Organic light emitting device and apparatus including the same
By optimizing the triplet state energy level difference between the double-layer electron transport region and the emission layer composed of a nitrogen ring compound with specific π electron depletion in an organic light-emitting device, the problem of inappropriate triplet exciton concentration was solved, and the luminescence efficiency and lifetime were improved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2020-09-09
- Publication Date
- 2026-03-27
AI Technical Summary
In existing organic light-emitting devices, improper concentration control of triplet excitons leads to insufficient luminescence efficiency and lifetime, and the design of the electron transport region fails to effectively prevent the leakage of triplet excitons.
A bilayer structure with electron transport region is adopted, in which the first auxiliary layer and the second auxiliary layer respectively contain nitrogen ring compounds with specific π electron depletion. The triplet energy level difference is optimized by density functional theory, the triplet exciton concentration is adjusted and leakage is reduced, and the triplet energy level difference is optimized by combining the host and dopant of the emitter layer to improve exciton utilization efficiency.
Effective control of triplet exciton concentration improves the luminous efficiency and lifespan of organic light-emitting devices, while reducing triplet exciton leakage and enhancing overall performance.
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Figure CN112490380B_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0113020, filed on September 11, 2019, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Technology
[0003] One or more embodiments of this disclosure relate to organic light-emitting devices and devices including the same. Technical Field
[0004] Organic light-emitting devices are self-emitting devices that generate full-color images, and compared with other devices in the field, they also have wide viewing angles, high contrast, short response times, and superior characteristics in terms of brightness, driving voltage, and response speed.
[0005] Examples of organic light-emitting devices 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., transitions or relaxations) to the ground state, thereby generating light. Summary of the Invention
[0006] One or more embodiments provide an organic light-emitting device and an apparatus including the same.
[0007] Further aspects of the implementation will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practice of the disclosed implementations presented.
[0008] Embodiments of this disclosure provide an organic light-emitting device comprising:
[0009] First electrode;
[0010] The second electrode facing the first electrode;
[0011] An organic layer between the first and second electrodes, including an emission layer; and
[0012] In the electron transport region between the emitter layer and the second electrode
[0013] The electron transport region includes a first auxiliary layer and a second auxiliary layer.
[0014] The first auxiliary layer is located between the emission layer and the second auxiliary layer.
[0015] The first auxiliary layer includes a first compound.
[0016] The second auxiliary layer includes a second compound,
[0017] The second compound includes at least one ring including a π-electron depleted nitrogen, and
[0018] The organic light emitting device satisfies equations: T1(EML) ≥ T1(AXL1) + 0.3 eV and T1(AXL2) ≥ T1(AXL1) + 0.5 eV,
[0019] wherein T1(EML) is a highest triplet energy level (eV) among triplet energy levels (eV) of compounds included in the emission layer,
[0020] T1(AXL1) is a lowest triplet excited energy level (eV) of the first compound,
[0021] T1(AXL2) is a lowest triplet excited energy level (eV) of the second compound, and
[0022] T1(EML), T1(AXL1), and T1(AXL2) are calculated using a density functional theory (DFT) method, wherein the compounds included in the emission layer, the first compound, and the second compound are structurally optimized at a level of B3LYP / 6-31G*(d,p).
[0023] Another aspect of embodiments of the disclosure provides an apparatus including an organic light emitting device and a thin film transistor, wherein the thin film transistor includes a source electrode, an active layer, and a drain electrode, and
[0024] The first electrode of the organic light emitting device is electrically connected to one of the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF DRAWINGS
[0025] The above and other aspects and features of certain embodiments of the disclosure will become more apparent from the following description, taken in conjunction with the accompanying drawings, in which:
[0026] Figure 1 is a schematic view of an organic light emitting device according to an embodiment; and
[0027] Figure 2 is a schematic view of an organic light emitting device according to another embodiment. DETAILED DESCRIPTION
[0028] The term "organic layer" as used herein refers to a single layer and / or multiple layers between the first electrode and the second electrode of the organic light emitting device. The materials included in the "organic layer" are not limited to organic materials. For example, the organic layer can include inorganic materials.
[0029] The expression "(organic layer) includes a compound represented by Formula 1" as used herein can include the case where "(organic layer) includes one compound of Formula 1 or two or more different compounds of Formula 1".
[0030] Hereinafter, embodiments of the present disclosure will be described in greater detail with reference to the accompanying drawings.
[0031] Figure 1 and Figure 2 Description
[0032] Figure 1 and Figure 2 Each of FIGS. 1 to 4 is a schematic view of an organic light emitting device 10 or an organic light emitting device 20 according to an embodiment, respectively. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190. The organic layer 150 can include an emission layer 151.
[0033] Referring to Figure 1 , the organic light emitting device 10 includes the first electrode 110; the second electrode 190 facing the first electrode 110; and the organic layer 150 between the first electrode 110 and the second electrode 190 and including the emission layer 151. The organic layer 150 includes an electron transport zone 170 between the emission layer 151 and the second electrode 190, and the electron transport zone 170 includes a first auxiliary layer 171 and a second auxiliary layer 172. The first auxiliary layer 171 is between the emission layer 151 and the second auxiliary layer 172 and includes a first compound, and the second auxiliary layer 172 includes a second compound, and the second compound includes at least one ring containing a π-electron depleted nitrogen.
[0034] The organic light emitting device 10 can satisfy the equations: T1(EML) ≥ T1(AXL1) + 0.3 eV and T1(AXL2) ≥ T1(AXL1) + 0.5 eV.
[0035] In the above equations, T1(EML) is the highest triplet energy level (eV) among triplet energy levels (eV) of a compound included in the emission layer 151,
[0036] T1(AXL1) is a lowest triplet excitation energy level (eV) of the first compound, and
[0037] T1(AXL2) is a lowest triplet excitation energy level (eV) of the second compound.
[0038] In the above equation, T1(EML), T1(AXL1), and T1(AXL2) are calculated (e.g., evaluated by using a density functional theory (DFT) method with a Gaussian program) using a density functional theory (DFT) method at the level of B3LYP / 6-31G*(d,p) (e.g., using a B3LYP hybrid functional and a 6-31G*(d,p) basis set), in which the compound (e.g., the compound included in the emission layer 151, the first compound, and the second compound) is structurally optimized.
[0039] When the first auxiliary layer 171 is between the emission layer 151 and the second auxiliary layer 172, and T1(EML) is higher than T1(AXL1) by 0.3 eV or more, the triplet exciton formed in the emission layer 151 can move to the triplet state level of the first auxiliary layer 171 having lower energy. As such, the concentration of the triplet exciton in the emission layer 151 can be adjusted, thereby preventing or reducing the deterioration of the emission layer material and improving the lifespan of the organic light emitting device 10 including the first compound in the first auxiliary layer 171.
[0040] The first compound included in the first auxiliary layer 171 is not particularly limited, and can include all compounds satisfying T1(EML) ≥ T1(AXL1) + 0.3 eV.
[0041] The first auxiliary layer 171 can directly contact (e.g., physically contact) the emission layer 151. For example, the first auxiliary layer 171 can exist at the interface between the emission layer 151 and the second auxiliary layer 172.
[0042] Because the first auxiliary layer 171 in the organic light emitting device 10 directly contacts (e.g., physically contacts) the emission layer 151, the concentration of the triplet exciton in the emission layer 151 can be appropriately or effectively adjusted, thereby improving the lifespan of the organic light emitting device 10.
[0043] Further, the second compound included in the second auxiliary layer 172 and the first compound included in the first auxiliary layer 171 can satisfy T1(AXL2) ≥ T1(AXL1) + 0.5 eV. As such, the triplet exciton moved from the emission layer 151 to the first auxiliary layer 171 can be prevented from moving to the second auxiliary layer 172 (or such movement can be reduced). For example, the triplet exciton formed in the emission layer 151 can be prevented from flowing to the second auxiliary layer 172 from the interface between the first auxiliary layer 171 and the second auxiliary layer 172 (or such flow of the electron can be reduced). Therefore, the excessive leakage of the triplet exciton can be prevented or reduced, and the concentration of the triplet exciton participating in light emission can be appropriately or suitably maintained.
[0044] Also, the second auxiliary layer 172 can prevent (or reduce) the injection of holes from the hole transport zone.
[0045] In an embodiment, the first auxiliary layer 171 can directly contact (e.g., physically contact) the second auxiliary layer 172. In one or more embodiments, the first auxiliary layer 171 can directly contact (e.g., physically contact) each of the emission layer 151 and the second auxiliary layer 172. For example, the first auxiliary layer 171 can exist at an interface between the emission layer 151 and the second auxiliary layer 172.
[0046] Because the first auxiliary layer 171 in the organic light emitting device 10 directly contacts (e.g., physically contacts) the second auxiliary layer 172, excitons formed in the emission layer 151 are substantially prevented from moving to the second auxiliary layer 172 (or such movement can be reduced), thereby appropriately or suitably adjusting the concentration of excitons in the emission layer 151 and the first auxiliary layer 171. Accordingly, the light emitting efficiency of the organic light emitting device 10 can be improved.
[0047] In an embodiment, T1(AXL1) can be less than 2.0 eV.
[0048] In an embodiment, the first auxiliary layer 171 and the second auxiliary layer 172 can each independently have a thickness of about to about When the thicknesses of the first auxiliary layer 171 and the second auxiliary layer 172 are within this range, an appropriate or desired life improvement effect of the organic light emitting device 10 can be obtained without significantly increasing the driving voltage.
[0049] The emission layer 151 can include (or consist of) a single compound, or can include two or more compounds.
[0050] In an embodiment, the emission layer 151 can include a host and a dopant.
[0051] In an embodiment, the emission layer 151 can include a host and a dopant, and can satisfy at least one of T1(host) ≥ T1(AXL1) + 0.3 eV and T1(dopant) ≥ T1(AXL1) + 0.3 eV.
[0052] T1(host) is the lowest triplet excited energy level (eV) of the host in the emission layer 151, T1(dopant) is the lowest triplet excited energy level (eV) of the dopant in the emission layer 151, and T1(host) and T1(dopant) are calculated (e.g., evaluated by using a DFT method) using a Gaussian program DFT method, in which the compounds (e.g., the host and the dopant) are structurally optimized at the level of B3LYP / 6-31G*(d,p) (e.g., using a B3LYP hybrid functional and a 6-31G*(d,p) basis set).
[0053] As described hereinabove, when the emission layer 151 of the organic light-emitting device 10 satisfies at least one selected from the equations T1(host) ≥ T1(AXL1) + 0.3 eV and T1(dopant) ≥ T1(AXL1) + 0.3 eV, the concentration of excitons in the emission layer 151 can be reduced, thereby improving the lifespan of the organic light-emitting device 10.
[0054] In one embodiment, the host in the emission layer 151 is not particularly limited and can include all compounds satisfying T1(EML) ≥ T1(AXL1) + 0.3 eV and / or T1(host) ≥ T1(AXL1) + 0.3 eV. The host in the emission layer 151 can be a single host or a mixed host in which two or more different compounds are mixed.
[0055] In one embodiment, the dopant in the emission layer 151 is not particularly limited and can include all compounds satisfying T1(EML) ≥ T1(AXL1) + 0.3 eV and / or T1(dopant) ≥ T1(AXL1) + 0.3 eV.
[0056] In one embodiment, the dopant can be a phosphorescent dopant, a fluorescent dopant, or a delayed fluorescent dopant.
[0057] As used herein, the term "delayed fluorescent dopant" refers to a compound satisfying ΔEst = S1 - T1 < 0.3 eV. Herein, S1 is a singlet energy level of the dopant, T1 is a triplet energy level of the dopant, and ΔEst is a difference between the singlet energy level and the triplet energy level.
[0058] Referring to Figure 2 The electron transport zone 170 can further include an electron transport layer 173 between the second auxiliary layer 172 and the second electrode 190. The electron transport layer 173 includes an electron transport material.
[0059] In one embodiment, the electron transport material can include a third compound including at least one ring containing a π-electron depleted nitrogen.
[0060] The second compound included in the second auxiliary layer 172 and the third compound included in the electron transport layer 173 can be the same as or different from each other. In one embodiment, the second compound included in the second auxiliary layer 172 and the third compound included in the electron transport layer 173 can be different from each other. The electron transport layer 173 will be understood by referring to the corresponding description presented herein.
[0061] In one embodiment, the first compound can be a compound represented by the following Formula 1-1, and the second compound can be a compound represented by the following Formula 1-2:
[0062] Formula 1-1
[0063]
[0064] Formula 1-2
[0065]
[0066] In Formula 1-1 and Formula 1-2,
[0067] A 11 may be selected from the group consisting of naphthyl, anthryl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, and perylenyl,
[0068] L 11 and L 21 to L 23 may each independently be selected from the group consisting of 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 C1-C 60 heteroaryl, substituted or unsubstituted non-aromatic fused polycyclic group, and substituted or unsubstituted non-aromatic fused heteropolycyclic group,
[0069] a11and a21to a23may each independently be selected from the group consisting of 0, 1, 2, and 3,
[0070] Ar 11 and Ar 21 to Ar 23 may each independently be selected from the group consisting of 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 C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
[0071] b11and b21to b23may each independently be selected from the group consisting of 1, 2, 3, and 4,
[0072] n11may be selected from the group consisting of 1, 2, 3, and 4,
[0073] X 21 may be N or CR21 X 22 Can be N or CR 22 And X 23 Can be N or CR 23 ,
[0074] R 11 and R 21 To R 23 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, 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 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), and
[0075] c11 can be an integer selected from 1 to 8.
[0076] In Equations 1-1 and 1-2, C3-C is substituted. 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-C60 alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10 heterocycloalkenyl, substituted C6-C 60 aryl, substituted C6-C 60 aryloxy, substituted C6-C 60 aralkyl, substituted C1-C 60 heteroaryl, substituted monovalent non-aromatic fused polycyclic group, substituted monovalent non-aromatic fused heteropolycyclic group, substituted C5-C 60 carbocyclic group and substituted C1-C 60 at least one substituent of the heterocyclyl group can be selected from:
[0077] deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 alkoxy;
[0078] each C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and 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, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=0)(Q 11 ), -S(=0)2(Q 11 ) and -P(=0)(Q 11 )(Q 12 );
[0079] C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group;
[0080] C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, 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, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ); and
[0081] -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 ), and -P(=O)(Q 31 )(Q 32 ), and
[0082] Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, 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, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, biphenyl, and terphenyl.
[0083] In one embodiment, L 11 and L 21 to L 23 may each independently be selected from the group consisting of:
[0084] phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, alexyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, tetracenyl, chrysenyl, perylenyl, pentaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthylidinyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, dibenzothiophyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzoxazolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzcabazolyl and dibenzocarbazolyl; and
[0085] phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, alexyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, tetracenyl, chrysenyl, perylenyl, pentaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthylidinyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, dibenzothiophyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzoxazolyl, benzimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzcabazolyl and dibenzocarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, C6-C 20 aryl, C1-C 20 heteroaryl, -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 ) and -P(=O)(Q 31 )(Q 32 ), and
[0086] Q 31 to Q 33 may each independently be selected from the group consisting of hydrogen, deuterium, C1-C 60 alkyl, C1-C 60 alkoxy, C6-C 60 aryl, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0087] In one embodiment, L 11 and L 21 to L 23 may each independently be selected from the group consisting of groups represented by the following formulae 3-1 to 3-39:
[0088]
[0089]
[0090] In formulae 3-1 to 3-39,
[0091] Y1may be O, S, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7),
[0092] Z1to Z7may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, C1-C 20 alkyl, C1-C 20 alkoxy, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzo-fluorenyl group, a dibenzo-fluorenyl group, a phenalene group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a naphthylidene group, a quinoxalyl group, a quinazolyl group, a carbazolyl group, a phenanthridyl group, an acridyl group, a phenanthrolinyl group, a phenoxazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), and -B(Q 31 )(Q 32 ),
[0093] d2may be 1 or 2,
[0094] d3may be an integer selected from 1 to 3,
[0095] d4may be an integer selected from 1 to 4,
[0096] d5may be an integer selected from 1 to 5,
[0097] d6may be an integer selected from 1 to 6,
[0098] d8may be an integer selected from 1 to 8,
[0099] Q 31 to Q 33 may each independently be selected from the group consisting of hydrogen, deuterium, C1-C 60 alkyl, C1-C 60 alkoxy, C6-C 60 aryl, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group, and
[0100] *, *’ and *” each indicate a binding site to an adjacent atom.
[0101] In one embodiment, L 11 and L 21 to L 23 may each independently be selected from the group consisting of a group represented by Formula 3-1, Formula 3-2, Formula 3-5 to Formula 3-9, Formula 3-25, and Formula 3-28 to Formula 3-39. In one embodiment, L 11 and L 21 to L 23 may each independently be selected from the group consisting of a group represented by Formula 3-1, Formula 3-2, Formula 3-6, and Formula 3-39.
[0102] In one or more embodiments, L 11 and L 21 to L 23 may each independently be selected from the group consisting of a group represented by Formula 4-1 to Formula 4-5 below:
[0103]
[0104] In Formula 4-1 to Formula 4-5,
[0105] *, *’ and *” each indicate a binding site to an adjacent atom.
[0106] When a11 is 0, *-(L 11 ) a11 *’ can be a single bond. When a11 is 2 or 3, two or three L 11 may be the same as or different from each other. When a21 is 0, *-(L 21 ) a21 *’ can be a single bond. When a21 is 2 or 3, two or three L 21may be the same or different from each other. When a22 is 0, *-(L 22 ) a22 may be a single bond. When a22 is 2 or 3, two or three L 22 may be the same or different from each other. When a23 is 0, *-(L 23 ) a23 may be a single bond. When a23 is 2 or 3, two or three L 23 may be the same or different from each other.
[0107] In one embodiment, a11 and a21 to a23 in Formula 1-1 and Formula 1-2 can each independently be 0 or 1.
[0108] In one embodiment, Ar 11 and Ar 21 to Ar 23 may each independently be selected from the group consisting of:
[0109] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalene, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, chrysenyl, naphthacene, pyromethene, perylenyl, pentaphenyl, periflanthene, pyrrolyl, thiophenyl, furanyl, thiazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthpyridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthpyridinyl, azafuorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and azadibenzothiazolyl; and
[0110] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, 1,2- benzophenanthryl, naphthacene, chrysene, pentaphene, periflanthene, pyrrolyl, thiophenyl, furanyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthpyridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzazolyl, benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthridinyl, azaf luorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and azadibenzosilolyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, C6-C 20 aryl, C1-C 20 heteroaryl, -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 ), and -P(=O)(Q 31 )(Q 32 ), and
[0111] Q 31 to Q 33 may each independently be selected from the group consisting of hydrogen, deuterium, C1-C 60 alkyl, C1-C 60 alkoxy, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl, and terphenyl.
[0112] In one implementation, Ar in Equations 1-1 and 1-2 11 and Ar 21 To Ar 23 Each group can be independently selected from those represented by formulas 5-1 to 5-79 below:
[0113]
[0114]
[0115]
[0116] In equations 5-1 to 5-79,
[0117] Y 31 It can be O, S, C(Z) 33 (Z) 34 ), N(Z 35 ) or Si(Z 36 (Z) 37 ),
[0118] Z 31 To Z 37 Each group 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, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, anthracene, fluoranyl, triphenylene, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[quinolinyl], naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophene, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ),
[0119] e2 can be 1 or 2.
[0120] e3 can be an integer selected from 1 to 3.
[0121] e4 can be an integer selected from 1 to 4.
[0122] e5 can be an integer selected from 1 to 5.
[0123] e6 can be an integer selected from 1 to 6,
[0124] e7 can be an integer selected from 1 to 7,
[0125] e9 can be an integer selected from 1 to 9,
[0126] Q 31 to Q 33 may each independently be selected from the group consisting of hydrogen, deuterium, C1-C 60 alkyl, C1-C 60 alkoxy, C6-C 60 aryl, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, and a terphenyl group, and
[0127] * indicates a bonding site to an adjacent atom.
[0128] In one embodiment, Ar 11 and Ar 21 to Ar 23 may each independently be selected from the group consisting of groups represented by the following Formulae 6-1 to 6-32:
[0129]
[0130] In Formulae 6-1 to 6-32,
[0131] Ph indicates a phenyl group, and
[0132] * indicates a bonding site to an adjacent atom.
[0133] In one embodiment, b11 and b21 to b23 in Formulae 1-1 and 1-2 may each independently be selected from 0, 1, and 2.
[0134] In one embodiment, n11 in Formula 1-1 can be 2.
[0135] When n11 is 2, 3, or 4, two, three, or four groups represented by *-[(L 11 ) a11 -(Ar 11 ) b11 may be the same as or different from each other.
[0136] In one embodiment, when A 11 is an anthryl group and n11 is 2, two, three, or four groups represented by *-[(L 11 ) a11 -(Ar 11 ) b11The two groups represented by ] can be different from each other.
[0137] In one implementation, when A in Equation 1-1 11 When n is pyrene-based and n11 is 2, by *-[(L 11 ) a11 -(Ar 11 ) b11 The two groups represented by ] can be the same as each other.
[0138] In one implementation, when X is selected from Equations 1-2 21 To X 23 When at least one of them is N, it is selected from X 21 To X 23 The two can each be N or X. 21 To X 23 Each can be N at the same time.
[0139] In one implementation, X 21 To X 23 Each can be N at the same time.
[0140] In one embodiment, R in Equations 1-1 and 1-2 11 and R 21 To R 23 Each can be selected independently:
[0141] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, phenatenyl, anthracene, fluoranyl, triphenylene, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indazoleyl, purine, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl , phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, benziisothiazolyl, benzooxazolyl, benziisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazole, benzocarbazole, dibenzocarbazole, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazole, azadibenzofuranyl, azadibenzothiophene, azadibenzothiopyrrolyl, biphenyl and terphenyl; and
[0142] Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, finadeninyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrrolyl, thiopheneyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indoleyl, purinel, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidyl Azolyl, benzofuranyl, benzothiophenyl, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothiopyrrolyl, biphenyl and terphenyl: 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, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, phenatenyl, anthracene, fluoranyl, triphenylene, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indazoleyl, purine, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl , phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, benziisothiazolyl, benzooxazolyl, benziisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxidazopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophene, azadibenzothiopyrrolyl, biphenyl and terphenyl.
[0143] In one embodiment, R in Equations 1-1 and 1-2 11 and R 21 To R23 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, C1-C 20 Alkoxy, phenyl, naphthyl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophene, biphenyl and terphenyl.
[0144] In one implementation, A in Equation 1-1 11 It can be anthraceneyl or pyreneyl.
[0145] In one embodiment, the first compound may be a compound represented by formula 1-11 or formula 1-12 below:
[0146] Formula 1-11
[0147]
[0148] Formula 1-12
[0149]
[0150] In equations 1-11 and 1-12,
[0151] L 111 L 121 and L 122 Each can be referenced and combined with L in Equation 1-1 11 To understand from the presented description,
[0152] a111, a121, and a122 can each be understood by referring to the description of a11 presented in Equation 1-1.
[0153] Ar 111 Ar 121 and Ar 122 Each can be referenced and combined with Ar in Equation 1-1 11 To understand from the presented description,
[0154] b111, b121, and b122 can each be understood by referring to the description of b11 presented in Equation 1-1.
[0155] n111 can be understood by referring to the description of n11 presented in Equation 1-1.
[0156] n121 and n122 can each be independently selected from 0, 1, and 2.
[0157] R 111 R 121 and R 122 Each can be referenced and combined with R in Equation 1-1 11The presented description for c11 in Formula 1-1 can be understood by reference to the presented description for c11,
[0158] The presented description for c11 in Formula 1-1 can be understood by reference to the presented description for c11,
[0159] c121 and c122 can each independently be selected from 0, 1, 2, 3, 4, and 5.
[0160] In one or more embodiments, the first compound can be a compound represented by Formula 1-11A or Formula 1-12A below:
[0161] Formula 1-11A
[0162]
[0163] Formula 1-12A
[0164]
[0165] In Formula 1-11A and 1-12A,
[0166] L 111 , L 112 , L 121 , and L 122 The presented description for L 11 in Formula 1-1 can be understood by reference to the presented description for L
[0167] a111, a112, a121, and a122 can each be understood by reference to the presented description for a11 in Formula 1-1,
[0168] Ar 111 , Ar 112 , Ar 121 , and Ar 122 The presented description for Ar 11 in Formula 1-1 can be understood by reference to the presented description for Ar
[0169] b111, b112, b121, and b122 can each be understood by reference to the presented description for b11 in Formula 1-1,
[0170] n121 and n122 can each independently be an integer selected from 0 to 2,
[0171] R 111 , R 121 , and R 122 The presented description for R 11 in Formula 1-1 can be understood by reference to the presented description for R
[0172] c111 can be understood by reference to the presented description for c11 in Formula 1-1, and
[0173] c121and c122may each be independently selected from 0, 1, 2, 3, and 4.
[0174] In one or more embodiments, the first compound can be a compound represented by Formula 1-11B or Formula 1-12B below:
[0175] Formula 1-11B
[0176]
[0177] Formula 1-12B
[0178]
[0179] In Formula 1-11B and Formula 1-12B,
[0180] L 111 , L 112 , L 121 , and L 122 may each be understood by reference to the description presented in L 11 in Formula 1-1,
[0181] a111, a112, a121, and a122may each be understood by reference to the description presented in a11in Formula 1-1,
[0182] Ar 111 , Ar 112 , Ar 121 , and Ar 122 may each be understood by reference to the description presented in Ar 11 in Formula 1-1,
[0183] b111, b112, b121, and b122may each be understood by reference to the description presented in b11in Formula 1-1, and
[0184] R 111 , R 112 , R 121 , and R 122 may each be understood by reference to the description presented in R 11 in Formula 1-1.
[0185] In Formula 1-11, Formula 1-12, Formula 1-11A, Formula 1-12A, Formula 1-11B, and Formula 1-12B,
[0186] L 111 , L 112 , L 121 , and L 122 may each be independently selected from a group represented by Formula 4-1 to Formula 4-5, and
[0187] Ar 111 , Ar 112 , Ar 121 , and Ar 122 may each independently be selected from the group represented by Formulae 6-1 to 6-32.
[0188] In one embodiment, the first compound can be selected from the following compounds:
[0189]
[0190] In one embodiment, the second compound can be selected from the following compounds:
[0191]
[0192] In one embodiment, when the emission layer 151 includes a host and a dopant, the host can include an anthracene-based compound.
[0193] Hereinafter, the structure of each of the organic light-emitting device 10 and the organic light-emitting device 20 according to the embodiments and a method of manufacturing the same will be described with reference to the accompanying drawings. Figure 1 and Figure 2 Hereinafter, the structure of each of the organic light-emitting device 10 and the organic light-emitting device 20 according to the embodiments and a method of manufacturing the same will be described with reference to the accompanying drawings.
[0194] The first electrode 110
[0195] In Figure 1 and Figure 2 , the substrate can be additionally under the first electrode 110 or over the second electrode 190. To serve as a substrate, the substrate can be a glass substrate or a plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0196] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from a material having a high work function to facilitate hole injection.
[0197] The first electrode 110 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and 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-reflective electrode or a semi-transmissive electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of this disclosure are not limited thereto.
[0198] The first electrode 110 may have a single-layer structure or a multi-layer structure comprising 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.
[0199] Organic layer 150
[0200] The organic layer 150 is on the first electrode 110. The organic layer 150 may include an emission layer 151 and an electron transport region 170 between the emission layer 151 and the second electrode 190.
[0201] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emitter layer 151.
[0202] Hole transport region in organic layer 150
[0203] The hole transport region may have i) a single-layer structure comprising a single layer (including a single material), ii) a single-layer structure comprising a single layer (including multiple different materials), or iii) a multi-layer structure having multiple layers (including multiple different materials).
[0204] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.
[0205] For example, the hole transport region may have a single-layer structure including a single layer (including a variety of different materials) or a multi-layer structure, which may have 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, wherein for each structure, the layers are stacked sequentially from the first electrode 110 in the order described, but the structure of the hole transport region is not limited to this.
[0206] The hole transport zone can comprise at least one selected from 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, and a compound represented by the following formula 202:
[0207]
[0208]
[0209] Formula 201
[0210]
[0211] Formula 202
[0212]
[0213] In the formula 201 and the formula 202,
[0214] L 201 to L 204 may each independently be selected from the group consisting of a substituted or unsubstituted C3-C 10 cycloalkylene group, a substituted or unsubstituted C1-C 10 heterocycloalkylene group, a substituted or unsubstituted C3-C 10 cycloalkenylene group, a substituted or unsubstituted C1-C 10 heterocycloalkenylene group, a substituted or unsubstituted C6-C 60 arylene group, a substituted or unsubstituted C1-C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
[0215] L 205 may be selected from the group consisting of *-O-*', *-S-*', *-N(Q 201 )-*', a substituted or unsubstituted C1-C 20 alkylene group, a substituted or unsubstituted C2-C 20 alkenylene group, a substituted or unsubstituted C3-C 10 cycloalkylene group, a substituted or unsubstituted C1-C 10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 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, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0216] xa1 to xa4 can each be an integer selected from 0 to 3 independently.
[0217] xa5 can be an integer selected from 1 to 10, and
[0218] R 201 To R 204 and Q 201 Each can be independently selected from 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0219] In one implementation, in formula 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 together by single bonds, dimethyl-methylene, or diphenyl-methylene bonds.
[0220] In one or more embodiments, in formulas 201 and 202,
[0221] L 201 To L 205 Each can be selected independently:
[0222] Phenylidene, pentylene, indene, naphthyl, azulene, heptadene, acenaphthene, fluorenene, spiro-difluorenene, benzo[a]fluorenene, dibenzo[a]fluorenene, phenanthroline, anthracene, fluorenyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenylene, fenenyl, perylene, perylene Pentofenyl, hexaphenylene, pentaphenylene, rubidylene, myristyl, oleophylene, thiophenyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzothiophenyl, and pyridylene; and
[0223] Each of the following substituted compounds is selected from at least one of the following: phenylene, pentyleneylene, indene, naphthylene, azuleneylene, heptadeneylene, acenaphtheneylene, fluoreneylene, spiro-difluoreneylene, benzo[a]fluoreneylene, dibenzo[a]fluoreneylene, phenenenylene, phenanthreneylene, anthraceneylene, fluoranthraceneylene, triphenylene, pyreneylene, 1,2-benzophenanthreneylene, tetraphenylene, fentanylene, perylene, pentyleneylene, hexaphenylene, etc. Benzenepentylene, Benzenerubinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinolylene and pyridylene: 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, indole-based, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, styrayl, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),and
[0224] Q 31 To Q 33 Each can be independently selected from C1-C10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0225] In one or more embodiments, each of xa1to xa4may be independently 0, 1, or 2.
[0226] In one or more embodiments, xa5may be 1, 2, 3, or 4.
[0227] In one or more embodiments, R 201 to R 204 and Q 201 may each be independently selected from:
[0228] phenyl, biphenyl, terphenyl, pentacenyl, indenyl, naphthyl, azulenyl, heptacenyl, indacene, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalene, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, tetracenyl, chrysenyl, pyranthryl, periflanthryl, pentaphenyl, hexacenyl, sapphyrinyl, coronatyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothianthryl, and pyridinyl; and
[0229] phenyl, biphenyl, terphenyl, pentacenyl, indenyl, naphthyl, azulenyl, heptacenyl, indacene, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalene, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, tetracenyl, chrysenyl, pyranthryl, periflanthryl, pentaphenyl, hexacenyl, sapphyrinyl, coronatyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothianthryl, and pyridinyl: 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, C1-C 10Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-based, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, styrayl, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),and
[0230] Q 31 To Q 33 Same as the description above in this article.
[0231] In one or more embodiments, R selected from Formula 201 201 To R 203 At least one of them can be independently selected from:
[0232] Fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and
[0233] Each of the following substituted groups is a fluorenyl group, a spiro-difluorenyl group, a carbazole group, a dibenzofuranyl group, or a dibenzothiophene group: 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, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl.
[0234] However, the embodiments disclosed herein are not limited thereto.
[0235] In one or more embodiments, in formula 202, i)R 201 and R 202 They can be connected to each other via single bonds, and / or ii)R 203 and R 204 They can be connected to each other via a single key.
[0236] In one or more embodiments, R selected from formula 202 201 To R 204at least one of R1and R2may each independently be selected from the group consisting of:
[0237] a carbazolyl group; and
[0238] a carbazolyl group substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a C1-C 20 a C1-C 20 alkyl group, a C1-C 10 alkyl group, a C1-C 10 alkyl group, a C1-C 10 alkyl group, a C1-C
[0239] However, embodiments of the present disclosure are not limited thereto.
[0240] The compound represented by formula 201 can be represented by the following formula 201-1:
[0241] Formula 201-1
[0242]
[0243] In one embodiment, the compound represented by formula 201 can be represented by the following formula 201-2, but embodiments of the present disclosure are not limited thereto:
[0244] Formula 201-2
[0245]
[0246] In one or more embodiments, the compound represented by formula 201 can be represented by the following formula 201-2(1), but embodiments of the present disclosure are not limited thereto:
[0247] Formula 201-2(1)
[0248]
[0249] In one or more embodiments, the compound represented by formula 201 can be represented by the following formula 201A:
[0250] Formula 201A
[0251]
[0252] 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:
[0253] Formula 201A(1)
[0254]
[0255] In one or more embodiments, the compound represented by Formula 201 can be represented by the following Formula 201A-1, although embodiments of the present disclosure are not limited thereto:
[0256] Formula 201A-1
[0257]
[0258] In one embodiment, the compound represented by Formula 202 can be represented by the following Formula 202-1:
[0259] Formula 202-1
[0260]
[0261] In one or more embodiments, the compound represented by Formula 202 can be represented by the following Formula 202-1(1):
[0262] Formula 202-1(1)
[0263]
[0264] In one or more embodiments, the compound represented by Formula 202 can be represented by the following Formula 202A:
[0265] Formula 202A
[0266]
[0267] In one or more embodiments, the compound represented by Formula 202 can be represented by the following Formula 202A-1:
[0268] Formula 202A-1
[0269]
[0270] In Formula 201-1, Formula 201-2, Formula 201-2(1), Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202-1, Formula 202-1(1), Formula 202A, Formula 202A-1,
[0271] L 201 to L 203 , xa1to xa3, xa5, and R 202 to R 204 may each be understood by reference to the corresponding description presented elsewhere herein,
[0272] L 205 may be selected from the group consisting of phenylene and fluorenylene,
[0273] X 211 may be selected from O, S, and N(R 211 ),
[0274] X 212 may be selected from O, S, and N(R 212 ),
[0275] R 211 and R 212 may each be understood by reference to the description presented for R 203 , and
[0276] R 213 through R 217 may each be independently selected from the group consisting of 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, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, pentacenyl, indenyl, naphthyl, azuleny, heptacenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzo phenanthryl, tetracenyl, chrysenyl, pyromethenyl, perimethenyl, perinaphthyl, oxepinyl, thiepinyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, and pyridinyl.
[0277] The hole transport zone can include at least one compound selected from the following compounds HT1 through HT48, but embodiments of the present disclosure are not limited thereto:
[0278]
[0279]
[0280]
[0281]
[0282]
[0283] The thickness of the hole transport zone can be about to about For example, about to about When the hole transport zone includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be about to about For example, about to about For example, about to about For example, about to about For example, about
[0284] The emission auxiliary layer can increase light emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport zone. The emission auxiliary layer and the electron blocking layer can include materials as described herein above.
[0285] p-dopant
[0286] 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.
[0287] The charge generating material can be, for example, a p-dopant.
[0288] In one embodiment, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0289] The p-dopant can include at least one selected from a quinone derivative, a metal oxide, and a compound containing a cyano group, but embodiments of the present disclosure are not limited thereto.
[0290] In one embodiment, the p-dopant can include at least one selected from the following:
[0291] a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0292] a metal oxide such as tungsten oxide or molybdenum oxide;
[0293] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0294] a compound represented by the following Formula 221:
[0295] but embodiments of the present disclosure are not limited thereto:
[0296] but embodiments of the present disclosure are not limited thereto:
[0297] Formula 221
[0298]
[0299] In Formula 221,
[0300] R 221 to R 223 may each independently be selected from the group consisting of a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein at least one of R 221 to R 223 may have at least one substituent selected from the group consisting of a cyano group, a -F group, a -Cl group, a -Br group, a -I group, a C1-C 20 alkyl group substituted with a -F group, a C1-C 20 alkyl group substituted with a -Cl group, a C1-C 20 alkyl group substituted with a -Br group, and a C1-C 20 alkyl group substituted with a -I group.
[0301] The emission layer 151 in the organic layer 150
[0302] When the organic light emitting device 10 or the organic light emitting device 20 is a full-color organic light emitting device, the emission layer 151 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 151 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., physically contact adjacent one of the two or more layers) or are 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 to emit white light.
[0303] The emission layer 151 can include a host and a dopant. The dopant can include at least one selected from a phosphorescent dopant, a fluorescent dopant, and a delayed fluorescent dopant.
[0304] In the emission layer, the amount of the dopant in the emission layer 151 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.
[0305] The thickness of the emission layer 151 can be in the range of about 1 nm to about 100 nm, but embodiments of the present disclosure are not limited thereto. to about For example, about to about When the thickness of the emission layer 151 is in the range, excellent light emission characteristics can be obtained without significantly increasing the driving voltage.
[0306] The host in the emission layer 151
[0307] The host can include a compound represented by the following Formula 301:
[0308] Formula 301
[0309] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0310] In Formula 301,
[0311] Ar 301 may be a substituted or unsubstituted C5-C 60 carbocyclyl, or a substituted or unsubstituted C1-C 60 heterocyclyl,
[0312] xb11may be 1, 2, or 3,
[0313] L 301 may be selected from the group consisting of 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 divalent non-aromatic fused polycyclyl, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclyl,
[0314] xb1may be an integer selected from 0 to 5,
[0315] R 301may be selected from the group consisting of 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 ), and -P(=O)(Q 301 )(Q 302 ),
[0316] xb21may be an integer selected from 1 to 5, and
[0317] Q 301 to Q 303 may each independently be selected from the group consisting of C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but embodiments of the present disclosure are not limited thereto.
[0318] In one embodiment, Ar 301 may be selected from the group consisting of:
[0319] naphthyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, naphthacene, chrysenyl, perylenyl, pentaphenyl, indanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0320] Each of the following substituted groups is selected from at least one of the following: naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, dibenzofuranyl, and dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, 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 ) and -P(=O)(Q 31 (Q) 32 ),and
[0321] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.
[0322] When xb11 in equation 301 is 2 or greater, two or more Ar 301 They can be connected to each other via a single key.
[0323] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:
[0324] Formula 301-1
[0325]
[0326] Formula 301-2
[0327]
[0328] In Equations 301-1 and 301-2,
[0329] A 301 To A 304Each ring can be independently selected from benzene ring, naphthyl ring, phenanthrene ring, fluoranthene ring, triphenylene ring, pyrene ring, cyclopentadiene 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, naphthanofuran ring, benzo[a]naphthanofuran ring, dinaphthanofuran ring, thiophene ring, benzo[a]thiophene ring, dibenzo[a]thiophene ring, naphthano[a]thiophene ring, benzo[a]naphthano[a]thiophene ring, and dinaphthano[a]thiophene ring.
[0330] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0331] R 311 To R 314 Each group 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, 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 ) and -P(=O)(Q 31 (Q) 32 ),
[0332] xb22 and xb23 can each be 0, 1, or 2 independently.
[0333] L 301 xb1, R 301 and Q 31 To Q 33 Each can be understood by referring to the corresponding descriptions presented in this article.
[0334] L 302 To L 304 Each can refer to and combine L 301 To understand from the presented description,
[0335] xb2 to xb4 can each be understood by referring to the description presented in conjunction with xb1, and
[0336] R 302 To R 304 Each can be combined with R through reference. 301The description presented to be understood.
[0337] L in Formulae 301, 301-1, and 301-2 301 to L 304 may each independently be selected from the group consisting of:
[0338] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, triphenylylene, pyrenylene, 1,2-phenanthrylene, pyrylenylene, pentaphenylene, hexa-phenylene, penta-phenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dithiophenolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthrydinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthrydinylene, pyrydinylene, phenarsazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and
[0339] each phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, triphenylylene, pyrenylene, 1,2-phenanthrylene, pyrylenylene, pentaphenylene, hexa-phenylene, penta-phenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dithiophenolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthrydinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthrydinylene, pyrydinylene, phenarsazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene, is each substituted with at least one selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexa-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, 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 ), and -P(=O)(Q 31 )(Q 32 ), and
[0340] Q 31 to Q 33 are the same as described above herein.
[0341] In one or more embodiments, R 301 to R 304 may each independently be selected from:
[0342] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexa-phenyl, pentacene-phenyl, 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, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0343] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexa-phenyl, pentacene-phenyl, 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, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, perylenyl, pentaphenyl, hexa-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, naphthridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzo-oxazolyl, benzoisoxazolyl, 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 ), and -P(=O)(Q 31 )(Q 32 ), and
[0344] Q 31 to Q 33 are the same as described above herein.
[0345] In one or more embodiments, the host can include an alkaline earth metal complex. For example, the host can be selected from a Be complex (e.g., compound H55), a Mg complex, and a Zn complex.
[0346] The host can include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-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), and compounds H1 to H55 below, but embodiments of the present disclosure are not limited thereto:
[0347]
[0348]
[0349]
[0350] Phosphorescent dopant in the emission layer 151
[0351] The phosphorescent dopant can include an organometallic complex represented by the following Formula 401:
[0352] Formula 401
[0353] M(L 401 ) xc1 (L 402 ) xc2 .
[0354] In Formula 401,
[0355] M can be selected from the group consisting of iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm),
[0356] 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,
[0357] L 402 may be an organic ligand, and xc2may be an integer selected from 0 to 4, wherein, when xc2is 2 or more, two or more L 402 may be the same as or different from each other,
[0358] Formula 402
[0359]
[0360] In Formula 402, X 401 to X 404 may each independently be nitrogen or carbon,
[0361] X 401 and X 403 may be connected to each other by a single bond or a double bond, and X 402 and X 404 may be connected to each other by a single bond or a double bond,
[0362] A 401 and A 402 may each independently be C5-C 60 carbocyclyl, or C1-C 60 heterocyclyl,
[0363] X 405 may be a single bond, *-O-*’, *-S-*’, *-C(=O)-*’, *-N(Q411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C(Q 411 )-*', where Q 411 and Q 412 It can be hydrogen, deuterium, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,
[0364] X 406 It can be a single bond, O, or S.
[0365] R 401 and R 402 Each can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, 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 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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 ) and -P(=O)(Q 401 (Q) 402 ), where Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10alkyl and C1-C 20 aryl and C1-C 20 heteroaryl,
[0366] xc11and xc12may each independently be an integer selected from 0 to 10, and
[0367] each of * and *' in formula 402 indicates a binding site to M in formula 401.
[0368] In one embodiment, A 401 and A 402 may each independently be selected from phenyl, naphthyl, fluorenyl, spiro- d ifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzo[c]thiophenyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl.
[0369] 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.
[0370] In one or more embodiments, R 401 and R 402 may each independently be selected from:
[0371] hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidinyl, hydrazinyl, hydrazone, C1-C 20 alkyl and C1-C 20 alkoxy;
[0372] C1-C 20 alkyl and C1-C 20 alkoxy each substituted with at least one selected from: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidinyl, hydrazinyl, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornenyl;
[0373] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0374] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and -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 ), and -P(=O)(Q 401 )(Q 402 ), and
[0375] Q 401 to Q 403 may each independently be selected from the group consisting of C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, and naphthyl, but embodiments of the present disclosure are not limited thereto.
[0376] In one or more embodiments, when xc1in Formula 401 is 2 or more, two or more A 401 in L 401 may be optionally linked to each other via X 407 which is a linking group, or two A 401 in L 402 may be optionally linked to each other via X 408 which is a linking group (see Compounds PD1 to PD4 and PD7). X 407 and X 408 may each independently be a single bond, -O-*, -S-*, -C(=O)-*, -N(Q 413 )-*, -C(Q 413 )(Q 414 )-*, or -C(Q413 )=C(Q 414 )-*'(where Q 413 and Q 414 Each can be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but not limited to these.
[0377] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The ligands can be selected from halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., pyridine carboxylate), -C (=O), isonitriles, -CN, and phosphorus-containing ligands (e.g., phosphine or phosphite), but the embodiments disclosed herein are not limited thereto.
[0378] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25 listed below, but embodiments of this disclosure are not limited thereto:
[0379]
[0380] Fluorescent dopant in emitter layer 151
[0381] Fluorescent dopants can emit fluorescence or delay fluorescence.
[0382] Fluorescent dopants may include aromatic amine compounds or styrene amine compounds.
[0383] Fluorescent dopants may include compounds represented by the following formula 501:
[0384] Formula 501
[0385]
[0386] In Equation 501,
[0387] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0388] L 501 To L 503 Each can be independently selected from 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-C10 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, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0389] xd1 to xd3 can each be an integer selected from 0 to 3 independently.
[0390] R 501 and R 502 Each can be independently selected from 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 group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, and
[0391] xd4 can be an integer selected from 1 to 6.
[0392] In one implementation, Ar in Formula 501 501 Optional from:
[0393] Naphthyl, heptadeninyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, and indoxanthryl; and
[0394] Each of the following substituted groups is selected from at least one of the following: naphthyl, heptalenyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, ind[a]anthryl, and ind[a]phenanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0395] In one or more embodiments, L in Formula 501 501 To L503 may each independently be selected from the group consisting of:
[0396] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, triphenylylene, pyrenylene, 1,2- benzophenanthrylene, pyrylenyl, pentaphenylene, hexa-phenylene, penta-phenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothianthrylene, and pyridinylene; and
[0397] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, triphenylylene, pyrenylene, 1,2- benzophenanthrylene, pyrylenyl, pentaphenylene, hexa-phenylene, penta-phenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothianthrylene, and pyridinylene: 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, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylyl, pyrenyl, 1,2- benzophenanthryl, pyrylenyl, pentaphenyl, hexa-phenyl, penta-phenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothianthryl, and pyridinyl.
[0398] In one or more embodiments, R 501 and R 502 may each independently be selected from the group consisting of:
[0399] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylyl, pyrenyl, 1,2- benzophenanthryl, pyrylenyl, pentaphenyl, hexa-phenyl, penta-phenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothianthryl, and pyridinyl; and
[0400] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexaphenyl, pentacenyl, pyridyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexaphenyl, pentacenyl, pyridyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 31 alkyl, C1-C 32 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexaphenyl, pentacenyl, pyridyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiazolyl, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 33 alkyl, C1-C
[0401] Q 31 to Q 33 may be each independently selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0402] In one or more embodiments, xd4in Formula 501 can be 2, but embodiments of the present disclosure are not limited thereto.
[0403] For example, the fluorescent dopant can be selected from the following compounds FD1 to FD22:
[0404]
[0405]
[0406]
[0407] In one or more embodiments, the fluorescent dopant can be selected from the following compounds, but embodiments of the present disclosure are not limited thereto.
[0408]
[0409] Electron transport zone 170 in organic layer
[0410] The electron transport zone 170 can have i) a single layer structure including a single layer (including a single material), ii) a single layer structure including 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).
[0411] The electron transport zone 170 can include a first auxiliary layer 171 and a second auxiliary layer 172.
[0412] The electron transport zone 170 can further include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer 173, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
[0413] For example, the electron transport zone 170 can have a structure of a first auxiliary layer 171 / second auxiliary layer 172 / electron transport layer 173 / electron injection layer, a structure of a first auxiliary layer 171 / second auxiliary layer 172 / hole blocking layer / electron transport layer 173 / electron injection layer, a structure of a first auxiliary layer 171 / second auxiliary layer 172 / electron control layer / electron transport layer 173 / electron injection layer, or a structure of a first auxiliary layer 171 / second auxiliary layer 172 / buffer layer / electron transport layer 173 / electron injection layer, in which, for each structure, the constituent layers are sequentially stacked from the emission layer 151 in the recited order, but embodiments of the present disclosure are not limited thereto.
[0414] The electron transport zone 170 (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport zone 170) can include a metal-free compound containing at least one ring containing a π-electron depleted nitrogen.
[0415] As used herein, the term “ring containing a π-electron depleted nitrogen” indicates a C1-C 60 heterocyclyl.
[0416] For example, the “ring containing a π-electron depleted nitrogen” can be i) a 5- to 7-membered heteromonocyclic group having at least one “*-N=*" moiety, ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one “*-N=*" moiety are fused to each other, or iii) a heteropolycyclic group in which at least one of 5- to 7-membered heteromonocyclic groups each having at least one “*-N=*" moiety is fused to at least one C5-C 60 C5-C12carbocyclyl.
[0417] 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.
[0418] For example, the electron transport zone 170 can include a compound represented by the following Formula 601:
[0419] Formula 601
[0420] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0421] In Formula 601,
[0422] Ar 601 may be a substituted or unsubstituted C5-C 60 carbocyclyl, or a substituted or unsubstituted C1-C 60 heterocyclyl,
[0423] xe11may be 1, 2, or 3,
[0424] L 601 may be selected from the group consisting of 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 divalent non-aromatic fused polycyclyl, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclyl,
[0425] xe1may be an integer selected from 0 to 5,
[0426] R 601 may be selected from the group consisting of 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 10heteroaryloxy, substituted or unsubstituted C1-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 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ),
[0427] Q 601 to Q 603 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0428] xe21may be an integer selected from 1 to 5.
[0429] In one embodiment, at least one of the number of Ar 601 and the number of R 601 in xe11may include a ring containing a π-electron depleted nitrogen.
[0430] In one embodiment, Ar 601 in formula 601may be selected from:
[0431] phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, tetracenyl, chrysenyl, perylenyl, pentaphenyl, indanthryl, dibenzo- furanyl, dibenzo-thiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthylidinyl, quinoxalyl, quinazolyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzo-oxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0432] phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, tetracenyl, chrysenyl, perylenyl, pentaphenyl, indanthryl, dibenzo- furanyl, dibenzo-thiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthylridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzo-oxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. 31 alkyl, C1-C 32 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. 33 alkyl, C1-C 31 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. 31 alkyl, C1-C 32 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0433] alkyl, C1-C 31 alkyl, C1-C 33 alkyl, C1-C 10 alkyl, C1-C 10 alkyl, C1-C
[0434] When xe11 in formula 601 is 2 or more, two or more Ar 601 may be connected to each other via a single bond.
[0435] In one or more embodiments, Ar 601 in formula 601 can be anthryl.
[0436] In one or more embodiments, the compound represented by formula 601 can be represented by the following formula 601-1:
[0437] Formula 601-1
[0438]
[0439] In formula 601-1,
[0440] X 614 may be N or C(R 614 ), X 615 may be N or C(R615 ), X 616 may be N or C(R 616 ), and is selected from X 614 to X 616 at least one of X
[0441] L 611 to L 613 may each be understood by reference to the description presented in connection with L 601 ,
[0442] xe611to xe613may each be understood by reference to the description presented in connection with xe1,
[0443] R 611 to R 613 may each be understood by reference to the description presented in connection with R 601 , and
[0444] R 614 to R 616 may each be independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0445] In one embodiment, L 601 and L 611 to L 613 may each be independently selected from the group consisting of:
[0446] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, triphenylylene, pyrenylene, 1,2- benzophenanthrylene, pyrylenylene, pentaphenylene, hexa-phenylene, penta-phenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phtalazinylene, naphthrydinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthrydinylene, pyrydinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and
[0447] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, triphenylylene, pyrenylene, pyrenylene, 1,2-benzophenylene, perylenylene, pentaphenylene, hexa- phenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilolylene, 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, and azacarbazolylene: 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-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylyl, pyrenyl, pyrenyl, 1,2-benzophenyl, perylenyl, pentaphenyl, hexaphenyl, pentacenyl, 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, naphthrydinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl,
[0448] However, embodiments of the present disclosure are not limited thereto.
[0449] In one or more embodiments, xe1and xe611to xe613in Formula 601 and Formula 601-1 can each independently be 0, 1, or 2.
[0450] In one or more embodiments, R 601 and R 611 to R 613 may each independently be selected from:
[0451] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexa-phenyl, pentacene-phenyl, 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, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0452] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzo-fluorenyl, dibenzo-fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, hexa-phenyl, pentacene-phenyl, 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, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, perylenyl, pentaphenyl, hexa-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, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthridinyl, quinoxalyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0453] -S(=O)2(Q 601 ) and -P(=O)(Q 601 )(Q 602 ), and
[0454] Q 601 and Q 602 are the same as described above herein.
[0455] The electron transport zone 170 can include at least one compound selected from the following compounds ET1 to ET37, but embodiments of the present disclosure are not limited thereto:
[0456]
[0457]
[0458]
[0459]
[0460] In one or more embodiments, the electron transport zone 170 can include at least one compound selected from 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), and NTAZ:
[0461]
[0462] 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 buffer layer, the hole blocking layer, and the electron control layer can have superior electron blocking characteristics or electron control characteristics without significantly increasing the driving voltage.
[0463] The thickness of the electron transport layer 173 can be in a range from about to about For example, the thickness of the electron transport layer 173 can be in a range from about to about When the thickness of the electron transport layer 173 is within the ranges described herein above, the electron transport layer 173 can have appropriate or satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0464] In addition to the materials described herein above, the electron transport region 170 (e.g., the electron transport layer 173 in the electron transport region 170) can further include a metal-containing material.
[0465] The metal-containing material can include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex can include a metal ion selected from a Li ion, a Na ion, a K ion, an Rb ion, and a Cs ion, and the alkaline earth metal complex can include a metal ion selected from a Be ion, a Mg ion, a Ca ion, an Sr ion, and a Ba ion. The ligand coordinated to the metal ion of the alkali metal complex or the alkaline earth metal complex can be selected from a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0466] For example, the metal-containing material can include a Li complex. The Li complex can include, for example, the following compound ET-D1 (lithium 8-hydroxyquinoline, LiQ) or compound ET-D2:
[0467]
[0468] The electron transport region 170 can include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer can directly contact (e.g., physically contact) the second electrode 190.
[0469] The electron injection layer can have i) a single layer structure including a single layer (including a single material), ii) a single layer structure including 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).
[0470] The electron injection layer can include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0471] The alkali metal can be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal can be Li, Na, or Cs. In one or more embodiments, the alkali metal can be Li or Cs, although embodiments of the present disclosure are not limited thereto.
[0472] The alkaline earth metal can be selected from Mg, Ca, Sr, and Ba.
[0473] The rare earth metal can be selected from Sc, Y, Ce, Tb, Yb, and Gd.
[0474] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound can be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal.
[0475] The alkali metal compound can be selected from alkali metal oxides such as Li2O, Cs2O, or K2O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compound can be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, although embodiments of the present disclosure are not limited thereto.
[0476] The alkaline earth metal compound can be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1), or Ba x Ca 1-x O (0 < x < 1). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO, and CaO, although embodiments of the present disclosure are not limited thereto.
[0477] The rare earth metal compound can be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound can be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, although embodiments of the present disclosure are not limited thereto.
[0478] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include ions of alkali metals, alkaline earth metals, and rare earth metals as described above herein, and the ligands coordinated to the metal ions of the alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.
[0479] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above (or consist of alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above). In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix comprising the organic material.
[0480] 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 significantly increasing the driving voltage when the thickness of the electron injection layer is within these ranges.
[0481] Second electrode 190
[0482] The second electrode 190 may be on the organic layer 150 having this structure. The second electrode 190 may be a cathode (which is an electron injection electrode), and in this regard, the material used to form the second electrode 190 may be selected from metals, alloys, conductive compounds and combinations thereof having relatively low work function.
[0483] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0484] The second electrode 190 can have a single layer structure, or a multi-layer structure including two or more layers.
[0485] The organic light emitting device 10 or the organic light emitting device 20 can further include a capping layer disposed in a direction in which light is emitted. The capping layer can increase external light emission efficiency according to a principle of constructive interference.
[0486] The capping layer can 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.
[0487] The capping layer can include at least one material selected from 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 containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, the capping layer can include an amine-based compound.
[0488] In one or more embodiments, the capping layer can include a compound represented by Formula 201 or a compound represented by Formula 202.
[0489] In one or more embodiments, the capping layer can include a compound selected from the following compounds HT28 to HT33 and compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto.
[0490]
[0491] Hereinafter, an organic light emitting device according to an embodiment has been described in conjunction with Figure 1 and Figure 2 However, embodiments of the present disclosure are not limited thereto.
[0492] The layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone can be formed in a certain region 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.
[0493] When the layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone are formed by vacuum deposition, 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 / second to about / second, by considering a material to be included in a layer to be formed and a structure of the layer to be formed.
[0494] 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 at a heat treatment temperature of about 80°C to 200°C, by taking into account the material to be included in the layer to be formed and the structure of the layer to be formed.
[0495] Apparatus
[0496] The organic light-emitting device can be included in various appropriate apparatuses.
[0497] Another aspect of an embodiment of the present disclosure provides an apparatus including the organic light-emitting device.
[0498] For example, the apparatus can be a light-emitting apparatus, an authentication apparatus, or an electronic apparatus, but embodiments of the present disclosure are not limited thereto.
[0499] The light-emitting apparatus can be used as various appropriate displays and / or light sources, etc.
[0500] The authentication apparatus can be, for example, a biometric authentication apparatus for authenticating an individual by using biometric information of a biometric body (e.g., a fingertip or a pupil, etc.).
[0501] The authentication apparatus can further include a biometric information collector in addition to the organic light-emitting device.
[0502] The electronic apparatus 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 aircraft, and a ship), and / or a projector, etc., but embodiments of the present disclosure are not limited thereto.
[0503] In one embodiment, the apparatus can further include a thin film transistor in addition to the organic light-emitting device. Here, the thin film transistor can include a source electrode, an active layer (e.g., an active region), and a drain electrode, in which the first electrode of the organic light-emitting device can electrically contact one of the source electrode and the drain electrode of the thin film transistor.
[0504] General definitions of at least some substituents
[0505] The term "C1-C 60 "alkyl" as used herein refers to a straight-chain or branched-chain aliphatic saturated hydrocarbon monovalent radical having from 1 to 60 carbon atoms, preferably "C1-C 20"alkyl", and examples of it include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is also used. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Alkyl groups are divalent groups with essentially the same structure.
[0506] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 A hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the end (e.g., terminal) of an alkyl group, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" refers to a hydrocarbon group with at least one carbon-carbon double bond at the main chain (e.g., in the middle) or terminal. 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Alkenes are divalent groups with essentially the same structure.
[0507] As used in this article, the term "C2-C" 60 "Alkyne group" refers to C2-C 60 A hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or end (e.g., 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 a group with a C2-C group. 60 The alkynyl group is a divalent group with essentially the same structure.
[0508] 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 The monovalent group represented by alkyl is preferred, especially "C1-C". 20 "Alkoxy", and examples of it include methoxy, ethoxy and isopropoxy.
[0509] 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 relevant. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Cycloalkyl groups are divalent groups with essentially the same structure.
[0510] 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..." 10Heteroalkyl refers to a divalent group having essentially the same structure as a C1-C 10 Heteroalkyl refers to a divalent group having essentially the same structure as a C1-C
[0511] The term "C3-C10cycloalkyl" as used herein refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring and no double bonds, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The term "C3-C10cycloalkyl" as used herein includes both saturated and partially unsaturated rings. 10 Cycloalkenyl refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring and at least one carbon-carbon double bond and no aromaticity, and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C10cycloalkenyl" as used herein includes both saturated and partially unsaturated rings. 10 Cycloalkenyl refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring and at least one carbon-carbon double bond and no aromaticity, and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C10cycloalkenyl" as used herein includes both saturated and partially unsaturated rings. 10 Cycloalkenyl refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring and at least one carbon-carbon double bond and no aromaticity, and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C10cycloalkenyl" as used herein includes both saturated and partially unsaturated rings.
[0512] The term "C1-C 10 Heterocycloalkenyl refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of C1-C 10 Heterocycloalkenyl refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of C1-C 10 Heterocycloalkenyl refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of C1-C 10 Heterocycloalkenyl refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of C1-C
[0513] The term "C6-C 60 Aryl refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), preferably "C6-C 20 Aryl refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), preferably "C6-C 60 Aryl refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), preferably "C6-C 60 Aryl refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), preferably "C6-C 60 Aryl refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), preferably "C6-C 60 When the aryl and C6-C
[0514] The term "C1-C 60 Heteroaryl refers to a monovalent group having a heterocyclic aromatic system (having 1 to 60 carbon atoms in addition to at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom), preferably "C1-C 20 Heteroaryl refers to a monovalent group having a heterocyclic aromatic system (having 1 to 60 carbon atoms in addition to at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom), preferably "C1-C 60"Heteroarylene" refers to a divalent radical of a heteroaromatic group (having 1 to 60 carbon atoms and at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to the carbon atoms). 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 Heteroaryl and C1-C 60 When heteroarylene groups each include two or more rings, the rings can be fused (e.g., combined together) with one another.
[0515] The term "C6-C 60 "Aryloxy" refers to -OA 102 (where A 102 is C6-C 60 aryl), and the term "C6-C 60 "Arylthio" refers to -SA 103 (where A 103 is C6-C 60 aryl).
[0516] 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., combined together) with one another, only carbon atoms as ring-forming atoms, and no aromaticity in its entire 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 substantially the same structure as a monovalent non-aromatic fused polycyclic group.
[0517] 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., combined together) with one another, at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms in addition to carbon atoms, and no aromaticity in its entire 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 substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0518] The term "C5-C 60 "Carbocyclyl" refers to a monocyclic or polycyclic radical of 5 to 60 carbon atoms having only carbon atoms as ring-forming atoms. The term "C5-C 60 "Carbocyclyl" refers to an aromatic carbocyclyl or a non-aromatic carbocyclyl. C5-C 60A carbocyclic group can be a ring, such as benzene; a monovalent group, such as phenyl; or a divalent group, such as phenylene. In one or more embodiments, the number of substituents of the carbocyclic group depends on whether the carbocyclic group is connected to a C5-C 60 The number of substituents of the carbocyclic group, C5-C 60 A carbocyclic group can be a trivalent group or a tetravalent group.
[0519] The term "C1-C 60 Heterocyclic group" refers to a group having substantially the same structure as a C5-C 60 A carbocyclic group can be a trivalent group or a tetravalent group.
[0520] In this specification, a substituted C5-C 60 Carbocyclic group, substituted C1-C 60 Heterocyclic group, substituted C3-C 10 Cycloalkylene group, substituted C1-C 10 Heterocycloalkylene group, substituted C3-C 10 Cycloalkenylene group, substituted C1-C 10 Heterocycloalkenylene group, substituted C6-C 60 Arylene group, substituted C1-C 60 Heteroarylene group, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused heteropolycyclic group, substituted C1-C 60 Alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted monovalent non-aromatic fused polycyclic group and substituted monovalent non-aromatic fused heteropolycyclic group can be selected from:
[0521] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group and C1-C 60 Alkoxy group;
[0522] Each is substituted by at least one of the following C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 );
[0523] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;
[0524] Each of the C3-C molecules is substituted by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60heteroaryl, monovalent non-aromatic fused polycyclic group, 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, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), and -P(=O)(Q 21 )(Q 22 ); and
[0525] -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 ), and -P(=O)(Q 31 )(Q 32 ), and
[0526] Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be selected from the group consisting of hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl, and terphenyl.
[0527] As used herein, the term "Ph" means phenyl, as used herein, the term "Me" means methyl, as used herein, the term "Et" means ethyl, as used herein, the term "ter-Bu" or "Bu t " means tert-butyl, and as used herein, the term "OMe" means methoxy.
[0528] As used herein, the term "biphenyl" means "phenyl substituted with phenyl". In other words, "biphenyl" is phenyl having C6-C 60 aryl as a substituent.
[0529] As used herein, the term "terphenyl" means "phenyl substituted with biphenyl". In other words, "terphenyl" is C6-C 60 aryl-substituted C6-C 60 aryl as a substituent.
[0530] As used herein, * and *', unless otherwise defined, each means a point of attachment to an adjacent atom in the corresponding formula.
[0531] Hereinafter, the compound according to the embodiments and the organic light emitting device according to the embodiments will be described in greater detail with reference to synthesis examples and examples. The phrase "use B instead of A" used in describing the synthesis examples means using the same molar equivalent of B instead of A.
[0532] Examples
[0533] Evaluation Example 1: Measurement of Triplet Energy Level
[0534] Quantum chemical calculation was performed on the compounds BH, BD, GH, and ET-1 to ET-5 used in the present example by using a quantum chemical calculation program Gaussian 09 (manufactured by Gaussian, Inc., USA). In the calculation, B3LYP hybrid functional was used for the structure optimization in the ground state, and 6-31G* (d, p) basis set was used as a subset of the function. Information on the structure / electronic features of the optimized structure was obtained, and the structure optimization was performed by using time-dependent density functional theory (TD-DFT) in order to obtain the features of the singlet excited state and the triplet excited state of the compounds, and the calculated value of the triplet state energy was obtained.
[0535] Table 1
[0536]
[0537] Device Example
[0538] Example 1-1
[0539] The structures of the compounds used in the examples are as follows.
[0540]
[0541] Corning ITO glass substrate (anode) was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonicated with isopropyl alcohol and pure water, each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition apparatus.
[0542] Compound HT1 was vacuum-deposited on the ITO glass substrate to form a first hole transport layer having a thickness of 100 nm, and compound HT2 was vacuum-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
[0543] Compound BH (host) and compound BD (dopant) were simultaneously vacuum-deposited on the second hole transport layer at a dopant concentration of 3 wt% based on the total weight of the host and the dopant to form an emission layer having a thickness of 20 nm.
[0544] Compound ET-1 was deposited on the emission layer to form a first auxiliary layer having a thickness of 5 nm, and compound ET-4 was deposited on the first auxiliary layer to form a second auxiliary layer having a thickness of 5 nm.
[0545] Compound ET-6 and LiQ were simultaneously vacuum-deposited on the second auxiliary layer in a weight ratio of 5:5 to form an electron transport layer having a thickness of 20 nm. LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and Mg:Ag was vacuum-deposited to form a cathode having a thickness of 10 nm, thereby completing the manufacture of the organic light-emitting device of Example 1-1.
[0546] Examples 1-2 to 1-6
[0547] The organic light-emitting devices of Examples 1-2 to 1-6 were manufactured in substantially the same manner as in Example 1-1, except that the compounds shown in Table 2 were used to form the first and second auxiliary layers, respectively.
[0548] Example 2-1
[0549] The organic light-emitting device of Example 2-1 was manufactured in substantially the same manner as in Example 1-1, except that Compound GH (host) and Compound GD (dopant) were simultaneously vacuum-deposited at a dopant concentration of 10 wt% to form an emission layer having a thickness of 40 nm.
[0550] Examples 2-2 to 2-6
[0551] The organic light-emitting devices of Examples 2-2 to 2-6 were manufactured in substantially the same manner as in Example 2-1, except that the compounds shown in Table 2 were used to form the first and second auxiliary layers, respectively.
[0552] Comparative Example 1-1
[0553] The organic light-emitting device of Comparative Example 1-1 was manufactured in substantially the same manner as in Example 1-1, except that Compound H1 was used to form the second auxiliary layer.
[0554] Compound H1
[0555]
[0556] Comparative Example 1-2
[0557] The organic light-emitting device of Comparative Example 1-2 was manufactured in substantially the same manner as in Example 1-1, except that the first auxiliary layer was not formed.
[0558] Comparative Example 2-1
[0559] The organic light-emitting device of Comparative Example 2-1 was manufactured in substantially the same manner as in Example 2-1, except that the first auxiliary layer was not formed.
[0560] Comparative Example 2-2
[0561] An organic light-emitting device of Comparative Example 2-2 was produced in substantially the same manner as in Example 2-1, except that Compound H1 was used in forming the second auxiliary layer.
[0562] Comparative Example 2-3
[0563] An organic light-emitting device of Comparative Example 2-3 was produced in substantially the same manner as in Example 2-1, except that Compound H1 and Compound G1 were used as the host and dopant, respectively, in forming the emission layer, and Compound H1 was used in forming the second auxiliary layer.
[0564] Compound G1
[0565]
[0566] Evaluation Example 2
[0567] The current efficiency and half-life of the organic light-emitting devices produced according to Examples 1-1 to 1-6 and 2-1 to 2-6 and Comparative Examples 1-1, 1-2, and 2-1 to 2-3 were measured by using Keithley SMU 236 and luminance meter PR650, and the results thereof are shown in Table 2.
[0568] Table 2
[0569]
[0570]
[0571] As can be seen from Table 2, the organic light-emitting devices of Examples 1-1 to 1-6 and 2-1 to 2-6 have superior current efficiency and lifespan compared to the organic light-emitting devices of Comparative Examples 1-1, 1-2, and 2-1 to 2-3.
[0572] An organic light-emitting device including a first auxiliary layer and a second auxiliary layer, in which the emission layer, the first auxiliary layer, and the second auxiliary layer satisfy a set or predetermined triplet energy level relationship, can inhibit or reduce the deterioration of the emission layer material and can have a long lifespan.
Claims
1. An organic light-emitting device, comprising: First electrode; The second electrode facing the first electrode; An organic layer between the first electrode and the second electrode, including an emission layer; and In the electron transport region between the emission layer and the second electrode, The electron transport region includes a first auxiliary layer and a second auxiliary layer. The first auxiliary layer is located between the transmitting layer and the second auxiliary layer. The first auxiliary layer includes a first compound. The second auxiliary layer includes a second compound. The second compound comprises at least one nitrogen ring containing π-electron-depleted nitrogen, and The organic light-emitting device satisfies the equations: T1(EML)≥T1(AXL1)+0.3eV and T1(AXL2)≥T1(AXL1)+0.5eV, where T1(AXL1) is less than 2.0eV. Where T1(EML) is the highest triplet energy level among the triplet energy levels of the compounds included in the emission layer. T1(AXL1) is the lowest triplet excitation energy level of the first compound. T1(AXL2) is the lowest triplet excitation energy level of the second compound, and T1(EML), T1(AXL1), and T1(AXL2) were calculated using density functional theory methods, wherein the compounds, the first compound, and the second compound included in the emitter layer were structurally optimized at the level of B3LYP / 6-31G*(d,p).
2. The organic light-emitting device according to claim 1, wherein the first auxiliary layer directly contacts the emitting layer.
3. The organic light-emitting device according to claim 1, wherein the first auxiliary layer directly contacts each of the emitting layer and the second auxiliary layer.
4. The organic light-emitting device according to claim 1, wherein the emitting layer is composed of a single compound, or comprises two or more compounds.
5. The organic light-emitting device according to claim 1, wherein, The emitter layer comprises a host and a dopant, and The emitter layer satisfies at least one equation selected from T1(body) ≥ T1(AXL1) + 0.3 eV and T1(dopant) ≥ T1(AXL1) + 0.3 eV. Where T1 (body) is the lowest triplet excitation energy level of the body in the emitter layer. T1 (dopant) is the lowest triplet excitation energy level of the dopant in the emitter layer, and T1 (body) and T1 (dopant) were calculated using density functional theory methods, wherein the body and the dopant were structurally optimized at the level of B3LYP / 6-31G*(d,p).
6. The organic light-emitting device according to claim 5, wherein the dopant is a phosphorescent dopant, a fluorescent dopant, or a delayed fluorescence dopant.
7. The organic light-emitting device according to claim 1, wherein, The electron transport region further includes an electron transport layer between the second auxiliary layer and the second electrode. The electron transport layer includes a third compound comprising at least one nitrogen ring containing π-electron-depleted nitrogen, and The second compound and the third compound are different from each other.
8. The organic light-emitting device according to claim 1, wherein the first compound is a compound represented by formula 1-1, and The second compound is a compound represented by formula 1-2: <Formula 1-1> <Equation 1-2> in, In Equations 1-1 and 1-2, A 11 Selected from naphthyl, anthraceneyl, triphenylene, pyrene, 1,2-benzophenanthryl, and perylene. L 11 and L 21 To L 23 Each is independently selected from 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 groups, substituted or unsubstituted non-aromatic fused polycyclic groups, and substituted or unsubstituted non-aromatic fused heterocyclic groups. a11 and a21 through a23 are each independently selected from 0, 1, 2, and 3. Ar 11 and Ar 21 To Ar 23 Each is independently selected from 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 groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, b11 and b21 to b23 are each independently selected from 1, 2, 3, and 4. n11 is selected from 1, 2, 3, and 4. X 21 For N or CR 21 X 22 For N or CR 22 And X 23 For N or CR 23 , R 11 and R 21 To R 23 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyne group, 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 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), c11 is an integer selected from 1 to 8. The substituted C3-C 10 Cycloalkylene, the substituted C1-C 10 Heterocyclic alkyl groups, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocyclic alkenyl groups, the substituted C6-C 60 aryl, the substituted C1-C 60 Hypoaryl, the substituted divalent non-aromatic fused polycyclic group, the substituted divalent non-aromatic fused heterocyclic group, the substituted C1-C 60 Alkyl groups, the substituted C2-C 60 alkenyl, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 Alkoxy groups, the substituted C3-C 10 cycloalkyl, the substituted C1-C 10 Heterocyclic alkyl groups, the substituted C3-C 10 cycloalkenyl, the substituted C1-C 10 Heterocyclic alkenyl groups, the substituted C6-C 60 Aryl, the substituted C6-C 60 aryloxy groups, the substituted C6-C 60 Arylthioyl, the substituted C1-C 60 The heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group are selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy; Each is substituted by at least one of the following C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 ); C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; Each of the C3-C molecules is substituted by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 ); as well as -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 ) and -P(=O)(Q 31 (Q) 32 ),and Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, 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, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.
9. The organic light-emitting device according to claim 8, wherein L 11 and L 21 To L 23 Each group is independently selected from those represented by formulas 3-1 to 3-39: in, In equations 3-1 to 3-39 Y1 can be O, S, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7). Z1 to Z7 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, anthracene, fluoranyl, triphenylene, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[quinolinyl], naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophene, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ), d2 is 1 or 2. d3 is an integer selected from 1 to 3. d4 is an integer selected from 1 to 4. d5 is an integer selected from 1 to 5. d6 is an integer selected from 1 to 6. d8 is an integer selected from 1 to 8. Q 31 To Q 33 Each is independently selected from hydrogen, deuterium, and C1-C. 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl, and *, *', and *” each indicate a binding site with an adjacent atom.
10. The organic light-emitting device according to claim 8, wherein a11 and a21 to a23 are each independently 0 or 1.
11. The organic light-emitting device according to claim 8, wherein Ar 11 and Ar 21 To Ar 23 Each is selected independently from: Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentanenyl, indole, naphthyl, azuleyl, heptanenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, phenatenyl, phenanthryl, anthraceneyl, fluoranyl, tri... Phenylidene, 1,2-benzophenanthrene, tetraphenyl, francyl, perylene, penfenyl, hexaphenyl, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzene quinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiapheneyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphridyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiapheneyl, and azadibenzothiazolyl; and Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentanenyl, indole, naphthyl, azuleyl, heptanenyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, spiro-cyclopentane-fluorenyl, spiro-cyclohexane-fluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, finalenyl, phenanthrene, anthraceneyl, fluoranthene. 1,2-Benzphenanthrene, Tetraphenyl, styrene, peryl, penfenyl, hexaphenyl, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoindoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthalene Pyridyl, quinoxalinyl, quinazolinyl, cyclolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiaphenyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl Dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiopheneyl, and azadibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, C6-C 20 Aryl, C1-C 20 heteroaryl, -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 ) and -P(=O)(Q 31 (Q) 32 ),and Q 31 To Q 33 Each is independently selected from hydrogen, deuterium, and C1-C. 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.
12. The organic light-emitting device according to claim 8, wherein Ar 11 and Ar 21 To Ar 23 Each group is independently selected from those represented by formulas 5-1 to 5-79: in, In equations 5-1 to 5-79, Y 31 is O, S, C(Z 33 )(Z 34 ), N(Z 35 ), or Si(Z 36 )(Z 37 ), Z 31 To Z 37 Each is independently selected from hydrogen, 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, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, anthracene, fluoranyl, triphenylene, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzo[quinolinyl], naphthidyl, quinoxalinyl, quinazolinyl, carbazole, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophene, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 ) and -B(Q 31 (Q) 32 ), e2 is 1 or 2. e3 is an integer selected from 1 to 3. e4 is an integer selected from 1 to 4. e5 is an integer selected from 1 to 5. e6 is an integer selected from 1 to 6. e7 is an integer selected from 1 to 7. e9 is an integer selected from 1 to 9. Q 31 To Q 33 Each is independently selected from hydrogen, deuterium, and C1-C. 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl, and * Indicates the binding site with adjacent atoms.
13. The organic light-emitting device according to claim 8, wherein Ar 11 and Ar 21 To Ar 23 Each group is independently selected from those represented by formulas 6-1 to 6-32: in, In equations 6-1 to 6-32, Ph indicates phenyl, and * Indicates the binding site with adjacent atoms.
14. The organic light-emitting device according to claim 8, wherein R 11 and R 21 To R 23 Each is selected independently from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, phenerenoyl, anthracene, fluoranyl, triphenylene, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indoleyl, purine, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazole, benzocarbazole, dibenzocarbazole, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazole, azadibenzofuranyl, azadibenzothiophene, azadibenzothiopyrrolyl, biphenyl and terphenyl; and Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, finadeninyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrrolyl, thiopheneyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indoleyl, purinel, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrynyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidyl Azolyl, benzofuranyl, benzothiophenyl, benzothiopyrrolyl, benzoisothiazolyl, benzooxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiopyrrolyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothiopyrrolyl, biphenyl and terphenyl: 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, naphthyl, fluorenyl, spiro-difluorenyl, spiro-fluorenyl-benzo[fluorenyl], benzo[fluorenyl], dibenzo[fluorenyl], pyrene, phenatenyl, anthracene, fluoranyl, triphenylene, pyrrolyl, thiophene, furanyl, thiophene, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoyindolyl, indazoleyl, purine, quinolinyl, isoquinolinyl, benzo[quinolinyl], phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl , phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiopyrrolyl, benziisothiazolyl, benzooxazolyl, benziisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, oxidazopyridyl, thiazopyridyl, benzonaphthidyl, azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophene, azadibenzothiopyrrolyl, biphenyl and terphenyl.
15. The organic light-emitting device according to claim 8, wherein X 21 To X 23 Each is N.
16. The organic light-emitting device according to claim 8, wherein the first compound is a compound represented by formula 1-11 or formula 1-12: <Formula 1-11> <Equation 1-12> in, In equations 1-11 and 1-12, L 111 L 121 and L 122 With L in combination 1-1 11 The same restrictions apply. a111, a121, and a122 are defined in the same way as a11 in associative formula 1-1. Ar 111 Ar 121 and Ar 122 With Ar in combination 1-1 11 The same restrictions apply. b111, b121, and b122 are defined in the same way as b11 in associative formula 1-1. n111 is defined in the same way as n11 in associative equation 1-1. n121 and n122 are each independently selected from 0, 1, and 2. R 111 R 121 and R 122 With R in combination 1-1 11 The same restrictions apply. c111 is defined in the same way as c11 in associative formula 1-1, and c121 and c122 are each independently selected from 0, 1, 2, 3, 4 and 5.
17. The organic light-emitting device according to claim 8, wherein the first compound is a compound represented by formula 1-11A or formula 1-12A: <Formula 1-11A> <Formula 1-12A> in, In equations 1-11A and 1-12A, L 111 L 112 L 121 and L 122 With L in combination 1-1 11 The same restrictions apply. a111, a112, a121, and a122 are defined in the same way as a11 in associative formula 1-1. Ar 111 Ar 112 Ar 121 and Ar 122 With Ar in combination 1-1 11 The same restrictions apply. b111, b112, b121, and b122 are the same as b11 defined in associative formula 1-1. n121 and n122 are each independent integers selected from 0 to 2. R 111 R 121 and R 122 With R in combination 1-1 11 The same restrictions apply. c111 is defined in the same way as c11 in associative formula 1-1, and c121 and c122 are each independently selected from 0, 1, 2, 3 and 4.
18. The organic light-emitting device according to claim 8, wherein the first compound is a compound represented by formula 1-11B or formula 1-12B: <Formula 1-11B> <Formula 1-12B> in, In Equations 1-11B and 1-12B, L 111 L 112 L 121 and L 122 With L in combination 1-1 11 The same restrictions apply. a111, a112, a121, and a122 are defined in the same way as a11 in associative formula 1-1. Ar 111 Ar 112 Ar 121 and Ar 122 With Ar in combination 1-1 11 The same restrictions apply. b111, b112, b121, and b122 are the same as b11 in associative formula 1-1, and R 111 R 112 R 121 and R 122 With R in combination 1-1 11 The same restrictions apply.
19. An apparatus comprising: The organic light-emitting device according to any one of claims 1-18; and Thin-film transistor, The thin-film transistor includes a source electrode, an active layer, and a drain electrode, and The first electrode of the organic light-emitting device is in electrical contact with one of the source electrode and the drain electrode of the thin-film transistor.
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