Organometallic compound and organic light emitting device comprising the same
By using organometallic compounds with specific structures and optimizing the combination of coordination and covalent bonds to form non-planar structures, the shortcomings of organic light-emitting devices in terms of color purity and lifetime are solved, and high-performance organic light-emitting devices are realized.
Patent Information
- Application Number
- CN202110375795.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-04-09
- Filing Date
- 2021-04-08
- Publication Date
- 2026-01-23
- Estimated Expiration
- 2041-04-08
AI Technical Summary
Existing organic light-emitting devices have shortcomings in color purity and lifespan, making it difficult to meet high-performance requirements.
By employing organometallic compounds with specific structures and optimizing the combination of coordination and covalent bonds, non-planar organometallic compounds can be formed, thereby enhancing the σ-bond stability of carbene-metal bonds and improving color purity and lifetime.
This achieves excellent color purity, low driving voltage, high efficiency, and long lifespan in organic light-emitting devices, thus improving the overall performance of the devices.
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Figure CN113512067B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0043600, filed on April 9, 2020, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference. TECHNICAL FIELD
[0002] One or more embodiments relate to an organometallic compound and an organic light emitting device including the same. BACKGROUND
[0003] An organic light emitting device (OLED) is a self-emitting device having excellent properties such as a wide viewing angle, high contrast, short response time, and / or excellent luminance, driving voltage, and / or response speed, as compared with devices in the related art.
[0004] An OLED can include a first electrode on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode can move toward the emission layer through the hole transport region, and electrons provided from the second electrode can move toward the emission layer through the electron transport region. Carriers such as holes and electrons are recombined in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. SUMMARY
[0005] Aspects according to one or more embodiments are directed to an organometallic compound having excellent color purity and long lifespan and an organic light emitting device using the same.
[0006] Additional aspects will be set forth in part in the description which follows, and in part will become apparent to those skilled in the art upon examination of the following disclosure or can be learned by practice of the presented embodiments.
[0007] According to embodiments of the disclosure, the organometallic compound is represented by Formula 1:
[0008] Formula 1
[0009]
[0010] wherein, in Formula 1,
[0011] M can be a transition metal,
[0012] L1may be a monodentate ligand,
[0013] Y1and Y2may each be C,
[0014] Y3may be C or N,
[0015] The bonds between Y1 and M, and between Y2 and M, can all be coordinate bonds, and the bonds between L1 and M, and between Y3 and M, can all be covalent bonds.
[0016] Rings CY1 to CY3 can all be independently C5-C. 30 Carbocyclic or C1-C 30 Heterocyclic group,
[0017] R1 to R3 can all be independently 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, 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, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0018] a1 to a3 can each be an independent integer from 0 to 20.
[0019] Depend on The group represented and composed of The groups represented can be different from each other.
[0020] * indicates the associativity bit with M in Equation 1, and *' and *" both indicate the associativity bit with ring CY3 in Equation 1.
[0021] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent among heteroaryl, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:
[0022] 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
[0023] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and 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 condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy
[0024] None of them are substituted, or they are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 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 condensed polycyclic and monovalent non-aromatic condensed heterocyclic, and
[0025] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31) and -P(=O)(Q 31 (Q) 32 ),
[0026] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently:
[0027] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 C1-C of at least one of alkyl, phenyl, and biphenyl 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 C6-C of at least one of alkyl, phenyl, and biphenyl 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heterocyclic group.
[0028] According to another embodiment of this disclosure, the organic light-emitting device includes: a first electrode,
[0029] The second electrode faces the first electrode, and
[0030] An organic layer, located between the first electrode and the second electrode, includes an emission layer.
[0031] Organic light-emitting devices include at least one organometallic compound represented by Formula 1. Attached Figure Description
[0032] The above and other aspects, features, and improvements of certain embodiments disclosed will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0033] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0034] Figure 2This is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0035] Figure 3 This is a schematic cross-sectional view of an organic light-emitting device according to an embodiment; and
[0036] Figure 4 This is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. Detailed Implementation
[0037] Referring now to embodiments in more detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals always denote the same elements. In this respect, the presented embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to explain aspects of this description. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Throughout this disclosure, the expression “at least one of a, b, and c” may refer to only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
[0038] The organometallic compounds according to embodiments of this disclosure can be represented by Formula 1.
[0039] Formula 1
[0040]
[0041] In Equation 1, M can be a transition metal.
[0042] For example, M can be selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), and osmium (Os).
[0043] In the embodiments, M can be Pt, Pd, or Au.
[0044] L1 in Equation 1 can be a monodentate ligand.
[0045] For example, L1 can be selected from hydrogen, deuterium (D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.
[0046] In one embodiment, L1 may be a cyano group, but the embodiments disclosed herein are not limited thereto.
[0047] In Equation 1, Y1 and Y2 can both be C, and Y3 can be C or N.
[0048] For example, Y3 can be C, but the embodiments of this disclosure are not limited thereto.
[0049] In Equation 1, the bonds between Y1 and M and between Y2 and M can both be coordinate bonds, and the bonds between L1 and M and between Y3 and M can both be covalent bonds.
[0050] In Equation 1, rings CY1 to CY3 can all be independently C5-C. 30 Carbocyclic or C1-C 30 Heterocyclic group.
[0051] For example, rings CY1 and CY2 can both be 5-membered rings, and ring CY3 can be a 6-membered ring.
[0052] In one embodiment, cyclo CY1 and cyclo CY2 can both be independently selected from pyrazole, imidazole, triazole, benzimidazole, cyclopentadiene, furan, thiophene, indole, pyrrole, oxazole, thiazole, oxadiazole, and thiadiazole groups.
[0053] In one or more embodiments, cycloCY3 may be selected from phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, benzo[9,10]phenanthrene groups, pyrene groups, etc. Groups, 1,2,3,4-tetrahydronaphthyl group, indene group, fluorene group, carbazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthrene-rhein group, and pyrazolopyridine group.
[0054] In one or more embodiments, both ring CY1 and ring CY2 may be imidazole groups or benzimidazole groups, and ring CY3 may be a phenyl group, but the embodiments disclosed herein are not limited thereto.
[0055] In Formula 1, R1 to R3 can all be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 The terms include heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2). Here, Q1 to Q3 can be understood by referring to the descriptions of Q1 to Q3 provided herein.
[0056] For example, R1 to R3 can all be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0057] All of these groups are substituted with substances ranging from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 10 The C1-C group selected from at least one of alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl is C1-C. 20 Alkyl and C1-C 20 Alkoxy;
[0058] All of these groups are substituted with substances ranging from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, indazoleyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cenolinyl, carbazoleyl, phenanthrololinyl, benzimidazoleyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The following are selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, inzolyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, carbazoleyl, phenanthrolinel, benzimidazoleyl, benzofuranyl Benzothiophene, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiophene, azafluorenyl, and azadibenzothiophene; and
[0059] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),
[0060] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently selected from:
[0061] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H and -CD2CDH2, as well as those that are not substituted or substituted with deuterium, C1-C 10 The compounds may be selected from at least one of alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridinyl, pyrazinyl, and triazinyl, including n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridinyl, pyrazinyl, and triazinyl, but the embodiments of this disclosure are not limited thereto.
[0062] In one embodiment, at least one of the a1 numbers of R1 and the a2 numbers of R2 can be independently either substituted or unsubstituted C6-C. 60 aryl, substituted or unsubstituted C1-C 60 The R3 group can be a heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic group, or a substituted or unsubstituted monovalent nonaromatic condensed heterocyclic group, and R3 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, or a substituted or unsubstituted C1-C group. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).
[0063] In one or more embodiments, R3 can be hydrogen or substituted or unsubstituted C1-C. 60 alkyl.
[0064] In one or more embodiments, at least one of the three R3s can each be independently substituted or unsubstituted C6-C. 60 aryl, substituted or unsubstituted C1-C60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic group, or substituted or unsubstituted monovalent nonaromatic condensed heterocyclic group.
[0065] In Equation 1, a1 to a3 can each be an integer from 0 to 20 independently.
[0066] In one embodiment, a1 to a3 can each be an integer from 0 to 5 independently.
[0067] In Equation 1, by The group represented and composed of The groups represented can be different from each other.
[0068] * indicates the associativity with M in Equation 1, and
[0069] Both *' and *" represent the binding position with ring CY3 in Equation 1.
[0070] In one embodiment, rings CY1 and CY2 can be different from each other.
[0071] In one or more embodiments, rings CY1 and CY2 may be identical to each other, a1 and a2 may each be an independent integer from 1 to 20, and one of the R1 values of a1 and one of the R2 values of a2 may be different from each other. For example, (R1) a1 It can be different from (R2). a2 .
[0072] In one or more embodiments, rings CY1 and CY2 can be identical to each other, a1 and a2 can be identical to each other, and one R1 of the number a1 in R1 and one R2 of the number a2 in R2 can be different from each other. For example, (R1) a1 It can be different from (R2). a2 .
[0073] In one embodiment, by The group represented can be one of the groups represented by formulas CY1-1 to CY1-24:
[0074]
[0075] R in equations CY1-1 to CY1-24 11 To R 15 It can be the same as that described in combination with R1, and R 12 To R 15 Each of the elements in the group can be non-hydrogen.
[0076] * indicates the associativity with M in Equation 1, and
[0077] *' indicates the binding position with ring CY3 in Equation 1.
[0078] In one or more embodiments, R in formulas CY1-1 to CY1-24 11 It doesn't have to be hydrogen.
[0079] In one or more embodiments, by The group represented can be one of the groups represented by formulas CY2-1 to CY2-24:
[0080]
[0081]
[0082] R in equations CY2-1 to CY2-24 21 To R 25 It can be the same as that described by combining R2, and R 22 To R 25 Each of the elements in the group can be non-hydrogen.
[0083] * indicates the associativity with M in Equation 1, and
[0084] * indicates the binding position with ring CY3 in Equation 1.
[0085] In one or more embodiments, R in formulas CY2-1 to CY2-24 21 It doesn't have to be hydrogen.
[0086] In one or more embodiments, by The group represented can be one of the groups represented by formulas CY3-1 to CY3-8:
[0087]
[0088] R in formulas CY3-1 to CY3-8 31 To R 33 It can be the same as that described in combination with R3, and R 31 To R 33 Each of them can be non-hydrogen, and
[0089] * indicates the associativity position with M in Equation 1.
[0090] *' indicates the binding position with ring CY1 in Equation 1, and
[0091] * indicates the binding position with ring CY2 in Equation 1.
[0092] In one embodiment, the organometallic compound represented by Formula 1 may be selected from compounds 1 to 49:
[0093]
[0094]
[0095] Organometallic compounds represented by Formula 1 can emit blue light.
[0096] Organometallic compounds represented by Formula 1 can have a minimum excited triplet energy level of 2.5 eV or greater and 3.1 eV or less.
[0097] Organometallic compounds represented by Formula 1 can emit blue light with a maximum emission wavelength of 400 nm to 500 nm.
[0098] Regarding organometallic compounds, i) in formula 1, ... The group represented and composed of The groups represented are different from each other; therefore, due to the non-planar structure, the excimer is suppressed, and the triplet state blue shift improves color purity. ii) Because Y1 and Y2 are both C, the bonds between Y1 and M and between Y2 and M are coordinate bonds, while the bonds between L1 and M and between Y3 and M are covalent bonds. Therefore, the σ bonds are strengthened through carbene-metal bonds, thus improving stability. Therefore, electronic devices (e.g., organic light-emitting devices including organometallic compounds) can possess excellent color purity, low driving voltage, high efficiency, and long lifetime.
[0099] The method for synthesizing organometallic compounds represented by Formula 1 can be understood by those skilled in the art by referring to the examples provided below.
[0100] At least one of such organometallic compounds represented by Formula 1 can be used between a pair of electrodes in an organic light-emitting device.
[0101] In one or more embodiments, the organic light-emitting device may include a first electrode, a second electrode facing the first electrode, and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes at least one organometallic compound represented by Formula 1.
[0102] In an embodiment, in an organic light-emitting device, the first electrode is the anode, the second electrode is the cathode, an organometallic compound is included in an organic layer, and the organic layer further includes a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode.
[0103] The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0104] In one embodiment, the emitter layer may include an organometallic compound.
[0105] In one or more embodiments, the emitter layer includes a host and a dopant, the host and the dopant being different from each other, the amount of the host being greater than the amount of the dopant, and an organometallic compound may be included in the dopant.
[0106] In one or more embodiments, the emitting layer of the organic light-emitting device may further include at least one of a second compound represented by Formula 2 and a third compound containing a group represented by Formula 3:
[0107] Formula 2
[0108]
[0109] Formula 3
[0110]
[0111] Among them, in equations 2 and 3,
[0112] CY 51 To CY 53 and CY 71 and CY 72 Each can be independently selected from C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic group,
[0113] L 51 To L 53 Each can be independently selected from substituted or unsubstituted C5-C. 30 Carbocyclic groups and substituted or unsubstituted C1-C 30 Heterocyclic group,
[0114] L 51 With CY 51 The key between, L 52 With CY 52 The key between, L 53 With CY 53 The key between two or more L 51 The key between two or more L 52 The key between two or more L 53 The bond between them, L in Formula 2 51 With X 54 and X 55 The bonds between carbon atoms, L in Formula 2 52 With X 54 and X 56 The bonds between carbon atoms and the L in Formula 2 53 With X55 and X 56 The bonds between carbon atoms can all be carbon-carbon single bonds.
[0115] b51 to b53 can all be independent integers from 0 to 5, where, when b51 is 0, *-(L 51 ) b51 -*' can be a single key; when b52 is 0, *-(L 52 ) b52 -*' can be a single key, and when b53 is 0, *-(L 53 ) b53 -*' can be a single key.
[0116] X 54 It can be N or C(R) 54 ), X 55 It can be N or C(R) 55 ), X 56 It can be N or C(R) 56 ), and from X 54 To X 56 At least one of the selected options can be N.
[0117] X 81 It can be a single bond, O, S, N(R) 81 ), B(R) 81 ), C(R 81a (R) 81b ) or Si(R 81a (R) 81b ),
[0118] R 51 To R 56 R 71 R 72 R 81 R 81a and R 81b Each group 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, 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 60aryl, substituted or unsubstituted C7-C 60 Alkyl 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 C2-C 60 Alkyl heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and bidentate organic ligands,
[0119] a51 to a53, a71, and a72 can all be independent integers from 0 to 20.
[0120] Both * and *' indicate bonding sites with adjacent atoms.
[0121] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 At least one substituent among alkyl heteroaryl, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:
[0122] 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;
[0123] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -O(Q) 11 -S(Q) 11 ), -Si(Q 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0124] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;
[0125] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -O(Q) 21 -S(Q) 21 ), -Si(Q 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heterocyclic group; and
[0126] -O(Q 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q)32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),
[0127] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, substituted with deuterium, -F, cyano, C1-C 60 C1-C of at least one of alkyl, phenyl, and biphenyl 60 Alkyl groups and substitutions include deuterium, -F, cyano, C1-C 10 C6-C of at least one of alkyl, phenyl, and biphenyl 60 Aryl.
[0128] For example, the ring CY in Equations 2 and 3 51 To CY 53 CY 71 and CY 72 Each of these can be independently: i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed together, iv) a condensed ring in which two or more second rings are condensed together, or v) a condensed ring in which one or more first rings and one or more second rings are condensed together.
[0129] The first ring can be selected from cyclopentyl groups, cyclopentadienyl groups, furan groups, thiophene groups, pyrrole groups, thiorrole groups, oxazole groups, isoxazole groups, oxadiazole groups, isoxadiazole groups, oxtriazole groups, isoxtriazole groups, thiazole groups, isothiazole groups, thiadiazole groups, isothiadiazole groups, thiatriazole groups, isothiadiazole groups, pyrazole groups, imidazole groups, triazole groups, tetraazole groups, azathiorrole groups, diazathiorrole groups, and triazathiorrole groups.
[0130] The second ring can be selected from adamantyl group, norbornel group, norbornene group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, oxasiline group, thiasiline group, dihydroazasiline group, dihydrodisiline group, dihydrosiline group, dioxene group, oxathiine group, oxazine group, pyran group, dithiine group, thiazine group, thiaran group, cyclohexene group, dihydropyridine group, and dihydropyrazine group.
[0131] In one or more embodiments, the ring CY in Formulas 2 and 3 51 To CY 53 CY 71 and CY 72 All can be independently selected from phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, benzo[9,10]phenanthrene groups, pyrene groups, Groups, cyclopentadienyl groups, 1,2,3,4-tetrahydronaphthalene groups, thiophene groups, furan groups, indole groups, benzoborane heterocyclopentadienyl groups, benzophosphane heterocyclopentadienyl groups, indene groups, benzothiophene groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenene groups, benzofuran groups, carbazole groups, dibenzoborane heterocyclopentadienyl groups, dibenzophosphane heterocyclopentadienyl groups, fluorene groups, dibenzothiophene groups, dibenzogermanium heterocyclopentadienyl groups, dibenzothiophene... Phenoyl group, dibenzoselenyl group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azidoindole group, azidobenzoborane group, azidobenzophosphacyclopentadien group, azidoindole group, azidobenzothiophene group, azidobenzogeraniumcyclopentadien group, azidobenzothiophene group, azidobenzofuran group, azidocarbazole group, azidodibenzoborane Cyclopentadienyl group, azadibenzophosphacyclopentadienyl group, azafluorene group, azadibenzothiophene group, azadibenzogermanium cyclopentadienyl group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group The groups include quinoxaline group, quinazolinine group, phenanthrene-rholine group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group and 5,6,7,8-tetrahydroquinoline group, but the embodiments of this disclosure are not limited thereto.
[0132] L in Equation 2 51 To L 53 Each can be independently selected from substituted or unsubstituted C5-C. 30 Carbocyclic groups and substituted or unsubstituted C1-C 30 Heterocyclic group.
[0133] For example, L 51 To L 53 Each can be independently selected from:
[0134] Phenylidene, naphthylene, anthracene, phenanthrene, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, cyclopentadienyl, furanyl, thiopheneyl, thiopheneyl, indeneyl, fluoreneyl, indoleyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzothiopheneyl, dibenzothiopheneyl, azirmonyl, azirmonyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, pyridinyl, pyridinyl Azinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, quinoxalinyl, quinoxalinyl, phenanthrolineyl, pyrrolyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazoleyl, benzimidazoleyl, benzioxazolyl, benzioxadiazolyl, and benzioxadiazolyl; and
[0135] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazole, phenylcarbazole, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, dimethyldibenzothiopyrrolyl, diphenyldibenzothiopyrrolyl, -O(Q) 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The at least one of the following selected: phenylene, naphthylene, anthraceneylene, phenanthrene, benzo[9,10]phenanthrene, pyreneylene, or phenylene oxide. alkyl, cyclopentadienyl, furanyl, thiopheneyl, thiopheneyl, indeneyl, fluoreneyl, indoleyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzothiopheneyl, dibenzothiopheneyl, azirmoneneyl, azirmonazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, pyridinyl, pyrimidinyl, pyrimidinyl Pyrazinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, quinoxalinyl, quinoxalinyl, phenanthrolineyl, pyrrolyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazoleyl, benzimidazoleyl, benzioxazolyl, benzioxadiazolyl, and benzioxadiazolyl.
[0136] Q 31 To Q 33 They can all be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, and triazinyl are used, but the embodiments of this disclosure are not limited thereto.
[0137] In Equation 2, L 51 With CY 51 The key between, L 52 With CY 52 The key between, L 53 With CY 53 The key between two or more L 51 The key between two or more L 52 The key between two or more L 53 The bond between them, L in Formula 2 51 With X 54 and X 55 The bonds between carbon atoms, L in Formula 2 52 With X 54 and X 56 The bonds between carbon atoms and the L in Formula 2 53 With X 55 and X 56 The bonds between carbon atoms can all be carbon-carbon single bonds, and
[0138] In Equation 2, b51 to b53 each represent L 51 To L 53 The number of elements, and each can be an independent integer from 0 to 5, where, when b51 is 0, *-(L 51 ) b51 -*' can be a single key; when b52 is 0, *-(L 52) b52 -*' can be a single key; when b53 is 0, *-(L 53 ) b53 -*' can be a single key, or two or more L's when b51 is 2 or greater. 51 They can be the same or different from each other, and when b52 is 2 or greater, two or more Ls 52 They can be the same or different from each other, and when b53 is 2 or greater, two or more Ls 53 They can be the same or different from each other. For example, b51 to b53 can each be 0, 1 or 2 independently.
[0139] In Equation 2, X 54 It can be N or C(R) 54 ), X 55 It can be N or C(R) 55 ), X 56 It can be N or C(R) 56 ), and from X 54 To X 56 At least one of the selected options can be N. R 54 To R 56 It can be the same as described above.
[0140] X in Equation 3 81 It can be a single bond, O, S, N(R) 81 ), B(R) 81 ), C(R 81a (R) 81b ) or Si(R 81a (R) 81b R 81 R 81a and R 81b It can be the same as described above.
[0141] R 51 To R 56 R 71 R 72 R 81 R 81a and R 81b Each group 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, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10Heterocyclic 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 C7-C 60 Alkyl 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 C2-C 60 Alkyl heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and bidentate organic ligands. Q1 to Q3 may be the same as those described in this specification.
[0142] For example, R 51 To R 56 R 71 R 72 R 81 R 81a and R 81b Each can be independently selected from:
[0143] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0144] All of these groups are substituted with substances ranging from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 10 The C1-C group selected from at least one of alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl is C1-C. 20 Alkyl and C1-C 20 Alkoxy;
[0145] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene The group consisting of: , isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiophenyl, and groups represented by Formula 91;
[0146] All of these groups are substituted with substances ranging from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, indazoleyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cenolinyl, carbazoleyl, phenanthrololyl, benzimidazoleyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, -O(Q) 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q)32 The following are selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, inzolyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cenolinyl, carbazoleyl, phenanthrololyl, benzimidazoleyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, di Benzothiophene, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophene, azafluorenyl, azadibenzothiophene, and groups represented by Formula 91; and -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),
[0147] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently selected from:
[0148] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CH3, -CD2CD3, -CD2CD2H and -CD2CDH2;
[0149] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, and triazinyl; and
[0150] All of them replace deuterium and C1-C 10 The group consisting of at least one of the following: alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridinyl, pyrazinyl, and triazinyl; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridinyl, pyrazinyl, and triazinyl.
[0151] However, the embodiments disclosed herein are not limited thereto:
[0152] Formula 91
[0153]
[0154] In Equation 91,
[0155] CY 91 and CY 92 Each can be independently selected from C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic group, X 91 It can be a single bond, O, S, N(R) 91 ), B(R) 91 ), C(R 91a (R) 91b ) or Si(R 91a (R) 91b ), R 91 R 91a and R 91b It can be combined with R respectively 81 R 81a and R 81b The descriptions are the same, and
[0156] * indicates a bonding site with an adjacent atom.
[0157] For example, in Equation 91,
[0158] CY 91 and CY 92 They can all be independently selected from phenyl groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, and triazine groups.
[0159] R 91 R 91a and R 91b Each can be independently selected from:
[0160] Hydrogen and C1-C 10 alkyl;
[0161] Phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, and triazinyl; and
[0162] All of them replace deuterium and C1-C 10 The phenyl, pyridyl, pyridyl, pyridinyl, pyrazinyl, and triazinyl groups selected from at least one of the following: alkyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, pyridinyl, and triazinyl.
[0163] However, the embodiments disclosed herein are not limited thereto.
[0164] In one or more embodiments, R 51 To R56 R 71 R 72 R 81 R 81a and R 81b The groups can be independently selected from hydrogen, deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of formulas 9-1 to 9-19, a group represented by one of formulas 10-1 to 10-243, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), and -P(=O)(Q1)(Q2) (where Q1 to Q3 can be the same as described above), but the embodiments of this disclosure are not limited thereto:
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172] In formulas 9-1 to 9-19 and 10-1 to 10-243, * indicates a bonding site with an adjacent atom, Ph can be (for example, denoted by ) phenyl, and TMS can be (for example, denoted by ) trimethylsilyl.
[0173] In one or more embodiments, R 51 To R 56 R 71 R 72 R 81 R 81a and R 81b Each of them may not be a bidentate organic ligand.
[0174] a51 to a53, a71, and a72 all represent R respectively. 51 To R 53 R 71 and R 72 The number of R, and can all be independent integers from 0 to 20 (e.g., integers from 0 to 5). When a51 is 2 or greater, two or more R 51They can be the same or different from each other, and this can be applied in the same way to a52, a53, a71, and a72, as well as R. 52 R 53 R 71 and R 72 That is to say, a52, a53, a71, and a72, and their corresponding R... 52 R 53 R 71 and R 72 Both can be used with a51 and R 51 It can be understood in the same way.
[0175] In one embodiment, Equation 2 is composed of... The group represented and composed of The group represented may not be phenyl.
[0176] In one embodiment, Equation 2 is composed of... The group represented and composed of The groups represented can be the same as each other.
[0177] In one or more embodiments, the ring CY in Formula 2 51 and CY 52 They can all be independently selected from phenyl groups, pyridine groups, pyrimidine groups, pyridazine groups, pyrazine groups, and triazine groups.
[0178] R 51 and R 52 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 C7-C 60 Alkyl 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 C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -C(Q1)(Q2)(Q3) and -Si(Q1)(Q2)(Q3),
[0179] Q1 to Q3 can all be independently selected from C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C10 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 condensed polycyclic, monovalent non-aromatic condensed heterocyclic, and substituted with deuterium, -F, cyano, C1-C 10 C6-C of at least one of alkyl, phenyl, and biphenyl 60 Aryl, and
[0180] a51 and a52 can each be 1, 2, or 3 independently.
[0181] In one or more embodiments, Equation 2 is derived from... The represented portion may be a group represented by one of formulas CY51-1 to CY51-17, and / or by... The represented portion may be a group represented by one of formulas CY52-1 to CY52-17, and / or by... The represented part can be a group represented by one of the formulas CY53-1 to CY53-18:
[0182]
[0183]
[0184]
[0185] Among them, in formulas CY51-1 to CY51-17, CY52-1 to CY52-17, and CY53-1 to CY53-18,
[0186] Y 63 It can be a single bond, O, S, N(R) 63 ), B(R) 63 ), C(R 63a (R) 63b ) or Si(R 63a (R) 63b ),
[0187] Y 64 It can be a single bond, O, S, N(R) 64 ), B(R) 64 ), C(R 64a (R) 64b ) or Si(R 64a (R) 64b ),
[0188] Y67 It can be a single bond, O, S, N(R) 67 ), B(R) 67 ), C(R 67a (R) 67b ) or Si(R 67a (R) 67b ), Y 68 It can be a single bond, O, S, N(R) 68 ), B(R) 68 ), C(R 68a (R) 68b ) or Si(R 68a (R) 68b ),
[0189] Y in formulas CY51-16 and CY51-17 63 and Y 64 Each element in the set can be a single key at the same time.
[0190] Y in formulas CY52-16 and CY52-17 67 and Y 68 Each element in the set can be a single key at the same time.
[0191] R 51a To R 51e R 61 To R 64 R 63a R 63b R 64a and R 64b They can all independently bind with R 51 The descriptions are the same, and R 51a To R 51e Each of the elements in R is not hydrogen, that is, R 51a To R 51e Neither of them are hydrogen.
[0192] R 52a To R 52e R 65 To R 68 R 67a R 67b R 68a and R 68b They can all independently bind with R 52 The descriptions are the same, and R 52a To R 52e It is not hydrogen, that is to say, R 52a To R 52e Neither of them are hydrogen.
[0193] R 53a To R 53e They can all independently bind with R53 The descriptions are the same, and R 53a To R 53e Each of the elements in R is not hydrogen, that is, R 53a To R 53e Neither of them are hydrogen, and
[0194] * indicates a bonding site with an adjacent atom.
[0195] For example,
[0196] R in formulas CY51-1 to CY51-15 and formulas CY52-1 to CY52-15 51a To R 51e and R 52a To R 52e Each can be independently selected from:
[0197] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene The group consisting of: , isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiophenyl, and groups represented by Formula 91;
[0198] All of these groups are substituted with substances ranging from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, inzolyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, carbazoleyl, phenanthrololinyl, benzimidazoleyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzyl The following are selected from at least one of the following groups: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, inzolyl, purineyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, carbazoleyl, phenanthrololinyl, benzimidazoleyl, benzofuranyl, benzothiopheneyl Isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiophenyl and groups represented by Formula 91; and
[0199] -C(Q1)(Q2)(Q3) and -Si(Q1)(Q2)(Q3);
[0200] Q1 to Q3 can all be independently selected from:
[0201] Phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, and triazinyl; and
[0202] All of them replace deuterium and C1-C 10 The alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, and triazinyl groups selected from at least one of the following: phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, and triazinyl groups.
[0203] In equations CY51-16 and CY51-17, i)Y 63 It can be O or S, Y 64 It can be Si(R) 64a (R) 64b ), or ii)Y 63It can be Si(R) 63a (R) 63b ), Y 64 It can be O or S, and
[0204] In equations CY52-16 and CY52-17, i)Y 67 It can be O or S, Y 68 It can be Si(R) 68a (R) 68b ), or ii)Y 67 It can be Si(R) 67a (R) 67b ), Y 68 It can be O or S, but the embodiments disclosed herein are not limited thereto.
[0205] In one or more embodiments, the third compound may be represented by one of Formulas 3-1 to 3-5:
[0206]
[0207]
[0208] Among them, in equations 3-1 to 3-5,
[0209] CY 71 CY 72 X 81 R 71 R 72 a71 and a72 can each be independently identical to those described in this specification.
[0210] CY 73 CY 74 R 73 R 74 a73 and a74 can each independently bind to the binding ring CY. 71 CY 72 R 71 R 72 A71 and A72 are described in the same way.
[0211] L 81 It can be selected from *-C(Q4)(Q5)-*', *-Si(Q4)(Q5)-*', substituted or unsubstituted C5-C 30 Carbocyclic groups and substituted or unsubstituted C1-C 30 Heterocyclic groups, and Q4 and Q5 can each be independently identical to those described by binding Q1.
[0212] b81 can be an integer from 0 to 5, where when b81 is 0, *-(L 81 )b81 -*' can be a single key, or two or more L's when b81 is 2 or greater. 81 They can be the same or different from each other.
[0213] X 82 It can be a single bond, O, S, N(R) 82 ), B(R) 82 ), C(R 82a (R) 82b ) or Si(R 82a (R) 82b ), X 83 It can be a single bond, O, S, N(R) 83 ), B(R) 83 ), C(R 83a (R) 83b ) or Si(R 83a (R) 83b ),
[0214] X in Equations 3-2 and 3-4 82 and X 83 Each of them is not a single key at the same time.
[0215] X 84 It can be C or Si.
[0216] R 80 R 82 R 83 R 82a R 82b R 83a R 83b and R 84 They can all independently bind with R 81 The descriptions are the same, and
[0217] Both * and *' represent bonding sites with adjacent atoms.
[0218] For example, L 81 It can be selected from:
[0219] *-C(Q4)(Q5)-*' and *-Si(Q4)(Q5)-*';
[0220] Phenylidene, naphthylene, anthracene, phenanthrene, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, cyclopentadienyl, furanyl, thiopheneyl, thiopheneyl, indeneyl, fluoreneyl, indoleyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzothiopheneyl, dibenzothiopheneyl, azirmonyl, azirmonyl, dibenzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, pyridinyl, pyridinyl Azinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, quinoxalinyl, quinoxalinyl, phenanthrolineyl, pyrrolyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazoleyl, benzimidazoleyl, benzioxazolyl, benzioxadiazolyl, and benzioxadiazolyl; and
[0221] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazole, phenylcarbazole, dibenzofuranyl, dibenzothiophene, dibenzothiopyrrolyl, dimethyldibenzothiopyrrolyl, diphenyldibenzothiopyrrolyl, -O(Q) 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The at least one of the following selected: phenylene, naphthylene, anthraceneylene, phenanthrene, benzo[9,10]phenanthrene, pyreneylene, or phenylene oxide. alkyl, cyclopentadienyl, furanyl, thiopheneyl, thiopheneyl, indeneyl, fluoreneyl, indoleyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzothiopheneyl, dibenzothiopheneyl, azirmoneneyl, azirmonazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, pyridinyl, pyrimidinyl, pyrimidinyl Pyrazinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, quinoxalinyl, quinoxalinyl, phenanthrolineyl, pyrrolyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazoleyl, benzimidazoleyl, benzioxazolyl, benzioxadiazolyl, and benzioxadiazolyl.
[0222] Among them, Q4, Q5 and Q 31 To Q 33 They can all be independently selected from hydrogen, deuterium, and C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, and triazinyl are used, but the embodiments of this disclosure are not limited thereto.
[0223] For example, in equations 3-1 and 3-2, by The represented part can be a group represented by one of the formulas CY71-1(1) to CY71-1(8).
[0224] In equations 3-1 and 3-3, by The represented part can be a group represented by one of the formulas CY71-2(1) to CY71-2(8).
[0225] In equations 3-2 and 3-4, by The part represented can be a group represented by one of the formulas CY71-3(1) to CY71-3(32).
[0226] In equations 3-3 to 3-5, by The represented part can be a group represented by one of the formulas CY71-4(1) to CY71-4(32), and
[0227] In equation 3-5, by The represented part may be a group represented by one of the formulas CY71-5(1) to CY71-5(8), but the embodiments of this disclosure are not limited thereto:
[0228]
[0229]
[0230]
[0231]
[0232] In equations CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
[0233] X 81 To X 84 R 80 and R 84 Each can be independently identical to that described in this specification.
[0234] X 85 It can be a single bond, O, S, N(R) 85 ), B(R) 85 ), C(R 85a (R) 85b ) or Si(R 85a (R) 85b ),
[0235] X 86 It can be a single bond, O, S, N(R) 86 ), B(R) 86 ), C(R 86a (R) 86b ) or Si(R 86a (R) 86b ),
[0236] X in equations CY71-1(1) to CY71-1(8) and equations CY71-4(1) to CY71-4(32) 85 and X 86 Each of them is not a single key at the same time.
[0237] X 87 It can be a single bond, O, S, N(R) 87 ), B(R) 87 ), C(R 87a (R) 87b ) or Si(R 87a (R) 87b ),
[0238] X 88 It can be a single bond, O, S, N(R) 88 ), B(R) 88 ), C(R 88a(R) 88b ) or Si(R 88a (R) 88b ),
[0239] In one embodiment, X in formulas CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8) 87 and X 88 Each of them can be a single bond at the same time, and
[0240] R 85 To R 88 R 85a R 85b R 86a R 86b R 87a R 87b R 88a and R 88b They can all independently bind with R 81 The descriptions are the same.
[0241] In one or more embodiments, the second compound may be selected from compounds H2-1 to H2-64:
[0242]
[0243]
[0244]
[0245] In one or more embodiments, the third compound may be selected from compounds H3-1 to H3-28:
[0246]
[0247]
[0248] In one embodiment, the hole transport region may include a p-doped material having a lowest unoccupied molecular orbital (LUMO) energy level of less than -3.5 eV.
[0249] In one embodiment, the electron transport region 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.
[0250] In one embodiment, the emitting layer is a first color light emitting layer (e.g., the emitting layer emits light of the first color).
[0251] The organic light-emitting device may further include, between the first electrode and the second electrode: i) at least one second-color light-emitting layer (e.g., at least one emitting layer emitting light of a second color) or ii) at least one second-color light-emitting layer and at least one third-color light-emitting layer (e.g., at least one emitting layer emitting light of a third color).
[0252] The maximum emission wavelengths of the first color light, the second color light, and the third color light may be the same as or different from each other, and
[0253] The first color light and the second color light can be emitted in the form of a mixed light, or the first color light, the second color light and the third color light can be emitted in the form of a mixed light.
[0254] According to another embodiment, an electronic device including an organic light-emitting device is provided. The electronic device may also include a thin-film transistor. In one or more embodiments, the electronic device may further include a thin-film transistor comprising a source electrode and a drain electrode, and a first electrode of the organic light-emitting device may be electrically connected to the source electrode or the drain electrode.
[0255] In this embodiment, the electronic device may be a flat panel display device.
[0256] As used herein, the term "organic layer" refers to a single layer and / or all layers between the first and second electrodes of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0257] For example, an organic light-emitting device may have: i) a stacked structure comprising a first electrode, an organic layer, a second electrode, and a second capping layer stacked sequentially in the order stated therein; ii) a stacked structure comprising a first capping layer, a first electrode, an organic layer, and a second electrode stacked sequentially in the order stated therein; or iii) a stacked structure comprising a first capping layer, a first electrode, an organic layer, a second electrode, and a second capping layer stacked sequentially in the order stated therein, and at least one selected from the first capping layer and the second capping layer may comprise an organometallic compound.
[0258] The expression "(organic layer) includes at least one of organometallic compounds" as used herein can include cases where "(organic layer) includes the same organometallic compound represented by Formula 1" and cases where "(organic layer) includes two or more different organometallic compounds, all represented by Formula 1". That is, the organic layer can include one organometallic compound represented by Formula 1 or two or more different organometallic compounds, all represented by Formula 1.
[0259] For example, the organic layer may be an organometallic compound (e.g., formed of an organometallic compound) and may include only compound 1. In this embodiment, compound 1 may be included in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as organometallic compounds. In this embodiment, compound 1 and compound 2 may be included in the same layer (e.g., both compound 1 and compound 2 may be included in the emitting layer) or may be included in different layers (e.g., compound 1 may be included in the emitting layer and compound 2 may be included in the electron transport layer).
[0260] Figure 1 Description
[0261] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0262] In the following text, we will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiments and the method of manufacturing the organic light-emitting device 10 are described.
[0263] First electrode 110
[0264] exist Figure 1 In this process, the substrate can be located below the first electrode 110 or above the second electrode 190. The substrate can be a glass substrate or a plastic substrate, both of which have excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0265] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from materials with high work function to facilitate hole injection.
[0266] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be 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-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can 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.
[0267] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited to this.
[0268] Organic layer 150
[0269] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emitter layer.
[0270] The organic layer 150 may also include a hole transport region located between the first electrode 110 and the emitter layer and an electron transport region located between the emitter layer and the second electrode 190.
[0271] Hole transport region in organic layer 150
[0272] The hole transport region may have: i) a single-layer structure comprising a single material (e.g., composed of a single material); ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure comprising multiple layers of multiple different materials.
[0273] 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.
[0274] For example, the hole transport region can have a single-layer structure or a multi-layer structure. The single-layer structure includes a variety of different materials, and the multi-layer structure has 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. For each structure, the layers are sequentially stacked from the first electrode 110 in the order stated therein, but the structure of the hole transport region is not limited to this.
[0275] In one embodiment, the hole transport region may include 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 / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by Formula 201 below, and compounds represented by Formula 202 below:
[0276]
[0277] Formula 201
[0278]
[0279] Formula 202
[0280]
[0281] Among them, in equations 201 and 202,
[0282] L 201 To L 204 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-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0283] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0284] xa1 to xa4 can each be an independent integer from 0 to 3.
[0285] xa5 can be an integer from 1 to 10, and
[0286] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.
[0287] For example, in equation 202, R 201 and R 202 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene, and R 203 and R 204 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene.
[0288] In one embodiment, in equations 201 and 202,
[0289] L 201 To L 205 Each can be independently selected from:
[0290] Phenylidene, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, adafenyl, acenaphthene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenenyl, anthracene, fluorenyl, benzo[9,10]phenenyl, pyrene, phenylene alkyl, benzotetraphenyl, purylene, perylene, pentaphenylene, benzohexaphenylene, benzopentaphenylene, benzobenzyl, benzoylene, oleophylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzothiopheneyl, and pyridylene; and
[0291] All are substituted with groups ranging from 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, terphenyl, substituted with C1-C 10Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adaninylene, fluoreneylene, spirodifluoreneylene, benzo[9,10]fluoreneylene, dibenzo[9,10]fluoreneylene, phenanthroline, anthraceneylene, fluoranthroline, benzo[9,10]phenanthroline, pyreneylene, etc. alkyl, tetraphenyl, arbutinyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, rubidinyl, benzoyl, oleophyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridylyl.
[0292] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0293] In one or more embodiments, xa1 to xa4 can each be independently 0, 1 or 2.
[0294] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0295] In one or more embodiments, R 201 To R 204 and Q 201 All of these can be independently selected from phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoydinoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and
[0296] All are substituted with groups ranging from 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, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, cyclopentadienyl, indole, naphthyl, chamomilecycloyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.
[0297] Among them, Q 31 To Q 33 Each can be independently the same as the above.
[0298] In one or more embodiments, R from formula 201 201 To R 203 At least one of the selected items can be independently selected from:
[0299] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl; and
[0300] All are substituted with groups ranging from 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, terphenyl, substituted with C1-C 10 The alkyl group of phenyl, the phenyl group substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl are selected from at least one of the following: fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl.
[0301] However, the embodiments disclosed herein are not limited thereto.
[0302] In one or more embodiments, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204 They can be connected to each other via a single key.
[0303] In one or more embodiments, R in formula 202 201 To R 204 At least one of them can be selected from:
[0304] Carbazolyl; and
[0305] Substitutions include 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, terphenyl, substituted with C1-C 10 The carbazoyl group selected from at least one of the following: alkyl phenyl, phenyl substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazoyl, dibenzofuranyl, and dibenzothiopheneyl.
[0306] However, the embodiments disclosed herein are not limited thereto.
[0307] In one or more embodiments, the compound represented by formula 201 can be represented by the following formula 201A:
[0308] Formula 201A
[0309]
[0310] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A(1), but the embodiments of this disclosure are not limited thereto:
[0311] Formula 201A(1)
[0312]
[0313] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A-1, but the embodiments of this disclosure are not limited thereto:
[0314] Formula 201A-1
[0315]
[0316] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A:
[0317] Formula 202A
[0318]
[0319] In one or more embodiments, the compound represented by formula 202 can be represented by the following formula 202A-1:
[0320] Formula 202A-1
[0321]
[0322] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0323] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 They can be the same as those mentioned above.
[0324] R 211 and R 212 They can all independently bind with R 203 The descriptions are the same, and
[0325] R 213 To R 217 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, terphenyl, substituted with C1-C 10Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, furanyl, perylene, pentyranyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophenyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl, and pyridyl.
[0326] The hole transport region may include at least one compound selected from compounds HT1 to HT39, but the compounds to be included in the hole transport region are not limited to these:
[0327]
[0328]
[0329]
[0330] The thickness of the hole transport region can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the range. When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within a certain range, the thickness of the hole transport layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage when the hole transport region, hole injection layer, and hole transport layer thickness are all within these ranges.
[0331] The emission assist layer can improve luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can include the materials described above.
[0332] p-doped agent
[0333] In addition to these materials, the hole transport region may also include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.
[0334] The charge-generating material can be, for example, a p-doped agent.
[0335] In one embodiment, the lowest unoccupied molecular orbital (LUMO) level of the p-doped agent can be -3.5 eV or lower.
[0336] p-dopers may include at least one selected from quinone derivatives, metal oxides and cyano-containing compounds, but the embodiments of this disclosure are not limited thereto.
[0337] In one embodiment, the p-doper may include at least one selected from the following compounds:
[0338] Quinone derivatives, such as tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ);
[0339] Metal oxides, such as tungsten oxide and / or molybdenum oxide;
[0340] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and
[0341] The compound represented by the following formula 221,
[0342] However, the embodiments disclosed herein are not limited thereto:
[0343]
[0344] Equation 221
[0345]
[0346] In Equation 221,
[0347] R 221 To R 223 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 C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and from R 221To R 223 At least one of the selected groups may have a C1-C group substituted with cyano, -F, -Cl, -Br, -I, or -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and substituted C1-C groups with -I 20 At least one substituent selected from alkyl groups.
[0348] Emission layer in organic layer 150
[0349] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer according to the sub-pixels. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers may be in contact with each other or may be separated from each other. In one or more embodiments, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0350] The emitter layer may include an organometallic compound represented by Formula 1.
[0351] The emitting layer may include a host and a light-emitting material (or dopant). The light-emitting material may include at least one of phosphorescent dopant and fluorescent dopant.
[0352] Based on about 100 parts by weight of the body, the amount of dopant in the emitter layer can be in the range of about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.
[0353] In this embodiment, the emitting layer may emit blue light or blue-green light.
[0354] In one embodiment, the organometallic compound of the emitting layer can emit blue or blue-green light with a maximum emission wavelength in the range of 400 nm to 500 nm.
[0355] The thickness of the emission layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within these ranges, excellent light-emitting characteristics can be obtained without significantly increasing the driving voltage when the thickness of the emitting layer is within these ranges.
[0356] The main body in the emission layer
[0357] The main body may also include compounds represented by formula 301.
[0358] Formula 301
[0359] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0360] In Equation 301,
[0361] Ar 301 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0362] xb11 can be 1, 2, or 3.
[0363] L 301 It can be 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-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0364] xb1 can be an integer from 0 to 5.
[0365] R 301 It can be selected from 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, 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, substituted or unsubstituted C6-C 60Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -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 ),and
[0366] xb21 can be an integer from 1 to 5.
[0367] Among them, Q 301 To Q 303 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.
[0368] In one embodiment, Ar in formula 301 301 It can be selected from:
[0369] Naphthalene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indoxane groups, dibenzofuran groups, and dibenzothiophene groups; and
[0370] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, 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) 32The following groups are selected from at least one of the following groups: naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl group, furan group, perylene group, pentylenetetrazol group, indene-anthracene group, dibenzofuran group and dibenzothiophene group,
[0371] Among them, 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.
[0372] When xb11 in equation 301 is 2 or greater, two or more Ar 301 It can be connected via a single key.
[0373] In one or more embodiments, the compound represented by formula 301 may be represented by one of formulas 301-1 and 301-2:
[0374] Formula 301-1
[0375]
[0376] Formula 301-2
[0377]
[0378] In Equations 301-1 and 301-2,
[0379] A 301 To A 304 They can all be independently selected from benzene rings, naphthalene rings, phenanthrene rings, fluoranthene rings, benzo[9,10]phenanthrene rings, pyrene rings, Rings, pyridine rings, pyrimidine rings, indene rings, fluorene rings, spirobisfluorene rings, benzo[a]fluorene rings, dibenzo[a]fluorene rings, indole rings, carbazole rings, benzo[a]carbazole rings, dibenzo[a]carbazole rings, furan rings, benzo[a]furan rings, dibenzo[a]furan rings, naphtho[a]furan rings, benzo[a]naphtho[a]furan rings, dinaphtho[a]furan rings, thiophene rings, benzo[a]thiophene rings, dibenzo[a]thiophene rings, naphtho[a]thiophene rings, benzo[a]naphtho[a]thiophene rings, and dinaphtho[a]thiophene rings.
[0380] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0381] R 311 To R 314Each 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 ),
[0382] xb22 and xb23 can each be independently 0, 1, or 2.
[0383] L 301 xb1, R 301 and Q 31 To Q 33 Each can be independently identical to the above.
[0384] L 302 To L 304 They can all independently bind with L 301 The descriptions are the same.
[0385] xb2 to xb4 can all be independently identical to those described in conjunction with xb1, and
[0386] R 302 To R 304 They can all independently bind with R 301 The descriptions are the same.
[0387] For example, L in Equations 301, 301-1, and 301-2 301 To L 304 Each can be independently selected from:
[0388] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0389] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, 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) 32The following are selected from at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,
[0390] Among them, Q 31 To Q 33 Each can be independently the same as the above.
[0391] In one embodiment, R in Equations 301, 301-1, and 301-2 301 To R 304 Each can be independently selected from:
[0392] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0393] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, 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 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.
[0394] Among them, Q 31 To Q 33 Each can be independently the same as the above.
[0395] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55), Mg complexes, and Zn complexes.
[0396] The main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:
[0397]
[0398]
[0399]
[0400] Phosphorescent dopants in the emission layer of organic layer 150
[0401] Phosphorescent dopants may include organometallic compounds represented by Formula 1.
[0402] In addition, phosphorescent dopants may include organometallic complexes represented by the following formula 401:
[0403] Formula 401
[0404] M(L 401 ) xc1 (L 402 ) xc2
[0405] Formula 402
[0406]
[0407] In Equations 401 and 402,
[0408] M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm).
[0409] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.
[0410] L402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 can be 2 or greater, two or more L 402 They can be the same or different from each other.
[0411] X 401 To X 404 They can each be nitrogen or carbon independently.
[0412] X 401 and X 403 It can be connected via a single or double key, X 402 and X 404 It can be connected via a single key or a double key.
[0413] A 401 and A 402 Each can be independently C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0414] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *', where Q 411 and Q 412 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,
[0415] X 406 It can be a single bond, O, or S.
[0416] R 401 and R 402 Each group 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 60aryl, 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 nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed 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 ), and Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,
[0417] xc11 and xc12 can both be independent integers from 0 to 3.
[0418] In Equation 402, * and *' both represent the binding position with M in Equation 401.
[0419] In one embodiment, A in Equation 402 401 and A 402 They can all be independently selected from phenyl groups, naphthyl groups, fluorene groups, spirodifluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaloline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzooxazole groups, isobenzooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, dibenzofuran groups, and dibenzothiophene groups.
[0420] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, X 402 It can be carbon, or ii)X 401 and X 402 Both can be nitrogen.
[0421] In one or more embodiments, R in Formula 402 401 and R 402 Each can be independently selected from:
[0422] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0423] All are substituted with at least one of the following C1-C groups selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl. 20 Alkyl and C1-C 20 Alkoxy;
[0424] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;
[0425] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 The cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups; and
[0426] -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 );
[0427] Among them, Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.
[0428] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two A's in 401 Optionally via X as a linker 407 Connected to each other, two A's 402 Optionally via X as a linker 408 They are interconnected (see compounds PD1 through PD4 and PD7). X 407 and X 408 They can all be independent single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments disclosed herein are not limited thereto.
[0429] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The components may be selected from halogens, diketones (e.g., acetylacetone (compound)), carboxylic acids (e.g., pyridinecarboxylic acid (salt)), -C (=O), isonitriles, -CN and phosphorus-containing substances (e.g., phosphine or phosphorous acid (salt)), but the embodiments disclosed herein are not limited thereto.
[0430] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but the embodiments of this disclosure are not limited thereto:
[0431]
[0432] Fluorescent dopants in the emission layer
[0433] Fluorescent dopants may include organometallic compounds represented by Formula 1.
[0434] Fluorescent dopants may also include arylamine compounds or styreneamine compounds.
[0435] Fluorescent dopants may also include compounds represented by the following formula 501:
[0436] Formula 501
[0437]
[0438] In Equation 501,
[0439] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0440] 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-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0441] xd1 to xd3 can each be an independent integer from 0 to 3.
[0442] 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, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.
[0443] xd4 can be an integer from 1 to 6.
[0444] In one embodiment, Ar in Formula 501 501 It can be selected from:
[0445] Naphthyl group, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, and indene-phenanthrene groups; and
[0446] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 The naphthyl group selected from at least one of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, penfenol group, indene-anthracene group and indene-phenanthrene group.
[0447] In one or more embodiments, L in Formula 501 501 To L 503 Each can be independently selected from:
[0448] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, and pyridylene; and
[0449] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, The following are selected from at least one of the following groups: phenylene, perylene, pentofenyl, nehexaphenyl, nepentylphenyl, thiophenyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenolyl, and pyridyl; phenylene, naphthylene, fluoreneylene, spirodifluoreneyl, benzo[9,10]fluoreneyl, dibenzo[9,10]fluoreneyl, phenanthreneyl, anthraceneylene, fluorenyleneyl, benzo[9,10]phenanthreneyl, pyreneyleneyl, etc. The compounds are: alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzothiopheneyl, dibenzothiopheneyl, and pyridylene.
[0450] In one or more embodiments, R in Formula 501 501 and R 502 Each can be independently selected from:
[0451] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl; and
[0452] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, The following groups are listed: alkyl, peryl, pentyranyl, benzohexaphenyl, benzopentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.
[0453] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0454] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of this disclosure are not limited thereto.
[0455] For example, fluorescent dopants can be selected from compounds FD1 to FD22:
[0456]
[0457]
[0458]
[0459] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of this disclosure are not limited thereto:
[0460]
[0461] Electron transport region in organic layer 150
[0462] The electron transport region may have: i) a single-layer structure comprising a single material (e.g., composed of a single material); ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure comprising multiple layers of multiple different materials.
[0463] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the embodiments of this disclosure are not limited thereto.
[0464] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein, for each structure, the layers are stacked sequentially from the emitter layer in the order stated herein. However, embodiments of the electron transport region structure are not limited to these.
[0465] In one embodiment, the electron transport region may include a buffer layer that is in direct contact with the emission layer, and the buffer layer may include an organometallic compound of Formula 1 as described above.
[0466] In one or more embodiments, the electron transport region may include a buffer layer, an electron transport layer, and an electron injection layer stacked in that order from the emitter layer, and the buffer layer may include an organometallic compound of Formula 1 as described above.
[0467] In one or more embodiments, the electron transport region (e.g., a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-deficient nitrogen-containing ring (or “π-electron-depleted nitrogen-containing ring”).
[0468] "π-electron-poor nitrogen-containing rings" refer to C1-C rings with at least one *-N=*' moiety as the cyclic component. 60 Heterocyclic group.
[0469] For example, a "nitrogen-containing ring depleted of π electrons" 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 condensed together; or iii) at least one 5- to 7-membered heteromonocyclic group, each having at least one *-N=*' moiety, and at least one C5-C 60 Heterocyclic groups formed by the condensation of carbocyclic groups.
[0470] Examples of π-electron-depleted nitrogen-containing rings include, but are not limited to, imidazole rings, pyrazole rings, thiazole rings, isothiazole rings, oxazole rings, isoxazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, indazole rings, purine rings, quinoline rings, isoquinoline rings, benzo[a]quinoline rings, phthalazine rings, naphthidine rings, quinoxaline rings, quinazoline rings, cyclophosphine rings, phenanthridine rings, acridine rings, phenanthrene-rhein rings, phenazine rings, benzimidazole rings, isobenzo[a]thiazole rings, benzo[a]oxazole rings, isobenzo[a]oxazole rings, triazole rings, tetraazole rings, oxadiazole rings, triazine rings, thiadiazole rings, imidazo[a]pyridine rings, imidazo[a]pyrimidine rings, and azacarbazole rings.
[0471] For example, the electron transport region may include a compound represented by the following formula 601:
[0472] Formula 601
[0473] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ]xe21 .
[0474] In Equation 601,
[0475] Ar 601 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0476] xe11 can be 1, 2, or 3.
[0477] L 601 It can be 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-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0478] xe1 can be an integer from 0 to 5.
[0479] R 601 It can be 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, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0480] Q 601 To Q 603 Each can be independently C1-C10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0481] xe21 can be an integer from 1 to 5.
[0482] In one embodiment, xe11 numbers of Ar 601 R with xe21 numbers 601 At least one of them may include a nitrogen-containing ring that is π-electron depleted.
[0483] In one embodiment, Ar in Formula 601 601 It can be selected from:
[0484] Phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indoxanthracene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthidine groups, quinoxaloline groups, quinazolinoline groups, cyclophosphine groups, phenanthridine groups, acridine groups, phenanthrene-rhein groups, phenazine groups, benzimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups; and
[0485] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 The phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, selected from at least one of the following: Groups, tetraphenyl group, styrene group, perylene group, pentylenetetrazol group, indoxanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazolinoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzooxazole group, isobenzooxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group,
[0486] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0487] When xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.
[0488] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.
[0489] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:
[0490] Formula 601-1
[0491]
[0492] In Equation 601-1,
[0493] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,
[0494] L 611 To L 613 They can all independently bind with L 601 The descriptions are the same.
[0495] xe611 to xe613 can all be independently identical to those described in conjunction with xe1.
[0496] R 611 To R 613 They can all independently bind with R 601 The descriptions are the same, and
[0497] R 614 To R 616 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, and naphthyl.
[0498] In one embodiment, L in Equation 601 601 L in Equation 601-1 611 To L 613 Each can be independently selected from:
[0499] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0500] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazine The following are at least one of the following groups selected from: phenylene, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrynyl, phenanthrinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrynyl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthrynyl, pyreneylyl, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,
[0501] However, the embodiments disclosed herein are not limited thereto.
[0502] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each be independently 0, 1 or 2.
[0503] In one or more embodiments, R in Formula 601 601 R in equation 601-1 611 To R 613 Each can be independently selected from:
[0504] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0505] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalyl The phenyl, biphenyl, terphenyl, naphthinyl, quinoxalinyl, quinazolinyl, terazolinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0506] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0507] Among them, Q 601 and Q 602 Each can be independently the same as the above.
[0508] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:
[0509]
[0510]
[0511]
[0512]
[0513] In one or more embodiments, the electron transport region may 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.
[0514]
[0515] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can all be independently set to approximately [value missing]. to approximately Within a certain range, for example, in approximately to approximately Within these ranges, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without significantly increasing the driving voltage when the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within these ranges.
[0516] The thickness of the electron transport layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the aforementioned range, when the thickness of the electron transport layer is within this range, the electron transport layer can exhibit satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0517] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include metallic materials.
[0518] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may include metal ions selected from Li, Na, K, Rb, and Cs ions, while alkaline earth metal complexes may include metal ions selected from Be, Mg, Ca, Sr, and Ba ions. The ligands coordinated to the metal ions of the alkali metal or alkaline earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.
[0519] For example, metallic materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:
[0520]
[0521] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0522] The electron injection layer can have: i) a single-layer structure comprising a single material (e.g., composed of a single material); ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure comprising multiple layers comprising multiple different materials.
[0523] 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.
[0524] In an embodiment, the electron injection layer may include Li, Na, K, Rb, Cs, Mg, Ca, Er, Tm, Yb, or any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0525] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0526] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0527] The rare earth metal may be selected from Sc, Y, Ce, Tm, Yb, Gd, and Tb.
[0528] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.
[0529] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, and / or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0530] The alkaline earth metal compound may be selected from alkaline earth metal oxides (such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and / or Ba x Ca 1-x O(0 < x < 1)). In one embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.
[0531] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.
[0532] 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, 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, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments disclosed herein are not limited thereto.
[0533] 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 (e.g., it may 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 also include organic materials. When the electron injection layer further includes organic materials, 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 including organic materials.
[0534] The thickness of the electron injection layer can be approximately to approximately Within a certain range, for example, in approximately to approximately Within the above range, when the thickness of the electron injection layer is within the above range, the electron injection layer can have satisfactory electron injection characteristics without significantly increasing the driving voltage.
[0535] In this embodiment, the electron transport region of the organic light-emitting device 10 includes a buffer layer, an electron transport layer, and an electron injection layer, and
[0536] At least one of the electron transport layer and electron injection layer may comprise 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.
[0537] Second electrode 190
[0538] The second electrode 190 is located on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode, and the material used for the second electrode 190 can be any metal, alloy, conductive compound, or any combination thereof, all having low work functions.
[0539] 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 this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0540] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0541] Figures 2 to 4 Description
[0542] Figure 2 The organic light-emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are stacked sequentially in the order stated herein. Figure 3 The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 stacked sequentially in the order stated herein. Figure 4 The organic light-emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 stacked sequentially in the order stated herein.
[0543] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be combined by reference. Figure 1 Use the given description to understand.
[0544] In each of the organic light-emitting devices 20 and 40, the light generated in the emission layer of the organic layer can pass outward through the first electrode 110, which serves as a semi-transparent electrode or a transmissive electrode, and the first capping layer 210. In each of the organic light-emitting devices 30 and 40, the light generated in the emission layer of the organic layer of the organic layer 150 can pass outward through the second electrode 190, which serves as a semi-transparent electrode or a transmissive electrode, and the second capping layer 220.
[0545] The first capping layer 210 and the second capping layer 220 can improve the external luminescence efficiency based on the principle of constructive interference.
[0546] The first capping layer 210 and the second capping layer 220 can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or a composite capping layer including both organic and inorganic materials.
[0547] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may optionally be substituted with substituents comprising at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine compound.
[0548] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.
[0549] In the above text, it has already been combined Figures 1 to 4 An organic light-emitting device according to an embodiment has been described. However, the embodiments disclosed herein are not limited thereto.
[0550] Layers constituting hole transport regions, emission regions, and electron transport regions can be formed in a specific area using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodget (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0551] When forming layers constituting hole transport regions, emitter layers, and electron transport regions by vacuum deposition, by considering the compounds to be included in the layers to be formed and the structure of the layers to be formed, deposition temperatures of approximately 100°C to approximately 500°C and approximately 10 -8 To about 10 -3 The vacuum degree and about to approximately Vacuum deposition was performed at a deposition rate of [value missing].
[0552] When spin coating is used to form layers constituting hole transport regions, emitter layers, and electron transport regions, spin coating can be performed at coating speeds of about 2,000 rpm to about 5,000 rpm and heat treatment temperatures of about 80°C to about 200°C, taking into account the compounds to be included in the layers to be formed and the structure of the layers to be formed.
[0553] General definition of substituents
[0554] As used herein, the term "C1-C"60 "alkyl" refers to a straight-chain or branched monovalent group of an aliphatic saturated hydrocarbon having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is used in conjunction with the alkyl group. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.
[0555] As used herein, 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 middle or end of an alkyl group, non-limiting examples of which include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Divalent groups with the same structure as alkenyl groups.
[0556] As used herein, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 A hydrocarbon group having at least one carbon-carbon triple bond at the middle or end of an alkyl group, non-limiting examples of which include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in conjunction with this. 60 "Immyneyl" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.
[0557] As used herein, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.
[0558] As used herein, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also used. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.
[0559] As used herein, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 10 carbon atoms, with non-limiting examples including 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10"Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.
[0560] As used herein, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic; non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also used. 10 "Biopylidene alkenyl" refers to a group that has a similar structure to C3-C4. 10 A divalent group with the same structure as a cycloalkenyl group.
[0561] As used herein, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom, one to ten carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.
[0562] As used here, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and as used herein, "C6-C" 60 "Aryl" refers to a divalent group that has a carbocyclic aromatic system with 6 to 60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, fluorenyl, and... Base. When C6-C 60 Aryl and C6-C 60 When each aryl group comprises two or more rings, the two or more rings may be fused together. As used herein, the term "C7-C" is relevant. 60 "alkylaryl" refers to a substituted compound having at least one C1-C group. 60 C6-C of alkyl groups 60 Aryl.
[0563] As used herein, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. As used herein, the term "C1-C" is also relevant. 60"Hypo-aryl" refers to a divalent group having a heterocyclic aromatic system, wherein the heterocyclic aromatic system has at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings may condense together. As used herein, the term "C2-C" is relevant. 60 "alkyl heteroaryl" refers to a substance with at least one C1-C substituted group. 60 C1-C of alkyl 60 Mixed aromatic compounds.
[0564] As used here, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), as used herein in the term "C6-C 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).
[0565] As used herein, the term "monovalent nonaromatic condensation polycyclic group" refers to a monovalent group having two or more rings condensed together, with only carbon atoms (e.g., having 8 to 60 carbon atoms) as cyclic atoms, and lacking aromaticity throughout its molecular structure. Non-limiting examples of monovalent nonaromatic condensation polycyclic groups include fluorenyl and adamantyl. As used herein, the term "divalent nonaromatic condensation polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic condensation polycyclic group.
[0566] As used herein, the term "monovalent non-aromatic condensed heterocyclic group" refers to a monovalent group having two or more rings condensed together, at least one heteroatom selected from N, O, Si, P, and S as cyclic atoms in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and lacking aromaticity throughout its molecular structure. Non-limiting examples of monovalent non-aromatic condensed heterocyclic groups include carbazolyl and azadamaneyl. As used herein, the term "divalent non-aromatic condensed heterocyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic condensed heterocyclic group.
[0567] As used herein, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group consisting of 5 to 60 carbon atoms, with only carbon atoms as cyclic atoms. (C5-C)60 The carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. (C5-C) 60 The 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, depending on the connection to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon cyclic group can be a trivalent or tetravalent group.
[0568] As used herein, the term "C1-C" 60 A "heterocyclic group" refers to a group that, in addition to using at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom (excluding carbon, which can range from 1 to 60 carbon atoms), has a cyclic structure similar to C5-C6. 60 Groups with the same structure as carbocyclic groups.
[0569] In this specification, C5-C is replaced. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 20 Alkylene, substituted C2-C 20 alkenyl, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 At least one substituent among alkyl heteroaryl, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:
[0570] 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;
[0571] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -O(Q) 11 -S(Q) 11 ), -Si(Q 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0572] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;
[0573] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -O(Q) 21 -S(Q) 21 ), -Si(Q 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heterocyclic group; and
[0574] -O(Q 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),
[0575] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, substituted with deuterium, -F, cyano, C1-C 60 C1-C of at least one of alkyl, phenyl, and biphenyl 60 Alkyl groups and substitutions include deuterium, -F, cyano, C1-C 10 C6-C of at least one of alkyl, phenyl, and biphenyl 60 Aryl.
[0576] As used herein, the term "Ph" refers to phenyl, as used herein, the term "Me" refers to methyl, as used herein, the term "Et" refers to ethyl, and as used herein, the terms "tert-Bu" or "Bu" refer to... t "Refers to tert-butyl, as the term "OMe" used herein refers to methyl methacrylate (MMA).
[0577] As used herein, the term "biphenyl" refers to a phenyl group that has a substituted phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C bond. 60 Aryl groups are substituted phenyl groups.
[0578] As used herein, the term "terphenyl" refers to a phenyl group substituted with biphenyl groups. In other words, "terphenyl" is a phenyl group having C6-C substitutions. 60 C6-C of aryl 60 Aryl groups are substituted phenyl groups.
[0579] Unless otherwise defined, *, *' and *” as used herein refer to the binding site with the adjacent atom in the corresponding expression.
[0580] In the following description, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in more detail with reference to the synthesis examples and examples. The expression "using B instead of A" used in the description of the synthesis examples means using the same molar equivalent of B instead of the same molar equivalent of A.
[0581] Synthesis Example
[0582] Synthesis Example 1: (Synthesis of Compound 1)
[0583]
[0584] (1) Synthesis of intermediate 131
[0585] Starting materials 111 (20 g, 55.3 mmol), 121 (9.2 g, 36.9 mmol), Ba(OH)₂ (0.63 g, 3.69 mmol), Pd(PPh₃)₄ (4.26 g, 3.69 mmol), and Na₂CO₃ (5.86 g, 55.3 mmol) were mixed and dissolved in 1,4-dioxane / H₂O (300 mL / 70 mL), and the resulting mixture was heated at 100 °C for 12 hours. The reaction product was cooled, and then 1,4-dioxane was distilled under low pressure and extracted with ethyl acetate (EA) and H₂O. The product was eluted with EA and hexane (1:9) using silica gel chromatography to synthesize intermediate 131 (white solid, 12.7 g, 79% yield). 1 H NMR confirmed intermediate 131.
[0586] (2) Synthesis of intermediate 141
[0587] Intermediate 131 (10 g, 22.9 mmol), 5,6-dimethylbenzimidazole (3.04 g, 20.8 mmol), CuI, N,N-dimethylglycine, K3PO4, and dimethyl sulfoxide (DMSO) were mixed and stirred, and kept at 120 °C for 1 day (e.g., 24 hours). The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added to it. The mixture was filtered with alkali-activated alumina to synthesize intermediate 141 (beige solid).
[0588] (3) Synthesis of intermediate 151
[0589] Intermediate 141 (5 g, 10.2 mmol), benzimidazole (1.09 g, 9.27 mmol), CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed and stirred, and maintained at 120 °C for 2 days (e.g., 48 hours). The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. The mixture was purified with dichloromethane (DCM) / MeOH (20:1) to synthesize intermediate 151.
[0590] (4) Synthesis of intermediate 161
[0591] Intermediate 151 (3.0 g, 4.69 mmol) and iodomethane-d3 (1.75 mL, 28.1 mmol) were dissolved in toluene and stirred while refluxed at 120 °C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 161.
[0592] (5) Synthesis of intermediate 171
[0593] Intermediate 161 (1 g, 1.56 mmol), NaOAc (0.19 g, 2.34 mmol), and PtCl2 (0.46 g, 1.72 mmol) were mixed with a 1,4-dioxane solution, and the mixture was stirred and kept at 120 °C overnight. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 171.
[0594] (6) Synthesis of Compound 1
[0595] The mixture comprising intermediate 171 (0.6 g, 0.75 mmol) and AgCN (0.11 mmol) was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 1 (0.36 g, 0.45 mmol, 60% yield).
[0596] Synthesis Example 2: (Synthesis of Compound 2)
[0597]
[0598] (1) Synthesis of intermediate 152
[0599] Intermediate 141 (5 g, 10.2 mmol), imidazole (0.63 g, 9.27 mmol), CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed and stirred, and kept at 120 °C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. The mixture was filtered through alkali-activated alumina, and ethyl acetate was added to synthesize intermediate 152 (white solid).
[0600] (2) Synthesis of intermediate 162
[0601] Intermediate 152 (3.0 g, 6.11 mmol) and iodomethane-d3 (2.31 mL, 36.7 mmol) were dissolved in toluene and stirred while refluxed at 120 °C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 162.
[0602] (3) Synthesis of intermediate 172
[0603] Intermediate 162 (1.7 g, 1.56 mmol), NaOAc (0.19 g, 2.34 mmol), and PtCl2 (0.46 g, 1.72 mmol) were mixed with a 1,4-dioxane solution, and the mixture was stirred and kept at 120 °C overnight. After extraction with DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 172.
[0604] (4) Synthesis of Compound 2
[0605] The mixture comprising intermediate 172 (0.6 g, 0.75 mmol) and AgCN (0.11 mmol) was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 2 (0.36 g, 0.47 mmol, yield 62%).
[0606] Synthesis Example 3: (Synthesis of Compound 3)
[0607]
[0608] (1) Synthesis of intermediate 153
[0609] Intermediate 141 (5 g, 10.2 mmol), 4,5-dimethylimidazole (0.98 g, 10.2 mmol), CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed and stirred, and kept at 120 °C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. The mixture was filtered through alkali-activated alumina, and ethyl acetate was added to synthesize intermediate 153 (white solid).
[0610] (2) Synthesis of intermediate 163
[0611] Intermediate 153 (3.3 g, 6.36 mmol) and iodomethane-d3 (2.42 mL, 36.7 mmol) were dissolved in toluene and stirred while refluxed at 120 °C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 163.
[0612] (3) Synthesis of intermediate 173
[0613] Intermediate 163 (1.9 g, 2.37 mmol), NaOAc (0.21 g, 2.61 mmol), and PtCl2 (0.69 g, 2.61 mmol) were mixed with a 1,4-dioxane solution, and the mixture was stirred and kept at 120 °C overnight. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 173.
[0614] (4) Synthesis of compound 3
[0615] A mixture comprising intermediate 173 (0.82 g, 1.05 mmol) and AgCN (0.16 g, 1.16 mmol) was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 3 (0.55 g, 0.7 mmol, yield 67%).
[0616] Synthesis Example 4: (Synthesis of Compound 4)
[0617]
[0618] (1) Synthesis of intermediate 144
[0619] Intermediate 131 (10 g, 22.9 mmol), benzimidazole (2.46 g, 20.8 mmol), CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed and stirred, and kept at 120 °C for 1 day. The reaction product was cooled to room temperature, and dichloromethane was added. The mixture was filtered with alkali-activated alumina to synthesize intermediate 144 (beige solid).
[0620] (2) Synthesis of intermediate 154
[0621] Intermediate 144 (5 g, 10.5 mmol), imidazole (0.69 g, 10.2 mmol), CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed and stirred, and kept at 120 °C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Ethyl acetate was then added to obtain intermediate 154 (white solid).
[0622] (3) Synthesis of intermediate 164
[0623] Intermediate 154 (4 g, 8.65 mmol) and iodomethane-d3 (3.23 mL, 51.9 mmol) were dissolved in toluene and stirred while refluxed at 120 °C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 164.
[0624] (4) Synthesis of intermediate 174
[0625] Intermediate 164 (2 g, 2.68 mmol), NaOAc (0.24 g, 2.95 mmol), and PtCl2 (0.78 g, 2.95 mmol) were mixed with a 1,4-dioxane solution, and the mixture was stirred and kept at 120 °C overnight. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 174.
[0626] (5) Synthesis of compound 4
[0627] A mixture comprising intermediate 174 (0.93 g, 1.29 mmol) and AgCN (0.19 g, 1.42 mmol) was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 4 (0.63 g, 0.88 mmol, yield 68%).
[0628] Synthesis Example 5: (Synthesis of Compound 5)
[0629]
[0630] (1) Synthesis of intermediate 144
[0631] Intermediate 131, benzimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 1 day. The reaction product was cooled to room temperature, and dichloromethane was added. The mixture was filtered with alkali-activated alumina to synthesize intermediate 144 (beige solid).
[0632] (2) Synthesis of intermediate 155
[0633] Intermediate 144, 4,5-dimethylimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Ethyl acetate was then added to obtain intermediate 155 (white solid).
[0634] (3) Synthesis of intermediate 165
[0635] Intermediate 155 and iodomethane-d3 were dissolved in toluene, and the resulting mixture was stirred and kept under reflux at 120°C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 165.
[0636] (4) Synthesis of intermediate 175
[0637] Intermediate 165, NaOAc, and PtCl2 were mixed in a 1,4-dioxane solution and stirred overnight at 120°C. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 175.
[0638] (5) Synthesis of compound 5
[0639] The mixture comprising intermediate 175 and AgCN was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 5 (0.63 g, 0.84 mmol, yield 66%).
[0640] Synthesis Example 6: (Synthesis of Compound 7)
[0641]
[0642] (1) Synthesis of intermediate 147
[0643] Intermediate 131, 4,5-dimethylimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 1 day. The reaction product was cooled to room temperature, and dichloromethane was added. The mixture was filtered with alkali-activated alumina to synthesize intermediate 147 (beige solid).
[0644] (2) Synthesis of intermediate 157
[0645] Intermediate 147, imidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Diethyl ether / ethyl acetate was then added to obtain intermediate 157 (white solid).
[0646] (3) Synthesis of intermediate 167
[0647] Intermediate 157 and iodomethane-d3 were dissolved in toluene, and the resulting mixture was stirred and kept under reflux at 120°C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 167.
[0648] (4) Synthesis of intermediate 177
[0649] Intermediate 167, NaOAc, and PtCl2 were mixed in a 1,4-dioxane solution and stirred overnight at 120°C. After extraction using DCM / H2O, the mixture was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 177.
[0650] (5) Synthesis of compound 7
[0651] The mixture comprising intermediate 177 and AgCN was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 7 (0.65 g, 0.84 mmol, yield 65%).
[0652] Synthesis Example 7: (Synthesis of Compound 8)
[0653]
[0654] (1) Synthesis of intermediate 148
[0655] Intermediate 138, 5,6-dimethylbenzimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 1 day. The reaction product was cooled to room temperature, and dichloromethane was added. The mixture was filtered with alkali-activated alumina to synthesize intermediate 148 (beige solid).
[0656] (2) Synthesis of intermediate 158
[0657] Intermediate 148, benzimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Ethyl acetate was then added to obtain intermediate 158 (white solid).
[0658] (3) Synthesis of intermediate 168
[0659] Intermediate 158 and iodomethane-d3 were dissolved in toluene, and the resulting mixture was stirred and kept under reflux at 120°C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 168.
[0660] (4) Synthesis of intermediate 178
[0661] Intermediate 168, NaOAc, and PtCl2 were mixed in a 1,4-dioxane solution and stirred overnight at 120°C. After extraction with DCM / H2O, the mixture was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 178.
[0662] (5) Synthesis of compound 8
[0663] The mixture comprising intermediate 178 and AgCN was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 8 (0.66 g, 0.85 mmol, yield 66%).
[0664] Synthesis Example 8: (Synthesis of Compound 9)
[0665]
[0666] (1) Synthesis of intermediate 148
[0667] Intermediate 138, 5,6-dimethylbenzimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 1 day. The reaction product was cooled to room temperature, and dichloromethane was added. The mixture was filtered with alkali-activated alumina to synthesize intermediate 148 (beige solid).
[0668] (2) Synthesis of intermediate 159
[0669] Intermediate 148, imidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Ethyl acetate was then added to obtain intermediate 159 (white solid).
[0670] (3) Synthesis of intermediate 169
[0671] Intermediate 159 and iodomethane-d3 were dissolved in toluene, and the resulting mixture was stirred and kept under reflux at 120°C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 169.
[0672] (4) Synthesis of intermediate 179
[0673] Intermediate 169, NaOAc, and PtCl2 were mixed in a 1,4-dioxane solution and stirred overnight at 120°C. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 179.
[0674] (5) Synthesis of compound 9
[0675] The mixture comprising intermediate 179 and AgCN was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 9 (0.64 g, 0.84 mmol, yield 66%).
[0676] Synthesis Example 9: (Synthesis of Compound 15)
[0677]
[0678] (1) Synthesis of intermediate 1415
[0679] Intermediate 1315, 5,6-dimethylbenzimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 1 day. The reaction product was cooled to room temperature, and the DMSO solvent was distilled under reduced pressure. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:2) to obtain intermediate 1415.
[0680] (2) Synthesis of intermediate 1515
[0681] Intermediate 1415, benzimidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Diethyl ether was then added to obtain intermediate 1515 (white solid).
[0682] (3) Synthesis of intermediate 1615
[0683] Intermediate 1515 and iodomethane-d3 were dissolved in toluene, and the resulting mixture was stirred and kept under reflux at 120°C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 1615.
[0684] (4) Synthesis of intermediate 1715
[0685] Intermediate 1615, NaOAc, and PtCl2 were mixed in a 1,4-dioxane solution and stirred overnight at 120°C. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 1715.
[0686] (5) Synthesis of compound 15
[0687] The mixture comprising intermediate 1715 and AgCN was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 15 (0.63 g, 0.89 mmol, yield 69%).
[0688] Synthesis Example 10: (Synthesis of Compound 16)
[0689]
[0690] (1) Synthesis of intermediate 1516
[0691] Intermediate 1415 (as described in the synthesis of compound 15), imidazole, CuI, N,N-dimethylglycine, K3PO4, and DMSO were mixed, stirred, and kept at 120°C for 2 days. The reaction product was cooled to room temperature, and 150 mL of dichloromethane was added. Diethyl ether was then added to obtain intermediate 1516 (white solid).
[0692] (2) Synthesis of intermediate 1616
[0693] Intermediate 1516 and iodomethane-d3 were dissolved in toluene, and the resulting mixture was stirred and kept under reflux at 120°C for 24 hours. The precipitate was washed with diethyl ether and filtered to synthesize intermediate 1616.
[0694] (3) Synthesis of intermediate 1716
[0695] Intermediate 1616, NaOAc, and PtCl2 were mixed in a 1,4-dioxane solution and stirred overnight at 120°C. After extraction using DCM / H2O, it was purified by chromatography using DCM / hexane (1:4) to obtain intermediate 1716.
[0696] (4) Synthesis of compound 16
[0697] The mixture comprising intermediate 1716 and AgCN was stirred and kept in DCM overnight. AgCl was removed from it with diatomaceous earth / silica gel, and the filtrate was collected. The resulting product was concentrated to synthesize compound 16 (0.61 g, 0.85 mmol, yield 65%).
[0698] The compounds synthesized according to Synthetic Examples 1 to 10 1 ¹H NMR and MS / FAB analyses are shown in Table 1. By referring to the above synthetic routes and starting materials, those skilled in the art can readily achieve suitable compounds other than those shown in Table 1.
[0699] Table 1
[0700]
[0701]
[0702] Evaluation Example 1
[0703] The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of each of compounds 1 to 5, 7 to 9, 15 and 16 were evaluated according to the method in Table 2, and the results are shown in Table 3.
[0704] Table 2
[0705]
[0706]
[0707] Table 3
[0708] Compound No. HOMO (eV) LUMO (eV) 1 -5.23 -2.04 2 -5.26 -2.05 3 -5.11 -2.11 4 -5.30 -2.22 5 -5.21 -2.05 7 -5.24 -2.05 8 -5.22 -2.21 9 -5.24 -2.23 15 -5.21 -2.23 16 -5.21 -2.25
[0709] Table 3 shows that compounds 1 to 5, 7 to 9, 15 and 16 have HOMO and LUMO energy levels suitable for manufacturing organic light-emitting devices.
[0710] Example
[0711] Example 1
[0712] As the anode, it has a strength of 15 Ω / cm. 2 The ITO glass substrate was cut to a size of 50mm × 50mm × 0.7mm, ultrasonicated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrate was then loaded onto a vacuum deposition apparatus.
[0713] Vacuum deposition of 2-TNATA on the anode to form a structure with A hole injection layer of a certain thickness is formed, and NPB is vacuum-deposited on the hole injection layer to form a hole injection layer with a certain thickness. A hole transport layer of a certain thickness.
[0714] Compound 1 as a dopant and H2-2:H3-2 as the main mixture in a 5:5 weight ratio were co-deposited on the hole transport layer to form a structure with... A blue fluorescent emitting layer of a certain thickness is formed, wherein the weight ratio of dopant to the mixed host is 10:90, and the emitting layer is a blue fluorescent emitting layer. Subsequently, H2-2 is vacuum deposited on it to form a layer with... A hole-blocking layer of a certain thickness is then deposited. Alq3 is then deposited on the hole-blocking layer to form a structure with… An electron transport layer of a certain thickness is formed, and then LiF (LiF is an alkali halide metal) is deposited on the electron transport layer to form an electron transport layer with a certain thickness. An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited on it to form a layer with [missing information]. A thick Al electrode (cathode) is formed, which in turn forms a LiF / Al electrode, thus completing the fabrication of the organic light-emitting device.
[0715]
[0716] Examples 2 through 10, and comparative examples A and B
[0717] The organic light-emitting device is fabricated in the same manner as in Example 1, except that compounds 2 to 5, 7 to 9, 15, 16, A and B are co-deposited as dopants to form the emission layer.
[0718] Evaluation Example 2
[0719] Using a Keithley MU 236 and a PR650 luminance meter, the organic light-emitting devices fabricated according to Examples 1 to 10, as well as Comparative Examples A and B, were measured at 1000 cd / m². 2 Drive voltage (V), current density (mA / cm²) 2 ), luminous efficacy (cd / A), maximum emission wavelength (nm), and lifetime (T) 90 The results are shown in Table 4. In Table 4, lifetime (T) 90 ( ) is a measure of the time taken for the brightness to reach 90% of the initial brightness.
[0720] Table 4
[0721]
[0722]
[0723]
[0724]
[0725] Table 4 confirms that, compared with the organic light-emitting devices of Comparative Example A and Comparative Example B, the organic light-emitting devices of Examples 1 to 10 have superior driving voltage characteristics, current density characteristics, and luminous efficiency characteristics, and also have superior lifetime characteristics.
[0726] In view of the above, organometallic compounds can be used to manufacture organic light-emitting devices with excellent color purity and long lifespan, and these organic light-emitting devices can be used to manufacture high-quality electronic devices with excellent color purity and long lifespan.
[0727] When describing embodiments of the invention, the use of "may" refers to "one or more embodiments of the invention." Furthermore, the term "exemplary" is intended to indicate examples or illustrations. It will be understood that when an element or layer is referred to as being "on" another element or layer, "connected to," "bonded to," or "adjacent to" another element or layer, the element or layer may be directly on, directly connected to, directly bonded to, or directly adjacent to the other element or layer, or one or more intermediate elements or layers may be present. Conversely, when an element or layer is referred to as being "directly on" another element or layer, "directly connected to," "directly bonded to," or "directly adjacent to" another element or layer, no intermediate elements or layers are present.
[0728] As used herein, the terms “substantially,” “approximately,” and similar terms are used as approximations rather than terms of degree and are intended to describe inherent deviations in measured or calculated values that would be recognized by one of ordinary skill in the art. Furthermore, any numerical range stated herein is intended to include all subranges of the same numerical precision contained within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between the stated minimum value of 1.0 and the stated maximum value of 10.0 (and includes both the stated minimum value of 1.0 and the stated maximum value of 10.0), i.e., having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all smaller numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all larger numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly state any subranges contained within the ranges expressly stated herein. All these ranges are intended to be inherently described in this specification such that modifications to any of these expressly enumerated subranges will be deemed appropriate.
[0729] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.
Claims
1. An organometallic compound, said organometallic compound being represented by Formula 1: Formula 1 in, In Equation 1, M is platinum. L1 is a cyano group. Both Y1 and Y2 are C. Y3 is C, The bonds between Y1 and M, and between Y2 and M, are independently coordinate bonds, and the bonds between L1 and M, and between Y3 and M, are independently covalent bonds. Both ring CY1 and ring CY2 are independently selected from imidazole and benzimidazole groups. The CY3 ring is a phenyl group. R1 and R2 are both independently hydrogen, deuterium, methyl, ethyl, or propyl. R3 is a phenyl group substituted with at least one methyl, ethyl, or propyl group, wherein the at least one methyl, ethyl, or propyl group is substituted at least at the ortho position of the binding site with ring CY3. a1 and a2 are both independent integers from 0 to 5. a3 is 1. Depend on The group represented and composed of The groups represented are different from each other. Depend on The group represented is a group represented by one of formulas CY1-4 and CY1-24: Depend on The group represented is a group represented by one of formulas CY2-4 and CY2-24: R in formulas CY1-4 and CY1-24 11 To R 15 Similar to the description in combination with R1, R in formulas CY2-4 and CY2-24 21 To R 25 Similar to the description in combination with R2, * indicates the binding bit with M in Equation 1, and *' and *" both indicate the binding bit with ring CY3 in Equation 1.
2. The organometallic compound according to claim 1, wherein, Ring CY1 is different from ring CY2.
3. The organometallic compound according to claim 1, wherein, Ring CY1 is the same as ring CY2. a1 and a2 are both independent integers from 1 to 5, and One R1 of a1 numbers in R1 and one R2 of a2 numbers in R2 are different from each other.
4. The organometallic compound according to claim 1, wherein, The organometallic compounds represented by Formula 1 are selected from compounds 1 to 21:
5. An organic light-emitting device, the organic light-emitting device comprising: First electrode; The second electrode faces the first electrode; as well as An organic layer, located between the first electrode and the second electrode, includes an emission layer. The organic layer comprises at least one organometallic compound represented by Formula 1: Formula 1 In Equation 1, M is platinum. L1 is a cyano group. Both Y1 and Y2 are C. Y3 is C, The bonds between Y1 and M, and between Y2 and M, are coordinate bonds, while the bonds between L1 and M, and between Y3 and M, are covalent bonds. Both ring CY1 and ring CY2 are independently selected from imidazole and benzimidazole groups. The CY3 ring is a phenyl group. R1 and R2 are both independently hydrogen, deuterium, methyl, ethyl, or propyl. R3 is a phenyl group substituted with at least one methyl, ethyl, or propyl group, wherein the at least one methyl, ethyl, or propyl group is substituted at least at the ortho position of the binding site with ring CY3. a1 and a2 are both independent integers from 0 to 5. a3 is 1. Depend on The group represented and composed of The groups represented are different from each other. Depend on The group represented is a group represented by one of formulas CY1-4 and CY1-24: Depend on The group represented is a group represented by one of formulas CY2-4 and CY2-24: R in formulas CY1-4 and CY1-24 11 To R 15 Similar to the description in combination with R1, R in formulas CY2-4 and CY2-24 21 To R 25 Similar to the description in combination with R2, * indicates the binding bit with M in Equation 1, and *' and *" both indicate the binding bit with ring CY3 in Equation 1.
Citation Information
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