Organometallic compound and organic light emitting device including the same
By using the organometallic compound represented by Formula 1 as the emission layer material, the problems of low blue light emission efficiency and short lifespan of existing organic light-emitting devices are solved, achieving high-efficiency blue light emission and improved device performance.
Patent Information
- Application Number
- CN202110047661.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-01-14
- Filing Date
- 2021-01-14
- Publication Date
- 2025-12-30
- Estimated Expiration
- 2041-01-14
AI Technical Summary
Existing organic light-emitting devices suffer from low efficiency and short lifespan when emitting blue light, especially due to the inadequate performance of the materials used in the emitting layer.
Organometallic compounds represented by Formula 1 are used as emission layer materials, including platinum (Pt) or palladium (Pd) as M1, iridium (Ir), ruthenium (Ru) or osmium (Os) as M2, and specific carbocyclic groups and heterocyclic groups are combined to form an emission layer with excellent performance.
It improves the luminous efficiency and lifetime of the blue light emitting layer, achieves high-efficiency blue light emission in the 400nm to 500nm range, and enhances the overall performance of organic light-emitting devices.
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Figure CN113121611B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0004944, filed on January 14, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The embodiments relate to organometallic compounds and organic light-emitting devices including the same. Background Technology
[0004] Compared with devices in the field, organic light-emitting devices are self-emitting devices that generate full-color images, and also have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] An organic light-emitting device may include a first electrode disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied from the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) recombine in the emitter layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the Invention
[0006] Novel organometallic compounds and organic light-emitting devices incorporating them are provided.
[0007] The implementation methods will be set forth in part in the description which follows, and will be apparent in part from the description, or may be learned by practicing the embodiments of this disclosure.
[0008] In the embodiments, organometallic compounds represented by Formula 1 are provided.
[0009] <Formula 1>
[0010]
[0011] In Equation 1,
[0012] M1 and M2 can be independently selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).
[0013] A1 to A4 and B1 to B4 can each be independently selected from substituted or unsubstituted C5-C. 60 Carbocyclic groups and substituted or unsubstituted C1-C60 Heterocyclic groups,
[0014] X 11 To X 16 Each can be independently C or N.
[0015] Y 10 Y 11 Y 12 Y 20 Y 21 Y 30 Y 31 Y 32 Y 40 Y 41 Y 50 Y 51 Y 60 Y 61 Y 70 Y 71 Y 80 and Y 81 Each can be independently C or N.
[0016] T1 can be selected from single bonds, *-O-*', *-S-*', *-C(R1)(R2)-*', *-C(R1)=*', *=C(R1)-*', *-C(R1)=C(R2)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R1)-*', *-N(R1)-*', *-P(R1)-*', *-Si(R1)(R2)-*', *-P(=O)(R1)-*', and *-Ge(R1)(R2)-*'.
[0017] R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 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-C10 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),
[0018] Choose freely from R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Two or more adjacent substituents in the group may optionally be linked together to form substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0019] a10, a20, a30, a40, a50, a60, a70, and a80 can each be an integer selected from 1 to 8 independently.
[0020] * and *' each indicate the binding site with the adjacent atom, and
[0021] Replacement C5-C 60 Carbocyclic groups, substituted C1-C 60 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 C6-C60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 The at least one substituent of the heteroaryl thio group, the substituted monovalent nonaromatic fused polycyclic group, and the substituted monovalent nonaromatic fused 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] Each is selected from at least one of the following C1-C substituted 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 ),
[0024] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups.
[0025] Each is substituted by at least one of the following 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 ),as well as
[0026] -Si(Q31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),
[0027] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.
[0028] In an embodiment, the organic light-emitting device may include: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes an organometallic compound.
[0029] In this embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer disposed between the first and second electrodes may further include a hole transport region disposed between the first electrode and the emitter layer, and an electron transport region disposed between the emitter layer and the second electrode. The hole transport region may include at least one selected from the group consisting of a hole injection layer, a hole transport layer, an emitter auxiliary layer, and an electron blocking layer. The electron transport region may include at least one selected from the group consisting of a hole blocking layer, an electron transport layer, and an electron injection layer.
[0030] In some embodiments, the emitter layer may include an organometallic compound.
[0031] In one embodiment, the emitting layer may emit blue light with a maximum emission wavelength of about 400 nm to about 500 nm.
[0032] In an implementation, the emitter layer may include a host and a dopant, and the dopant may include an organometallic compound.
[0033] In one embodiment, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of less than about -3.5 eV.
[0034] In an embodiment, the electron transport region may include an electron transport layer and an electron injection layer, and at least one of the electron transport layer and the electron injection layer may further include at least one selected from the group consisting 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, and rare earth metal complexes. Attached Figure Description
[0035] The above and other aspects, features and advantages of the embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings.
[0036] Figures 1 to 4 Each is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. Detailed Implementation
[0037] The embodiments will now be described in detail with reference to the accompanying drawings, examples of which are illustrated. In this regard, embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, embodiments are described below with reference to the figures to explain various aspects of the invention.
[0038] The same reference numerals refer to the same elements throughout the drawings. In the drawings, the dimensions of the structures have been enlarged for clarity. It will be understood that although the terms first, second, etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. Therefore, without departing from the teachings of the invention, a first element may be referred to as a second element. Similarly, a second element may be referred to as a first element. As used herein, the singular forms are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0039] As used herein, for the purposes of its meaning and interpretation, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Throughout this disclosure, the expression “at least one of a, b, and c” indicates 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. For example, “A and / or B” can be understood to mean either A and B or A and B. The terms “and” and “or” can be used in a connecting or separating sense and can be understood as equivalent to “and / or”.
[0040] For the purposes of its meaning and interpretation, the phrase "at least one" is intended to include the meaning of "at least one selected from a group consisting of...". For example, "at least one of A and B" can be understood to mean A, B, or A and B. When preceding a list of elements, the term "at least one" modifies the entire list of elements rather than a single element in that list.
[0041] It will be further understood that the terms “comprises,” “comprising,” “includes,” and / or “including,” when used in this specification, indicate the presence of the stated features, figures, steps, operations, elements, components, or combinations thereof, but do not exclude the presence or addition of one or more other features, figures, steps, operations, elements, components, or combinations thereof.
[0042] It will be further understood that when a layer, film, region, plate, etc., is referred to as being "on" or "above" another component, it can be directly on the other component, or there may be intermediate elements present. It will also be understood that when a layer, film, region, plate, etc., is referred to as being "below" or "under" another component, it can be directly below the other component, or there may be intermediate elements present. When an element is referred to as being disposed on another element, it can be disposed below the other element.
[0043] For ease of description, spatial relative terms such as “below,” “under,” “down,” “above,” or “on” may be used herein to describe the relationship between one element or component and another element or component as shown in the accompanying drawings. It will be understood that spatial relative terms are intended to cover different orientations of the apparatus in use or operation other than those depicted in the accompanying drawings. For example, in cases where the apparatus shown in the accompanying drawings is flipped, the apparatus located “below” or “under” another apparatus may be placed “on top” of the other apparatus. Therefore, the descriptive term “below” may include both lower and upper positions. The apparatus may also be oriented in other directions, and thus the spatial relative terms may be interpreted differently depending on the orientation.
[0044] Unless otherwise specified, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should be further understood that terms (such as those defined in a common dictionary) shall be interpreted as having the meaning consistent with their meaning in the context of the relevant field and shall not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.
[0045] This disclosure provides organometallic compounds represented by the following formula 1:
[0046] <Formula 1>
[0047]
[0048] In Formula 1, M1 and M2 can be independently selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).
[0049] According to the implementation method, M1 can be Pt or Pd. For example, M1 can be Pt. For example, M1 can be Pd.
[0050] According to the implementation method, M2 can be selected from Rh, Ir, Os, and Ru. For example, M2 can be Ir.
[0051] In Formula 1, A1 to A4 and B1 to B4 can each be independently selected from substituted or unsubstituted C5-C. 60 Carbocyclic groups and substituted or unsubstituted C1-C 60 Heterocyclic groups.
[0052] In the embodiments, A1 to A4 and B1 to B4 may each be independently selected from phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, furanyl, thiopheneyl, thiopheneyl, indoleyl, fluorenyl, indoleyl, carbazoleyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzothiopheneyl, dibenzothiopheneyl, indoleylpyridinyl, indoleylpyridinyl, benzofuranylpyridinyl, benzothiopheneylpyridinyl, benzothiopheneylpyridinyl, dihydropyridinyl, pyridinyl, pyrimidinyl, and pyrazinyl. , pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrene-rholineyl, pyrrolyl, pyrazolyl, imidazoleyl, 2,3-dihydroimidazolyl, triazolyl, 2,3-dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, 2,3-dihydrobenzimidazolyl, imidazopyridyl, 2,3-dihydroimidazopyridyl, imidazopyrimidinyl, 2,3-dihydroimidazopyrimidinyl, imidazopyrazinyl, 2,3-dihydroimidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl and 5,6,7,8-tetrahydroquinolinyl.
[0053] According to the implementation method, A1 to A4 and B1 to B4 can each be independently selected from one of the groups represented by formula 2-1 to formula 2-43.
[0054]
[0055]
[0056]
[0057] In equations 2-1 to 2-43,
[0058] X 21 To X 23 Each can be independently selected from C(Z) 24 ) and C-*, where selected from X 21 To X 23 At least two of them can be C-*.
[0059] X 24 It can be N-*, and X 25 and X 26 Each can be independently selected from C(Z) 24 ) and C-*, where selected from X 25 and X 26 At least one of them can be C-*.
[0060] X 27 and X 28 Each can be independently selected from N, N(Z) 25 ) and N-*, and X 29 Optional from C(Z) 24 ) and C-*, where i) is selected from X 27 and X 28 At least one of them is N-* and X 29 For C-*, or ii)X 27 and X 28 Each can be N-* and X 29 It can be C(Z) 24 ),
[0061] Z 21 To Z 25 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0062] Each is selected from at least one of the following C1-C substituted 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl;
[0063] Phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], carbazole, acridineyl, dibenzofuranyl, dibenzothiophenyl, benzo[carbazole], and dibenzo[carbazole]; and
[0064] Each of the following substituted phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azyl, indole, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], carbazole, acridineyl, dibenzofuranyl, dibenzothiophenyl, benzo[carbazole], and dibenzo[carbazole]: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, and biphenyl
[0065] c21 can be an integer selected from 1 to 3.
[0066] c22 can be an integer selected from 1 to 5.
[0067] c23 can be an integer selected from 1 to 4.
[0068] c24 can be 1 or 2, and
[0069] * Indicates the binding site with adjacent atoms.
[0070] According to the implementation method, B1 to B4 can each be independently a group represented by one of Formula 3-1 and Formula 3-2:
[0071]
[0072] In equations 3-1 and 3-2,
[0073] X 31 To X 36 Each can be independently represented as C(Z) 32 ) or N,
[0074] Z 31 and Z 32 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0075] Each is selected from at least one of the following C1-C substituted 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl;
[0076] Phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], carbazole, acridineyl, dibenzofuranyl, dibenzothiophenyl, benzo[carbazole], and dibenzo[carbazole]; and
[0077] Each of the following substituted phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azyl, indole, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], carbazole, acridineyl, dibenzofuranyl, dibenzothiophenyl, benzo[carbazole], and dibenzo[carbazole]: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, and biphenyl, and
[0078] * and *' each indicate the binding site with the adjacent atom.
[0079] According to the embodiments, A1 to A4 and B1 to B4 may each be independently selected from phenyl, pyridyl, imidazolyl, 2,3-dihydroimidazolyl, imidazopyrimidinyl and benzimidazolyl.
[0080] For example, A1 to A4 can each be independently selected from phenyl and pyridinyl. In embodiments, B1 to B4 can each be independently selected from imidazolyl, 2,3-dihydroimidazolyl, imidazopyrimidinyl, and benzimidazolyl.
[0081] X in Equation 1 11 To X 16 Each can be either C or N independently.
[0082] According to the implementation method, X 11 To X 16 Each can be C.
[0083] Y in Equation 1 10 Y 11 Y 12 Y 20 Y 21 Y 30 Y 31 Y 32 Y 40 Y 41 Y 50 Y 51 Y 60 Y 61 Y 70 Y 71 Y 80 and Y 81 Each can be either C or N independently.
[0084] M1 and X 11 The key between M1 and Y 10 The key between M1 and Y 50 The key between M1 and Y 60 The bonds between them can be either covalent or coordinate bonds, each independently.
[0085] According to the implementation method, M1 and X 11 The key between M1 and Y 10 The key between M1 and Y 50 The key between M1 and Y 60 Two of the bonds between them can be covalent bonds, and the other two bonds can be coordinate bonds.
[0086] For example, M1 and X 11 The bond between M1 and Y can be a covalent bond. 10 The bond between M1 and Y can be a covalent bond. 50 The bond between them can be a coordinate bond, and M1 and Y 60 The bond between them can be a coordinate bond.
[0087] M2 and X 14 The bond between M2 and Y 20The bond between M2 and Y 30 The bond between M2 and Y 40 The bond between M2 and Y 70 The key between M2 and Y 80 The bonds between them can be either covalent or coordinate bonds, each independently.
[0088] According to the implementation method, M2 and X 14 The bond between M2 and Y 20 The bond between M2 and Y 30 The bond between M2 and Y 40 The bond between M2 and Y 70 The key between M2 and Y 80 Three of the bonds between them can be covalent bonds, and the other three bonds can be coordinate bonds.
[0089] For example, M2 and X 14 The bond between M2 and Y can be a covalent bond. 20 The bond between M2 and Y can be a covalent bond. 30 The bond between them can be a coordinate bond, M2 and Y 40 The bond between M2 and Y can be a covalent bond. 70 The bond between them can be a coordinate bond, and M2 and Y 80 The bond between them can be a coordinate bond.
[0090] According to the implementation method, M1 and X 11 The key between M1 and Y 10 The key between M1 and Y 50 The key between M1 and Y 60 Two of the bonds between M2 and X are covalent bonds, and the other two are coordinate bonds. 14 The bond between M2 and Y 20 The bond between M2 and Y 30 The bond between M2 and Y 40 The bond between M2 and Y 70 The key between M2 and Y 80 Three of the bonds between the molecules can be covalent, and the other three can be coordinate. Therefore, organometallic compounds do not exist in salt form, including cations and anions, and can be electrically neutral.
[0091] In Equation 1, T1 can be selected from single bond, *-O-*', *-S-*', *-C(R1)(R2)-*', *-C(R1)=*', *=C(R1)-*', *-C(R1)=C(R2)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R1)-*', *-N(R1)-*', *-P(R1)-*', *-Si(R1)(R2)-*', *-P(=O)(R1)-*', and *-Ge(R1)(R2)-*'.
[0092] According to the implementation method, T1 can be selected from single bond, *-O-*', *-S-*', *-N(R1)-*', *-C(R1)(R2)-*', *-Si(R1)(R2)-*' and *-B(R1)-*'.
[0093] According to the implementation method, T1 can be selected from *-O-*' and *-S-*'. For example, T1 can be *-O-*'. In the implementation method, T1 can be *-S-*'.
[0094] In Equation 1, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 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 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2).
[0095] According to the implementation method, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0096] Each is selected from at least one of the following C1-C substituted 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl;
[0097] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, indole-enyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentaphenyl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isoindoleyl, indazolyl, purineyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenanthridineyl Azinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiopyrrolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiopyrrolyl, benzocarbazoleyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothiopyrrolyl, dibenzo benzo[carbazolyl], dinaphthofuranyl, dinaphthothienyl, dinaphthothiolyl, imidazo[pyridyl], imidazo[pyrimidinyl], oxazolo[pyridyl], thiazo[pyridyl], benzo[naphridyl], azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzo[thienyl], azadibenzo[thiolyl], indole[pyridyl], indole[carbazolyl] and indole[carbazolyl];
[0098] Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranthryl, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentaphenyl, pyrroleyl, thiopheneyl, furfural. yl, thiolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isindoleyl, indazoleyl, purineyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, phenanthridineyl, acridineyl, phenanthroxalinyl, phenazinyl, benzyl Imidazolyl, benzofuranyl, benzothiophenel, benzothiopyrrolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazolel, dibenzofuranyl, dibenzothiophenel, dibenzothiopyrrolyl, benzocarbazolel, naphthobenzofuranyl, naphthobenzothiophenel, naphthobenzothiopyrrolyl, dibenzocarbazolel, dinaphthofuranyl, di Naphthothienyl, dinaphthothiol, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphridyl, azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiol, indolepyrrolyl, indolepyrrolyl, indolecarbazolyl and indolecarbazolyl: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentaphenyl, pyrroleyl, thiopheneyl, furanyl, thiopheneyl Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indoleyl, isindoleyl, indazolyl, purineyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, phenazinyl, acridineyl, phenanthrolineyl, phenazine Benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazoleyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiolyl, benzocarbazoleyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothiolyl, dibenzocarbazole , dinaphthofuranyl, dinaphthothienyl, dinaphthothiolyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphridyl, azafluorenyl, azaspiro-difluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiolyl, indolepyrrolyl, indolepyrrolyl, indolepyrrolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) and -P(=S)(Q 31 (Q) 32 );as well as
[0099] -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),
[0100] Among them, Q1 to Q3 and Q 31 To Q33 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 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, C1-C groups substituted with at least one of deuterium, -F, and cyano groups 60 Alkyl group, C6-C group substituted with at least one of deuterium, -F and cyano groups 60 Aryl, biphenyl, and terphenyl.
[0101] According to the implementation method, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0102] Each is selected from at least one of the following C1-C substituted 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl; and
[0103] A group represented by one of formulas 5-1 to 5-26 and 6-1 to 6-55:
[0104]
[0105]
[0106]
[0107] In equations 5-1 to 5-26 and equations 6-1 to 6-55,
[0108] X 51 and X 52 Each can be independently represented as O, S, C(Z) 53 (Z) 54 ), N(Z 53 ) or Si(Z 53 (Z) 54 ),
[0109] Z 51 To Z 54 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 alkenyl, C1-C 20 alkynyl group, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, phenanthryl, anthraceneyl, triphenylene, pyridyl, pyrimidinyl, carbazoleyl, and triazineyl.
[0110] e2 can be 1 or 2.
[0111] e3 can be an integer selected from 1 to 3.
[0112] e4 can be an integer selected from 1 to 4.
[0113] e5 can be an integer selected from 1 to 5.
[0114] e6 can be an integer selected from 1 to 6.
[0115] e7 can be an integer selected from 1 to 7.
[0116] e9 can be an integer selected from 1 to 9, and
[0117] * Indicates the binding site with adjacent atoms.
[0118] According to the implementation method, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0119] Each is selected from at least one of the following C1-C substituted20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl;
[0120] Phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azyl, indoleyl, acenaphthyl, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], carbazole, acridineyl, dibenzofuranyl, dibenzothiophenyl, benzo[carbazole], and dibenzo[carbazole]; and
[0121] Each of the following substituted phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azyl, indole, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], carbazole, acridineyl, dibenzofuranyl, dibenzothiophenyl, benzo[carbazole], and dibenzo[carbazole]: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, and biphenyl.
[0122] According to the implementation method, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkyl group.
[0123] Choose R1, R2, and R from free form 1. 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Two or more adjacent substituents in the group may optionally be linked together to form substituted or unsubstituted C5-C. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups.
[0124] According to the implementation method, R1, R2, and R are selected. 10 R 20 R 30 R 40 R 50 R 60 R 70 and R80 Two or more adjacent substituents in the group may optionally be linked together to form a group selected from any one of the following: cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazine, and carbazole; and
[0125] Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazine, and carbazole: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, and biphenyl.
[0126] According to the implementation method, R1, R2, and R are selected. 10 R 20 R 30 and R 40 Two or more adjacent substituents in the group may optionally be linked together to form cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazine, or carbazolyl.
[0127] According to the implementation method, R1, R2, and R are selected. 10 R 20 R 30 and R 40 Two or more adjacent substituents in the group may optionally be linked together to form phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazine, or carbazolyl.
[0128] In Equation 1, a10, a20, a30, a40, a50, a60, a70, and a80 can each be an integer selected from 1 to 8 independently.
[0129] According to the embodiments, organometallic compounds can be represented by Formula 2:
[0130] <Formula 2>
[0131]
[0132] In Equation 2,
[0133] Y 23 It can be C(R) 23 ) or N,
[0134] Y 43 It can be C(R) 43 ) or N,
[0135] R 11 To R 13 It can be combined with R in Formula 1 10 The descriptions are the same.
[0136] R 21 To R 24 It can be combined with R in Formula 1 20 The descriptions are the same.
[0137] R 31 To R 33 It can be combined with R in Formula 1 30 The descriptions are the same.
[0138] R 41 To R 44 It can be combined with R in Formula 1 40 The descriptions are the same.
[0139] R 51 To R 53 It can be combined with R in Formula 1 50 The descriptions are the same.
[0140] R 61 To R 63 It can be combined with R in Formula 1 60 The descriptions are the same.
[0141] R 71 To R 73 It can be combined with R in Formula 1 70 The descriptions are the same, and
[0142] R 81 To R 83 It can be combined with R in Formula 1 80 The descriptions are the same.
[0143] According to the embodiments, the organometallic compound represented by Formula 1 may be selected from compounds BD1 to BD21, but the embodiments are not limited to these:
[0144]
[0145]
[0146]
[0147] Organometallic compounds represented by Formula 1 contain two metal atoms, and ligands coordinated to these metal atoms are interconnected, thus providing excellent molecular stability due to their rigid structure. In organometallic compounds represented by Formula 1, the formation of excited-state molecules is suppressed due to the structure in which the angles of the ligands are tilted relative to the metal atoms. Therefore, the efficiency and lifetime of organic light-emitting devices using organometallic compounds can be improved.
[0148] Organometallic compounds can emit blue light. For example, organometallic compounds can emit blue light with a maximum emission wavelength of about 400 nm to about 500 nm. For example, the maximum emission wavelength can be about 440 nm to about 470 nm (0.05 CIE). x,y (Color coordinates), but the implementation is not limited to this. Therefore, the organometallic compound represented by Formula 1 can be used in the manufacture of organic light-emitting devices.
[0149] The method for synthesizing the organometallic compounds represented by Formula 1 can be recognized by those skilled in the art by referring to the examples provided below.
[0150] At least one of the organometallic compounds represented by Formula 1 can be used between a pair of electrodes in an organic light-emitting device. For example, the organometallic compound can be included in the emitting layer. The organometallic compound included in the emitting layer can act as a dopant. In an embodiment, the organometallic compound of Formula 1 can be used as a material for a capping layer located outside a pair of electrodes in an organic light-emitting device.
[0151] This disclosure provides an organic light-emitting device that may include: a first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode; and at least one organometallic compound represented by Formula 1. For example, the organic layer includes at least one organometallic compound.
[0152] The expression “(organic layer) includes at least one of organometallic compounds” as used herein may 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 represented by Formula 1”.
[0153] For example, the organic layer may include an organometallic compound, and may include only compound 1 as an organometallic compound. In this regard, compound 1 may be present only in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as organometallic compounds. In this regard, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer) or in different layers (e.g., compound 1 may be present in the emitting layer and compound 2 may be present in the electron transport region).
[0154] In the implementation,
[0155] The first electrode of an organic light-emitting device can be the anode.
[0156] The second electrode of an organic light-emitting device can be a cathode, and
[0157] The organic layer may further include a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode.
[0158] The hole transport region may include at least one selected from the group consisting of a hole injection layer, a hole transport layer, an emission assist layer, and an electron blocking layer, and
[0159] The electron transport region may include at least one selected from the group consisting of a hole blocking layer, an electron transport layer, and an electron injection layer.
[0160] 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. The materials included in the "organic layer" are not limited to organic materials.
[0161] In an embodiment, the emitter layer may include an organometallic compound represented by Formula 1. The emitter layer may further include a host, and the amount of the host in the emitter layer may be greater than the amount of the organometallic compound in the emitter layer.
[0162] In an embodiment, the hole transport region may include an electron blocking layer, and the electron blocking layer may include an organometallic compound represented by Formula 1; or
[0163] The electron transport region may include a hole blocking layer, and the hole blocking layer may include an organometallic compound represented by Formula 1.
[0164] In an implementation, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0165] In an embodiment, the electron transport region may include an electron transport layer and an electron injection layer, and
[0166] At least one of the electron transport layer and the electron injection layer may further include at least one selected from the group consisting 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, and rare earth metal complexes.
[0167] [ Figure 1 [Description]
[0168] 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.
[0169] The following text 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.
[0170] [First Electrode 110]
[0171] exist Figure 1 In this process, the substrate can be additionally disposed below the first electrode 110 or above the second electrode 190. The substrate can be a glass substrate or a plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0172] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from a material with a high work function to facilitate hole injection.
[0173] The first electrode 110 may 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 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments 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 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments are not limited thereto.
[0174] 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.
[0175] [Organic layer 150]
[0176] An organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emitter layer.
[0177] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emitter layer, and an electron transport region between the emitter layer and the second electrode 190.
[0178] [Hole transport region in organic layer 150]
[0179] The hole transport region may have i) a single-layer structure comprising a single layer (including a single material), ii) a single-layer structure comprising a single layer (including different materials), or iii) a multi-layer structure comprising multiple layers comprising different materials.
[0180] 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.
[0181] For example, the hole transport region may have a single-layer structure including a single layer (including different materials), or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated therein, but the structure of the hole transport region is not limited to this.
[0182] The hole transport region may include at least one selected from the following: 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:
[0183]
[0184]
[0185] <Form 201>
[0186]
[0187] <Form 202>
[0188]
[0189] In equations 201 and 202,
[0190] 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 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0191] L 205 Optional 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 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0192] xa1 to xa4 can each be an integer selected from 0 to 3 independently.
[0193] xa5 can be an integer selected from 1 to 10, and
[0194] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0195] For example, in equation 202, R 201 and R 202 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene bonds, and R 203 and R 204 They can be optionally linked together by single bonds, dimethyl-methylene, or diphenyl-methylene bonds.
[0196] In the implementation, in formulas 201 and 202,
[0197] L 201 To L 205 Each can be selected independently from:
[0198] Phenylidene, pentylene, indene, naphthyl, azulene, heptadene, acenaphthene, fluorenene, spiro-difluorenene, benzo[a]fluorenene, dibenzo[a]fluorenene, phenanthroline, anthracene, fluorenyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenylene, fenenyl, perylene, perylene Pentofenyl, hexaphenylene, pentaphenylene, rubidylene, myristyl, oleophylene, thiophenyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzothiophenyl, and pyridylene; and
[0199] Each of the following substituted compounds is selected from at least one of the following: phenylene, pentyleneylene, indene, naphthylene, azulene, heptadeneylene, acenaphthene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenenenyl, phenanthrene, anthracene, fluorenyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenylene, fentanyl, perylene, pentyleneyl, hexaphenylene. Benzenepentylene, Benzenerubinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinylene, Benzenemylinolylene and pyridylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-based, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, styrayl, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),
[0200] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0201] In one or more embodiments, xa1 to xa4 may each be 0, 1 or 2 independently.
[0202] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0203] In one or more embodiments, R 201 To R 204 and Q 201 Each of these can be independently selected from: phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-glycol, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, styryl, peryl, pentanyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, ovoleyl, thiopheneyl, furanyl, carbazoleyl, indoleyl, isoyindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl; and
[0204] Each of the following substituted phenyl, biphenyl, terphenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indoleyl, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, framyl, peryleneyl, pentanfenyl, hexaphenyl Pentaphenyl, rutinyl, keratyl, ovolenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indole, naphthyl, azuleyl, heptenyl, indole-based, acenaphthel, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthreneyl, tetraphenyl, styrayl, peryl, pentanfenyl, hexaphenyl, pentaphenyl, rutinyl, keratyl, ovoleyl, thiopheneyl, furanyl, carbazoyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 ),
[0205] Q 31 To Q 33 Same as described above.
[0206] In one or more embodiments, selected from R 201 To R 203 At least one of them can be independently selected from:
[0207] Fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and
[0208] Each of the following substituted fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl groups is selected from at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl.
[0209] However, the implementation methods are not limited to this.
[0210] In one or more embodiments, in formula 202, i)R 201 and R 202 They can be connected to each other via single bonds, and / or ii)R 203 and R 204 They can be connected to each other via a single key.
[0211] In one or more embodiments, R in formula 202 201 To R 204 Optional from:
[0212] Carbazolyl; and
[0213] The carbazoyl group is substituted with at least one of the following: 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, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-difluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl.
[0214] However, the implementation methods are not limited to this.
[0215] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A:
[0216] <Form 201A>
[0217]
[0218] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A(1), but the embodiments are not limited thereto:
[0219] <Formula 201A(1)>
[0220]
[0221] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A-1, but the embodiments are not limited thereto:
[0222] <Form 201A-1>
[0223]
[0224] In one or more embodiments, the compound represented by formula 202 may be represented by the following formula 202A:
[0225] <Form 202A>
[0226]
[0227] In one or more embodiments, the compound represented by formula 202 may be represented by the following formula 202A-1:
[0228] <Formula 202A-1>
[0229]
[0230] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0231] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 Same as described above,
[0232] R 211 and R 212 With R 203 The descriptions are the same, and
[0233] 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, C1-C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentanenyl, indyl, naphthyl, azuleyl, heptenyl, indole-based, acenaphtheyl, fluorenyl, spiro-difluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], phenatenyl, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyreneyl, 1,2-benzophenanthreneyl, tetraphenyl, furanyl, peryl, pentanyl, hexaphenyl, pentaphenyl, rubidyl, kosyl, ovoidyl, thiopheneyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[carbazoyl], dibenzo[carbazoyl], dibenzothiopheneyl, and pyridyl.
[0234] 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:
[0235]
[0236]
[0237]
[0238] The thickness of the hole transport region can be approximately to approximately Within a certain range. For example, the thickness of the hole transport region can be 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, and the thickness of the hole transport layer can be approximately... to approximately Within a certain range. For example, the thickness of the hole injection layer can be approximately... to approximately Within a certain range. For example, the thickness of the hole transport layer can be approximately... to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within these ranges.
[0239] The emission assist layer can increase light emission 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 comprise the materials described above.
[0240] [p-dopant]
[0241] In addition to these materials, the hole transport region may further include charge-generating materials for improving conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region.
[0242] The charge-generating material can be, for example, a p-doped agent.
[0243] In an implementation, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant can be -3.5 eV or less.
[0244] p-dopers may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the implementation is not limited thereto.
[0245] In an embodiment, the p-doper may include at least one selected from the following:
[0246] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);
[0247] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0248] 1,4,5,8,9,12-hexaazatriphenylene-hexanitrile (HAT-CN); and
[0249] The compound represented by the following formula 221,
[0250] However, the implementation method is not limited to this:
[0251]
[0252] In Equation 221,
[0253] 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 groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, and selected from R 221 To R 223 At least one of them may have at least one substituent selected from the following: cyano, -F, -Cl, -Br, -I, C1-C substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with –Br 20 Alkyl groups and -I-substituted C1-C 20 alkyl.
[0254] [Emitting layer in organic layer 150]
[0255] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned as a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixels. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from red, green, and blue emission layers, wherein the two or more layers are in contact with or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from red, green, and blue luminescent materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0256] The emitting layer may include a host and a dopant. The dopant may include at least one selected from phosphorescent dopant and fluorescent dopant.
[0257] Based on approximately 100 parts by weight of the main body, the amount of dopant in the emitter layer can range from approximately 0.01 parts by weight to approximately 15 parts by weight, but the implementation is not limited to this.
[0258] The thickness of the emission layer can be approximately to approximately Within a certain range. For example, the thickness of the emission layer can be approximately... to approximately Within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within this range.
[0259] [The main body in the emission layer]
[0260] In one or more embodiments, the body may include a compound represented by the following formula 301.
[0261] <Formula 301>
[0262] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0263] In Equation 301,
[0264] Ar 301 C5-C can be substituted or unsubstituted. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0265] xb11 can be 1, 2, or 3.
[0266] L 301 C3-C can be self-substituted or unsubstituted. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0267] xb1 can be an integer selected from 0 to 5.
[0268] R 301 The group can be 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 C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 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
[0269] xb21 can be an integer selected from 1 to 5.
[0270] 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 implementation methods are not limited to these.
[0271] In the implementation method, Ar in formula 301 301 Optional from:
[0272] Naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenatenyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, dibenzofuranyl, and dibenzothiopheneyl; and
[0273] Each of the following substituted groups is selected from at least one of the following: naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, styrene, peryl, penfenyl, indoxanthryl, dibenzofuranyl, and dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q)31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),
[0274] 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 implementation methods are not limited to these.
[0275] When xb11 in equation 301 is 2 or greater, two or more Ar 301 It can be connected via a single button.
[0276] In one or more embodiments, the compound represented by formula 301 may be represented by one of formulas 301-1 and 301-2:
[0277] <Formula 301-1>
[0278]
[0279] <Formula 301-2>
[0280]
[0281] In Equations 301-1 and 301-2,
[0282] A 301 To A 304 Each ring can be independently selected from benzene ring, naphthyl ring, phenanthrene ring, fluoranthene ring, triphenylene ring, pyrene ring, 1,2-benzophenanthrene ring, pyridine ring, pyrimidine ring, indene ring, fluorene ring, spiro-difluorene ring, benzo[a]fluorene ring, dibenzo[a]fluorene ring, indole ring, carbazole ring, benzo[a]carbazole ring, dibenzo[a]carbazole ring, furan ring, benzo[a]furan ring, dibenzo[a]furan ring, naphtholane ring, benzo[a]naphtholane ring, dinaphtholane ring, benzo[a]naphtholane ring, and dinaphtholane ring.
[0283] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0284] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),
[0285] xb22 and xb23 can each be 0, 1, or 2 independently.
[0286] L 301 xb1, R 301 and Q 31 To Q 33 Same as described above,
[0287] L 302 To L 304 Each independently and in combination with L 301 The descriptions are the same.
[0288] xb2 to xb4 can each be independently identical to the one described in combination with xb1, and
[0289] R 302 To R 304 Each can independently combine with R 301 The descriptions are the same.
[0290] For example, L in Equations 301, 301-1, and 301-2 301 To L 304 Each can be selected independently from:
[0291] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazolyl, thiopheneyl Azolyl, iminothiazolyl, iminooxazolyl, iminooxazolyl, iminothiadiazolyl, iminooxadiazolyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, triazinyl, iminopyrinyl, iminopyrinyl, iminopyrinyl, benzoquinolineyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, and iminopyrazoleyl; and
[0292] Each of the following substituted compounds is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthylene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, etc. Oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisoxazolyl, benzisisoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyridyl Azolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisoxazolyl, benzisisothiazolyl, 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 ),
[0293] Q 31 To Q 33 Same as described above.
[0294] In the implementation, R in formulas 301, 301-1 and 301-2 301 To R 304 Each can be selected independently from:
[0295] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazole , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazolyl; and
[0296] Each of the following substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazoleyl, dibenzo[a]carbazoleyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl Oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyridyl Azolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisoxazolyl, benzisisothiazolyl, 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 ),
[0297] Q 31 To Q 33 Same as described above.
[0298] 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.
[0299] 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 are not limited thereto:
[0300]
[0301]
[0302]
[0303] [The phosphorescent dopant included in the emission layer of organic layer 150]
[0304] Phosphorescent dopants may include organometallic complexes represented by the following formula 401:
[0305] <Formula 401>
[0306] M(L 401 ) xc1 (L 402 ) xc2
[0307] In Equation 401,
[0308] 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).
[0309] 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.
[0310] L 402 It can be an organic ligand, and xc2 can be an integer selected from 0 to 4, wherein when xc2 can be 2 or greater, two or more L 402 They can be the same or different from each other.
[0311] <Formula 402>
[0312]
[0313] In Equation 402, X 401 To X 404 They can be nitrogen or carbon independently.
[0314] X 401 and X 403 It can be connected via a single or double key, and X 402 and X 404 It can be connected via a single key or a double key.
[0315] A 401 and A 402 Each can be independently classified as C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,
[0316] 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 It can be hydrogen, deuterium, or C1-C. 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,
[0317] X 406 It can be a single bond, O, or S.
[0318] 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 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ), where Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20Mixed aromatics,
[0319] xc11 and xc12 can each be an integer selected from 0 to 3 independently, and
[0320] In Equation 402, * and *' each indicate the binding site with M in Equation 401.
[0321] In the implementation, A in formula 402 401 and A 402 Each of the following can be independently selected from phenyl, naphthyl, fluorenyl, spiro-difluorenyl, indyl, pyrroleyl, thiopheneyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, carbazoleyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl, benzo[c]thiopheneyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiopheneyl.
[0322] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen and X 402 It can be carbon, or ii)X 401 and X 402 Each can be nitrogen at the same time.
[0323] In one or more embodiments, R in formula 402 401 and R 402 Each can be selected independently from:
[0324] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0325] Each is selected from at least one of the following C1-C substituted 20 Alkyl and C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl;
[0326] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;
[0327] Each of the following substituted groups is selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornel, norbornel-enyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, adamantyl, norbornel, norbornel-alkenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl; and
[0328] -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 ),
[0329] 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 implementation methods are not limited to these.
[0330] 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 linking group X 407 Connected to each other, two A's 402 Optionally via linking group X 408 They are interconnected (see compounds PD1 through PD4 and PD7). X 407 and X 408 Each can be independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q)-*', or *-N(Q)-*'. 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414)-*'(where Q 413 and Q 414 Each can be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl), but the implementation methods are not limited to these.
[0331] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The ligands can be selected from halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., pyridine carboxylates), -C (=O), isonitriles, -CN, and phosphorus-containing ligands (e.g., phosphine or phosphites), but the implementation is not limited thereto.
[0332] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but the embodiments are not limited thereto:
[0333]
[0334]
[0335] Fluorescent dopants in the emitter layer
[0336] Fluorescent dopants may include aromatic amine compounds or styrene amine compounds.
[0337] Fluorescent dopants may include compounds represented by the following formula 501.
[0338] <Form 501>
[0339]
[0340] In Equation 501,
[0341] Ar 501 C5-C can be substituted or unsubstituted. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0342] 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 60Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0343] xd1 to xd3 can each be an integer selected from 0 to 3 independently.
[0344] 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 groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, and
[0345] xd4 can be an integer selected from 1 to 6.
[0346] In the implementation, Ar in Formula 501 501 Optional from:
[0347] Naphthyl, heptadeninyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, lavany, perylene, penfenyl, indoxanthryl, and indoxanthryl; and
[0348] Each of the following substituted groups is selected from at least one of the following: naphthyl, heptalenyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenyl, styrene, peryl, penfenyl, ind[a]anthryl, and ind[a]phenanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0349] In one or more embodiments, L in Formula 501 501 To L 503 Each can be selected independently from:
[0350] Phenylidene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, and pyridylene; and
[0351] Each of the following substituted groups is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, and pyridylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indolyl, isoindolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.
[0352] In one or more embodiments, R in formula 501 501 and R 502 Each can be selected independently from:
[0353] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and
[0354] Each of the following substituted groups is selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, and -Si(Q) 31 (Q) 32 (Q) 33 ),
[0355] Q 31 To Q 33 Optional from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0356] In one or more embodiments, xd4 in Formula 501 may be 2, but the embodiments are not limited thereto.
[0357] For example, fluorescent dopants can be selected from compounds FD1 to FD22:
[0358]
[0359]
[0360]
[0361] In one or more embodiments, the fluorescent dopant may be selected from the compounds listed below, but the embodiments are not limited thereto.
[0362]
[0363] [Electron transport region in organic layer 150]
[0364] The electron transport region may have i) a single-layer structure comprising a single layer (including a single material), ii) a single-layer structure comprising a single layer (including different materials), or iii) a multi-layer structure comprising multiple layers comprising different materials.
[0365] 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 implementation is not limited thereto.
[0366] 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 constituent layers are stacked sequentially from the emitter layer. However, the implementation of the electron transport region structure is not limited to this.
[0367] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one ring of nitrogen with depleted π electrons.
[0368] "A ring containing nitrogen with depleted π electrons" indicates a C1-C ring with at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic groups.
[0369] For example, "a ring containing nitrogen with depleted π electrons" can be i) a 5- to 7-membered heterocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group wherein two or more 5- to 7-membered heterocyclic groups each having at least one *-N=*' moiety are fused together, or iii) a heteropolycyclic group wherein at least one of the 5- to 7-membered heterocyclic groups each having at least one *-N=*' moiety is combined with at least one C5-C 60 Fusing of carbocyclic groups.
[0370] Examples of rings containing nitrogen with depleted π electrons 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, benziisothiazole rings, benziisoxazole rings, benziisoxazole rings, triazole rings, tetraazole rings, oxadiazole rings, triazine rings, thiadiazole rings, imidazo[a]pyridine rings, imidazo[a]pyrimidine rings, and azacarbazole rings.
[0371] For example, the electron transport region may include a compound represented by the following formula 601:
[0372] <Formula 601>
[0373] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0374] In Equation 601,
[0375] Ar 601 C5-C can be substituted or unsubstituted. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 The heterocyclic group, xe11, can be 1, 2, or 3.
[0376] L 601 C3-C can be self-substituted or unsubstituted. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0377] xe1 can be an integer selected from 0 to 5.
[0378] R 601 C3-C can be self-substituted or unsubstituted. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 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 groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0379] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0380] xe21 can be an integer selected from 1 to 5.
[0381] In the implementation method, the quantity of Ar is xe11. 601 and R with a quantity of xe21 601 At least one of them may include a nitrogen ring containing π electrons depleted.
[0382] In the implementation method, Ar in formula 601 601 Optional from:
[0383] Phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, lavany, perylene, penfenyl, indoxane, dibenzofuranyl, dibenzothiopheneyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridyl Azinyl, indazole, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and
[0384] Each of the following substituted groups is selected from at least one of the following: phenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthrene, tetraphenyl, lavany, perylene, penfenyl, indoxaneyl, dibenzofuranyl, dibenzothiopheneyl, carbazole, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazole, purine. Quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 ),
[0385] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0386] 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.
[0387] In one or more embodiments, Ar in Formula 601 601 It can be anthracene.
[0388] In one or more embodiments, the compound represented by formula 601 may be represented by formula 601-1:
[0389] <Formula 601-1>
[0390]
[0391] In Equation 601-1,
[0392] 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 selected from X 614 To X 616 At least one of them can be N,
[0393] L 611 To L 613 Each can be independently combined with L 601 The descriptions are the same.
[0394] xe611 to xe613 can each be independently identical to the description in conjunction with xe1.
[0395] R 611 To R 613 Each can independently combine with R 601 The descriptions are the same, and
[0396] R 614To 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.
[0397] In the implementation, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Each can be selected independently from:
[0398] Phenylidene, naphthylene, fluorenelene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthracene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazolyl, thiopheneyl Azolyl, iminothiazolyl, iminooxazolyl, iminooxazolyl, iminothiadiazolyl, iminooxadiazolyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, triazinyl, iminopyrinyl, iminopyrinyl, iminopyrinyl, benzoquinolineyl, iminopyrazinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, iminopyridinyl, and iminopyrazoleyl; and
[0399] Each of the following substituted compounds is selected from at least one of the following: phenylene, naphthylene, fluorene, spiro-difluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthylene, triphenylene, pyrene, 1,2-benzophenanthrene, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, etc. Oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, quinoxalinyl, phenanthrinyl, acridineyl, phenanthrolineyl, phenazinyl, benzimidazolyl, benzisisothiazolyl, benzisisoxazolyl, benzisisoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl and zazacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazole Pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.
[0400] However, the implementation methods are not limited to this.
[0401] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each be 0, 1 or 2 independently.
[0402] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Each can be selected independently from:
[0403] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyridyl Azolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzisothiazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0404] Each of the following substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentofenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzo[a]carbazoleyl, dibenzo[a]carbazoleyl, dibenzothiopheneyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl Oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, phenanthridine, acridineyl, phenanthrolinel, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentafenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, pyridyl, 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, benzisothiazolyl, benzoxoxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; and
[0405] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0406] Q 601 and Q 602 Same as described above.
[0407] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but the implementation is not limited thereto:
[0408]
[0409]
[0410]
[0411]
[0412] 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.
[0413]
[0414] The thicknesses of the buffer layer, the hole-blocking layer, and the electronic control layer can each be independently set at approximately [value missing]. to approximately Within a certain range. For example, the thickness of the buffer layer, the hole blocking layer, and the electronic control layer can each be independently within approximately [a certain range]. to approximately When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are each within these ranges, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without a significant increase in the driving voltage.
[0415] The thickness of the electron transport layer can be approximately to approximately Within a certain range. For example, the thickness of the electron transport layer can be 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 a significant increase in driving voltage.
[0416] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.
[0417] 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, and alkaline earth metal complexes may include metal ions selected from Be, Mg, Ca, Sr, and Ba ions. The ligand coordinating with the metal ion of the alkali metal or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments are not limited thereto.
[0418] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2:
[0419]
[0420] 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 contact (e.g., directly contact) the second electrode 190.
[0421] The electron injection layer may have i) a single-layer structure comprising a single layer (including a single material), ii) a single-layer structure comprising a single layer (including different materials), or iii) a multilayer structure comprising multiple layers comprising different materials.
[0422] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0423] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In an 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 are not limited thereto.
[0424] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0425] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
[0426] The alkali metal compound, the alkaline earth metal compound, and the 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.
[0427] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In an embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments are not limited thereto.
[0428] 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) or Ba x Ca 1-x O(0 < x < 1). In an embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments are not limited thereto.
[0429] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In an embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments are not limited thereto.
[0430] 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 with the metal ions of the alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments are not limited thereto.
[0431] The electron injection layer may be composed of alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include organic materials. When the electron injection layer further includes organic materials, the alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix comprising the organic materials.
[0432] The thickness of the electron injection layer can be approximately to approximately Within a certain range. For example, the thickness of the electron-injected layer can be approximately... to approximately Within the aforementioned range, when the thickness of the electron injection layer is within this range, the electron injection layer can exhibit satisfactory electron injection characteristics without a significant increase in driving voltage.
[0433] [Second electrode 190]
[0434] The second electrode 190 is located on the organic layer 150 having this structure. The second electrode 190 may be a cathode (which is an electron injection electrode), and in this regard, the material used to form the second electrode 190 may be selected from metals, alloys, conductive compounds and combinations thereof having relatively low work function.
[0435] 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 the embodiments are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0436] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0437] [ Figures 2 to 4[Description]
[0438] 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 arranged 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, which are arranged 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, which are arranged sequentially in the order stated herein.
[0439] for Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be bonded by reference. Figure 1 Use the presented description to understand.
[0440] In the respective organic layers 150 of organic light-emitting devices 20 and 40, light generated in the emitting layer can pass through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer 210 toward the outside, and in the respective organic layers 150 of organic light-emitting devices 30 and 40, light generated in the emitting layer can pass through the second electrode 190 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer 220 toward the outside.
[0441] Based on the principle of constructive interference, the first capping layer 210 and the second capping layer 220 can increase the external emission efficiency.
[0442] The first capping layer 210 and the second capping layer 220 can each be 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.
[0443] 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, amino compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalenephthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amino compounds may optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amino compound.
[0444] In an 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.
[0445] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments are not limited thereto.
[0446]
[0447] The above text has already combined Figures 1 to 4 An organic light-emitting device according to an embodiment has been described. However, the embodiments are not limited thereto.
[0448] The layers constituting the hole transport region, the emission layer, and the electron transport region can be formed in a region using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0449] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are formed by vacuum deposition, the deposition can be carried out at a deposition temperature of about 100°C to about 500°C, and at a deposition temperature of about 10°C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed. -8 To about 10 -3 The vacuum degree and about / seconds to approximately The deposition was carried out at a rate of / second.
[0450] When the layer constituting the hole transport region, the emitter layer, and the layer constituting the electron transport region are formed by spin coating, spin coating can be carried out at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.
[0451] [Definition of substituents]
[0452] As used in this article, the term "C1-C" 60 "alkyl" refers to a straight-chain or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, preferably "C1-C". 20 "alkyl", and examples of which 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 other alkyl groups. 60 "alkylene" refers to C1-C 60 Alkyl groups have the same structure as divalent groups.
[0453] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60The alkyl group has at least one carbon-carbon double bond at the middle or end, preferably "C2-C". 20 "Alkenyl", and examples of it include vinyl, propenyl and butenyl. As used herein, the term "C2-C" is... 60 "Alkenyl" refers to C2-C 60 Alkenes have divalent groups with the same structure.
[0454] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 The alkyl group has at least one carbon-carbon triple bond at the middle or end, preferably "C2-C". 20 "Alynyl", and examples of it include ethynyl and propynyl. As used herein, the term "C2-C" is used in this context. 60 "Immyneyl" refers to C2-C 60 The alkynyl group is a divalent group with the same structure.
[0455] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 The monovalent group represented by alkyl is preferred, especially "C1-C". 20 "Alkoxy", and examples of it include methoxy and isopropoxy.
[0456] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic hydrocarbon group with 3 to 10 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have the same divalent structure.
[0457] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom and 1 to 10 carbon atoms, and examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with the same structure.
[0458] The term "C3-C" used in this article 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, and examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant.10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.
[0459] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.
[0460] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (with 6 to 60 carbon atoms), and the "C6-C" used in this article... 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system (with 6 to 60 carbon atoms). C6-C 60 Examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and 1,2-benzophenanthryl. When C6-C... 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings can fused together.
[0461] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system (in addition to 1 to 60 carbon atoms, it has at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom). As used herein, the term "C1-C" is also relevant. 60 "Hypo-heteroaryl" refers to a divalent group that has a heterocyclic aromatic system (in addition to 1 to 60 carbon atoms, it has at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom). C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings can fused together.
[0462] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60Aryl), and the “C6-C” used in this article 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).
[0463] As used in this article, the term "C1-C" 60 "Heteroaryloxy" refers to -OA 104 (where A) 104 For C1-C 60 (Heteroaryl), and the “C6-C” used in this article 60 "Heteroarylsulfonyl" refers to -SA 105 (where A) 105 For C1-C 60 (Miscellaneous aromatic compounds).
[0464] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) that has two or more rings fused together, with only carbon atoms as cyclic atoms, and which is not aromatic throughout its molecular structure. A detailed example of a monovalent nonaromatic fused polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.
[0465] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) that has two or more rings fused together, and in addition to carbon atoms, has at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, and is not aromatic throughout its molecular structure. An example of a monovalent nonaromatic fused heterocyclic group is the carbazoyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.
[0466] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group consisting of 5 to 60 carbon atoms, with carbon as the only ring-forming atom. (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 benzene ring, a monovalent group (such as a phenyl group), or a divalent group (such as a phenylene group). In one or more embodiments, depending on the linkage to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbocyclic group can be trivalent or tetravalent. For example, the term "phenyl" can refer to a benzene ring, phenyl, phenylene, or its corresponding trivalent or tetravalent group.
[0467] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to C5-C 60 Carbocyclic groups are groups with the same structure, except that, in addition to carbon (the number of carbon atoms can range from 1 to 60), at least one heteroatom selected from N, O, Si, P and S is used as the cyclic atom.
[0468] The instruction manual states that it replaces C5-C. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hypoaryl, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be selected from:
[0469] Deuterium (-D), -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;
[0470] Each is selected from at least one of the following C1-C substituted 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60Alkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 ) and -P(=O)(Q 11 (Q) 12 );
[0471] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;
[0472] Each is substituted by at least one of the following C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 );as well as
[0473] -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 ),
[0474] 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 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl and terphenyl.
[0475] As used herein, “Ph” refers to phenyl, “Me” refers to methyl, “Et” refers to ethyl, and “tert-Bu” or “Bu” refers to ethyl. t "Refers to tert-butyl, and as used herein, the term "OMe" refers to methyl methacrylate (MMA).
[0476] As used in this article, the term "biphenyl" refers to a phenyl group that has been substituted with a phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C2 bond. 60 Aryl groups are substituted phenyl groups.
[0477] As used in this article, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group." In other words, "terphenyl" is a phenyl group with a C6-C substituted biphenyl group. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.
[0478] Unless otherwise defined, as used herein, * and *' refer to the binding sites with adjacent atoms in the corresponding formulas.
[0479] In the following text, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in detail with reference to synthesis examples and embodiments. The phrase "using B instead of A" used in describing the synthesis examples means using the same molar equivalent of B instead of A.
[0480] [Synthesis example]
[0481] Synthesis Example 1: Synthesis of Compound BD1
[0482] (1) Synthesis of intermediate 1-1
[0483]
[0484] Starting materials 1-0, 1,2,4,5-tetrabromobenzene (CAS No.: 636-28-2), and BPPO were reacted at 160 °C in the presence of CuI, K3PO4, and DMSO solvents. Intermediate 1-1 was identified by LC-MS.
[0485] C 12 H6Br4O: M+1 481.75
[0486] (2) Synthesis of intermediates 1-2
[0487]
[0488] Intermediate 1-1 was reacted with imidazole (CAS No.: 288-13-1) and potassium carbonate to synthesize intermediate 1-2. Intermediate 1-2 was confirmed by LC-MS.
[0489] C 24 H 18 N8O: M+1 434.19
[0490] (3) Synthesis of intermediates 1-3
[0491]
[0492] Intermediates 1-2 were reacted with iodomethane (CAS No.: 74-88-4) in the presence of acetone as a solvent to synthesize intermediate 1-3. Intermediates 1-3 were identified by LC-MS.
[0493] C 28 H 30 I4N8O: M+1 1001.89
[0494] (4) Synthesis of intermediates 1-4
[0495]
[0496] Intermediates 1-3 were reacted with dichloro(1,5-cyclooctadiene)platinum(II) at 160 °C in the presence of sodium acetate and dioxane solvent. Intermediates 1-4 were identified by LC-MS.
[0497] C 28 H 26 I2N8OPt: M+1 939.25
[0498] (5) Synthesis of intermediate 2-1
[0499]
[0500] Starting material 2-0 was reacted with 2,6-dibromopyridine (CAS No.: 626-05-1), Pd2(dba)3, Sphos, and K3PO4 at 120 °C in the presence of toluene solvent. Intermediate 2-1 was identified by LC-MS.
[0501] C 15 H7F4N3: M+1 305.09
[0502] (6) Synthesis of compound BD1
[0503]
[0504] Intermediates 1-4, 2-1, IrCl3·3H2O, and K2CO3 were dissolved in propionic acid, and the mixture was stirred at 140 °C for 12 hours. After the reaction was complete, the solvent was removed under reduced pressure, and the mixture was extracted with dichloromethane and distilled water. The organic layer was washed three times with distilled water, dried over magnesium sulfate, filtered under reduced pressure, and concentrated. Compound BD1 was identified by LC-MS.
[0505] C 43 H 28 F4IrN 11 OPt: M+1 1178.17
[0506] Synthesis Example 2: Synthesis of compounds BD2 to BD8
[0507] Compounds BD2 through BD8 were synthesized using essentially the same method as the intermediates used to synthesize compound BD1, except for the starting materials.
[0508] pass 1 The compounds synthesized according to the above synthesis example were identified by 1H NMR and MS / FAB, and the results are shown in Table 1 below.
[0509] [Table 1]
[0510]
[0511]
[0512] The methods for synthesizing compounds other than those shown in Table 1 can also be readily understood by those skilled in the art by referring to the above-described synthetic mechanisms and starting materials.
[0513] [Example]
[0514] Example 1
[0515] As the substrate and anode, it has a 15Ωcm 2 The ITO glass substrate (manufactured by Corning Incorporated) was cut to a size of 50mm × 50mm × 0.7mm and ultrasonically treated with isopropanol and pure water for 5 minutes each, then irradiated with ultraviolet (UV) light for 30 minutes and exposed to ozone for cleaning. The resulting glass substrate was then loaded onto a vacuum deposition apparatus.
[0516] 2-TNATA was vacuum deposited onto an ITO anode on a glass substrate 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 layer with [missing information]. A hole transport layer of a certain thickness.
[0517] Bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS) and (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA) (BCPDS to POPCPA in a weight ratio of 1:1, serving as the co-substrate) and compound BD1 (a dopant) were co-deposited on the hole transport layer at a weight ratio of 90:10 to form a structure with... The thickness of the emission layer.
[0518] Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed, and Alq3 is deposited on the hole-blocking layer to form a hole-blocking layer with [missing information]. An electron transport layer of a certain thickness is formed by depositing LiF on the electron transport layer to create an electron transport layer with... An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited onto the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is used to complete the fabrication of an organic light-emitting device.
[0519]
[0520] Examples 2 to 5 and Comparative Examples 1 to 3
[0521] The organic light-emitting device was manufactured in the same manner as in Example 1, except that when forming the emission layer, the corresponding compound shown in Table 1 was used instead of compound BD1 as a dopant.
[0522] Evaluation Example 2
[0523] The driving voltage, current density, luminance, emission efficiency, emission color, and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Examples 1 to 3 were measured using a Kethley SMU 236 and a luminance photometer PR650, and the results are shown in Table 2.
[0524] [Table 2]
[0525]
[0526]
[0527] Referring to Table 2, it is confirmed that the organic light-emitting devices of Examples 1 to 5 have low driving voltage, high current density, and high emission efficiency. Compared with the organic light-emitting devices of Comparative Examples 1 to 3, the organic light-emitting devices of Examples 1 to 5 exhibit lower driving voltage and higher current density.
[0528] Organic light-emitting devices, including organometallic compounds, can have low driving voltage, high brightness, high efficiency, high color purity, and long lifespan.
[0529] It should be understood that the embodiments described herein are for descriptive purposes 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 figures, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.
Claims
1. An organometallic compound represented by Formula 2: <Formula 2> wherein in Formula 2, M1 is Pt, and M2 is Ir, T1 is selected from the group consisting of *-O-* and *-S-*, * and *' each indicate a bonding site to an adjacent atom. a group represented by one of Formulae 5-1 to 5-12: Y 23 and Y 43 each independently is N, and R 11 to R 13 , R 21 to R 24 , R 31 to R 33 , R 41 to R 44 , R 51 to R 53 , R 61 to R 63 , R 71 to R 73 , and R 81 to R 83 are each independently selected from: hydrogen, deuterium, -F, -CI, -Br, -I, Ci-C 20 alkyl, Ci-C 20 alkoxy and C6-C 60 aryl, wherein the C6-C 60 aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl or 1,2- benzophenanthryl, C1-C4alkyl and C1-C4alkoxy, each substituted with at least one member selected from the group consisting of deuterium, -F, -CI, -Br, -I, phenyl, and biphenyl; 20 C1-C4alkyl and C1-C4alkoxy, each substituted with at least one member selected from the group consisting of deuterium, -F, -CI, -Br, -I, phenyl, and biphenyl; 20 C1-C4alkyl and C1-C4alkoxy, each substituted with at C6-C substituted by at least one of the following 60 Aryl groups: deuterium, -F, -Cl, -Br, -I, Cl-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, and biphenyl; two or more adjacent substituents selected from the group consisting of R 11 to R 13 , R 21 to R 24 , R 31 to R 33 , R 41 to R 44 , R 51 to R 53 , R 61 to R 63 , R 71 to R 73 , and R 81 to R 83 are optionally linked together to form any one radical selected from the group consisting of cyclopentane, cyclohexane, phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazinyl, and carbazolyl, wherein in Formulae 5-1 to 5-12, 2. The organometallic compound according to claim 1, wherein R 11 to R 13 , R 21 to R 24 , R 31 to R 33 , R 41 to R 44 , R 51 to R 53 , R 61 to R 63 , R 71 to R 73 , and R 81 to R 83 are each independently selected from: hydrogen, deuterium, -F and C1-C4alkyl; 20 alkyl; C1-C4alkyl substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, phenyl, and biphenyl; 20 C1-C4alkyl; and e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, two or more adjacent substituents selected from the group consisting of R 11 to R 13 , R 21 to R 24 , R 31 to R 33 , R 41 to R 44 , R 51 to R 53 , R 61 to R 63 , R 71 to R 73 , and R 81 to R 83 are optionally linked together to form any one radical selected from the group consisting of cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazinyl, and carbazolyl, e5 is an integer selected from 1 to 5, Z 51 to Z 52 each independently is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, e9 is an integer selected from 1 to 9, and * indicates a bonding site to an adjacent atom. a phenyl group or a naphthyl group; and 4. An organometallic compound, wherein the organometallic compound is one of Compounds BD1 to BD16 and BD21:
5. An organic light-emitting device comprising:
3. The organometallic compound of claim 1, wherein R 11 to R 13 , R 21 to R 24 , R 31 to R 33 , R 41 to R 44 , R 51 to R 53 , R 61 to R 63 , R 71 to R 73 , and R 81 to R 83 are each independently selected from: hydrogen, deuterium, -F and C1-C4alkyl; 20 alkyl; C1-C4alkyl substituted by at least one member selected from the group consisting of: 20 alkyl: deuterium, -F, -CI, -Br, -I, phenyl, and biphenyl; a first electrode; phenyl or naphthyl, each substituted by at least one member selected from the group consisting of deuterium, -F, -CI, -Br, -I, Ci-C 20 alkyl, Ci-C 20 alkoxy, phenyl and biphenyl, and two or more adjacent substituents selected from the group consisting of R 11 to R 13 , R 21 to R 24 , R 31 to R 33 , R 41 to R 44 , R 51 to R 53 , R 61 to R 63 , R 71 to R 73 , and R 81 to R 83 are optionally linked together to form a phenyl, naphthyl, fluorenyl, pyridyl, pyrimidinyl, triazinyl, or carbazolyl. a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes the organometallic compound according to any one of claims 1 to 4.
6. The organic light-emitting device according to claim 5, wherein: the first electrode is an anode, the second electrode is a cathode, and the organic layer includes: a hole transport zone disposed between the first electrode and the emission layer, and including a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof; and an electron transport zone disposed between the emission layer and the second electrode, and including a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
7. The organic light-emitting device according to claim 5, wherein the emission layer includes the organometallic compound.
8. The organic light-emitting device according to claim 5, wherein: the emission layer includes a host and a dopant, and the dopant includes the organometallic compound.
9. The organic light-emitting device according to claim 6, wherein the electron transport zone includes the electron transport layer and the electron injection layer, and at least one of the electron transport layer and the electron injection layer further includes at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, and a rare earth metal compound.
10. The organic light-emitting device according to claim 9, wherein the alkali metal compound is an alkali metal complex, the alkaline earth metal compound is an alkaline earth metal complex, and the rare earth metal compound is a rare earth metal complex.
Citation Information
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