / or ii) in Formula 1, X3may be C, and the group represented by may be a group represented by one of Formula A3-1(44) to Formula A3-1(55).
[0227] In one or more embodiments, L2in Formula 1 can be a ligand represented by one of Formula A4-1(1) to Formula A4-1(4):
[0228]
[0229] In Formula A4-1(1) to Formula A4-1(4),
[0230] X4may be the same as described herein above,
[0231] X 40a may be a single bond, O, S, S(=O)2, C(R 40a )(R 40b ), Si(R 40a )(R 40b ), N(R 40a ), or B(R 40a ),
[0232] X 40c may be O, S, C(R 40c )(R 40d ), Si(R 40c )(R 40d ), or N(R 40c ),
[0233] X 40e may be O, S, C(R 40e )(R 40f ), Si(R 40e )(R 40f ), or N(R 40e ),
[0234] X 40g may be N, B, or P,
[0235] X 41 may be N or C(R 41 ), X42 may be N or C(R 42 ), X 43 may be N or C(R 43 ), X 44 may be N or C(R 44 ), X 45 may be N or C(R 45 ), X 46 may be N or C(R 46 ), X 47 may be N or C(R 47 ), X 48 may be N or C(R 48 ), and X 49 may be N or C(R 49 ),
[0236] R 40a to R 40f and R 41 to R 49 may each independently be the same as defined in connection with R4, and
[0237] * indicates the binding site to M in Formula 1.
[0238] In one or more embodiments, L2in Formula 1may be a ligand represented by one of Formula CY4-1to Formula CY4-8:
[0239]
[0240] In Formula CY4-1to Formula CY4-8,
[0241] X4may be the same as described herein above,
[0242] R 40a , R 40c , R 40e , R 41 , R 42 and R 48 may each independently be the same as defined in connection with R4, and
[0243] * indicates the binding site to M in Formula 1.
[0244] In one embodiment, in Formula CY4-1to Formula CY4-8,
[0245] X4may be N,
[0246] R 40a , R 40c and R 40e may each independently be phenyl unsubstituted or substituted with deuterium, C1-C20 Alkyl, phenyl, or any combination thereof, and
[0247] R 41 R 42 and R 48 They can be independently:
[0248] Hydrogen or cyano; or
[0249] Unsubstituted or substituted C1-C 20 Alkyl: -F, cyano, or any combination thereof.
[0250] In one or more embodiments, the first compound may be represented by formula 1A, formula 1B or formula 1C:
[0251]
[0252] In equations 1A to 1C,
[0253] M, L2, X1 to X3, T1 and T2 can each be independently identical to those described in this document.
[0254] X 12 It can be O, S or N(R) 12 ), X 13 It can be N or C(R) 13 ), X 14 It can be N or C(R) 14 ), X 15 It can be N or C(R) 15 ), X 16 It can be N or C(R) 16 ), and R 12 To R 16 Each can be independently identical to the one defined by R1.
[0255] X 21 It can be N or C(R) 21 ), X 22 It can be N or C(R) 22 ), X 23 It can be N or C(R) 23 ), and R 21 To R 23 Each can be independently identical to the one defined by R2.
[0256] X 32 It can be O, S or N(R) 32 ), X 33 It can be N or C(R) 33 ), X 34 It can be N or C(R) 34 ), X 35It can be N or C(R) 35 ), X 36 It can be N or C(R) 36 ), and R 32 To R 36 Each can be independently identical to the one defined by R3.
[0257] R 12 To R 16 Two or more of them may be optionally connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 30 Heterocyclic group,
[0258] R 21 To R 23 Two or more of them may be optionally connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 30 Heterocyclic groups, and
[0259] R 32 To R 36 Two or more of them may be optionally connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 30 Heterocyclic group.
[0260] R 10a It can be the same as described above.
[0261] In one embodiment, L2 in Formulas 1A to 1C can be a ligand represented by Formula A4-1(1) or Formula A4-1(2) (or a ligand represented by one of Formulas CY4-1 to CY4-8).
[0262] In one or more embodiments, X in Formulas 1A to 1C 22 It can be C(R) 22 ), where R 22 C3-C can be substituted or unsubstituted. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10substituted or unsubstituted C6-C 60 substituted or unsubstituted C7-C 60 substituted or unsubstituted C6-C 60 substituted or unsubstituted C6-C 60 substituted or unsubstituted C1-C 60 substituted or unsubstituted C2-C 60 substituted or unsubstituted C6-C
[0263] In Formula 2, the group represented by *-(L 51 ) b51 -R 51 and the group represented by *-(L 52 ) b52 -R 52 may not be phenyl.
[0264] In one embodiment, in Formula 2, the group represented by *-(L 51 ) b51 -R 51 and the group represented by *-(L 52 ) b52 -R 52 may be the same as each other.
[0265] In one or more embodiments, in Formula 2, the group represented by *-(L 51 ) b51 -R 51 and the group represented by *-(L 52 ) b52 -R 52 may be different from each other.
[0266] In one or more embodiments, in Formula 2, b51 and b52 can be 1, 2, or 3, L 51 and L 52 may each independently be phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl, each unsubstituted or each substituted with at least one R 10a , but embodiments of the present disclosure are not limited thereto.
[0267] R 10a may be the same as described herein above. For example, in Formula 2, R 51 and R 52 may each independently be substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q1)(Q2)(Q3), or -Si(Q1)(Q2)(Q3), and
[0268] Q1to Q3may each independently be: C1-C 60 alkyl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C3-C 10 cycloalkyl; C1-C 10 heterocycloalkyl; C3-C 10 cycloalkenyl; C1-C 10 heterocycloalkenyl; C6-C 60 aryl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C6-C 60 aryloxy; C6-C 60 arylthio; C1-C 60 heteroaryl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heteropolycyclic group,
[0269] In one embodiment,
[0270] in Formula 2, the group represented by *-(L 51 ) b51 -R 51 may be a group represented by one of Formula CY51-1 to Formula CY51-22, and / or
[0271] in Formula 2, the group represented by *-(L 52 ) b52 -R 52The group represented by R
[0272] The group represented by R 53 ) b53 The group represented by R 53 The group represented by R
[0273]
[0274]
[0275]
[0276] In Formulae CY51-1 to CY51-22, CY52-1 to CY52-22, and CY53-1 to CY53-18,
[0277] The group represented by R 63 may be a single bond, O, S, N(R 63 ), B(R 63 ), C(R 63a )(R 63b ), or Si(R 63a )(R 63b ),
[0278] The group represented by R 64 may be a single bond, O, S, N(R 64 ), B(R 64 ), C(R 64a )(R 64b ), or Si(R 64a )(R 64b ),
[0279] The group represented by R 67 may be a single bond, O, S, N(R 67 ), B(R 67 ), C(R 67a )(R 67b ), or Si(R 67a )(R 67b ),
[0280] The group represented by R 68 may be a single bond, O, S, N(R 68 ), B(R 68 ), C(R 68a )(R 68b ), or Si(R 68a )(R68b ),
[0281] In Formula CY51-16 and Formula CY51-17, Y 63 and Y 64 may not be a single bond at the same time,
[0282] In Formula CY52-16 and Formula CY52-17, Y 67 and Y 68 may not be a single bond at the same time,
[0283] R 51a to R 51e , R 61 to R 64 , R 63a , R 63b , R 64a and R 64b may each independently be the same as defined in connection with R 51 , where each of R 51a to R 51e may not be hydrogen,
[0284] R 52a to R 52e , R 65 to R 68 , R 67a , R 67b , R 68a and R 68b may each independently be the same as defined in connection with R 52 , where each of R 52a to R 52e may not be hydrogen,
[0285] R 53a to R 53e may each independently be the same as defined in connection with R 53 , where each of R 53a to R 53e may not be hydrogen, and
[0286] * indicates a binding site to an adjacent atom.
[0287] For example,
[0288] In Formula CY51-1 to CY51-22 and Formula CY52-1 to CY52-22, R 51a to R 51e and R 52a to R 52e may each independently be:
[0289] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, benzo[a]phenanthryl, pyrene, tyl, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthryl, benzimidazolyl, benzofuranyl, benzo[a]thiophene, benzo[a]isothiazolyl, benzo[a]oxazolyl, benzo[a]isooxazolyl Triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiophenyl or groups represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, benzo[a]phenanthryl, pyrene, tyl, pyrroloyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthrolyl, benzimidazolyl, benzofuranyl, benzo[a]thiophene, benzo[a]isothiazolyl, benzo[a]oxazolyl, benzo[a]isooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzo[a]carbazole, dibenzo[a]carbazole, imidazo[a]pyridyl, imidazo[a]pyrimidinyl, or any combination thereof; or
[0290] -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3), and
[0291] Q1 to Q3 can each be independently unsubstituted or substituted with one of the following: phenyl, naphthyl, pyridyl, pyridyl, pyrimidinyl, pyridazinyl, or triazinyl: deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0292] In Formula CY51-16 and Formula CY51-17, i) Y 63 may be O or S, and Y 64 may be Si(R 64a )(R 64b ), or ii) Y 63 may be Si(R 63a )(R 63b ), and Y 64 may be O or S.
[0293] In Formula CY52-16 and Formula CY52-17, i) Y 67 may be O or S, and Y 68 may be Si(R 68a )(R 68b ), or ii) Y 67 may be Si(R 67a )(R 67b ), and Y 68 may be O or S, but embodiments of the present disclosure are not limited thereto.
[0294] In one embodiment, the third compound can be represented by one of Formula 3-1 to Formula 3-5:
[0295]
[0296] In Formula 3-1 to Formula 3-5,
[0297] Ring CY 71 , Ring CY 72 , X 81 , R 71 , R 72 , a71 and a72 can each independently be the same as described herein,
[0298] Ring CY 73 , Ring CY 74 , R 73 , R 74 , a73 and a74 can each independently be the same as defined in connection with Ring CY 71 , Ring CY 72 , R 71 , R 72 , a71 and a72,
[0299] L 81 may be *-C(Q4)(Q5)-*, *-Si(Q4)(Q5)-*, C5-C 10a carbocyclyl, or C6-C 30 aryl, which is unsubstituted or substituted by at least one R10a substituted C1-C 30 heterocyclyl, wherein Q4and Q5may each independently be the same as defined in connection with Q1,
[0300] R 10a may be the same as described herein above,
[0301] b81may be one of an integer from 0 to 5, wherein, when b81is 0, *-(L 81 ) b81 *’may be a single bond, and when b81is 2 or more, two or more L 81 may be the same as or different from each other,
[0302] X 82 may be a single bond, O, S, N(R 82 ), B(R 82 ), C(R 82a )(R 82b ), or Si(R 82a )(R 82b ),
[0303] X 83 may be a single bond, O, S, N(R 83 ), B(R 83 ), C(R 83a )(R 83b ), or Si(R 83a )(R 83b ),
[0304] X 82 and X 83 may not be a single bond at the same time,
[0305] X 84 may be C or Si,
[0306] R 80 , R 82 , R 83 , R 82a , R 82b , R 83a , R 83b , and R 84 may each independently be the same as defined in connection with R 81 , and
[0307] *and *’each indicate a bonding site to an adjacent atom.
[0308] For example, L 81 may be:
[0309] *-C(Q4)(Q5)-*' or *-Si(Q4)(Q5)-*'; or
[0310] The following are unsubstituted or substituted: phenyl, naphthyl, anthraceneyl, phenanthrene, benzo[a]phenanthrene, pyrene, tyl, cyclopentadienyl, furanyl, thiophene, thiopyrrolyl, indole, fluorenyl, indole, carbazole, benzo[a]furanyl, dibenzo[a]furanyl, benzo[a]thiophene, dibenzo[a]thiophene, benzo[a]thiopyrrolyl, azirfluorenyl, azircarbazoyl, azirdibenzofuranyl, azirdibenzo[a]thiophene, azirdibenzo[a]thiopyrrolyl, pyridyl, pyrimidinyl, Pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolineyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazoleyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl or benzothiazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazole, phenylcarbazole, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, dimethyldibenzothiopyrrolyl, diphenyldibenzothiopyrrolyl, -O(Q) 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, and
[0311] Q4, Q5 and Q 31 To Q 33 They can each be independently hydrogen, deuterium, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl, but the embodiments disclosed herein are not limited thereto.
[0312] In one embodiment, equations 3-1 and 3-2 are derived from... The group represented by the symbol R
[0313] The group represented by the symbol R The group represented by the symbol R
[0314] The group represented by the symbol R The group represented by the symbol R
[0315] The group represented by the symbol R The group represented by the symbol R
[0316] The group represented by the symbol R The group represented by the symbol R
[0317]
[0318]
[0319]
[0320]
[0321] In Formulae CY71-1(1) to CY71-1(8), Formulae CY71-2(1) to CY71-2(8), Formulae CY71-3(1) to CY71-3(32), Formulae CY71-4(1) to CY71-4(32), and Formulae CY71-5(1) to CY71-5(8),
[0322] X 81 to X 84 , R 80 , and R 84 may each independently be the same as described herein,
[0323] X 85 may be a single bond, O, S, N(R 85 ), B(R 85 ), C(R 85a )(R 85b ), or Si(R 85a )(R 85b ),
[0324] X86 may be a single bond, O, S, N(R 86 ), 86 may be a single bond, O, S, N(R 86a ), 86b ), 86a ), 86b ,
[0325] X 85 and X 86 may not simultaneously be a single bond,
[0326] X 87 may be a single bond, O, S, N(R 87 ), 87 ), 87a ), 87b ), 87a ), 87b ,
[0327] X 88 may be a single bond, O, S, N(R 88 ), 88 ), 88a ), 88b ), 88a ), 88b ,
[0328] X 87 and X 88 may not simultaneously be a single bond, and
[0329] R 85 to R 88 , 85a , 85b , 86a , 86b , 87a , 87b , 88a and R 88b may each independently be the same as defined in connection with R 81 .
[0330] In Formula 1, L2may not be attached to adjacent R1and / or R3. In other words, Formula 1 has one tridentate ligand and one monodentate ligand (e.g., L2).
[0331] In an embodiment, the first compound can be selected from the group consisting of Compound BD1 to Compound BD105, but embodiments of the present disclosure are not limited thereto:
[0332]
[0333]
[0334]
[0335]
[0336]
[0337]
[0338] In one or more embodiments, the second compound can be selected from the group consisting of Compound ETH1 to Compound ETH80, but embodiments of the present disclosure are not limited thereto:
[0339]
[0340]
[0341]
[0342] In one or more embodiments, the third compound can be selected from the group consisting of Compound HTH1 to Compound HTH28, but embodiments of the present disclosure are not limited thereto:
[0343]
[0344] In an embodiment, the weight ratio of the second compound to the third compound can be in the range of 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, or 4:6 to 6:4.
[0345] In an embodiment, the organic light emitting device can satisfy at least one of the following conditions 1 to 4:
[0346] Condition 1
[0347] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound > the LUMO energy level (eV) of the first compound
[0348] Condition 2
[0349] The LUMO energy level (eV) of the first compound > the LUMO energy level (eV) of the second compound
[0350] Condition 3
[0351] the highest occupied molecular orbital (HOMO) level of the first compound > the HOMO level of the third compound (eV)
[0352] Condition 4
[0353] the HOMO level of the third compound > the HOMO level of the second compound (eV)
[0354] The HOMO level and the LUMO level of each of the first compound, the second compound, and the third compound are negative values, and can be actually measured by any suitable method, such as, for example, the method described in Evaluation Example 1.
[0355] In one or more embodiments, the absolute value of the difference between the LUMO level of the first compound and the LUMO level of the second compound can be about 0.1 eV or greater and about 1.0 eV or less. The absolute value of the difference between the LUMO level of the first compound and the LUMO level of the third compound can be about 0.1 eV or greater and about 1.0 eV or less. The absolute value of the difference between the HOMO level of the first compound and the HOMO level of the second compound can be about 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or greater). The absolute value of the difference between the HOMO level of the first compound and the HOMO level of the third compound can be about 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or greater).
[0356] When the organic light emitting device satisfies the relationship between the LUMO level and the HOMO level described herein, hole and electron injection balance to the emission layer can be achieved.
[0357] The organic light emitting device can be prepared according to the first embodiment or according to the second embodiment, but the present disclosure is not limited thereto.
[0358] First Embodiment
[0359] In the organic light emitting device according to the first embodiment, the first compound can be included in the emission layer, the emission layer can further include a host, the first compound and the host can be different from each other, and the emission layer can be configured to emit blue light emitted from the first compound.
[0360] For example, in the first embodiment, the first compound can act as a phosphorescent emitter (or a phosphorescent dopant).
[0361] In the first embodiment, the blue light can be blue phosphorescence emitted from the first compound.
[0362] Second Embodiment
[0363] In the organic light-emitting device according to the second embodiment, a first compound may be included in an emission layer, the emission layer may further include a host and a dopant (or emitter), the first compound, the host and the dopant may be different from each other, and the emission layer may be configured to emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
[0364] For example, in a second embodiment, the first compound may not act as an emitter, but rather as an auxiliary dopant for transferring energy to the dopant (or emitter).
[0365] In the second embodiment, the first compound can act as an emitter and also as an auxiliary dopant for transferring energy to the dopant (or emitter).
[0366] For example, in the second embodiment, the phosphorescence or fluorescence emitted from the dopant (or emitter) can be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
[0367] In the organic light-emitting device according to the second embodiment, a first compound may be included in an emission layer, which may further include a host and a fluorescent dopant (e.g., a delayed fluorescent dopant). The fluorescent dopant does not include a transition metal. The first compound, the host, and the fluorescent dopant may be different from each other. The emission layer may be configured to emit both phosphorescence from the first compound and fluorescence (e.g., delayed fluorescence) from the fluorescent dopant.
[0368] In the second embodiment, the dopant (or emitter) can be any suitable phosphorescent dopant material (e.g., an organometallic compound represented by Formula 1, an organometallic complex represented by Formula 401, or any combination thereof) or any suitable fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, or any combination thereof).
[0369] In the first and second embodiments, the blue light can be blue light having a maximum emission wavelength of about 390 nm or greater and about 500 nm or less (e.g., about 430 nm or greater and about 470 nm or less).
[0370] In the first and second embodiments, the main body can be any suitable main body material (e.g., a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof).
[0371] Equations 401, 501, 502, 301, 301-1, and 301-2 will be described in detail below.
[0372] In the first and second embodiments, the host can be the second compound, the third compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
[0373] In the first and second embodiments, the host can be any suitable host material (e.g., compound ETH2, compound ETH77, compound HTH2, compound HTH4, or any combination thereof), but embodiments of the present disclosure are not limited thereto.
[0374] Another aspect of embodiments of the present disclosure provides an organometallic compound represented by Formula 1. Formula 1 can be the same as described herein above.
[0375] i) at least one of X1to X3in Formula 1 is a carbon atom (C) of a carbene moiety, ii) L2in Formula 1 is not -F, -Cl, -Br, and -I as described above, iii) M in Formula 1 is not iridium. Although the present disclosure is not limited to any particular mechanism or theory, when a film is formed by using an organometallic compound represented by Formula 1, the organometallic compound represented by Formula 1 (e.g., an organometallic compound represented by Formula 1 in which at least one R2(e.g., the number a2of R2) is a substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group) can be minimized or reduced. Accordingly, an electronic device (e.g., an organic light emitting device) including an organometallic compound represented by Formula 1 (or a first compound) can have high light emitting efficiency and / or long lifespan.
[0376] Another aspect of embodiments of the present disclosure provides an electronic device including an organic light emitting device. The electronic device can further include a thin film transistor. For example, the electronic device can further include a thin film transistor including a source electrode and a drain electrode, and the first electrode of the organic light emitting device can be electrically coupled with the source electrode or the drain electrode of the thin film transistor.
[0377] Figure 1 Description
[0378] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0379] In the following text, we will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiments and the method of manufacturing the organic light-emitting device 10 are described.
[0380] First electrode 110
[0381] exist Figure 1 In this process, the substrate may be located below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0382] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material used for the first electrode 110 can be a material with a high work function to facilitate hole injection.
[0383] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof, but the embodiments of this disclosure are not limited thereto.
[0384] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.
[0385] Organic layer 150
[0386] The organic layer 150 is on the first electrode 110. The organic layer 150 may include an emitter layer.
[0387] The organic layer 150 can include a hole transport zone between the first electrode 110 and the emission layer and an electron transport zone between the emission layer and the second electrode 190.
[0388] The hole transport zone in the organic layer 150
[0389] The hole transport zone can have i) a single layer structure including a single layer containing a single material, ii) a single layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0390] The hole transport zone can include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
[0391] For example, the hole transport zone can have a single layer structure including a single layer having a plurality of different materials or a multi-layer structure having 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 / electron blocking layer structure, in which, for each structure, the constituent layers are stacked in the order of the statement, but the structure of the hole transport zone is not limited thereto.
[0392] The hole transport zone can include m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, a compound represented by the following Formula 202, or any combination thereof:
[0393]
[0394] Formula 201
[0395]
[0396] Formula 202
[0397]
[0398] In Formula 201 and Formula 202,
[0399] L 201To L 204 Each can be independently substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0400] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0401] xa1 to xa4 can each be an integer from 0 to 3 independently.
[0402] xa5 can be any integer from 1 to 10, and
[0403] R 201 To R 204 and Q 201 Each can be independently substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0404] For example, in equation 202, R 201 and R 202 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene bonds, and R 203 and R 204 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene.
[0405] In one implementation, in equations 201 and 202,
[0406] L 201 To L 205 They can be independently:
[0407] The unsubstituted or substituted of each of the following: phenylene, pentyleneylene, indenylene, naphthylene, azuleneylene, heptyleneylene, acenaphtheneylene, fluoreneylene, spiro-difluoreneylene, benzo[a]fluoreneylene, dibenzo[a]fluoreneylene, phenanthrenylene, anthraceneylene, fluoranthrenylene, benzo[a]phenanthreneylene, pyreneylene, trehalylene, tetraphenylene, fentanylene, perylene, pentyleneylene, hexaphenylene, pentaphenylene alkyl, benzo[a]benzyl, benzo[a]benzyl, benzo[a]thienyl, benzo[a]furanyl, benzo[a]carbazoyl, benzo[a]indolyl, benzo[a]isoindolyl, benzo[a]furanyl, benzo[a]thienyl, benzo[a]thienyl, benzo[a]carbazoyl, benzo[a]carbazoyl, benzo[a]thiolyl or pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], phenanthreneyl, anthraceneyl, fluoranyl, benzo[phenanthreneyl], pyreneyl, trefyl, tetraphenyl, styryl, peryl, pentanyl, hexaphenyl, pentaphenyl, rubiginyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) or any combination thereof, and
[0408] Q 31 to Q 33 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0409] In one or more embodiments, xa1to xa4may each independently be 0, 1, or 2.
[0410] In one or more embodiments, xa5may be 1, 2, 3, or 4.
[0411] In one or more embodiments, R 201 to R 204 and Q 201 may each independently be: phenyl, biphenyl, terphenyl, pentacenyl, indacenyl, naphthacenyl, azulenyl, heptacenyl, indacenyl, acenaphthyl, fluorenyl, spiro- dluorenyl, benzofluorenyl, dibenzofluorenyl, phenalene, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysenyl, perilenyl, pentaphenyl, hexaphenyl, pentaphene, coronene, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, or pyridinyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, pentacenyl, indacenyl, naphthacenyl, azulenyl, heptacenyl, indacenyl, acenaphthyl, fluorenyl, spiro-dluorenyl, benzofluorenyl, dibenzofluorenyl, phenalene, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysenyl, perilenyl, pentaphenyl, hexaphenyl, pentaphene, coronene, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, pyridinyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), or any combination thereof, and
[0412] Q 31 to Q 33The same as described herein above.
[0413] In one or more embodiments, in Formula 201, R 201 to R 203 each independently can be fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl, each unsubstituted or each substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
[0414] In one or more embodiments, in Formula 202, i) R 201 and R 202 may be connected to each other via a single bond, and / or ii) R 203 and R 204 may be connected to each other via a single bond.
[0415] In one or more embodiments, in Formula 202, R 201 to R 204 each independently can be carbazolyl unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
[0416] In one embodiment, the compound represented by Formula 201 can be represented by the following Formula 201A, but embodiments of the present disclosure are not limited thereto:
[0417] Formula 201A
[0418]
[0419] In one or more embodiments, the compound represented by Formula 201 can be represented by the following Formula 201A(1), but embodiments of the present disclosure are not limited thereto:
[0420] Formula 201A(1)
[0421]
[0422] In one or more embodiments, the compound represented by Formula 201 can be represented by Formula 201A-1, but embodiments of the present disclosure are not limited thereto:
[0423] Formula 201A-1
[0424]
[0425] In one embodiment, the compound represented by Formula 202 can be represented by Formula 202A, but embodiments of the present disclosure are not limited thereto:
[0426] Formula 202A
[0427]
[0428] In one or more embodiments, the compound represented by Formula 202 can be represented by Formula 202A-1, but embodiments of the present disclosure are not limited thereto:
[0429] Formula 202A-1
[0430]
[0431] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,
[0432] L 201 to L 203 , xa1to xa3, xa5, and R 202 to R 204 are the same as described herein above,
[0433] R 211 and R 212 can be understood by referring to the description provided herein in connection with R 203 , and
[0434] R 213 to R 217 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10alkyl-substituted phenyl, phenyl substituted with -F, pentacenyl, indenyl, naphthyl, azulenyl, heptacenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysenyl, naphthacene, pyromethene, coronene, pentaphene, hexacene, pentacene, triphenylene, chrysene, tetracene, azulene, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, bisbenzocarbazolyl, bisbenzothiophorolyl, or pyridyl.
[0435] The thickness of the hole transport zone can be about 1 nm to about 1000 nm. to about 1000 nm. For example, about 1 nm to about 1000 nm. to about 1000 nm. For example, about 1 nm to about 1000 nm. to about 1000 nm. For example, about 1 nm to about 1000 nm. to about 1000 nm. For example, about 1 nm to about 1000 nm. to about 1000 nm. For example, about 1 nm to about 1000 nm. to about 1000 nm. When the thickness of the hole transport zone, the hole injection layer, and the hole transport layer is within these ranges, suitable or satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.
[0436] The emission auxiliary layer can increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted from the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport zone. The emission auxiliary layer and the electron blocking layer can include materials as described above.
[0437] p-dopant
[0438] In addition to these materials, the hole transport zone can further include a charge generating material for improving conductive properties. The charge generating material can be uniformly or non-uniformly dispersed in the hole transport zone.
[0439] The charge generating material can be, for example, a p-dopant.
[0440] In one embodiment, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV or less.
[0441] The p-dopant can include at least one selected from a quinone derivative, a metal oxide, and a cyano-containing compound, but embodiments of the present disclosure are not limited thereto.
[0442] In one embodiment, the p-doper may include at least one selected from the following:
[0443] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);
[0444] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0445] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and
[0446] The compound represented by formula 221,
[0447] However, the implementation methods of this disclosure are not limited thereto:
[0448] HAT-CN F4-TCNQ
[0449]
[0450] Equation 221
[0451]
[0452] In Equation 221,
[0453] R 221 To R 223 Each can be independently substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein R 221 To R 223 At least one of them may have at least one substituent selected from the following: cyano, -F, -Cl, -Br, -I, C1-C substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and -I-substituted C1-C 20 alkyl.
[0454] Emission layer in organic layer 150
[0455] When the emission layer includes a dopant (or emitter) and an auxiliary dopant as described above, the dopant (or emitter) and the auxiliary dopant can be different from each other.
[0456] In the present specification, the first compound can be used as a dopant (or emitter) or an auxiliary dopant.
[0457] In the emission layer, the amount of the dopant (or emitter) can be in the range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0458] The thickness of the emission layer can be in the range of about to about For example, the thickness of the emission layer can be in the range of about to about When the thickness of the emission layer is in the range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.
[0459] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to a sub-pixel. In one or more embodiments, the emission layer can have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers are in contact with each other (e.g., in physical contact with each other) or separated from each other. In one or more embodiments, the emission layer can include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer configured to emit white light.
[0460] The host in the emission layer
[0461] In one or more embodiments, the host can include a compound represented by the following Formula 301:
[0462] Formula 301
[0463] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0464] In Formula 301,
[0465] Ar 301 may be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,
[0466] xb11may be 1, 2, or 3,
[0467] L 301 may be substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted bivalent non-aromatic fused polycyclic group, or substituted or unsubstituted bivalent non-aromatic fused heteropolycyclic group,
[0468] xb1may be one of an integer from 0 to 5,
[0469] R 301 may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic 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 ),
[0470] xb21 can be one of an integer from 1 to 5, and
[0471] Q 301 to Q 303 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, but embodiments of the present disclosure are not limited thereto.
[0472] In one embodiment, in formula 301, Ar 301 may be each unsubstituted or each substituted naphthyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysenyl, naphthacene, pyranthryl, indenanthryl, dibenzofuranyl, or dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof, and
[0473] Q 31 to Q 33 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, but embodiments of the present disclosure are not limited thereto.
[0474] When xb11 in formula 301 is 2 or more, two or more Ar 301 may be connected to each other via a single bond.
[0475] In one or more embodiments, the compound represented by formula 301 can be represented by the following formula 301-1 or formula 301-2:
[0476] Formula 301-1
[0477]
[0478] Formula 301-2
[0479]
[0480] In Equations 301-1 and 301-2,
[0481] Ring A 301 To Ring A 304 Each of these rings can independently be a benzene ring, naphthyl ring, phenanthrene ring, fluoranthene ring, benzo[a]phenanthrene ring, pyrene ring, pyridine ring, pyrimidine ring, indene ring, fluorene ring, spiro-difluorene ring, benzo[a]fluorene ring, dibenzo[a]fluorene ring, indole ring, carbazole ring, benzo[a]carbazole ring, dibenzo[a]carbazole ring, furan ring, benzo[a]furan ring, dibenzo[a]furan ring, naphtholane ring, benzo[a]naphtholane ring, dinaphtholane ring, thiophene ring, benzo[a]thiophene ring, dibenzo[a]thiophene ring, naphtholane ring, benzo[a]naphtholane ring, or dinaphtholane ring.
[0482] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0483] R 311 To R 314 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ),
[0484] xb22 and xb23 can each be 0, 1, or 2 independently.
[0485] L 301 xb1, R 301 and Q 31 To Q 33 As described above,
[0486] L 302 To L 304 Each can be independently combined with L 301 The same as the specified ones,
[0487] xb2to xb4may each independently be the same as defined in connection with xb1, and
[0488] R 302 to R 304 may each independently be the same as defined in connection with R 301 .
[0489] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 to L 304 may each independently be phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzophenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexa- phenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzospiro- thiophenylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthrydinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenoxazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, azacarbazolylene, each unsubstituted or each substituted with -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C20alkyl, C1-C20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzospiro-thiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthrydinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 20 )(Q 20 alkyl, C1-C20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzospiro-thiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthrydinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, and
[0490] Q 31 To Q 33 Same as described above.
[0491] In one embodiment, in formulas 301, 301-1, and 301-2, R 301 To R 304 Each of these can be independently unsubstituted or substituted with one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene, tyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzo[a]furanyl, benzo[a]thienyl, dibenzo[a]furanyl, dibenzo[a]thienyl, benzo[a]carbazoleyl, dibenzo[a]carbazoleyl, dibenzo[a]thiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl. alkyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzoxazolyl, benzisisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl or azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, heptaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof, and
[0492] Q 31 to Q 33 are the same as described herein above.
[0493] In one or more embodiments, the host can include an alkaline earth metal complex. For example, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0494] The host can include 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphth-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-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), one of compounds H1 to H55, or any combination thereof, although embodiments of the present disclosure are not limited thereto:
[0495]
[0496]
[0497]
[0498]
[0499] In one embodiment, the host can include a silicon-containing compound (e.g., BCPDS, etc.), a phosphine oxide-containing compound (e.g., POPCPA, etc.), or any combination thereof.
[0500] However, embodiments of the present disclosure are not limited thereto. In one embodiment, the host can include only one compound, or two or more different compounds (e.g., the host includes BCPDS and POPCPA).
[0501] Phosphorescent dopant included in an emission layer in the organic layer 150
[0502] The phosphorescent dopant can be an organometallic complex containing a transition metal.
[0503] For example, the phosphorescent dopant can include an organometallic complex represented by the following Formula 401:
[0504] Formula 401
[0505] M(L 401 ) xc1 (L 402 ) xc2 .
[0506] In Formula 401,
[0507] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), or thulium (Tm)),
[0508] L 401 may be selected from a ligand represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1is 2 or more, two or more L 401 may be the same as or different from each other,
[0509] Formula 402
[0510]
[0511] L 402 may be an organic ligand, and xc2may be one of integers from 0 to 4, wherein, when xc2is 2 or more, two or more L 402may be identical or different from each other,
[0512] in formula 402,
[0513] X 401 to X 404 may each independently be nitrogen or carbon,
[0514] X 401 and X 403 may be connected via a single or double bond, and X 402 and X 404 may be connected via a single or double bond,
[0515] A 401 and A 402 may each independently be selected from C5-C 60 carbocyclyl or C1-C 60 heterocyclyl,
[0516] X 405 may 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=*, wherein Q 411 and Q 412 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,
[0517] X 406 may be a single bond, O or S,
[0518] R 401 and R 402 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 20 alkyl, substituted or unsubstituted C1-C 20 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60substituted or unsubstituted C6-C 60 substituted or unsubstituted C1-C 60 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 402 substituted or unsubstituted C6-C 403 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 402 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 402 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 402 substituted or unsubstituted C6-C 401 substituted or unsubstituted C6-C 403 substituted or unsubstituted C6-C 10 substituted or unsubstituted C6-C 10 substituted or unsubstituted C6-C 20 substituted or unsubstituted C6-C 20 substituted or unsubstituted C6-C
[0519] xc11and xc12may each independently be one of an integer from 0 to 10, and
[0520] * and *' in formula 402 each indicate a binding site to M in formula 401.
[0521] In one embodiment, A 401 and A 402 may each independently be phenyl, naphthyl, fluorenyl, spiro-difluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothienyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, or dibenzothienyl.
[0522] In one or more embodiments, in formula 402, i) X 401 may be nitrogen, and X 402 may be carbon, or ii) X 401 and X 402 may each simultaneously be nitrogen.
[0523] In one or more embodiments, R 401 and R 402 may each independently be:
[0524] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl or C1-C 20 alkyl or C1-C
[0525] C1-C 20 alkyl or C1-C 20 alkyl or C1-C
[0526] each unsubstituted or each substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkyl, C1-C
[0527] -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 ), and
[0528] Q 401 to Q 403 may each independently be C1-C 10 alkyl, C1-C 10 alkyl, C1-C
[0529] In one or more embodiments, in Formula 401, when xci is 2 or more, two or more L 401 of two A 401 may be optionally connected to each other via a linking group X 407 , or when xci is 2 or more, two or more L 401 of two A 402 may be optionally connected to each other via a linking group X 408 (see Compounds PD1 to PD4 and PD7). X 407 and X 408 may each independently be a single bond, *-O-*', *-S-*', *-C(=O)-*', 413 *-N(Q 413 )-*', *-C(Q 414 )(Q 413 )-*' or *-C(Q 414 )=C(Q 413 )-*' (where Q 414 and Q 20 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 402 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but embodiments of the present disclosure are not limited thereto.
[0530] L 402 in Formula 401 can be a monovalent, divalent or trivalent organic ligand. For example, L 402 may be selected from the group consisting of halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), -C(=O), isonitrile, -CN and phosphorus (e.g., phosphine or phosphite), but embodiments of the present disclosure are not limited thereto.
[0531] In one or more embodiments, the phosphorescent dopant can be selected from, for example, Compounds PD1 to PD25, but embodiments of the present disclosure are not limited thereto:
[0532]
[0533]
[0534] The fluorescent dopant included in the emission layer in the organic layer 150
[0535] The fluorescent dopant can include an arylamine compound, a styrylamine compound, a boron-containing compound or any combination thereof.
[0536] For example, the fluorescent dopant can include a compound represented by the following Formula 501, a compound represented by the following Formula 502 or any combination thereof:
[0537] Formula 501
[0538]
[0539] Formula 502
[0540]
[0541] In Formula 501 and Formula 502,
[0542] Ar 501 may be substituted or unsubstituted C5-C 60 carbocyclyl, or substituted or unsubstituted C1-C 60 heterocyclyl,
[0543] A 501 to A 503 may each independently be C5-C 60 carbocyclyl, or C1-C 60 heterocyclyl,
[0544] L 501 to L 505 may each independently be substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted bivalent non-aromatic fused polycyclic group, or substituted or unsubstituted bivalent non-aromatic fused heteropolycyclic group,
[0545] xd1 to xd3 can each independently be one of an integer from 0 to 3,
[0546] a501 to a505 can each independently be one of an integer from 0 to 3,
[0547] R 501 and R 502 may each independently be substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
[0548] R 503 to R 507 may each independently be substituted or unsubstituted C3-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
[0549] xd4may be one of an integer from 1 to 6, and
[0550] c11to c13may each independently be one of an integer from 0 to 6.
[0551] In one embodiment, Ar 501 may be naphthyl, heptacenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysenyl, naphthacene, pyranthryl, perylenyl, pentaphenyl, indanthryl, or indenanthracenyl, each unsubstituted or each substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof.
[0552] In one or more embodiments, A 501 to A 503 may each independently be phenyl, naphthyl, heptacenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, chrysenyl, naphthacene, pyranthryl, perylenyl, pentaphenyl, indanthryl, indenanthracenyl, or a group represented by Formula 503:
[0553] Formula 503
[0554]
[0555] In Formula 503,
[0556] A 504 to A 506 may each independently be the same as described in connection with A 501 in Formula 502,
[0557] L 504 to L 508 may each independently be the same as described in connection with L 501 in Formula 502,
[0558] a504 to a508 can each independently be the same as described in connection with a501 in Formula 502,
[0559] R 506 to R 510 may each independently be the same as described in connection with R 503 in Formula 502, and
[0560] c14 to c16 can each independently be the same as described in connection with c11 in Formula 502.
[0561] In one or more embodiments, in Formula 501 and Formula 502, L 501 to L 505 may each independently be phenylene, naphthylene, fluorenylene, spiro- dibluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzophenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexa- phenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothianolylene, or pyridinylene, each unsubstituted or each substituted with: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-dibluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothianolyl, pyridinyl, or any combination thereof.
[0562] In one or more embodiments, R 501 and R502 each independently unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophophenyl, or pyridinyl: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophophenyl, pyridinyl, -Si(Q 31 )(Q 32 )(Q 33 or any combination thereof, and
[0563] Q 31 to Q 33 each independently unsubstituted C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0564] In one or more embodiments, R 503 to R 507 each independently unsubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophophenyl, or pyridinyl: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20alkyl, C1-C6alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, perylenyl, pentaphenyl, hexaphenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, -Si(Q 31 32 33 or any combination thereof, and
[0565] Q 31 to Q 33 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0566] In one or more embodiments, xd4in Formula 501 can be 2, but embodiments of the present disclosure are not limited thereto.
[0567] In one or more embodiments, c11to c13in Formula 502 can be 0 or 1, but embodiments of the present disclosure are not limited thereto.
[0568] For example, the fluorescent dopant can be selected from the group consisting of Compounds FD1 to FD27:
[0569]
[0570]
[0571]
[0572]
[0573] In one or more embodiments, the fluorescent dopant can be selected from the group consisting of the following compounds, but embodiments of the present disclosure are not limited thereto:
[0574]
[0575] The electron transport region in the organic layer 150
[0576] The electron transport region can have i) a single layer structure including a single layer containing a single material, ii) a single layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0577] The electron transport zone can include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
[0578] For example, the electron transport zone can have a structure of an electron transport layer / electron injection layer, a structure of a hole blocking layer / electron transport layer / electron injection layer, a structure of an electron control layer / electron transport layer / electron injection layer, or a structure of a buffer layer / electron transport layer / electron injection layer, in which, for each structure, the constituent layers are sequentially stacked from the emission layer. However, embodiments of the structure of the electron transport zone are not limited thereto.
[0579] The electron transport zone can include the second compound as described above.
[0580] In one embodiment, the electron transport zone can include a buffer layer. The buffer layer can directly contact (e.g., physically contact) the emission layer, and can include the second compound.
[0581] In one or more embodiments, the electron transport zone can include a buffer layer, an electron transport layer, and an electron injection layer, which are stacked on the emission layer in the order of the recitation, and the buffer layer can include the second compound as described above.
[0582] The electron transport zone (e.g., a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport zone) can include a metal-free compound including at least one ring containing a π-electron depleted nitrogen.
[0583] As used herein, the term "ring containing a π-electron depleted nitrogen" refers to a C1-C 60 heterocyclyl.
[0584] For example, the "ring containing a π-electron depleted nitrogen" can be i) a five- to seven-membered heteromonocyclic group having at least one *-N=* portion; ii) a heteropolycyclic group in which two or more five- to seven-membered heteromonocyclic groups each having at least one *-N=* portion are fused (e.g., bonded together); or iii) a heteropolycyclic group in which at least one of the five- to seven-membered heteromonocyclic groups each having at least one *-N=* portion is fused (e.g., bonded together) with at least one C5-C 60 carbocyclyl.
[0585] Examples of rings containing a π-electron depleted nitrogen include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthylidine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenoxazine, benzimidazole, benzoisothiazole, benzoxazole, benzoisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but are not limited thereto.
[0586] For example, the electron transport region can include a compound represented by the following formula 601:
[0587] Formula 601
[0588] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0589] In formula 601,
[0590] Ar 601 may be a substituted or unsubstituted C5-C 60 carbocyclyl, or a substituted or unsubstituted C1-C 60 heterocyclyl,
[0591] xe11may be 1, 2, or 3,
[0592] L 601 may be a substituted or unsubstituted C3-C 10 cycloalkylene, a substituted or unsubstituted C1-C 10 heterocycloalkylene, a substituted or unsubstituted C3-C 10 cycloalkenylene, a substituted or unsubstituted C1-C 10 heterocycloalkenylene, a substituted or unsubstituted C6-C 60 arylene, a substituted or unsubstituted C1-C 60 heteroarylene, a substituted or unsubstituted bivalent non-aromatic fused polycyclic group, or a substituted or unsubstituted bivalent non-aromatic fused heteropolycyclic group,
[0593] xe1may be one of integers from 0 to 5,
[0594] R 601 may be a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C 10 cycloalkenyl, a substituted or unsubstituted C1-C 10 heterocycloalkenyl, a substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),and
[0595] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0596] xe21 can be any integer from 1 to 5.
[0597] In one implementation, Ar 601 (For example, Ar in quantity xe11) 601 ) and R 601 (For example, R with a quantity of xe21) 601 At least one of them may include a ring containing nitrogen with depleted π electrons.
[0598] In one implementation, Ar in Formula 601 601 It can be phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, benzo[a]phenanthrene, pyrene, trefyl, tetraphenyl, styrene, peryl, penfenyl, indoxane, dibenzofuranyl, dibenzothiopheneyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazole, purine, quinyl Phinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cyclolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl or azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20alkyl, C1-C6alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof, and
[0599] Q 31 to Q 33 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.
[0600] In Formula 601, when xe11 is 2 or more, two or more Ar 601 may be connected via a single bond.
[0601] In one or more embodiments, Ar 601 in Formula 601 can be an anthracenyl group.
[0602] In one or more embodiments, the compound represented by Formula 601 can be represented by the following Formula 601-1:
[0603] Formula 601-1
[0604]
[0605] In Formula 601-1,
[0606] X 614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X 616 may be N or C(R 616 ), and at least one of X 614 to X 616 may be N,
[0607] L 611 to L 613 may each independently be the same as described in connection with L 601 ,
[0608] xe611to xe613may each independently be the same as defined in connection with xe1,
[0609] R 611 to R 613 may each independently be the same as described in connection with R 601 , and
[0610] R 614 To R 616 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0611] In one embodiment, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Each of these can be independently unsubstituted or substituted with one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylene, benzo[a]phenanthrene, pyrene, trehalyl, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, etc. Oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisoxazolyl, benzisisoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl or zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[a]phenanthryl, pyrene, tyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[a]carbazole, dibenzo[a]carbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl The following compounds are used: oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cyclolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, or any combination thereof, but the embodiments disclosed herein are not limited thereto.
[0612] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be 0, 1 or 2 independently.
[0613] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Each of these can be independently unsubstituted or substituted with one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, benzo[a]phenanthryl, pyrene, tyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzo[a]furanyl, benzo[a]thienyl, dibenzo[a]furanyl, dibenzo[a]thienyl, benzo[a]carbazoleyl, dibenzo[a]carbazoleyl, dibenzo[a]thiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl. alkyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzoxazolyl, benzisisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl or azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzophenanthryl, pyrenyl, pentalenyl, perylenyl, hexaperi-phenyl, pentacene, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzo-oxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, or any combination thereof; or
[0614] -S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ), and
[0615] Q 601 and Q 602 are the same as described herein above.
[0616] The electron transport zone can include one of compounds ET1 to ET36 or any combination thereof, but embodiments of the present disclosure are not limited thereto:
[0617]
[0618]
[0619]
[0620] In one or more embodiments, the electron transport zone can include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, or any combination thereof:
[0621]
[0622] The thickness of the buffer layer, the hole blocking layer, or the electron control layer can be about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the hole blocking layer or the electron control layer can have excellent hole blocking characteristics or electron control characteristics without a significant increase in driving voltage.
[0623] The thickness of the electron transport layer can be about 1 nm to about 100 nm. to about 50 nm. For example, the thickness of the electron transport layer can be about 1 nm to about 50 nm. to about 50 nm. When the thickness of the electron transport layer is within the above range, the electron transport layer can have appropriate or satisfactory electron transport characteristics without a significant increase in driving voltage.
[0624] In addition to the above-described materials, the electron transport zone (e.g., the electron transport layer in the electron transport zone) can further include a metal-containing material.
[0625] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The alkali metal complex can include a metal ion from Li ion, Na ion, K ion, Rb ion, or Cs ion, and the alkaline earth metal complex can include a metal ion from 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 alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl-oxazole, hydroxyphenyl-thiazole, hydroxyphenyl-oxadiazole, hydroxyphenyl-thiadiazole, hydroxyphenyl-pyridine, hydroxyphenyl-benzimidazole, hydroxyphenyl-benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
[0626] For example, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1 (LiQ) or compound ET-D2:
[0627]
[0628] The electron transport zone can include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer can directly contact the second electrode 190.
[0629] The electron injection layer can have i) a single layer structure composed of a single layer (composed of a single material), ii) a single layer structure composed of a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0630] The electron injection layer can 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.
[0631] The alkali metal can include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal can include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal can include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0632] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound can include oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal.
[0633] The alkali metal-containing compound can include alkali metal oxides (such as Li2O, Cs2O, or K2O), alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof). The alkaline earth metal-containing compound can include alkaline earth metal compounds, such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1) or Ba x Ca 1-x O (0 < x < 1). The rare earth metal-containing compound can include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof.
[0634] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex can include i) one of the ions of the alkali metal, the alkaline earth metal, and the rare earth metal as described above, and ii) a ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth metal complex, or the rare earth metal complex, and examples of the ligand include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl-oxazole, hydroxyphenyl-thiazole, hydroxyphenyl-oxadiazole, hydroxyphenyl-thiadiazole, hydroxyphenyl-pyridine, hydroxyphenyl-benzimidazole, hydroxyphenyl-benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0635] As described above, the electron injection layer can be composed of the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof. In one or more embodiments, the electron injection layer can further include an organic material (e.g., a compound represented by Formula 601). When the electron injection layer further includes the organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof can be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0636] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately Within these ranges, appropriate or satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron-injected layer is within these ranges.
[0637] Second electrode 190
[0638] The second electrode 190 may be on the organic layer 150 having the structure described above. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this respect, the material used to form the second electrode 190 may be a metal, alloy, conductive compound, or any combination thereof having a relatively low work function.
[0639] The second electrode 190 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, IZO, or any combination thereof, but the embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0640] The second electrode 190 may have a single-layer structure comprising a single layer, or a multi-layer structure comprising two or more layers.
[0641] Capping layer
[0642] The first capping layer may be located outside the first electrode 110, and / or the second capping layer may be located outside the second electrode 190. More specifically, the organic light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the organic layer 150, and the second electrode 190 are stacked in the order stated herein; or a structure in which the first capping layer, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer are stacked in the order stated herein; or a structure in which the first capping layer, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer are stacked in the order stated herein.
[0643] Light generated in the emitting layer of the organic layer 150 of the organic light-emitting device 10 can pass through the first electrode 110 and the first capping layer toward the outside, wherein the first electrode 110 can be a semi-transparent electrode or a transmissive electrode. Light generated in the emitting layer of the organic layer 150 of the organic light-emitting device 10 can pass through the second capping layer toward the outside, wherein the second electrode 190 can be a semi-transparent electrode or a transmissive electrode.
[0644] Based on the principle of constructive interference, the first and second capping layers can increase the external luminescence efficiency.
[0645] The first capping layer and the second capping layer can each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0646] At least one of the first capping layer and the second capping layer can each independently include a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. The carbocyclic compound, the heterocyclic compound, and the amine-based compound can be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0647] In an embodiment, at least one of the first capping layer and the second capping layer can each independently include an amine group-containing compound.
[0648] For example, at least one of the first capping layer and the second capping layer can each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0649] Apparatus
[0650] The organic light emitting device 10 can be included in various appropriate apparatuses. For example, a light emitting apparatus, an authentication apparatus, or an electronic apparatus including the organic light emitting device 10 can be provided.
[0651] In addition to the organic light emitting device 10, the authentication apparatus can further include a biometric information collector. The thin film transistor can include a source electrode, a drain electrode, and an active layer, and one of the source electrode and the drain electrode can be electrically coupled with one of the first electrode 110 and the second electrode 190 of the organic light emitting device 10.
[0652] The thin film transistor can further include a gate electrode, a gate insulating layer, etc.
[0653] The active layer can include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc., but embodiments of the present disclosure are not limited thereto.
[0654] The apparatus including the organic light emitting device 10 can further include a sealing member sealing the organic light emitting device 10. The sealing member can be between the color filter and the organic light emitting device 10. The sealing member can be a transparent glass substrate or a plastic substrate. The sealing member can be a thin film encapsulation layer including a plurality of organic layers and / or a plurality of inorganic layers. When the sealing member is a thin film encapsulation layer, the organic light emitting device 10 can be flexible.
[0655] The light emitting apparatus can be used as various appropriate displays, light sources, etc.
[0656] The authentication device can be, for example, a biometric authentication device for authenticating an individual by using biometric information of a biometric body (e.g., a fingertip, a pupil, etc.).
[0657] The authentication device can further include a biometric information collector in addition to the organic light emitting device 10.
[0658] The electronic device can be applied to a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notebook, an electronic dictionary, an electronic game machine, a medical instrument (e.g., an electronic thermometer, a sphygmomanometer, a blood glucose meter, a pulse measurement device, a pulse wave measurement device, an electrocardiogram (ECG) display, an ultrasonic diagnostic device, or an endoscope display), a fish finder, various appropriate measuring instruments, a meter (e.g., a meter for a vehicle, an airplane, and a ship), a projector, etc., but embodiments of the present disclosure are not limited thereto.
[0659] Preparation method
[0660] The layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone can be formed in a certain zone by using one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0661] When the layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone are formed by vacuum deposition, the deposition can be performed at a deposition temperature of about 100°C to about 500°C, a vacuum degree of about 10 -8 tor to about 10 -3 tor, and a deposition rate of about 0.1 A / sec to about 10 A / sec, in consideration of a material to be included in a layer to be formed and a structure of the layer to be formed. to about tor, and a deposition rate of about 0.1 A / sec to about 10 A / sec, in consideration of a material to be included in a layer to be formed and a structure of the layer to be formed.
[0662] When the layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone are formed by spin coating, the spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, in consideration of a material to be included in a layer to be formed and a structure of the layer to be formed.
[0663] General definitions of at least some substituents
[0664] The term "C1-C 60 alkyl" as used herein refers to a straight-chain or branched aliphatic saturated hydrocarbon monovalent radical having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, and hexyl. The term "C1-C 60 alkylene" as used herein refers to a straight-chain or branched aliphatic saturated hydrocarbon divalent radical having 1 to 60 carbon atoms, and examples thereof include methylene, ethylene, propylene, isobutylene, sec-butylene, t-butylene, pentylene, isopentylene, and hexylene. 60Alkyl groups have essentially the same divalent structure.
[0665] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 An alkyl group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the end (e.g., at the terminal) of the alkyl group, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to C2-C 60 Alkenes have divalent groups with essentially the same structure.
[0666] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 A hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the end (e.g., at the terminal) of an alkyl group, and examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to C2-C 60 The alkynyl group is a divalent group with essentially the same structure.
[0667] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy, ethoxy and isopropoxy.
[0668] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also used. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have divalent groups with essentially the same structure.
[0669] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom and 1 to 10 carbon atoms, and examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with essentially the same structure.
[0670] As used in this article, the term "C3-C" 10"Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic (e.g., not aromatic), and examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is also used as a whole. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with essentially the same structure.
[0671] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups have divalent groups with essentially the same structure.
[0672] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (with 6 to 60 carbon atoms), and as used herein, "C6-C". 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system (with 6 to 60 carbon atoms). C6-C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and trefyl. When C6-C... 60 Aryl and C6-C 60 When each aryl group comprises two or more rings, these rings can fused together (e.g., bonded together). This is as used herein with the term "C7-C". 60 "alkylaryl" refers to an alkyl group consisting of at least one C1-C2 group. 60 Alkyl-substituted C6-C 60 Aryl.
[0673] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system (which, in addition to 1 to 60 carbon atoms, has at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom). As used herein, the term "C1-C" is similar. 60 "Hypo-heteroaryl" refers to a divalent group that has a heterocyclic aromatic system (in addition to 1 to 60 carbon atoms, it has at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom). C1-C 60Non-limiting examples of heteroaryl groups include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 heteroaryl groups each include two or more rings, the rings can be fused (e.g., bonded together). The term "C2-C 60 heteroaryl groups each include two or more rings, the rings can be fused (e.g., bonded together). The term "C2-C 60 alkylheteroaryl" refers to a C1-C 60 alkyl-substituted C1-C 60 heteroaryl.
[0674] The term "C6-C 60 aryloxy" refers to -OA 102 (where A 102 is a C6-C 60 aryl group), and the term "C6-C 60 arylthio" refers to -SA 103 (where A 103 is a C6-C 60 aryl group).
[0675] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused (e.g., bonded together) to one another, only carbon atoms as ring-forming atoms, and which does not have aromaticity throughout its molecular structure (e.g., the entire molecular structure is not aromatic). An example of a monovalent non-aromatic fused polycyclic group is fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having essentially the same structure as a monovalent non-aromatic fused polycyclic group.
[0676] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused (e.g., bonded together) to one another, at least one heteroatom selected from N, O, Si, P, S, and B in addition to carbon atoms as ring-forming atoms, and which does not have aromaticity throughout its molecular structure (e.g., the entire molecular structure is not aromatic). An example of a monovalent non-aromatic fused heteropolycyclic group is carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having essentially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0677] The term "C5-C 60 carbocyclyl" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms in which the ring-forming atoms are only carbon atoms. The term "C5-C 60 carbocyclyl" refers to an aromatic carbocyclic group or a non-aromatic carbocyclic group. C5-C60 The carbocyclic group can be a ring (e.g., benzene), a monovalent group (e.g., phenyl), or a divalent group (e.g., phenylene). In one or more embodiments, depending on the linkage to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbocyclic group can be a trivalent or tetravalent group. In one or more embodiments, C5-C is preferred. 30 Carbon cyclic group.
[0678] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to C5-C 60 Carbocyclic groups have substantially the same structure, except that, in addition to carbon (the number of carbon atoms can range from 1 to 60), at least one heteroatom selected from N, O, Si, P, and S is used as the cyclizing atom. In one or more embodiments, C1-C is preferred. 30 Heterocyclic group.
[0679] In this specification, C5-C is replaced. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hypoaryl, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 At least one substituent of the alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group can be:
[0680] deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy;
[0681] each unsubstituted or substituted by deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic, fused polycyclic group, monovalent non-aromatic, fused heteropolycyclic group, -O(Q 11 ), -S(Q 11 ), -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -P(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0682] each unsubstituted or substituted by deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -O(Q 21 ), -S(Q 21 ), -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -P(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ) or any combination thereof;
[0683] -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 ) or any combination thereof.) or -P(=O)(Q 31 ) or -P(=O)(Q 32 ) or -P(=O)(Q
[0684] or any combination thereof.
[0685] In the present specification, Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazino; hydrazono; C1-C 60 alkyl unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; C3-C 10 cycloalkyl; C1-C 10 heterocycloalkyl; C3-C 10 cycloalkenyl; C1-C 10 heterocycloalkenyl; C6-C 60 aryl unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C6-C 60 aryloxy; C6-C 60 arylthio; C1-C 60 heteroaryl unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.
[0686] The term “Ph” as used herein means phenyl, the term “Me” as used herein means methyl, the term “Et” as used herein means ethyl, the term “ter-Bu” or “Bu t ” as used herein means tert-butyl, and the term “OMe” as used herein means methoxy.
[0687] The term “biphenyl” as used herein means “phenyl substituted by phenyl”. In other words, “biphenyl” is phenyl substituted with C6-C 60 aryl as a substituent.
[0688] The term "triphenyl" as used herein refers to "a phenyl group substituted with a biphenyl group". In other words, "triphenyl" is a phenyl group having a C6-C12biphenyl group substituted at the ortho position. 60 C6-C12aryl-substituted C6-C12aryl. 60 C6-C12aryl-substituted C6-C12aryl.
[0689] Unless otherwise defined, and as used herein, * and * each refer to the point of attachment to the adjacent atom in the respective formula.
[0690] Hereinafter, the compound according to the embodiment and the organic light emitting device according to the embodiment will be described in more detail with reference to synthesis examples and embodiments. The phrase "use B instead of A" used when describing the synthesis examples refers to using the same molar equivalent of B instead of A.
[0691] EMBODIMENT
[0692] SYNTHESIS EXAMPLE 1 (SYNTHESIS OF COMPOUND BD2)
[0693]
[0694] Compound BD2(1) (1.00 g, 1.71 mmol), 9H-carbazole-3,6-dicarbonitrile (0.45 g, 2.05 mmol), and NaOH (0.10 g, 2.57 mmol) were mixed with acetone (300 mL) and stirred at room temperature for 3 hours, and an organic layer was extracted therefrom three times by adding dichloromethane and water thereto. The extracted organic layer was dried by using magnesium sulfate, filtered by using celite, and subjected to chromatography to obtain compound BD2 (0.79 g, 1.03 mmol) (yield = 60%).
[0695] SYNTHESIS EXAMPLE 2 (SYNTHESIS OF COMPOUND BD7)
[0696]
[0697] Compound BD7 (0.94 g, 1.08 mmol) was synthesized in substantially the same manner as in Synthesis Example 1, except that compound BD7(1) (1.17 g, 1.71 mmol) was used instead of compound BD2(1) (yield = 63%).
[0698] SYNTHESIS EXAMPLE 3 (SYNTHESIS OF COMPOUND BD67)
[0699]
[0700] Compound BD67 (0.85 g, 0.89 mmol) was synthesized in substantially the same manner as in Synthesis Example 1, except that compound BD67(1) (1.33 g, 1.71 mmol) was used instead of compound BD2(1) (yield = 52%).
[0701] Synthesis Example 4 (Synthesis of Compound BD102)
[0702]
[0703] Compound BD102(1) (1.33 g, 1.71 mmol) and AgCN (0.27 g, 2.05 mmol) were mixed with dichloromethane (300 mL) and stirred at room temperature for 12 hours, and an organic layer was extracted therefrom three times by adding water thereto. The extracted organic layer was dried by using magnesium sulfate, and filtered by using celite, and chromatography was performed thereon to obtain compound BD102 (0.92 g, 1.20 mmol) (yield = 70%).
[0704] The HOMO and LUMO energy levels of the compounds synthesized according to synthesis examples 1 to 4 are shown in Table 1. 1 H NMR and MALDI-TOF MS data.
[0705] In addition to the compounds synthesized according to synthesis examples 1 to 4, compounds other than the compounds synthesized according to synthesis examples 1 to 4 can also be synthesized by referring to the above-described synthesis mechanism and raw materials.
[0706] Table 1
[0707]
[0708]
[0709] Evaluation Example 1
[0710] The HOMO and LUMO energy levels of compound BD2, compound BD7, compound BD67, compound BD102, compound ETH2, compound ETH77, compound HTH2, and compound HTH4 were evaluated according to the method of Table 2, and the results thereof are shown in Table 3.
[0711] Table 2
[0712]
[0713] Table 3
[0714] Compound No. HOMO (eV) LUMO (eV) BD2 -5.20 -2.08 BD7 -5.23 -2.13 BD67 -5.25 -2.16 BD102 -5.30 -2.32 ETH2 -6.50 -2.72 ETH77 -5.75 -2.65 HTH2 -5.51 -1.91 HTH4 -5.64 -2.13
[0715]
[0716] As can be seen from Table 3, compound BD2, compound BD7, compound BD67, compound BD102, compound ETH2, compound ETH77, compound HTH2, and compound HTH4 have HOMO and LUMO energy levels suitable for manufacturing an organic light emitting device.
[0717] Example 1
[0718] As the anode, Corning 15Ω / cm 2 An ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, cleaned by ultrasonic treatment with isopropanol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. Then, the ITO glass substrate was supplied to a vacuum deposition apparatus.
[0719] 2-TNATA was vacuum deposited on the anode to form a hole injection layer having a thickness of 10 nm, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 40 nm. Compound BD2 (first compound), compound ETH2 (second compound), and compound HTH2 (third compound) were vacuum deposited on the hole transport layer to form an emission layer having a thickness of 20 nm. The amount of compound BD2 was 10 wt% based on 100 wt% of the emission layer, and the weight ratio of compound ETH2 to compound HTH2 was adjusted to 5:5.
[0720] Compound ETH2 was vacuum deposited on the emission layer to form a buffer layer having a thickness of 10 nm, Alq3 was vacuum deposited on the buffer layer to form an electron transport layer having a thickness of 40 nm, LiF was vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and Al was vacuum deposited on the electron injection layer to form a cathode having a thickness of 100 nm, thereby completing the manufacture of the organic light-emitting device.
[0721] Compound ETH2 was vacuum deposited on the emission layer to form a buffer layer having a thickness of 10 nm, Alq3 was vacuum deposited on the buffer layer to form an electron transport layer having a thickness of 40 nm, LiF was vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and Al was vacuum deposited on the electron injection layer to form a cathode having a thickness of 100 nm, thereby completing the manufacture of the organic light-emitting device.
[0722]
[0723] The organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 4 were used as the first compound, the second compound, and the third compound when forming the emission layer, respectively.
[0724] Evaluation Example 2
[0725] The organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 4 were used as the first compound, the second compound, and the third compound when forming the emission layer, respectively.
[0726] The organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 4 were used as the first compound, the second compound, and the third compound when forming the emission layer, respectively. 2 The driving voltage (V), current density (mA / cm 2 ), luminous efficiency (cd / A), maximum emission wavelength (nm), and lifetime (T 90 ) of the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 and 2 were measured, and the results thereof are shown in Table 4. In Table 4, the lifetime (T 90 ) indicates the amount of time (hr) elapsed when the luminance is 90% of the initial luminance (100%). The wavelength-emission intensity graph and the luminance-luminous efficiency graph of the organic light-emitting devices manufactured according to Example 5 and Comparative Examples 1 and 2 are shown in FIGS. 5 and 6, respectively. Figure 2 Figure 3
[0727] Table 4
[0728]
[0729]
[0730] As can be seen from Table 4, the organic light-emitting devices of Examples 1 to 7 have excellent or comparable driving voltage and current density compared to the organic light-emitting devices of Comparative Examples 1 and 2, and the organic light-emitting devices of Examples 1 to 7 have excellent luminous efficiency and lifetime characteristics compared to the organic light-emitting devices of Comparative Examples 1 and 2.
[0731] Example 8
[0732] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that instead of vacuum depositing the compound BD2 (first compound), the compound ETH2 (second compound), and the compound HTH2 (third compound) on the hole transport layer, the compound BD2 (first compound or dopant) and the compound HTH4 (host) were vacuum deposited on the hole transport layer to form an emission layer having a thickness of 30 nm. In forming the emission layer, the amount of the compound BD2 was adjusted to 10 wt% based on 100 wt% of the emission layer.
[0733] Examples 9 to 11 and Comparative Examples 3 and 4
[0734] An organic light-emitting device was manufactured in substantially the same manner as in Example 8, except that the compounds shown in Table 5 were used as the dopant and the host in forming the emission layer, respectively.
[0735] Evaluation Example 3
[0736] The driving voltage (V), current density (mA / cm 2 The driving voltage (V) and current density (mA / cm²) of the organic light-emitting devices manufactured according to Examples 8 to 11 and Comparative Examples 3 and 4 were measured. 2 ), luminous efficacy (cd / A), maximum emission wavelength (nm), and lifetime (T) 90 The results are shown in Table 5. In Table 5, lifetime (T) 90 This indicates the amount of time (hr) that has elapsed when the brightness is 90% of the initial brightness (100%).
[0737] [Table 5]
[0738]
[0739] As can be seen from Table 5, compared with the organic light-emitting devices of Comparative Examples 3 and 4, the organic light-emitting devices of Examples 8 to 11 have excellent or comparable driving voltage and current density, and compared with the organic light-emitting devices of Comparative Examples 3 and 4, Examples 8 to 11 have excellent luminous efficiency and lifetime characteristics.
[0740] Example 12
[0741] The organic light-emitting device was fabricated in essentially the same manner as in Example 1, except that instead of vacuum-depositing compounds BD2 (first compound), ETH2 (second compound), and HTH2 (third compound) onto the hole transport layer to form a structure with... Instead of a thick emission layer, compounds BD2 (first compound, auxiliary dopant), ETH2 (second compound), HTH2 (third compound), and FD24 (fluorescent dopant, fluorescent emitter) are vacuum-deposited onto the hole transport layer to form a layer with... A thick emission layer. When forming the emission layer, based on a 100wt% emission layer, the amount of fluorescent dopant compound FD24 was adjusted to 0.5wt%, and the weight ratio of compound BD2 (first compound), compound ETH2 (second compound), and compound HTH2 (third compound) was adjusted to 9.5:45:45.
[0742] Examples 13 to 18
[0743] The organic light-emitting device was manufactured in essentially the same manner as in Example 12, except that the compounds shown in Table 6 were used as the first compound, the second compound, the third compound, and the fluorescent dopant, respectively, when forming the emission layer.
[0744] Evaluation Example 4
[0745] Using a Keithley MU 236 and a PR650 luminance meter at 1,000 cd / m² 2The driving voltage (V) and current density (mA / cm²) of the organic light-emitting devices in Examples 12 to 18 were measured. 2 ), luminous efficacy (cd / A), maximum emission wavelength (nm), and lifetime (T) 90 The results are shown in Table 6. In Table 6, lifetime (T) 90 The value indicates the amount of time (hr) that has elapsed when the brightness reaches 90% of the initial brightness (100%). The wavelength-emission intensity diagrams of the organic light-emitting devices manufactured according to Examples 5 and 12 to 15, the wavelength-emission intensity diagrams of the organic light-emitting devices manufactured according to Examples 16 to 18, the brightness-luminous efficiency diagrams of the organic light-emitting devices manufactured according to Examples 5 and 12 to 18, and the time-brightness diagrams of the organic light-emitting devices manufactured according to Examples 12 to 18 are shown in the figures. Figure 4 to Figure 7 The diagram is shown in the image.
[0746] [Table 6]
[0747]
[0748]
[0749] As can be seen from Table 6, the organic light-emitting devices of Examples 12 to 18 have excellent driving voltage, current density, luminous efficiency and lifetime characteristics.
[0750] Evaluation Example 5
[0751] While applying voltage pulses (pulse widths ranging from 100 ns to 1 ms) using an AVTECCH AV-1011-B pulse generator, the time-resolved electroluminescence (TREL) spectra of each organic light-emitting device in Examples 14 and 17 were measured using a Tektronix TDS 460 four-channel digital oscilloscope, and the results are shown in... Figure 8 From Figure 8 The decay times calculated from the TREL spectrum are shown in Table 7.
[0752] Table 7
[0753] Decay time [τ1 (μs)] [tau]2 (μs) [CDATA[τ3 (μs)]]> Example 14 2 5 29 Example 17 2 10 70
[0754] from Figure 8 As can be seen from Table 7, the organic light-emitting devices of Examples 14 and 17 emit both phosphorescence and delayed fluorescence.
[0755] Organic light-emitting devices can exhibit low driving voltage, high current density, high luminous efficiency, and long lifetime, and can be used to manufacture high-quality electronic devices. This organometallic compound can be used to manufacture organic light-emitting devices with high luminous efficiency and long lifetime.
[0756] It is to be understood that the embodiments described herein are to be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should be considered as available for other similar features or aspects in other embodiments.
[0757] It will be understood that, although the terms“first,”“second,”“third,” etc. can be used herein to describe various elements, components, regions, layers and / or sections, these elements, components, regions, layers and / or sections should not be limited by these terms. These terms are used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus,“first,”“second,”“third,” and / or other similar terms can be used interchangeably to describe various elements, components, regions, layers and / or sections.
[0758] For ease of explanation, spatially relative terms, such as“beneath,”“below,”“lower,”“bottom,”“on,”“above,”“upper” and the like, can be used herein for describing elemental and / or feature relationships when the apparatus is illustrated in the figures. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientations depicted in the figures. For example, if the device in the figures is turned over, elements described as“below” or“beneath” other elements or features would then be oriented“above” the other elements or features. Thus, the example term“below” can encompass both an orientation of above and below. The device can be otherwise oriented (e.g., rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein interpreted accordingly.
[0759] It will be understood that when an element or layer is referred to as being“on,”“connected to,” or“coupled to” another element or layer, it can be directly on, connected or coupled to the other element or layer, or one or more intervening elements or layers can be present. In addition, it will also be understood that when an element or layer is referred to as being“between” two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers can also be present.
[0760] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the present disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. It will be further understood that the terms "comprises", "comprising", "includes" and "including" when used in this specification, specify the presence of stated features, integers, actions, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, integers, actions, operations, elements, components, and / or groups thereof.
[0761] As used herein, the terms "substantially", "about" and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. Further, when describing embodiments of the present disclosure using "may", it is meant to mean "one or more embodiments of the present disclosure". As used herein, the terms "use", "using" and "used" can be taken in their broadest possible context as being synonymous with "utilize", "utilizing" and "utilized", respectively. Also, the term "exemplary" is intended to mean an example or an illustration.
[0762] Also, any numerical range recited herein is intended to include all sub-ranges of the same whole number recited, as well as an endpoint range of either the same whole number or an endpoint range including or excluding the same whole number. For example, a range of "1.0 to 10.0" is intended to include the whole number recited "1.0" and the whole number recited "10.0" between and including the endpoints (i.e., a minimum of 1.0 and a maximum of 10.0), as well as an endpoint range of either the same whole number, or an endpoint range including or excluding the same whole number. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations falling within the same range, and any minimum numerical limitation recited in the specification is intended to include all higher numerical limitations falling within the same range. Accordingly, the applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range falling within the ranges expressly recited in this specification.
[0763] While one or more embodiments have been described with reference to the attached figures, those of ordinary skill in the art will appreciate that various changes in form and detail can be made without departing from the spirit and scope of the disclosure as defined by the appended claims and their equivalents.
Claims
1. An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes a first compound represented by Formula 1: Formula 1 wherein, in Formula 1, M is Pt, Pd, or Au, and L2 is a ligand represented by one of Formula A4-1(1) and Formula A4-1(3): wherein, in Formula 1, Formula A4-1(1), and Formula A4-1(3), X1 to X3 are each independently C, X4 is N, X1 and M are directly connected to each other, X2 and M are directly connected to each other, and X3 and M are directly connected to each other, T 11 to T 13 each independently is a bond, two of the bonds selected from i) the bond between X1 and M, ii) the bond between X2 and M, and iii) the bond between X3 and M are each a coordination bond, and the other two bonds are each a covalent bond, T1 is a single bond, T2 is a single bond, rings CY1 and CY3 are each independently an imidazolyl group, a benzimidazolyl group, or an azabenzimidazolyl group, ring CY2 is a phenyl group, R2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted chrysenyl group, R1and R3are each independently hydrogen, deuterium, -F, -CI, -Br, -I, substituted or unsubstituted C1-C 20 alkyl or substituted or unsubstituted C1-C 20 alkoxy, a1 to a3 are each independently one of integers from 0 to 5, two or more R1s are the same as or different from each other when a1 is 2 or more; two or more R2s are the same as or different from each other when a2 is 2 or more; and two or more R3s are the same as or different from each other when a3 is 2 or more, * indicates a binding site with M in Formula 1, X 40a is a single bond, S(=0)2or B(R 40a ), X 41 is N or C(R 41 ), X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), X 44 is N or C(R 44 ), X 45 is N or C(R 45 ), X 46 is N or C(R 46 ), X 47 is N or C(R 47 ), X 48 is N or C(R 48 ), and X 49 is N or C(R 49 ), R 40a and R 41 to R 49 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C 20 alkyl, substituted or unsubstituted C1-C 20 alkoxy, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrenyl, or substituted or unsubstituted chrysenyl, 2. The organic light-emitting device according to claim 1, wherein said substituted C1-C 20 alkyl, said substituted C1-C 20 alkyl, said substituted C1-C 60 alkyl, said substituted C1-C 60 alkyl, said substituted C1-C the organic layer further includes a second compound represented by Formula 2, a third compound including a group represented by Formula 3, or any combination thereof, and the second compound is different from the third compound: Formula 2 Formula 3 wherein, in Formula 2 and Formula 3, a71 and a72 are each independently one of integers from 0 to 20, ring CY 71 and ring CY 72 each independently C5-C 30 carbocyclyl or C1-C 30 heterocyclyl, L 51 to L 53 each independently unsubstituted or substituted by at least one R 10a substituted C5-C 30 carbocyclyl, or unsubstituted or substituted by at least one R 10a substituted C1-C 30 heterocyclyl, b51 to b53 are each independently one of an integer from 0 to 5, wherein, when b51 is 0, *-(L 51 ) b51 -*' is a single bond, when b52 is 0, *-(L 52 ) b52 -*' is a single bond, and when b53 is 0, *-(L 53 ) b53 -*' is a single bond, two or more L's are the same or different from each other; and when b51 is 2 or more, two or more L's are the same or different from each other 51 two or more L's are the same or different from each other; and when b52 is 2 or more, two or more L's are the same or different from each other 52 two or more L's are the same or different from each other; and when b53 is 2 or more, two or more L's are the same or different from each other 53 two or more L's are the same or different from each other X 54 is N or C(R 54 ), X 55 is N or C(R 55 ), X 56 is N or C(R 56 ), and X 54 is N or C(R 56 ) at least one of X X 81 is a single bond, O, S, N(R 81 ), B(R 81 ), C(R 81a )(R 81b ) or Si(R 81a )(R 81b ), R 51 to R 56 , R 71 , R 72 , R 81 , R 81a , and R 81b are each independently hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted C8-C 60 monovalent non-aromatic fused polycyclic group, substituted or unsubstituted C1-C 60 monovalent non-aromatic fused heteropolycyclic 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), R 10a is deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 aralkylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted C8-C 60 monovalent non-aromatic fused polycyclic group, substituted or unsubstituted C1-C 60 monovalent non-aromatic fused heteropolycyclic 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), * and *' each indicate a binding site with an adjacent atom, when a71 is 2 or more, two or more R 71 are the same or different from each other; and when a72 is 2 or more, two or more R 72 are the same or different from each other, any combination thereof, and said substituted C1-C 60 alkyl, said substituted C2-C 60 alkenyl, said substituted C2-C 60 alkynyl, said substituted C1-C 60 alkoxy, said substituted C3-C 10 cycloalkyl, said substituted C1-C 10 heterocycloalkyl, said substituted C3-C 10 cycloalkenyl, said substituted C1-C 10 heterocycloalkenyl, said substituted C6-C 60 aryl, said substituted C7-C 60 alkylaryl, said substituted C6-C 60 aryloxy, said substituted C6-C 60 arylthio, said substituted C1-C 60 heteroaryl, said substituted C2-C 60 alkylheteroaryl, said substituted C8-C 60 monovalent non-aromatic fused polycyclic groups and said substituted C1-C 60 substituents of said monovalent non-aromatic fused heteropolycyclic groups are: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy; Each of the following C1-C is replaced 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C8-C 60 Monovalent non-aromatic fused polycyclic groups, C1-C 60 Monovalent non-aromatic fused heterocyclic groups, -O(Q) 11 -S(Q) 11 ), -Si(Q 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof; Each of the following C3-Cs that are not substituted or are substituted by: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C8-C 60 Monovalent non-aromatic fused polycyclic groups or C1-C 60 Monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C8-C 60 Monovalent non-aromatic fused polycyclic groups, C1-C 60 Monovalent non-aromatic fused heterocyclic groups, -O(Q) 21 -S(Q) 21 ), -Si(Q 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; -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 ), or -P(=O)(Q 31 )(Q 32 ); or 3. The organic light-emitting device according to claim 1, wherein Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently hydrogen; deuterium; -F; -CI; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazino; hydrazono; unsubstituted or substituted C1-C 60 alkyl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; C3-C 10 cycloalkyl; C1-C 10 heterocycloalkyl; C3-C 10 cycloalkenyl; C1-C 10 heterocycloalkenyl; unsubstituted or substituted C6-C 60 aryl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C6-C 60 aryloxy; C6-C 60 arysthiyl; unsubstituted or substituted C1-C 60 heteroaryl: deuterium, -F, cyano, C1-C 60 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C8-C 60 monovalent non-aromatic fused polycyclic group; or C1-C 60 monovalent non-aromatic fused heteropolycyclic group. M in Formula 1 is Pt.
4. The organic light-emitting device according to claim 1, wherein the first compound is represented by Formula 1A, Formula 1B, or Formula 1C: wherein, in Formula 1A to Formula 1C, M, L2, X1 to X3, T1, and T2 are each independently the same as described in claim 1, 5. The organic light-emitting device according to claim 4, wherein X 12 is O, S or N(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ), and R 12 to R 16 each independently are the same as defined in claim 1 in connection with R1, X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), and R 21 through R 23 each independently are the same as defined in claim 1 in connection with R2, X 32 is O, S or N(R 32 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), and R 32 to R 36 each independently are the same as defined in claim 1 in connection with R3.
6. The organic light-emitting device according to claim 2, wherein In Formula 1A to Formula 1C, X 22 is C(R 22 ), and R 22 is the same as defined in connection with R2 in claim 1. wherein, in Formula CY51-1 to Formula CY51-22, Formula CY52-1 to Formula CY52-22, and Formula CY53-1 to Formula CY53-18, the group represented by *-(L 51 ) b51 -R 51 the group represented by *-(L one of formula CY51-1 to formula CY51-22, the group represented by *-(L 52 ) b52 -R 52 the group represented by *-(L one of formula CY52-1 to formula CY52-22, and In Equation 2, *-(L 53 ) b53 -R 53 The represented group is one of the groups represented by formulas CY53-1 to CY53-18, -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3): * indicates a binding site with an adjacent atom. Y 63 is a single bond, O, S, N(R 63 ), B(R 63 ), C(R 63a )(R 63b ) or Si(R 63a )(R 63b ), Y 64 is a single bond, O, S, N(R 64 ), B(R 64 ), C(R 64a )(R 64b ) or Si(R 64a )(R 64b ), Y 67 is a single bond, O, S, N(R 67 ), B(R 67 ), C(R 67a )(R 67b ) or Si(R 67a )(R 67b ), Y 68 is a single bond, O, S, N(R 68 ), B(R 68 ), C(R 68a )(R 68b ) or Si(R 68a )(R 68b ), Y in formula CY51-16 and formula CY51-17 63 and Y 64 are not simultaneously a single bond, Y in formula CY52-16 and formula CY52-17 67 and Y 68 are not simultaneously a single bond, R 51a to R 51e , R 61 to R 64 , R 63a , R 63b , R 64a and R 64b are each independently the same as defined in claim 2 in connection with R 51 , wherein each of R 51a to R 51e is other than hydrogen, R 52a to R 52e , R 65 to R 68 , R 67a , R 67b , R 68a and R 68b are each independently the same as defined in claim 2 in connection with R 52 , wherein each of R 52a to R 52e is other than hydrogen, R 53a to R 53e each independently is as defined in claim 2 in connection with R 53 , wherein each of R 53a to R 53e is other than hydrogen, and the third compound is represented by one of Formula 3-1 to Formula 3-5:
7. The organic light emitting device according to claim 2, wherein, wherein, in Formula 3-1 to Formula 3-5, Ring CY 71 , Ring CY 72 , X 81 , R 71 , R 72 , a71and a72are each independently the same as described in claim 2, ring CY 73 , ring CY 74 , R 73 , R 74 , a73and a74are each independently defined as in claim 2 in connection with ring CY 71 , ring CY 72 , R 71 , R 72 , a71and a72are the same as defined in claim 2 in connection with ring CY L 81 is *-C(Q4)(Q5)-*, *-Si(Q4)(Q5)-*, unsubstituted or substituted C5-C 10a substituted C5-C 30 carbocyclyl, or unsubstituted or substituted C1-C 10a substituted C1-C 30 heterocyclyl, wherein Q4and Q5are each independently the same as defined in claim 2 in connection with Q1. b81 is one of an integer from 0 to 5, wherein, when b81 is 0, *-(L 81 ) b81 * is a single bond, and when b81 is 2 or more, two or more L 81 are the same or different from each other, X 82 is a single bond, O, S, N(R 82 ), B(R 82 ), C(R 82a )(R 82b ) or Si(R 82a )(R 82b ), X 83 is a single bond, O, S, N(R 83 ), B(R 83 ), C(R 83a )(R 83b ) or Si(R 83a )(R 83b ), X in formula 3-2 and formula 3-4 82 and X 83 are not simultaneously a single bond, X 84 is C or Si, R 80 , R 82 , R 83 , R 82a , R 82b , R 83a , R 83b and R 84 are each independently the same as defined in claim 2 in connection with R 81 , R 10a the same as defined in claim 2, and * and * each indicate a binding site to an adjacent atom.
8. The organic light emitting device according to claim 7, wherein, the group represented by in formula 3-1 and formula 3-2 is a group represented by one of formula CY71-1(1) to formula CY71-1(8), the group represented by in formula 3-1 and formula 3-3 is a group represented by one of formula CY71-2(1) to formula CY71-2(8), the group represented by in formula 3-2 and formula 3-4 is a group represented by one of formula CY71-3(1) to formula CY71-3(32), the group represented by formula CY71-4(1) to formula CY71-4(32) and the group represented by one of formula CY71-5(1) to formula CY71-5(8): wherein, 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), X 81 to X 84 , R 80 and R 84 each independently is the same as described in claim 7, X 85 is a single bond, O, S, N(R 85 ), B(R 85 ), C(R 85a )(R 85b ) or Si(R 85a )(R 85b ), X 86 is a single bond, O, S, N(R 86 ), B(R 86 ), C(R 86a )(R 86b ) or Si(R 86a )(R 86b ), X in the formulae CY71-1 (1 ) to CY71-1 (8) and CY71-4 (1 ) to CY71-4 (32) 85 and X 86 are not simultaneously a single bond, X 87 is a single bond, O, S, N(R 87 ), B(R 87 ), C(R 87a )(R 87b ) or Si(R 87a )(R 87b ), X 88 is a single bond, O, S, N(R 88 ), B(R 88 ), C(R 88a )(R 88b ), or Si(R 88a )(R 88b ), X in formula CY71-2(1) to formula CY71-2(8), formula CY71-3(1) to formula CY71-3(32), and formula CY71-5(1) to formula CY71-5(8) 87 and X 88 are not simultaneously a single bond, and R 85 to R 88 , R 85a , R 85b , R 86a , R 86b , R 87a , R 87b , R 88a and R 88b each independently are the same as defined in claim 2 in connection with R 81 .
9. The organic light emitting device according to claim 1, wherein, the emission layer includes the first compound, the emission layer further includes a host, the first compound and the host are different from each other, and the emission layer is configured to emit blue light emitted from the first compound.
10. The organic light emitting device according to claim 1, wherein, the emission layer includes the first compound, the emission layer further includes a host and a dopant, the first compound, the host, and the dopant are different from each other, and the emission layer is configured to emit phosphorescence or fluorescence emitted from the dopant.
11. An organometallic compound represented by formula 1: Formula 1 wherein, in formula 1, M is Pt, Pd, or Au, and wherein, L2 is a ligand represented by one of formula A4-1 (1) to formula A4-1 (3): wherein, in formula 1, formula A4-1 (1), and formula A4-1 (3), X1 to X3 are each independently C, and X4 is N X1 and M are directly connected to each other, X2 and M are directly connected to each other, and X3 and M are directly connected to each other, two of the bonds selected from i) the bond between X1 and M, ii) the bond between X2 and M, and iii) the bond between X3 and M are each a coordinate bond, and the other two bonds are each a covalent bond, T 11 to T 13 each independently a bond, T1 is a single bond, T2 is a single bond, ring CY1 and ring CY3 are each independently an imidazolyl group, a benzimidazolyl group, or an azabenzimidazolyl group, ring CY2 is a phenyl group, R2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted chrysenyl group, a1 to a3 are each independently one of an integer of 0 to 5, R1and R3are each independently hydrogen, deuterium, -F, -CI, -Br, -I, substituted or unsubstituted C1-C 20 alkyl or substituted or unsubstituted C1-C 20 alkoxy, two or more R1 are the same as or different from each other when a1 is 2 or more; two or more R2 are the same as or different from each other when a2 is 2 or more; and two or more R3 are the same as or different from each other when a3 is 2 or more, * indicates a binding site to M in formula 1, 12. The organometallic compound according to claim 11, wherein, X 40a is a single bond, S(=0)2or B(R 40a ), X 41 is N or C(R 41 ), X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), X 44 is N or C(R 44 ), X 45 is N or C(R 45 ), X 46 is N or C(R 46 ), X 47 is N or C(R 47 ), X 48 is N or C(R 48 ), and X 49 is N or C(R 49 ), R 40a and R 41 to R 49 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C 20 alkyl or substituted or unsubstituted C1-C 20 alkoxy, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrenyl, or substituted or unsubstituted chrysenyl, M is Pt. said substituted C1-C 20 alkyl, said substituted C1-C 20 alkoxy, said substituted phenyl, said substituted biphenyl, said substituted naphthyl, said substituted fluorenyl, said substituted phenanthryl, said substituted anthryl, said substituted fluoranthenyl, said substituted benzophenanthryl, said substituted pyrenyl and said substituted chrysenyl are: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 alkyl or C1-C 60 alkoxy.
13. The organometallic compound according to claim 11, wherein, the organometallic compound is represented by formula 1A, formula 1B, or formula 1C: wherein, in formula 1A to formula 1C, M, L2, X1 to X3, T1, and T2 are each independently the same as described in claim 11, X 12 is O, S or N(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ), and R 12 to R 16 each independently are the same as defined in claim 11 in connection with R1, X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), and R 21 to R 23 each independently are the same as defined in claim 11 in connection with R2, X 32 is O, S or N(R 32 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), and R 32 to R 36 each independently are the same as defined in claim 11 in connection with R3.
14. The organometallic compound of claim 11, wherein, the organometallic compound is selected from the group consisting of compound BD1 to compound BD105:
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