Organometallic compound, organic light-emitting device, electronic device, and consumer article including same
By using organometallic compounds of specific structures as the emission layer material, the shortcomings of existing organic light emitting devices in terms of color purity, luminous efficiency and life are solved, and efficient blue and green light emission is achieved, and the overall performance of the organic light emitting device is improved.
Patent Information
- Application Number
- CN202510130028.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-01-31
- Filing Date
- 2025-02-05
- Publication Date
- 2025-08-01
AI Technical Summary
Existing organic light emitting devices have shortcomings in color purity, luminous efficiency and lifetime, especially when emitting blue and green light, it is difficult to achieve efficient and stable optical performance.
The organometallic compound represented by Formula 1 is used as the material of the emission layer, and its structure is regulated to separate the highest occupied molecular orbital and the lowest unoccupied molecular orbital, color purity and luminescence efficiency are improved, and the formation of excited complexes is suppressed in the emission layer.
An organic light emitting device with high color purity, high luminous efficiency and long life is achieved, especially when blue and green light is emitted, with excellent optical performance.
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Figure CN120398961A_ABST
Abstract
Description
[0001] Cross - reference to related applications
[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2024 - 0015182, filed with the Korean Intellectual Property Office on January 31, 2024, the entire contents of which are incorporated herein by reference. Technical field
[0003] Embodiments relate to an organometallic compound, an organic light - emitting device including the same, an electronic device, and a consumer product. Background art
[0004] An organic light - emitting device is a self - emitting device, which has a wide viewing angle, high contrast ratio, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to conventional devices, and generates a full - color image.
[0005] In an example, an organic light - emitting device may have the following structure, in which a first electrode is disposed on a substrate, and a hole - transporting region, an emission layer, an electron - transporting region, and a second electrode may be sequentially formed on the first electrode. Holes provided from the first electrode move through the hole - transporting region toward the emission layer, and electrons provided from the second electrode move through the electron - transporting region toward the emission layer. Charge carriers, such as holes and electrons, recombine in the emission layer to generate excitons. The excitons may transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background art section is intended to provide, in part, useful background for understanding the technology. However, this background art section may also include ideas, concepts, or cognitions that were not known or understood by those skilled in the relevant art before the effective filing date of the corresponding subject matter disclosed herein. Summary of the invention
[0007] Embodiments include an organometallic compound, an organic light - emitting device including the same, an electronic device, and a consumer product.
[0008] Additional aspects will be set forth in part in the following description, and in part will be obvious from the description, or may be learned by practice of the embodiments of the present disclosure.
[0009] According to an embodiment, the organometallic compound may be represented by Formula 1.
[0010] [Formula 1]
[0011]
[0012] In Formula 1,
[0013] M1 can be 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) or thulium (Tm),
[0014] A 10 can be an unsubstituted or at least one R 10 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group,
[0015] A 20 can be an unsubstituted or at least one R 20 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group,
[0016] A 30 can be an unsubstituted or at least one R 30 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group,
[0017] A 40 to A 42 can each independently be an unsubstituted or at least one R 40 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group,
[0018] A 43 and A 44 can each independently be an unsubstituted or at least one R 40 substituted 5-membered carbocyclic group or 5-membered heterocyclic group,
[0019] Y<� 10 、Y 20 、Y 30 and Y 40 can each independently be C or N,
[0020] T1 to T4 can each independently be a chemical bond,
[0021] L 11 to L 14 It should be noted that there is a possible incorrect symbol "<� 10 " in the original text which is retained as is during translation. You may want to check the accuracy of this symbol in the original.may each independently be a 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)-*' or *-Ge(R1)(R2)-*',
[0022] a11 to a14 can each independently be 0, 1, 2, 3, 4 or 5,
[0023] R1, R2, R 10 、R 20 、R 30 and R 40 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted by at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused polycyclic group, an unsubstituted or substituted monovalent non-aromatic fused polycyclic group, 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -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), or -P(═S)(Q1)(Q2),
[0024] R1, R2, R 10 、R 20 、R 30 and R 40 Two or more adjacent groups in the group may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 heterocyclic group,
[0025] R 10a Can be:
[0026] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;
[0027] Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q11 ), -S(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), -P(=S)(Q 11 )(Q 12 ) or any combination thereof;
[0028] Each unsubstituted or substituted by the following C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group or C1-C 60 heteroarylthio group: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group, C1-C 60 heteroarylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ) or any combination thereof; or
[0029] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q31 )(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 ) or -P(=S)(Q 31 )(Q 32 ) and
[0030] Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amidino; hydrazino; hydrazono; C1-C 60 alkyl; C2-C 60 60 alkynyl; C1-C 60 alkoxy; or a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group that is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof.
[0031] In an embodiment, M1 can be Pt, Pd, Cu, Ag, or Au.
[0032] In an embodiment, A 10 、A 20 、A 30 and A 40 to A 42 can each independently be a group represented by one of Formulas 2-1 to 2-43 as explained below.
[0033] In an embodiment, L 11 to L 14 can each independently be a single bond, *-O-*', *-S-*', *-N(R1)-*', *-C(R1)(R2)-*', *-Si(R1)(R2)-*', or *-B(R1)-*'.
[0034] In an embodiment, a11 can be 0.
[0035] In an embodiment, R1, R2, R 10 , R 20 , R 30 and R 40 may each independently be:
[0036] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl or C1-C 20 alkoxy;
[0037] C1-C each independently substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof 20 alkyl or C1-C 20 alkoxy; or
[0038] a group represented by one of Formula 5-1 to Formula 5-26 and Formula 6-1 to Formula 6-55, and
[0039] R1, R2, R 10 , R 20 , R 30 and R 40 two or more adjacent groups among them may optionally be bonded to each other to form:
[0040] cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl; or
[0041] cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl each independently substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof, wherein Formula 5-1 to Formula 5- 26 and Formula 6-1 to Formula 6-55 are explained below.
[0042] In an embodiment, the organometallic compound may be represented by Formula 11 explained below.
[0043] In an embodiment, the organometallic compound may be represented by one of Formula 21 to Formula 28 explained below.
[0044] In an embodiment, the organometallic compound may be electrically neutral.
[0045] In an embodiment, the organometallic compound may be one of Compound 1 to Compound 192 explained below.
[0046] According to an embodiment, the organic light-emitting device may include a first electrode, a second electrode facing the first electrode, a sandwich layer between the first electrode and the second electrode and including an emission layer, and an organometallic compound explained herein.
[0047] In an embodiment, the first electrode may be an anode,
[0048] the second electrode may be a cathode,
[0049] The interlayer may further include: a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode.
[0050] The hole transport region may include at least one of a hole injection layer, a hole transport layer, an emission assist layer, and an electron blocking layer, and
[0051] The electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
[0052] In an embodiment, the emission layer may include an organometallic compound.
[0053] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include an organometallic compound.
[0054] In an embodiment, the emission layer may emit blue light or green light each having a maximum emission wavelength in the range of about 400 nm to about 580 nm.
[0055] In an embodiment, the host may include a first host compound and a second host compound, the first host compound may be a hole transport host, and the second host compound may be an electron transport host.
[0056] According to an embodiment, the electronic device may include an organic light emitting device.
[0057] In an embodiment, the electronic device may further include a thin film transistor, wherein the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the organic light emitting device may be electrically connected to at least one of the source electrode and the drain electrode.
[0058] According to an embodiment, a consumer product (e.g., an electronic device) may include an organic light emitting device.
[0059] In an embodiment, the consumer product may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall including a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0060] It should be understood that the above-described embodiments are described only in a general and illustrative sense and not for the purpose of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0061] The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. By referring to the accompanying drawings and describing the embodiments of the present disclosure in detail, the above and other aspects and features of the present disclosure will become more apparent, where:
[0062] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0063] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0064] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0065] Figure 4 is a schematic perspective view of a consumer product including an organic light-emitting device according to an embodiment;
[0066] Figure 5 is a schematic view of the exterior of a vehicle as a consumer product including an organic light-emitting device according to an embodiment; and
[0067] Figures 6A to 6C are each a schematic view of the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION OF THE EMBODIMENTS
[0068] The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the present disclosure to those skilled in the art.
[0069] In the drawings, for ease of description and for clarity, the dimensions (e.g., thickness), ratios, and dimensions of elements may be enlarged. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0070] In the description, it will be understood that when an element (or region, layer, portion, etc.) is referred to as being "on", "connected to", or "coupled to" another element (or region, layer, portion, etc.), it can be directly on, connected to, or coupled to the other element (or region, layer, portion, etc.), or there can be one or more intervening elements (or regions, layers, portions, etc.) between them. In a similar sense, when an element (or region, layer, portion, etc.) is described as "covering" another element (or region, layer, portion, etc.), it can directly cover the other element (or region, layer, portion, etc.), or there can be one or more intervening elements (or regions, layers, portions, etc.) between them.
[0071] In the description, when an element is "directly on", "directly connected to", or "directly coupled to" another element, there are no intervening elements. For example, "directly on" can mean that two layers or two elements are disposed without another element (such as an adhesive element) between them.
[0072] As used herein, expressions used in the singular form, such as "a", "an", and "the", are intended to also include the plural forms unless the context clearly indicates otherwise.
[0073] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B". The terms "and" and "or" can be used in a conjunctive or disjunctive sense and can be understood to be equivalent to "and / or".
[0074] In the specification and claims, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of...", for purposes of its meaning and interpretation. For example, "at least one of A, B, and C" can be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of..." modifies the entire list of elements and not individual elements of the list.
[0075] It will be understood that although terms such as first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, without departing from the teachings of the present disclosure, a first element can be referred to as a second element. Similarly, without departing from the scope of the present disclosure, a second element can be referred to as a first element.
[0076] For ease of description, spatial relative terms such as "below", "beneath", "under", "above", or "over" may be used herein to describe the relationship between one element or component and another element or component as illustrated in the figures. It will be understood that the spatial relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, in the case of flipping the device illustrated in the figures, a device that is "below" or "beneath" another device may be positioned "above" the other device. Accordingly, the illustrative term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and thus the spatial relative terms may be interpreted differently depending on the orientation.
[0077] As used herein, the term "about" or "approximate" includes the recited value and means within an acceptable deviation range of the recited value as determined by one of ordinary skill in the art in view of the measurements discussed and the error associated with the measurement of the recited quantity (i.e., the limitations of the measurement system). For example, "about" may mean within one or more standard deviations of the recited value, or within ±20%, ±10%, or ±5% of the recited value.
[0078] It should be understood that the terms "comprise", "comprising", "include", "including", "have", "having", "contains", and "containing" and the like are intended to specify the presence of the stated features, integers, steps, operations, elements, components, or any combination thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or any combination thereof.
[0079] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless clearly defined in the specification.
[0080] According to an embodiment, the organometallic compound may be represented by Formula 1:
[0081] [Formula 1]
[0082]
[0083] In Formula 1, M1 can be 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), or thulium (Tm).
[0084] In an embodiment, M1 can be Pt, Pd, Cu, Ag, or Au.
[0085] In an embodiment, M1 can be Pt or Pd.
[0086] In Formula 1,
[0087] A 10 can be an unsubstituted or at least one R 10 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group,
[0088] A 20 can be an unsubstituted or at least one R 20 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group, and
[0089] A 30 can be an unsubstituted or at least one R 30 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group, and
[0090] A 40 to A 42 can each independently be an unsubstituted or at least one R 40 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group.
[0091] In an embodiment, A 10 can be an unsubstituted or at least one R 10Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, indolopyridyl, indolopyridinyl, benzofuropyridinyl, benzothienopyridinyl, benzosilolopyridinyl, indolopyrimidinyl, indolopyrimidinyl, benzofuropyrimidinyl, benzothienopyrimidinyl, benzosilolopyrimidinyl, dihydropyridyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, 2,3-dihydroimidazolyl, triazolyl, 2,3-dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, 2,3-dihydrobenzimidazolyl, imidazopyridyl, 2,3-dihydroimidazopyridyl, imidazopyrimidinyl, 2,3-dihydroimidazopyrimidinyl, imidazopyrazinyl, 2,3-dihydroimidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
[0092] In an embodiment, A 20 may each be unsubstituted or substituted by at least one R 20 Substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, indolopyridyl, indolopyridinyl, benzofuropyridinyl, benzothienopyridinyl, benzosilolopyridinyl, indolopyrimidinyl, indolopyrimidinyl, benzofuropyrimidinyl, benzothienopyrimidinyl, benzosilolopyrimidinyl, dihydropyridyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, 2,3-dihydroimidazolyl, triazolyl, 2,3-dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, 2,3-dihydrobenzimidazolyl, imidazopyridyl, 2,3-dihydroimidazopyridyl, imidazopyrimidinyl, 2,3-dihydroimidazopyrimidinyl, imidazopyrazinyl, 2,3-dihydroimidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
[0093] In an embodiment, A 30 may each be unsubstituted or substituted by at least one R 30 and be phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, indolopyridinyl, indolopyridinyl, benzofuranopyridinyl, benzothiophenopyridinyl, benzosilolopyridinyl, indolopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, benzosilolopyrimidinyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, 2,3-dihydroimidazolyl, triazolyl, 2,3-dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, 2,3-dihydrobenzimidazolyl, imidazopyridinyl, 2,3-dihydroimidazopyridinyl, imidazopyrimidinyl, 2,3-dihydroimidazopyrimidinyl, imidazopyrazinyl, 2,3-dihydroimidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
[0094] In an embodiment, A 40 to A 42 may each independently be unsubstituted or substituted by at least one R 40A substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, indolopyridinyl, indolopyridinyl, benzofuranopyridinyl, benzothiophenopyridinyl, benzosilolopyridinyl, indolopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, benzosilolopyrimidinyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, 2,3-dihydroimidazolyl, triazolyl, 2,3-dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, 2,3-dihydrobenzimidazolyl, imidazopyridinyl, 2,3-dihydroimidazopyridinyl, imidazopyrimidinyl, 2,3-dihydroimidazopyrimidinyl, imidazopyrazinyl, 2,3-dihydroimidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
[0095] In an embodiment, A 10 , A 20 , A 30 and A 40 to A 42 may each independently be a group represented by one of Formulae 2-1 to 2-43.
[0096]
[0097]
[0098] In Formulae 2-1 to 2-43,
[0099] X 21 to X 23 may each independently be C(Z 24 ) or C-*,
[0100] X 21 to X 23 at least two of which may each be C-*,
[0101] X 24 may be N-*,
[0102] X 25 and X 26 may each independently be C(Z 24 ), C-*, C(Z 24)(Z 25 ) or C(Z 24 )-*,
[0103] X 25 and X 26 at least one of which may be C-* or C(Z 24 )-*,
[0104] X 27 and X 28 may each independently be N, N(Z 25 ) or N-*,
[0105] X 29 may be C(Z 24 ), C-*, C(Z 24 )(Z 25 ) or C(Z 24 )-*,
[0106] wherein for X 27 to X 29 : one of X 27 and X 28 may be N-*, and X 29 may be C-* or C(Z 24 )-*; or X 27 and X 28 may each be N-*, and X 29 may be C(Z 24 ) or C(Z 24 )(Z 25 ),
[0107] Z 21 to Z 25 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthryl, triphenylene, pyridyl, pyrimidinyl, carbazolyl or triazinyl,
[0108] c21 may be 1, 2 or 3,
[0109] c22 may be 1, 2, 3, 4 or 5,
[0110] c23 may be 1, 2, 3 or 4,
[0111] c24 may be 1 or 2, and
[0112] * indicates the binding site to the adjacent atom.
[0113] In Formula 1, A 43 and A 44 may each independently be an unsubstituted or at least one R 40 substituted 5-membered carbocyclic group or 5-membered heterocyclic group.
[0114] In an embodiment, A 43 and A 44 may each independently be an unsubstituted or at least one R 40 substituted furyl, thienyl, selenophenyl, pyrrolyl or cyclopent-1,3-dienyl.
[0115] In Formula 1, Y 10 , Y 20 , Y 30 and Y 40 may each independently be C or N.
[0116] In Formula 1, T1 to T4 may each independently be a chemical bond.
[0117] In an embodiment, T1 to T4 may each independently represent a coordination bond or a covalent bond.
[0118] In an embodiment, T1 to T4 may each independently represent a single bond or a double bond.
[0119] In an embodiment, any two of T1 to T4 may each be a coordination bond, and the remaining two of T1 to T4 may each be a covalent bond. Accordingly, the organometallic compound may be electrically neutral and not in the form of a salt composed of a cation and an anion.
[0120] In an embodiment, T1 and T2 may each be a coordination bond, and T3 and T4 may each be a covalent bond.
[0121] In Formula 1, L 11 to L 14 may each independently be a 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)-*' or *-Ge(R1)(R2)-*'.
[0122] In an embodiment, L 11 to L 14Each of them can independently be a single bond, *-O-*, *-S-*, *-N(R1)-*, *-C(R1)(R2)-*, *-Si(R1)(R2)-* or *-B(R1)-*.
[0123] In an embodiment, L 12 to L 14 can each be a single bond.
[0124] In an embodiment, L 13 can be *-O-*, *-S-*, *-N(R1)-* or *-C(R1)(R2)-*.
[0125] In Formula 1, a11 to a14 can each independently be 0, 1, 2, 3, 4 or 5.
[0126] In an embodiment, a11 can be 0 or 1.
[0127] In an embodiment, a11 can be 0.
[0128] In an embodiment, a12 to a14 can each be 1.
[0129] In Formula 1, R1, R2, R 10 , R 20 , R 30 and R 40 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 10 cycloalkyl, unsubstituted or substituted by at least one R 10a substituted C1-C 10 heterocycloalkyl, unsubstituted or substituted by at least one R 10a substituted C3-C 10 cycloalkenyl, unsubstituted or substituted by at least one R 10a substituted C1-C 10 heterocycloalkenyl, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryl, unsubstituted or substituted by at least one R10a Substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heteroaryl, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heteroaryloxy, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heteroarylthio, unsubstituted or substituted by at least one R 10a Substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -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) or -P(=S)(Q1)(Q2).
[0130] In Formula 1, two or more adjacent groups among R1, R2, R 10 , R 20 , R 30 and R 40 may optionally be bonded to each other to form an unsubstituted or R-substituted C5-C 10a carbocyclic group or an unsubstituted or R-substituted C1-C 60 heterocyclic group. 10a Substituted C1-C 60 heterocyclic group.
[0131] R 10a may be:
[0132] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0133] Each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60Heteroaralkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 )、-P(=S)(Q 11 )(Q 12 ) or any combination thereof;
[0134] Each unsubstituted or substituted by the following C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, C1-C 60 Heteroaryloxy or C1-C 60 Heteroarylthio: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)(Q 21 )、-S(=O)2(Q 21)、 -P(=O)(Q 21 )(Q 22 )、 -P(=S)(Q 21 )(Q 22 ) or any combination thereof; or
[0135] -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 ) or -P(=S)(Q 31 )(Q 32 ).
[0136] In an embodiment, Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amidino; hydrazino; hydrazono; C1-C 60 alkyl; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; or a C3-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof, unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 carbocyclic group or C1-C 60 heterocyclic group.
[0137] In an embodiment, R1, R2, R 10 , R 20 , R 30 and R 40 can each independently be:
[0138] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl or C1-C 20 alkoxy;
[0139] C1-C, each substituted by deuterium, -F, -Cl, -Br, -I, -CDH2, -CD2H, -CD3, cyano, phenyl, biphenyl or any combination thereof 20 alkyl, C1-C 20 alkoxy or C3-C 10 cycloalkyl;
[0140] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentacenyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentacenyl, pyrrolyl, thienyl, furyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafuranyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, indolopyrrolyl, indolopyrrolyl, indolocarbazolyl or indolocarbazolyl;
[0141] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentacenyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentacenyl, pyrrolyl, thienyl, furyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafuranyl,azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, indolopyrrolyl, indolopyrrolyl, indolocarbazolyl or indolocarbazolyl: deuterium, -F, -Cl, -Br, -I, -CDH2, -CD2H, -CD3, cyano, C1-C 20 alkyl, C1-C 20 alkoxy, C3-C 10Cycloalkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentacenyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, quinquephenyl, pyrrolyl, thienyl, furyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafuranyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, indolopyrrolyl, indolocarbazolyl, -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 ), -P(=S)(Q 31 )(Q 32 ) or any combination thereof; or
[0142] -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) or -P(=S)(Q1)(Q2).
[0143] In an embodiment, R1, R2, R 10 , R20 , R 30 and R 40 may each independently be:
[0144] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl or C1-C 20 alkoxy;
[0145] C1-C alkyl or C1-C alkoxy each independently substituted with deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof; or 20 alkyl or C1-C 20 alkoxy; or
[0146] a group represented by one of Formulae 5-1 to 5-26 and Formulae 6-1 to 6-55:
[0147]
[0148] X
[0149]
[0150]
[0151] In Formulae 5-1 to 5-26 and Formulae 6-1 to 6-55,
[0152] Y 31 and Y 32 may each independently be O, S, C(Z 33 )(Z 34 ), N(Z 33 ), or Si(Z 33 )(Z 34 ),
[0153] Z 31 to Z 34 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthryl, triphenylene, pyridyl, pyrimidinyl, carbazolyl or triazinyl,
[0154] e2 may be 1 or 2,
[0155] e3 may be an integer selected from 1 to 3,
[0156] e4 may be an integer selected from 1 to 4,
[0157] e5 can be an integer selected from 1 to 5,
[0158] e6 can be an integer selected from 1 to 6,
[0159] e7 can be an integer selected from 1 to 7,
[0160] e9 can be an integer selected from 1 to 9, and
[0161] * indicates the binding site to the adjacent atom.
[0162] In an embodiment, two or more adjacent groups among R1, R2, R 10 , R 20 , R 30 and R 40 can optionally be bonded to each other to form:
[0163] A cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl group, each unsubstituted or substituted by at least one R 10a .
[0164] In an embodiment, two or more adjacent groups among R1, R2, R 10 , R 20 , R 30 and R 40 can optionally be bonded to each other to form:
[0165] A cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl group; or
[0166] A cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl group, each substituted by deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof.
[0167] In an embodiment, R1, R2, R 10 , R 20 , R 30 and R 40 can each independently be:
[0168] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl or C1-C 20 alkoxy;
[0169] C1-C 20 alkyl or C1-C 20 alkoxy, each substituted by deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof;
[0170] phenyl, biphenyl, terphenyl, pentaphenylenyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, acridinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl or dibenzocarbazolyl; or
[0171] phenyl, biphenyl, terphenyl, pentaphenylenyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, carbazolyl, acridinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl or dibenzocarbazolyl, each substituted with: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, C1-C 20 alkyl substituted with deuterium, phenyl substituted with deuterium or any combination thereof.
[0172] In an embodiment, the organometallic compound can be represented by Formula 11:
[0173] [Formula 11]
[0174]
[0175] In Formula 11,
[0176] M1, A 10 、A 20 、A 30 、Y 10 、Y 20 、Y 30 、Y 40 、T1 to T4, L 11 to L 14 and a11 to a14 can each be the same as those described herein,
[0177] One of X1 and X2 can be a single bond,
[0178] The other of X1 and X2 can be O, S, Se, N(R 52 ) or C(R 52 )(R 53 ),
[0179] One of X3 and X4 can be a single bond,
[0180] The other of X3 and X4 can be O, S, Se, N(R 54 ) or C(R 54 )(R 55 ),
[0181] Y 41 can be C(R 41)、C or N, Y42 can be C(R 42 ), or N, Y 43 can be C(R 43 ), or N, Y 44 can be C(R 44 ), or N, Y 45 can be C(R 45 ), or N, Y 46 can be C(R 46 ), or N, Y 47 can be C(R 47 ), or N, Y 48 can be C(R 48 ), or N, Y 49 can be C(R 49 ), or N, Y 50 can be C(R 50 ), or N, Y 51 can be C(R 51 ), or N, and
[0182] R 41 to R 55 can each independently be the same as those described for R 40 in Reference Formula 1.
[0183] In an embodiment, the organometallic compound represented by Formula 1 can be represented by one of Formulas 21 to 28:
[0184] [Formula 21]
[0185]
[0186] [Formula 22]
[0187]
[0188] [Formula 23]
[0189]
[0190] [Formula 24]
[0191]
[0192] [Formula 25]
[0193]
[0194] [Formula 26]
[0195]
[0196] [Formula 27]
[0197]
[0198] [Equation 28]
[0199]
[0200] In Equations 21 to 28,
[0201] M1, T1 to T4 and L 12 may each be the same as described herein,
[0202] X1 and X2 can each independently be O, S, Se, N (R 52 ) or C(R 52 )(R 53 ),
[0203] X3 and X4 can each independently be O, S, Se, N (R 54 ) or C(R 54 )(R 55 ),
[0204] Y 11 Can be C(R 11 ) or N, Y 12 Can be C(R 12 ) or N, Y 13 Can be C(R 13 ) or N, and Y 14 Can be C(R 14 ) or N,
[0205] Y 22 Can be C(R 22 ) or N, Y 23 Can be C(R 23 ) or N, Y 24 Can be C(R 24 ) or N, Y 25 Can be C(R 25 ) or N, Y 26 Can be C(R 26 ) or N, and Y 27 Can be C(R 27 ) or N,
[0206] Y 31 Can be C(R 31 ) or N, Y 32 Can be C(R 32 ) or N, and Y 33 Can be C(R 33 ) or N,
[0207] Y 42 Can be C(R 42 ) or N, Y 43 Can be C(R43 ) or N, Y 44 may be C(R 44 ) or N, Y 45 may be C(R 45 ) or N, Y 46 may be C(R 46 ) or N, Y 47 may be C(R 47 ) or N, Y 48 may be C(R 48 ) or N, Y 49 may be C(R 49 ) or N, Y 50 may be C(R 50 ) or N, and Y 51 may be C(R 51 ) or N,
[0208] R 11 to R 14 may each independently be the same as those described for R in Reference Formula 1 10 described,
[0209] R 21 to R 27 may each independently be the same as those described for R in Reference Formula 1 20 described,
[0210] R 31 to R 33 may each independently be the same as those described for R in Reference Formula 1 30 described, and
[0211] R 42 to R 55 may each independently be the same as those described for R in Reference Formula 1 40 described.
[0212] In an embodiment, the organometallic compound may be electrically neutral.
[0213] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 192, but the embodiment is not limited thereto:
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224] The organometallic compound represented by Formula 1 has the structure of a tetradentate organometallic compound, in which a bulky fused ring structure can be arranged on the portion of the ligand corresponding to the highest occupied molecular orbital (HOMO). This structure allows the separation of HOMO and the lowest unoccupied molecular orbital (LUMO) within the organometallic compound structure, resulting in a narrow full width at half maximum (FWHM), high color purity, and high luminous efficiency. This structure can have improved structural stability, so that when the organometallic compound represented by Formula 1 is used in the emission layer of an organic light-emitting device, the organic light-emitting device can have a long lifespan, and can suppress the formation of an excimer complex with the host in the emission layer, resulting in high luminous efficiency characteristics.
[0225] Accordingly, when the organometallic compound represented by Formula 1 is applied to an organic light-emitting device, color purity, luminous efficiency, and lifespan characteristics can be improved. For example, when the organometallic compound represented by Formula 1 is included in an emission layer, an organic light-emitting device emitting deep blue light, blue light, and / or green light with excellent color purity, luminous efficiency, and lifespan characteristics can be realized.
[0226] The organometallic compound represented by Formula 1 may emit blue light or green light. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 400 nm to about 580 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 400 nm to about 490 nm (bottom emission CIE values of 0.15, 0.05 to 0.15). x,y Color coordinates) or the organic metal compound represented by Formula 1 can emit green light having a maximum emission wavelength in the range of about 500 nm to about 580 nm, but the embodiment is not limited thereto. Therefore, the organic metal compound represented by Formula 1 can be used to manufacture an organic light-emitting device that emits blue light or green light.
[0227] In an embodiment, the organometallic compound represented by Formula 1 may emit deep blue light having a maximum emission wavelength in the range of about 410 nm to about 465 nm.
[0228] A method of synthesizing the organometallic compound represented by Formula 1 may be easily understood by those of ordinary skill in the art by referring to the examples described herein.
[0229] According to an embodiment, an organic light-emitting device may include a first electrode, a second electrode facing the first electrode, a sandwich layer between the first electrode and the second electrode and including an emission layer, and an organometallic compound represented by Formula 1.
[0230] In an embodiment, in the organic light-emitting device,
[0231] the first electrode may be an anode,
[0232] the second electrode may be a cathode,
[0233] the sandwich layer may further include: a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode,
[0234] the hole transport region may include at least one of a hole injection layer, a hole transport layer, an emission assist layer, and an electron blocking layer, and
[0235] the electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
[0236] In an embodiment, the electron transport region may include a hole blocking layer.
[0237] In an embodiment, the hole blocking layer may contact (e.g., directly contact) the emission layer.
[0238] In an embodiment, the hole blocking layer may include a phosphine oxide-containing compound, a silyl-containing compound, or any combination thereof.
[0239] In an embodiment, the emission layer may include an organometallic compound represented by Formula 1. In an embodiment, the emission layer may emit blue light or green light each having a maximum emission wavelength in the range of about 400 nm to about 580 nm.
[0240] In an embodiment, the emission layer of the organic light-emitting device may include a dopant and a host, and the dopant may include an organometallic compound represented by Formula 1. For example, the organometallic compound represented by Formula 1 may be used as a dopant. The emission layer may emit, for example, blue light or green light. The blue light may have, for example, a maximum emission wavelength in the range of about 400 nm to about 490 nm. The green light may have, for example, a maximum emission wavelength in the range of about 500 nm to about 580 nm.
[0241] In an embodiment, the emission layer may emit deep blue light having a maximum emission wavelength in the range of about 410 nm to about 465 nm.
[0242] In an embodiment, the emission layer may include a host and a dopant.
[0243] In an embodiment, in the emission layer, based on weight, the amount of the host may be greater than the amount of the dopant.
[0244] In an embodiment, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0245] In an embodiment, the host may be the host described herein.
[0246] Therefore, an organic light-emitting device including an organometallic compound represented by Formula 1 may have high color purity, high luminous efficiency, low driving voltage, and long lifetime characteristics.
[0247] In an embodiment, the organometallic compound represented by Formula 1 may emit green light or blue light. For example, the organometallic compound represented by Formula 1 may emit green light or blue light having a maximum emission wavelength in the range of about 390 nm to about 580 nm. For example, the organometallic compound represented by Formula 1 may emit green light or blue light having a maximum emission wavelength in the range of about 400 nm to about 580 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 390 nm to about 500 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 410 nm to about 500 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 410 nm to about 490 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 430 nm to about 480 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 440 nm to about 475 nm. For example, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in the range of about 455 nm to about 470 nm.
[0248] As another example, the organometallic compound represented by Formula 1 may emit green light having a maximum emission wavelength in the range of about 500 nm to about 580 nm. For example, the organometallic compound represented by Formula 1 may emit green light having a maximum emission wavelength in the range of about 510 nm to about 570 nm. For example, the organometallic compound represented by Formula 1 may emit green light having a maximum emission wavelength in the range of about 520 nm to about 560 nm. For example, the organometallic compound represented by Formula 1 may emit green light having a maximum emission wavelength in the range of about 530 nm to about 550 nm.
[0249] In an embodiment, the organometallic compound represented by Formula 1 may have a bottom emission CIE xThe color purity with color coordinates in the range of about 0.12 to about 0.15. For example, the organometallic compound represented by Formula 1 may have a bottom emission CIE therein x The color purity with color coordinates in the range of about 0.13 to about 0.14. In an embodiment, the organometallic compound represented by Formula 1 may have a bottom emission CIE therein y The color purity with color coordinates in the range of about 0.06 to about 0.25. For example, the organometallic compound represented by Formula 1 may have a bottom emission CIE therein y The color purity with color coordinates in the range of about 0.10 to about 0.20. For example, the organometallic compound represented by Formula 1 may have a bottom emission CIE therein y The color purity with color coordinates in the range of about 0.13 to about 0.20.
[0250] As used herein, the term "interlayer" may refer to a single layer and / or multiple layers between the first electrode and the second electrode of an organic light-emitting device.
[0251] According to an embodiment, an electronic device may include an organic light-emitting device. In an embodiment, the electronic device may further include a thin-film transistor. In an embodiment, the electronic device may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the organic light-emitting device may be electrically connected to at least one of the source electrode and the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. The electronic device may be the electronic device described herein.
[0252] According to an embodiment, a consumer product may include an organic light-emitting device.
[0253] In an embodiment, the consumer product may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall including a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0254] Figure 1 description]
[0255] Figure 1 FIG. 0 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 interlayer 130, and a second electrode 150.
[0256] Hereinafter, reference Figure 1 is made to describe the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10.
[0257] [First Electrode 110]
[0258] In Figure 1 the substrate may further be included under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0259] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0260] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0261] The first electrode 110 may have a single-layer structure composed of a single layer or a multi-layer structure including multiple layers. In an embodiment, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0262] [Interlayer 130]
[0263] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0264] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
[0265] In addition to various organic materials, the interlayer 130 may further include a metal-containing compound (such as an organometallic compound) or an inorganic material (such as a quantum dot), etc.
[0266] In an embodiment, the interlayer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between adjacent units of the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer as described above, the organic light-emitting device 10 may be a tandem organic light-emitting device.
[0267] [Hole transport region in the interlayer 130]
[0268] The hole transport region may have a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multilayer structure including multiple layers (including different materials).
[0269] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0270] In an embodiment, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where the layers of each structure may be stacked from the first electrode 110 in their respective specified order, but the structure of the hole transport region is not limited thereto.
[0271] In an embodiment, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0272] [Formula 201]
[0273]
[0274] [Formula 202]
[0275]
[0276] In Formula 201 and Formula 202,
[0277] L 201 to L 204 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0278] L 205 can be *-O-*, *-S-*, *-N(Q 201 )-*, an unsubstituted or at least one R-substituted C1-C 10a alkylene, an unsubstituted or at least one R-substituted C2-C 20 alkenylene, an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 20 heterocyclic group, 10a substituted C3-C 60 substituted C1-C 10a substituted C2-C 60 heterocyclic group,
[0279] xa1 to xa4 can each independently be an integer selected from 0 to 5,
[0280] xa5 can be an integer selected from 1 to 10,
[0281] R 201 to R 204 and Q 201 can each independently be an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a substituted C1-C 60 heterocyclic group,
[0282] R 201 and R 202 can optionally be connected to each other via a single bond, an unsubstituted or at least one R-substituted C1-C5 alkylene or an unsubstituted or at least one R-substituted C2-C5 alkenylene to form an unsubstituted or at least one R-substituted C8-C 10a substituted polycyclic group (e.g., carbazolyl) (e.g., compound HT16), 10a substituted C2-C5 alkenylene to form an unsubstituted or at least one R-substituted C8-C 10a substituted polycyclic group, and 60 substituted polycyclic group, and
[0283] R 203 and R 204 can optionally be connected to each other via a single bond, an unsubstituted or at least one R-substituted C1-C5 alkylene or an unsubstituted or at least one R-substituted C2-C5 alkenylene to form an unsubstituted or at least one R-substituted C8-C 10a substituted polycyclic group, and 10a substituted C2-C5 alkenylene to form an unsubstituted or at least one R-substituted C8-C 10a substituted polycyclic group, and 60 substituted polycyclic group, and
[0284] na1 can be an integer selected from 1 to 4.
[0285] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formula CY201 to Formula CY217:
[0286]
[0287] In Formulas CY201 to CY217, R 10b and R 10c may each independently be the same as described with reference to R 10a , ring CY 201 to ring CY 204 may each independently be a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group, and at least one hydrogen in Formulas CY201 to CY217 may be unsubstituted or substituted by R as described herein 10a .
[0288] In an embodiment, in Formulas CY201 to CY217, ring CY 201 to ring CY 204 may each independently be phenyl, naphthyl, phenanthryl or anthryl.
[0289] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY203.
[0290] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217.
[0291] In an embodiment, in Formula 201, xa1 may be 1, R 201 may be a group represented by one of Formulas CY201 to CY203, xa2 may be 0, and R 202 may be a group represented by one of Formulas CY204 to CY207.
[0292] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formulas CY201 to CY203.
[0293] [[ID=G49]]In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formulas CY201 to CY203, and may each independently include at least one of the groups represented by Formulas CY204 to CY217.
[0294] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY217.
[0295] In an embodiment, the hole transport region may include one of Compounds HT1 to HT46, 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), or any combination thereof:
[0296]
[0297]
[0298]
[0299]
[0300]
[0301] The thickness of the hole transport region may be in the range of about to about For example, the thickness of the hole transport region may be in the range of about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in the range of about to about and the thickness of the hole transport layer may be in the range of about to about For example, the thickness of the hole injection layer may be in the range of about to about For example, the thickness of the hole transport layer may be in the range of about [[ID=4)3]]to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the above ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0302] The emission assisting layer can increase the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the leakage of electrons from the emission layer to the hole transport region. The materials that can be included in the hole transport region can be included in the emission assisting layer and the electron blocking layer.
[0303] [p-dopant]
[0304] In addition to these materials, the hole transport region can further include a charge generation material for improving the conductive properties. The charge generation material can be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generation material).
[0305] The charge generation material can be, for example, a p-dopant.
[0306] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be less than or equal to about -3.5 eV.
[0307] In an embodiment, the p-dopant can include a quinone derivative, a cyanide-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
[0308] Examples of the quinone derivative can include TCNQ and F4-TCNQ.
[0309] Examples of the cyanide-containing compound can include HAT-CN and the compound represented by Formula 221.
[0310]
[0311] [Formula 221]
[0312]
[0313] In Formula 221,
[0314] R 221 to R 223 can each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, and
[0315] R 221 to R 223 at least one of which can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group each substituted by: cyano; -F; -Cl; -Br; -I; a C1-C substituted by cyano, -F, -Cl, -Br, -I, or any combination thereof20 alkyl; or any combination thereof.
[0316] In a compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
[0317] Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
[0318] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0319] Examples of non-metals may include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).
[0320] Examples of compounds including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0321] Examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and rhenium oxides (e.g., ReO3, etc.).
[0322] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0323] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
[0324] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
[0325] Examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), ferrous halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).
[0326] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.) and tin halides (e.g., SnI2, etc.).
[0327] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, etc.
[0328] Examples of metalloid halides may include antimony halides (e.g., SbCl5, etc.).
[0329] Examples of metal tellurides may include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[0330] [Emission layer in interlayer 130]
[0331] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to sub-pixels. In an embodiment, the emission layer may have a stacked structure of two or more layers among a red emission layer, a green emission layer, and a blue emission layer, where the two or more layers may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emission layer may include two or more materials among a red light-emitting material, a green light-emitting material, and a blue light-emitting material, where the two or more materials may be mixed with each other in a single layer to emit white light.
[0332] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0333] Based on 100 parts by weight of the host, the amount of the dopant in the emission layer may be in the range of about 0.01 part by weight to about 15 parts by weight.
[0334] In an embodiment, the emission layer may include quantum dots.
[0335] In an embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or a dopant in the emission layer.
[0336] The thickness of the emission layer may be about to about in the range. For example, the thickness of the emission layer may be about to about When the thickness of the emission layer is within any of the above ranges, excellent light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0337] [Host]
[0338] In an embodiment, the host may include a compound represented by Formula 301:
[0339] [Formula 301]
[0340] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21 .
[0341] In Formula 301,
[0342] Ar 301 and L 301 may each independently be an unsubstituted or at least one R 10a -substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a -substituted C1-C 60 heterocyclic group,
[0343] xb11 may be 1, 2, or 3,
[0344] xb1 may be an integer selected from 0 to 5,
[0345] R 301 may be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an unsubstituted or at least one R 10a -substituted C1-C 60 alkyl group, an unsubstituted or at least one R 10a -substituted C2-C 60 alkenyl group, an unsubstituted or at least one R 10a -substituted C2-C 60 alkynyl group, an unsubstituted or at least one R 10a -substituted C1-C 60 alkoxy group, an unsubstituted or at least one R 10a -substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a -substituted C1-C 60 heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0346] xb21 can be an integer selected from 1 to 5, and
[0347] Q 301 to Q 303 can each independently be the same as described with reference to Q1.
[0348] In an embodiment, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0349] In an embodiment, the host can include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0350] [Formula 301-1]
[0351]
[0352] [Formula 301-2]
[0353]
[0354] In Formula 301-1 and Formula 301-2,
[0355] Ring A 301 to Ring A 304 can each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0356] X 301 can be O, S, N[(L 304 ) xb4 -R 304 , C(R 304 )(R 305 ), or Si(R 304 )(R 305 ),
[0357] xb22 and xb23 can each independently be 0, 1, or 2,
[0358] L 301, xb1, and R 301 may each be the same as described in the specification,
[0359] L 302 to L 304 may each independently be the same as that referenced to L 301 described,
[0360] xb2 to xb4 may each independently be the same as that referenced to xb1 described, and
[0361] R 302 to R 305 and R 311 to R 314 may each independently be the same as that referenced to R 301 described.
[0362] In an embodiment, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. In an embodiment, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0363] In an embodiment, the host may include one of compounds H1 to H126, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-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-carbazolyl)benzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:
[0364]
[0365]
[0366]
[0367]
[0368]
[0369]
[0370] In an embodiment, the host may include a first host compound and a second host compound.
[0371] In an embodiment, the first host compound may be a hole-transporting host.
[0372] In an embodiment, the second host compound may be an electron-transporting host.
[0373] In an embodiment, the "hole transport host" may be a compound including a hole transport moiety.
[0374] In an embodiment, the "electron transport host" may be not only a compound including an electron transport moiety but also a compound having bipolar properties.
[0375] In the specification, the terms "hole transport host" and "electron transport host" may be understood respectively based on the relative difference between the hole mobility in the hole transport host and the electron mobility in the electron transport host. For example, even when the electron transport host does not include an electron transport moiety, a bipolar compound exhibiting an electron mobility relatively higher than the hole mobility of the hole transport host may be the electron transport host.
[0376] In an embodiment, the hole transport host may be represented by one of Formulae 311-1 to 311-6, and the electron transport host may be represented by one of Formulae 312-1 to 312-4 and Formula 313.
[0377] [Formula 311-1]
[0378]
[0379] [Formula 311-2]
[0380]
[0381] [Formula 311-3]
[0382]
[0383] [Formula 311-4]
[0384]
[0385] [Formula 311-5]
[0386]
[0387] [Formula 311-6]
[0388]
[0389] [Formula 312-1]
[0390]
[0391] [Formula 312-2]
[0392]
[0393] [Formula 312-3]
[0394]
[0395] [Formula 312-4]
[0396]
[0397] [Formula 313]
[0398]
[0399] [Formula 313A]
[0400]
[0401] In Formulas 311-1 to 311-6, 312-1 to 312-4, 313 and 313A,
[0402] Ar 301 may be unsubstituted or substituted by at least one R 10a to form a C3-C 60 carbocyclic group or may be unsubstituted or substituted by at least one R 10a to form a C1-C 60 heterocyclic group,
[0403] A 301 to A 304 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0404] X 301 may be O, S, N[(L 304 ) xb4 -R 304 , C[(L 304 ) xb4 -R 304 [(L 305 ) xb5 -R 305 or Si[(L 304 ) xb4 -R 304 [(L 305 ) xb5 -R 305 ,
[0405] X 302 、Y 301 and Y 302 may each independently be a single bond, O, S, N[(L 305 ) xb5 -R 305 , C[(L 304 ) xb4 -R304 [(L 305 ) xb5 -R 305 、Si[(L 304 ) xb4 -R 304 [(L 305 ) xb5 -R 305 or S(=O)2,
[0406] xb1 to xb5 can each independently be 0, 1, 2, 3, 4 or 5,
[0407] xb6 can be 1, 2, 3, 4 or 5,
[0408] X 321 to X 328 can each independently be N or C[(L 324 ) xb24 -R 324 ,
[0409] Y 321 can be *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 -*', *-C[(L 325 ) xb25 -R 325 [(L 326 ) xb26 -R 326 -*', *-C[(L 325 ) xb25 -R 325 =C[(L 326 ) xb26 -R 326 -*', *-C[(L 325 ) xb25 -R 325 =N-*' or *-N=C[(L 326 ) xb26 -R 326 -*',
[0410] k21 can be 0, 1 or 2, where when k21 is 0, Y 321 does not exist,
[0411] xb21 to xb26 can each independently be 0, 1, 2, 3, 4 or 5,
[0412] A 31 、A 32 and A 34 can each independently be C3-C 60A carbocyclic group or a C1-C 30 heterocyclic group,
[0413] A 33 may be a group represented by Formula 313A,
[0414] X 31 may be N[(L 335 ) xb35 -(R 335 )], O, S, Se, C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )] or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )],
[0415] xb31 to xb36 may each independently be 0, 1, 2, 3, 4 or 5,
[0416] xb42 to xb44 may each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
[0417] L 301 to L 306 、L 321 to L 326 and L 331 to L 336 may each independently be a single bond, an unsubstituted or at least one R 10a substituted C1-C 20 alkylene, an unsubstituted or at least one R 10a substituted C2-C 20 alkenylene, an unsubstituted or at least one R 10a substituted C2-C 20 alkynylene, an unsubstituted or at least one R 10a substituted C3-C 10 cycloalkylene, an unsubstituted or at least one R 10a substituted C1-C 10 heterocycloalkylene, an unsubstituted or at least one R 10a substituted C3-C 10 cycloalkenylene, an unsubstituted or at least one R 10a substituted C1-C 10 heterocycloalkenylene, an unsubstituted or at least one R 10a substituted C6-C60 Arylene, unsubstituted or substituted by at least one R 10a to C1-C 60 Heteroarylene, unsubstituted or substituted by at least one R 10a Substituted divalent non-aromatic fused polycyclic group or unsubstituted or substituted by at least one R 10a Substituted divalent non-aromatic fused heteropolycyclic group,
[0418] R 301 to R 305 , R 311 to R 314 , R 321 to R 326 and R 331 to R 336 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, unsubstituted or substituted by at least one R 10a to C1-C 60 Alkyl, unsubstituted or substituted by at least one R 10a to C2-C 60 Alkenyl, unsubstituted or substituted by at least one R 10a to C2-C 60 Alkynyl, unsubstituted or substituted by at least one R 10a to C1-C 60 Alkoxy, unsubstituted or substituted by at least one R 10a to C3-C 10 Cycloalkyl, unsubstituted or substituted by at least one R 10a to C1-C 10 Heterocycloalkyl, unsubstituted or substituted by at least one R 10a to C3-C 10 Cycloalkenyl, unsubstituted or substituted by at least one R 10a to C1-C 10 Heterocycloalkenyl, unsubstituted or substituted by at least one R 10a to C6-C 60 Aryl, unsubstituted or substituted by at least one R 10a to C6-C 60 Aryloxy, unsubstituted or substituted by at least one R 10a to C6-C 60 Arylthio, unsubstituted or substituted by at least one R 10a to C1-C 60 Heteroaryl, unsubstituted or substituted by at least one R 10a to C1-C 60 Heteroaryloxy, unsubstituted or substituted by at least one R 10a to C1-C 60Heteroarylthio, unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused polycyclic group, an unsubstituted or substituted monovalent non-aromatic fused polycyclic group, 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -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), or -P(═S)(Q1)(Q2),
[0419] R 321 to R 326 Two or more adjacent groups in the group may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, R 10a Can be:
[0420] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;
[0421] Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 ),-S(=O)(Q 11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ),-P(=S)(Q11 )(Q 12 ) or any combination thereof;
[0422] Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group or C1-C 60 heteroarylthio group: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group, C1-C 60 heteroarylthio group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 )、-P(=S)(Q 21 )(Q 22 ) or any combination thereof; or
[0423] -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 ) or -P(=S)(Q 31 )(Q 32 ),and
[0424] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each of them can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or each unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
[0425] In an embodiment, the first host compound and the second host compound may form an exciplex.
[0426] [Phosphorescent dopant]
[0427] The phosphorescent dopant may include at least one transition metal as a central metal.
[0428] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0429] The phosphorescent dopant may be electrically neutral.
[0430] In an embodiment, the phosphorescent dopant may be an organometallic compound represented by Formula 1.
[0431] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0432] [Formula 401]
[0433] M(L 401 ) xc1 (L 402 ) xc2
[0434] [Formula 402]
[0435]
[0436] In Formula 401 and Formula 402,
[0437] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0438] L 401 can be a ligand represented by Formula 402, and xc1 can be 1, 2, or 3, where when xc1 is 2 or greater, two or more L 401 can be the same as or different from each other,
[0439] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, where when xc2 is 2 or greater, two or more L 402 can be the same as or different from each other,
[0440] X 401 and X 402 can each independently be nitrogen or carbon,
[0441] Ring A 401 and Ring A 402 can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0442] T 401 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 = *',
[0443] X 403 and X 404 can each independently be a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ), or Si(Q 413 )(Q 414 ),
[0444] Q 411 to Q414 may each independently be the same as described with reference to Q1,
[0445] R 401 and R 402 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 20 alkyl, unsubstituted or substituted with at least one R 10a C1-C 20 alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), or -P(=O)(Q 401 )(Q 402 ),
[0446] Q 401 to Q 403 may each independently be the same as described with reference to Q1,
[0447] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0448] * and *' in Formula 402 each indicate the binding site to M in Formula 401.
[0449] For example, in Formula 402, X 401 may be nitrogen and X 402 may be carbon, or X 401 and X 402 may each be nitrogen.
[0450] In an embodiment, in Formula 401, when xc1 is 2 or greater, two or more of the two ring A 401 s in L 401 may optionally be linked together via T 402 as a linking group, and the two ring A 402 s may optionally be linked together via T 403Linked together (see Compound PD1 to Compound PD4 and Compound PD7). T 402 and T 403 may each independently be the same as that described with reference to T 401 described.
[0451] In Formula 401, L 402 may be an organic ligand. In an embodiment, L 402 may include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isocyano group, a -CN group, a phosphorus-containing group (e.g., phosphine group, phosphite group, etc.) or any combination thereof.
[0452] In an embodiment, the phosphorescent dopant may include, for example, one or any combination of Compounds PD1 to PD39:
[0453]
[0454]
[0455]
[0456] [Fluorescent dopant]
[0457] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound or any combination thereof.
[0458] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0459] [Formula 501]
[0460]
[0461] In Formula 501,
[0462] Ar 501 、L 501 to L 503 、R 501 and R 502 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0463] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0464] xd4 may be 1, 2, 3, 4, 5 or 6.
[0465] In an embodiment, in Formula 501, Ar 501 may be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthryl, 1,2-benzoanthryl, pyrenyl, etc.).
[0466] In an embodiment, in Formula 501, xd4 may be 2.
[0467] In an embodiment, the fluorescent dopant may include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
[0468]
[0469]
[0470]
[0471] [Thermally activated delayed fluorescence material]
[0472] The emission layer may further include a thermally activated delayed fluorescence material.
[0473] The thermally activated delayed fluorescence material may be selected from compounds capable of emitting thermally activated delayed fluorescence based on a thermally activated delayed fluorescence emission mechanism.
[0474] Depending on the type of other materials included in the emission layer, the thermally activated delayed fluorescence material included in the emission layer may be used as a host or a dopant.
[0475] In an embodiment, the difference between the triplet energy level (eV) of the thermally activated delayed fluorescence material and the singlet energy level (eV) of the thermally activated delayed fluorescence material may be in the range of 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the thermally activated delayed fluorescence material and the singlet energy level (eV) of the thermally activated delayed fluorescence material satisfies the above range, upconversion from the triplet state to the singlet state of the thermally activated delayed fluorescence material may occur effectively. Thus, the organic light-emitting device 10 may have improved luminous efficiency.
[0476] In an embodiment, the thermally activated delayed fluorescence material may include: a material including at least one electron donor (e.g., a π-electron rich C3-C 60 cyclic group such as a carbazolyl group) and at least one electron acceptor (e.g., a sulfinyl group, a cyano group, and a π-electron deficient nitrogen-containing C1-C 60 cyclic group, etc.); or a material including a C8-C 60 polycyclic group in which at least two cyclic groups are fused together while sharing boron (B).
[0477] In an embodiment, the thermally activated delayed fluorescence material may include, for example, at least one of Compounds DF1 to DF9:
[0478]
[0479] [Quantum dots]
[0480] The emission layer may include quantum dots.
[0481] In the specification, the quantum dots may be crystals of semiconductor compounds and may include any material capable of emitting light of various emission wavelengths according to the size of the crystals.
[0482] The diameter of the quantum dots may be in the range of, for example, about 1 nm to about 10 nm.
[0483] The quantum dots may be synthesized by a wet chemical process, a metalorganic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any process similar thereto.
[0484] The wet chemical process is a method including mixing precursor materials with an organic solvent and growing quantum dot particle crystals. When the quantum dot particle crystals grow, the organic solvent naturally serves as a dispersant coordinated on the surface of the quantum dot particle crystals and controls the growth of the quantum dot particle crystals so that the growth of the quantum dot particle crystals can be controlled by a process that is less costly and easier to perform than vapor deposition methods (such as metalorganic chemical vapor deposition or molecular beam epitaxy).
[0485] The quantum dots may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds, or any combination thereof.
[0486] Examples of group II-VI semiconductor compounds may include: binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
[0487] Examples of group III-V semiconductor compounds may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In an embodiment, the group III-V semiconductor compound may further include a group II element. Examples of group III-V semiconductor compounds further including a group II element may include InZnP, InGaZnP, or InAlZnP.
[0488] Examples of group III-VI semiconductor compounds may include: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; ternary compounds such as InGaS3 or InGaSe3; or any combination thereof.
[0489] Examples of group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, etc.; or any combination thereof.
[0490] Examples of group IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
[0491] Examples of group IV elements or compounds may include: single-element materials such as Si or Ge; binary compounds such as SiC or SiGe; or any combination thereof.
[0492] Each element included in a compound (such as a binary compound, ternary compound, or quaternary compound) may be present in the particles at a uniform concentration or a non-uniform concentration.
[0493] In an embodiment, the quantum dots may have a single structure (wherein the concentration of each element in the quantum dots is uniform), or may have a core-shell structure. In an embodiment, when the quantum dots have a core-shell structure, the material included in the core and the material included in the shell may be different from each other.
[0494] The shell of the quantum dots can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can be used as a charging layer to impart electrophoretic properties to the quantum dots. The shell can be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient, where the concentration of the material present in the shell decreases towards the center of the core.
[0495] Examples of the shell of the quantum dots may include metal oxides, metalloid oxides, non-metal oxides, semiconductor compounds, or any combination thereof. Examples of metal oxides, metalloid oxides, or non-metal oxides may include: binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; or any combination thereof.
[0496] Examples of semiconductor compounds may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, or any combination thereof as described herein. In an embodiment, the semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0497] The quantum dots may have a full width at half maximum (FWHM) of the emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dots may have an FWHM of the emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dots may have an FWHM of the emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of the quantum dots is within any of these ranges, the quantum dots may have improved color purity or improved color reproducibility. The light emitted by the quantum dots can be emitted in all directions so that a wide viewing angle can be improved.
[0498] In an embodiment, the quantum dots may be in the form of a sphere, a cone, a multi-arm form, or a cube form, or the quantum dots may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0499] Since the band gap can be adjusted by controlling the size of the quantum dots, light with various wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, an organic light emitting device that emits light with various wavelength bands can be realized. For example, the size of the quantum dots can be selected to emit red, green, and / or blue light. In an embodiment, the size of the quantum dots can be configured to emit white light by combining lights of various colors.
[0500] [Electron transport region in the interlayer 130]
[0501] The electron transport region can have a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).
[0502] The electron transport region can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0503] In an embodiment, the electron transport region can 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, and the layers of each structure can be stacked from the emission layer in their respective specified order, but the structure of the electron transport region is not limited thereto.
[0504] The electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) can include a metal-free compound including at least one nitrogen-containing C1-C 60 ring group lacking π electrons.
[0505] In an embodiment, the electron transport region can include a compound represented by Formula 601.
[0506] [Formula 601]
[0507] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21
[0508] In Formula 601,
[0509] Ar 601 and L 601 can each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a Substituted C1-C 60 heterocyclic group,
[0510] xe11 can be 1, 2 or 3,
[0511] xe1 can be 0, 1, 2, 3, 4 or 5,
[0512] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ),-C(=O)(Q 601 )、-S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0513] Q 601 To Q 603 can be independently the same as described with reference to Q1,
[0514] xe21 can be 1, 2, 3, 4, or 5, and
[0515] Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or replaced by at least one R 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic group.
[0516] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 Can be linked together via a single bond.
[0517] In an embodiment, in Formula 601, Ar 601 It may be unsubstituted or substituted with at least one R 10a substituted anthracenyl.
[0518] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0519] [Formula 601-1]
[0520]
[0521] In formula 601-1,
[0522] X614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X 616 may be N or C(R 616 ), and X 614 to X 616 at least one of which may each be N,
[0523] L 611 to L 613 may each independently be the same as described with reference to L 601 .
[0524] xe611 to xe613 may each independently be the same as described with reference to xe1,
[0525] R 611 to R 613 may each independently be the same as described with reference to R 601 , and
[0526] R 614 to R 616 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group.
[0527] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0528] In an embodiment, the electron transport region may include one of Compounds ET1 to ET46, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0529]
[0530]
[0531]
[0532]
[0533] The thickness of the electron transport region can be in the range of about to about For example, the thickness of the electron transport region can be in the range of about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be in the range of about to about and the thickness of the electron transport layer can be in the range of about to about For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be in the range of about to about For example, the thickness of the electron transport layer can be in the range of about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and / or the electron transport region is within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0534] In addition to the above materials, the electron transport region (e.g., the electron transport layer in the electron transport region) can further include a metal-containing material.
[0535] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex can be a Li ion, a Na ion, a K ion, an Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex can be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion.
[0536] The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0537] In an embodiment, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1(Liq) or compound ET-D2:
[0538]
[0539] The electron transport region can include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer can contact (e.g., directly contact) the second electrode 150.
[0540] The electron injection layer may have a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).
[0541] 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.
[0542] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0543] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, alkaline earth metal, and rare earth metal, or any combination thereof.
[0544] The alkali metal compound may include: alkali metal oxides such as Li2O, Cs2O, or K2O; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1). The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
[0545] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include: alkali metal ions, alkaline earth metal ions, or rare earth metal ions; and ligands bonded to the metal ions (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof).
[0546] The electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0547] In an embodiment, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide), and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a co-deposited layer of KI:Yb, a co-deposited layer of RbI:Yb, a co-deposited layer of LiF:Yb, etc.
[0548] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0549] The thickness of the electron injection layer may be in the range of about to about . For example, the thickness of the electron injection layer may be in the range of about to about . When the thickness of the electron injection layer is within any of the above ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0550] [Second Electrode 150]
[0551] The second electrode 150 may be disposed on the interlayer 130. The second electrode 150 may be a cathode serving as an electron injection electrode. When the second electrode 150 is a cathode, the material used to form the second electrode 150 may include materials having a low work function, such as metals, alloys, conductive compounds, or any combination thereof.
[0552] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0553] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0554] [Capping layer]
[0555] The organic light-emitting device 10 may include a first capping layer outside the first electrode 110 and / or a second capping layer outside the second electrode 150. For example, the organic light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this specified order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this specified order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this specified order.
[0556] The light generated in the emission layer of the interlayer 130 of the organic light-emitting device 10 may pass through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and pass through the first capping layer to the outside. The light generated in the emission layer of the interlayer 130 of the organic light-emitting device 10 may pass through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and pass through the second capping layer to the outside.
[0557] The first capping layer and the second capping layer may each increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the organic light-emitting device 10 is increased, so that the light-emitting efficiency of the organic light-emitting device 10 can be increased.
[0558] The first capping layer and the second capping layer may each include a material having a refractive index greater than or equal to 1.6 (relative to a wavelength of about 589 nm).
[0559] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0560] At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amino group-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amino group-containing compound may each optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amino group-containing compound.
[0561] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0562] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of Compound HT28 to Compound HT33, one of Compound CP1 to Compound CP6, β-NPB, or any combination thereof:
[0563]
[0564] [Film]
[0565] The organometallic compound represented by Formula 1 may be included in various films. Thus, according to an embodiment, the film may include the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or a light control device) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, or a quantum dot-containing layer, etc.), a light-blocking member (e.g., a light reflection layer or a light absorption layer, etc.), or a protective member (e.g., an insulating layer or a dielectric layer, etc.).
[0566] [Electronic Device]
[0567] The organic light-emitting device may be included in various electronic devices. For example, the electronic device including the organic light-emitting device may be a light-emitting device, an authentication device, etc.
[0568] In addition to the organic light-emitting device, the electronic device (e.g., a light-emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be disposed in at least one traveling direction of the light emitted from the organic light-emitting device. For example, the light emitted from the organic light-emitting device may be blue light or white light. The organic light-emitting device may be the organic light-emitting device described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.
[0569] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixels, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.
[0570] The pixel defining film may be disposed between the plurality of sub-pixel regions to define each sub-pixel.
[0571] The color filter may further include a plurality of color filter regions and a light-shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern disposed between the plurality of color conversion regions.
[0572] The color filter region (or color conversion region) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. In an embodiment, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the quantum dots described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0573] In an embodiment, the organic light-emitting device may emit a first light, the first region may absorb the first light to emit a first-first color light, the second region may absorb the first light to emit a second-first color light, and the third region may absorb the first light to emit a third-first color light. In an embodiment, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0574] In addition to the organic light-emitting device described above, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device.
[0575] The thin-film transistor may further include a gate electrode, a gate insulating film, etc.
[0576] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc.
[0577] The electronic device may further include a sealing portion for sealing the organic light-emitting device. The sealing portion may be disposed between the color filter and / or color conversion layer and the organic light-emitting device. The sealing portion may allow light from the organic light-emitting device to be extracted to the outside, and may prevent environmental air and / or moisture from penetrating into the organic light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one layer of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0578] In addition to the color filter and / or color conversion layer, various functional layers may be further included on the sealing portion according to the use of the electronic device. The functional layer may include a touch screen layer, a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
[0579] In addition to the organic light-emitting device as described above, the authentication device may further include a biometric information collector. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., fingertip, pupil, etc.).
[0580] The electronic device may be applied to various displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game machines, medical tools (e.g., electronic thermometers, sphygmomanometers, glucometers, pulse measurement devices, pulse wave measurement devices, electrocardiogram monitors, ultrasonic diagnostic devices, or endoscope monitors), fish finders, various measuring tools, meters (e.g., meters for vehicles, aircraft, and ships), and projectors, etc.
[0581] Figure 2 and Figure 3 description of]
[0582] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0583] Figure 2 The electronic device of may include a substrate 100, a thin film transistor (TFT), an organic light-emitting device, and a sealing portion 300 for sealing the organic light-emitting device.
[0584] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0585] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0586] The active layer 220 may include an inorganic semiconductor (such as silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0587] The gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220, and the gate electrode 240 may be disposed on the gate insulating film 230.
[0588] The interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and may be disposed between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0589] The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may respectively contact the exposed portions of the source region and the drain region of the active layer 220.
[0590] The TFT may be electrically connected to the organic light-emitting device to drive the organic light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The organic light-emitting device is provided on the passivation layer 280. The organic light-emitting device includes a first electrode 110, an interlayer 130, and a second electrode 150.
[0591] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a part of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0592] The pixel defining film 290 including an insulating material may be disposed on the first electrode 110. The pixel defining film 290 may expose a region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic acid-based organic film. Although not shown in Figure 2 , at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining film 290 and may be provided in the form of a common layer.
[0593] The second electrode 150 may be disposed on the interlayer 130, and a capping layer 170 may further be included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0594] The sealing part 300 may be located on the capping layer 170. The sealing part 300 may be disposed on the organic light-emitting device to protect the organic light-emitting device from moisture and / or oxygen. The sealing part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate or polyacrylic acid, etc.), an epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or any combination of an inorganic film and an organic film.
[0595] Figure 3 FIG. is a schematic cross-sectional view of an electronic device according to another embodiment.
[0596] Figure 3 The electronic device of Figure 2 may be different from the electronic device of Figure 2 at least in that a light-shielding pattern 500 and a functional region 400 are further included on the sealing part 300. The functional region 400 may be a color filter region, a color conversion region, or a combination of a color filter region and a color conversion region. In an embodiment, Figure 3 the organic light-emitting device included in the electronic device of Figure 3 may be a tandem organic light-emitting device.
[0597] Figure 4 description of
[0598] Figure 4 FIG. is a schematic perspective view of a consumer product 1 including an organic light-emitting device according to an embodiment. The consumer product 1, which may be a device for displaying moving images or still images, may be not only a portable electronic device such as a mobile phone, a smart phone, a tablet computer, a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile PC (UMPC), but also various products such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IoT) device. The consumer product 1 may be such a product or any part thereof.
[0599] The consumer product 1 may be a wearable device such as a smart watch, a watch phone, a glasses-type display, or a head-mounted display (HMD), or a part of a wearable device. However, the embodiment is not limited thereto.
[0600] In an embodiment, the consumer product 1 may be an instrument panel of a vehicle, a center information display (CID) disposed on a center console or instrument panel of the vehicle, an in-vehicle rearview mirror display replacing a sideview mirror of the vehicle, an entertainment display for a rear seat of the vehicle, a display disposed on a backrest of a front seat of the vehicle, a head-up display (HUD) mounted in front of the vehicle or projected on a windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 illustrates an embodiment in which the consumer product 1 is a smart phone.
[0601] The consumer product 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may implement an image through a two-dimensional array of pixels disposed in the display area DA.
[0602] The non-display area NDA may be an area where no image is displayed and may surround (e.g., completely surround) the display area DA. A driver for supplying an electrical signal or power to a display element disposed in the display area DA may be disposed in the non-display area NDA. A pad may be disposed in the non-display area NDA, and the pad may be electrically connected to an electronic component or a printed circuit board.
[0603] In the consumer product 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. In an embodiment, as Figure 4 shown, the length in the x-axis direction may be smaller than the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be larger than the length in the y-axis direction.
[0604] Figure 5 and Figures 6A to 6C description]
[0605] Figure 5 FIG. 1000 is a schematic perspective view of the exterior of a vehicle 1000 as a consumer product including an organic light-emitting device according to an embodiment. Figures 6A to 6C FIGS. 1001 and 1002 are schematic views of the interior of the vehicle 1000 according to an embodiment, respectively.
[0606] Refer to Figure 5 、 Figure 6A 、 Figure 6B and Figure 6C , embodiments of the vehicle 1000 may include various devices for moving an object (such as a person, an object, or an animal) to be transported from a starting point to a target point. Examples of the vehicle 1000 may include vehicles traveling on roads or tracks, boats moving on oceans or rivers, and airplanes flying in the air by the action of air, etc.
[0607] The vehicle 1000 can travel on roads or tracks. The vehicle 1000 can move in an optional direction according to the rotation of at least one wheel. Examples of the vehicle 1000 can include three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, prime mover devices, bicycles, and trains traveling on tracks.
[0608] The vehicle 1000 can include a body having an interior and an exterior, and a chassis in addition to the body in which mechanical equipment required for driving is installed. The exterior of the body can include a front panel, a hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between the doors, etc. The chassis of the vehicle 1000 can include a power generation device, a power transmission device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, and front and rear wheels, left and right wheels, etc.
[0609] The vehicle 1000 can include side window glass 1100, front window glass 1200, side mirrors 1300, an instrument cluster 1400, a center console 1500, a passenger seat dashboard 1600, and a display device 2.
[0610] The side window glass 1100 and the front window glass 1200 can be separated by pillars arranged between the side window glass 1100 and the front window glass 1200.
[0611] The side window glass 1100 can be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 can be installed on the door of the vehicle 1000. A plurality of side window glasses 1100 can be provided and can face each other. In an embodiment, the side window glass 1100 can include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 can be arranged adjacent to the instrument cluster 1400, and the second side window glass 1120 can be arranged adjacent to the passenger seat dashboard 1600.
[0612] In an embodiment, the side window glasses 1100 can be spaced apart from each other in the x-axis direction or the -x-axis direction (a direction opposite to the x-axis direction). In an embodiment, the first side window glass 1110 and the second side window glass 1120 can be spaced apart from each other in the x-axis direction or the -x-axis direction. For example, a virtual straight line L connecting the side window glasses 1100 can extend in the x-axis direction or the -x-axis direction. In an embodiment, a virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 can extend in the x-axis direction or the -x-axis direction.
[0613] The front window glass 1200 can be installed in the front of the vehicle 1000. The front window glass 1200 can be arranged between the side window glasses 1100 facing each other.
[0614] The side mirror 1300 can provide a rear view of the vehicle 1000. The side mirror 1300 can be mounted on the exterior of the vehicle body. In an embodiment, a plurality of side mirrors 1300 can be provided. Any one of the plurality of side mirrors 1300 can be arranged outside the first side window glass 1110, and another one of the plurality of side mirrors 1300 can be arranged outside the second side window glass 1120.
[0615] The instrument cluster 1400 can be arranged in front of the steering wheel. The instrument cluster 1400 can include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a speed recorder, an automatic shift lever indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0616] The center console 1500 can include a control panel, and buttons for adjusting an audio device, an air conditioning device, and a seat heater can be provided on the control panel. The center console 1500 can be arranged beside the instrument cluster 1400.
[0617] The passenger seat instrument panel 1600 can be spaced apart from the instrument cluster 1400, and the center console 1500 is arranged between the passenger seat instrument panel 1600 and the instrument cluster 1400. In an embodiment, the instrument cluster 1400 can be arranged corresponding to the driver's seat (not shown), and the passenger seat instrument panel 1600 can be arranged corresponding to the passenger seat (not shown). In an embodiment, the instrument cluster 1400 can be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 can be adjacent to the second side window glass 1120.
[0618] In an embodiment, the display device 2 can include a display panel 3, and the display panel 3 can display an image. The display device 2 can be arranged inside the vehicle 1000. In an embodiment, the display device 2 can be arranged between the side window glasses 1100 facing each other. The display device 2 can be arranged on at least one of the instrument cluster 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0619] The display device 2 can include an organic light emitting display, an inorganic electroluminescent display, a quantum dot display, etc. Hereinafter, as the display device 2 according to an embodiment, an organic light emitting display device including an organic light emitting device will be described as an example. However, various types of display devices as described above can be used in the embodiment.
[0620] See Figure 6A , the display device 2 can be arranged on the center console 1500. In an embodiment, the display device 2 can display navigation information. In an embodiment, the display device 2 can display information about audio settings, video settings, or vehicle settings.
[0621] SeeFigure 6B , the display device 2 can be arranged on the instrument cluster 1400. In an embodiment, the instrument cluster 1400 can display driving information and the like through the display device 2. For example, the instrument cluster 1400 can digitally implement driving information and the like. The instrument cluster 1400 operated digitally can display vehicle information and driving information as images. In an embodiment, the pointer and instrument of the tachometer and various appropriate warning lights or icons can be displayed through digital signals.
[0622] See Figure 6C , the display device 2 can be arranged on the passenger seat instrument panel 1600. The display device 2 can be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 can display an image related to the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 can display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500.
[0623] [Manufacturing Method]
[0624] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a selected region by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0625] When forming the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region by vacuum deposition, depending on the material to be included in the layer to be formed and the structure of the layer to be formed, at a deposition temperature in the range of about 100 °C to about 500 °C, at a vacuum degree in the range of about 10 -8 torr to about 10 -3 torr and at a deposition rate in the range of about to about .
[0626] [Definition of Terms]
[0627] As used herein, the term "C3-C 60 carbocyclic group" can be a cyclic group composed of only carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms. For example, C3-C 50 carbocyclic group, C3-C 40 carbocyclic group, C3-C 30 carbocyclic group, C3-C 20 carbocyclic group, or C3-C 10 carbocyclic group, and as used herein, the term "C1-C 60"Heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and may further include at least one heteroatom as a ring-forming atom in addition to carbon atoms. For example, C1-C 50 heterocyclic group, C1-C 40 heterocyclic group, C1-C 30 heterocyclic group, C1-C 20 heterocyclic group or C1-C 10 heterocyclic group. C3-C 60 carbocyclic group and C1-C 60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. For example, C1-C 60 heterocyclic group may have 3 to 61 ring-forming atoms.
[0628] As used herein, the term "cyclic group" may be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group.
[0629] As used herein, the term "π-electron-rich C3-C 60 cyclic group" may be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a ring-forming moiety, and as used herein, the term "π-electron-deficient nitrogen-containing C1-C 60 cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming moiety.
[0630] In an embodiment,
[0631] C3-C 60 carbocyclic group may be a T1 group, or a group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentaphenylenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentaphenyl, heptaphenylenyl, tetracenyl, picenyl, hexaphenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthrenyl or indenanthracenyl),
[0632] C1-C 60The heterocyclic group may be a T2 group, a group in which two or more T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indolocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl, benzothienodibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuryl, etc.),
[0633] π - electron - rich C3 - C 60 The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C3 - C 60 carbocyclic group, 1H - pyrrolyl, silolyl, borole, 2H - pyrrolyl, 3H - pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indolocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl or benzothienodibenzothienyl, etc.),
[0634] π - electron - deficient nitrogen - containing C1 - C 60The cyclic group may be a T4 group, a group in which two or more T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorene, azadibenzothiophene, azadibenzothiophene and azadibenzofuran, etc.),
[0635] The T1 group may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl) group, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl or phenyl,
[0636] The T2 group may be furyl, thienyl, 1H-pyrrolyl, silolyl, borolyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridyl, dihydropyridyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,
[0637] The T3 group may be furyl, thienyl, 1H-pyrrolyl, silolyl or borolyl, and
[0638] The T4 group may be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0639] As used herein, the terms "cyclic group", "C3-C 60 carbocyclic group", "C1-C 60 heterocyclic group", "π-electron-rich C3-C 60 cyclic group" or "π-electron-deficient nitrogen-containing C1-C 60 cyclic group" may each be a group that is fused to any cyclic group or not fused to any cyclic group according to the structure of the formula using the corresponding term, or may each be a monovalent group or a polyvalent group (e.g., divalent group, trivalent group, tetravalent group, etc.). In an embodiment, "phenyl" may be benzyl, phenyl or phenylene, etc., and those of ordinary skill in the art can easily understand these groups according to the structure of the formula including "phenyl".
[0640] In an embodiment, examples of the monovalent C3-C 60 carbocyclic group or monovalent C1-C 60 heterocyclic group may include C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group.
[0641] Examples of the divalent C3-C 60 carbocyclic group or divalent C1-C 60 heterocyclic group may include C3-C 10 cycloalkylene, C1-C 10 heterocycloalkylene, C3-C 10 cycloalkenylene, C1-C 10 heterocycloalkenylene, C6-C 60 arylene, C1-C 60 heteroarylene, divalent non-aromatic fused polycyclic group and divalent non-aromatic fused heteropolycyclic group.
[0642] As used herein, the term "C1-C 60 alkyl" may be a straight-chain or branched-chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, e.g., C1-C 50 alkyl, C1-C 30 alkyl, C1-C 20 alkyl or C1-C 10An alkyl group, and examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl.
[0643] As used herein, the term "C1-C 60 alkylene" may be a divalent group having substantially the same structure as a C1-C 60 alkyl group.
[0644] As used herein, the term "C2-C 60 alkenyl" may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of a C2-C 60 alkyl group, for example, C2-C 30 alkenyl, C2-C 20 alkenyl, or C2-C 10 alkenyl, and examples thereof may include vinyl, propenyl, and butenyl. As used herein, the term "C2-C 60 alkenylene" may be a divalent group having substantially the same structure as a C2-C 60 alkenyl group.
[0645] As used herein, the term "C2-C 60 alkynyl" may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of a C2-C 60 alkyl group, for example, C2-C 30 alkynyl, C2-C 20 alkynyl, or C2-C 10 alkynyl, and examples thereof may include ethynyl and propynyl. As used herein, the term "C2-C 60 alkynylene" may be a divalent group having substantially the same structure as a C2-C 60 alkynyl group.
[0646] As used herein, the term "C1-C 60 alkoxy" may be a monovalent group represented by -O(A 101 )(where A 101 may be a C1-C 60 alkyl group), for example, C1-C 30 alkoxy, C1-C 20 alkoxy, or C1-C 10 alkoxy, and examples thereof may include methoxy, ethoxy, and isopropoxy.
[0647] As used herein, the term "C3-C 10 cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. As used herein, the term "C3-C 10 cycloalkylene" may be a divalent group having substantially the same structure as C3-C 10 cycloalkyl.
[0648] As used herein, the term "C1-C 10 heterocycloalkyl" may be a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof may include 1,2,3,4-oxadiazolyl, tetrahydrofuryl, and tetrahydrothienyl. As used herein, the term "C1-C 10 heterocycloalkylene" may be a divalent group having substantially the same structure as C1-C 10 heterocycloalkyl.
[0649] As used herein, the term "C3-C 10 cycloalkenyl" may be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its cyclic structure and having no aromaticity, and examples thereof may include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 cycloalkenylene" may be a divalent group having substantially the same structure as C3-C 10 cycloalkenyl.
[0650] As used herein, the term "C1-C 10 heterocycloalkenyl" may be a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and having at least one double bond in its cyclic structure. Examples of C1-C 10 heterocycloalkenyl may include 4,5-dihydro-1,2,3,4-oxadiazolyl, 2,3-dihydrofuryl, and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 heterocycloalkenylene" may be a divalent group having substantially the same structure as C1-C 10 heterocycloalkenyl.
[0651] As used herein, the term "C6-C 60 aryl" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, C6-C 50 aryl, C6-C40 Aryl, C6-C 30 Aryl, C6-C 20 Aryl or C6-C 15 Aryl, and as used herein the term "C6-C 60 arylene" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. C6-C 60 Examples of aryl may include phenyl, pentaphenylenyl, naphthyl, azulenyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentaphenyl, heptaphenylenyl, tetracenyl, picenyl, hexaphenyl, pentacenyl, rubicenyl, coronenyl, and ovalenyl. When C6-C 60 aryl and C6-C 60 arylene each include two or more rings, the two or more respective rings may be fused to each other.
[0652] As used herein the term "C1-C 60 heteroaryl" may be a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, e.g., C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl or C1-C 10 heteroaryl. As used herein the term "C1-C 60 heteroarylene" may be a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. C1-C 60 Examples of heteroaryl may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. When C1-C 60 heteroaryl and C1-C 60 heteroarylene each include two or more rings, the two or more respective rings may be fused to each other.
[0653] As used herein the term "monovalent non-aromatic fused polycyclic group" may be a monovalent group having two or more rings fused to each other, only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms, and having no aromaticity in its molecular structure when considered as a whole, e.g., C8-C 60 monovalent non-aromatic fused polycyclic group, C8-C 50Monovalent non-aromatic fused polycyclic group, C8-C 40 Monovalent non-aromatic fused polycyclic group, C8-C 30 Monovalent non-aromatic fused polycyclic group or C8-C 20 Monovalent non-aromatic fused polycyclic group. Examples of the monovalent non-aromatic fused polycyclic group may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenoanthracenyl, and indenoanthracenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" may be a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.
[0654] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" may be a monovalent group having two or more rings fused to each other, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity in its molecular structure when considered as a whole. For example, C1-C 60 Monovalent non-aromatic fused heteropolycyclic group, C1-C 50 Monovalent non-aromatic fused heteropolycyclic group, C1-C 40 Monovalent non-aromatic fused heteropolycyclic group, C1-C 30 Monovalent non-aromatic fused heteropolycyclic group or C1-C<0x 20 Monovalent non-aromatic fused heteropolycyclic group. Examples of the monovalent non-aromatic fused heteropolycyclic group may include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuryl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl, and benzothienodibenzothienyl. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" may be a divalent group having substantially the same structure as the monovalent non-aromatic fused heteropolycyclic group.
[0655] As used herein, the term "C6-C 60 aryloxy" may be -O(A 102 )(where A102 can be a group represented by C6-C 60 (aryl), for example, C6-C 50 aryloxy, C6-C 40 aryloxy, C6-C 30 aryloxy, C6-C 20 aryloxy or C6-C 15 aryloxy, and as used herein, the term "C6-C 60 arylthio" can be a group represented by -S(A 103 )(where A 103 can be a group represented by C6-C 60 (aryl), for example, C6-C 50 arylthio, C6-C 40 arylthio, C6-C 30 arylthio, C6-C 20 arylthio or C6-C 15 arylthio.
[0656] As used herein, the term "C7-C 60 aralkyl" can be a group represented by -(A 104 )(A 105 (where A 104 can be C1-C 54 alkylene, and A 105 can be C6-C 59 aryl), for example, C7-C 50 aralkyl, C7-C 40 aralkyl, C7-C 30 aralkyl, C7-C 20 aralkyl or C7-C 15 aralkyl, and as used herein, the term "C2-C 60 heteroaralkyl" can be a group represented by -(A 106 )(A 107 (where A 106 can be C1-C 59 alkylene, and A 107 can be C1-C 59 heteroaryl), for example, C2-C 50 heteroaralkyl, C2-C 40 heteroaralkyl, C2-C 30 heteroaralkyl, C2-C 20 heteroaralkyl or C2-C 15 heteroaralkyl.
[0657] As used herein, the term "C1-C 60 heteroaryloxy" can be a group represented by -O(A 108 (where A108 It may be a group represented by C1-C 60 (heteroaryl), for example, C1-C 50 heteroaryloxy, C1-C 40 heteroaryloxy, C1-C 30 heteroaryloxy or C1-C 20 heteroaryloxy, and as used herein, the term "C1-C 60 heteroarylthio" may be -S(A 109 )(where A 109 may be a group represented by C1-C 60 heteroaryl), for example, C1-C 50 heteroarylthio, C1-C 40 heteroarylthio, C1-C 30 heteroarylthio or C1-C 20 heteroarylthio.
[0658] In the specification, the group "R 10a " may be:
[0659] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0660] each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 )、-P(=S)(Q 11 )(Q12 ) or any combination thereof;
[0661] Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group or C1-C 60 heteroarylthio group: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group, C1-C 60 heteroarylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ) or any combination thereof; or
[0662] -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 ) or -P(=S)(Q 31 )(Q 32 ).
[0663] In the specification, the groups Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amidino; hydrazino; hydrazono; C1-C 60 alkyl; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; or C3-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof, unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
[0664] As used herein, the term "heteroatom" can be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se or any combination thereof.
[0665] In the specification, the term "Ph" refers to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, the terms "tert-Bu" and "Bu t " each refer to tert-butyl, and the term "OMe" refers to methoxy.
[0666] As used herein, the term "biphenyl" can be "phenyl substituted by phenyl". For example, "biphenyl" can be a substituted phenyl having a C6-C 60 aryl as a substituent.
[0667] As used herein, the term "terphenyl" can be "phenyl substituted by biphenyl". For example, "terphenyl" can be a substituted phenyl having a C6-C 60 aryl substituted by a C6-C 60 aryl as a substituent.
[0668] In the specification, the terms "x-axis", "y-axis", and "z-axis" are not limited to the three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and can be interpreted in a broader sense than the aforementioned three axes in an orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may describe axes that are orthogonal to each other, or may describe axes in different directions that are not orthogonal to each other.
[0669] Unless otherwise defined, the symbols *, *' and *" as used herein each refer to a binding site to the adjacent atom in the corresponding formula or moiety.
[0670] Hereinafter, the compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A in the same molar equivalent.
[0671] [Synthesis example]
[0672] Synthesis Example 1: Synthesis of Compound 1
[0673] (1) Preparation Example 1: Synthesis of Intermediate 1-1
[0674]
[0675] 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (10 g, 0.029 mol), iodobenzene (13 g, 0.064 mol) and sodium tert-butoxide (8.35 g, 0.087 mol) were dissolved in 180 mL of anhydrous 1,4-dioxane and in an N2 atmosphere, palladium acetate (II) (0.32 g, 0.001 mol) and tri-tert-butylphosphine (0.59 g, 0.003 mol) were added. The mixture was reacted at 100 ° C for 24 hours and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 8.2 g of intermediate 1-1 (yield: 57%) as a white solid in a volume ratio of CH2Cl2: hexane = 1:5 and 1:1.
[0676] (2) Preparation Example 2: Synthesis of Intermediate 1-2
[0677]
[0678] The solution obtained by dissolving NBS (3.15 g, 0.018 mol) in 50 mL of DMF was slowly added dropwise to the solution obtained by dissolving Intermediate 1-1 (8 g, 0.016 mol) in 500 mL of CHCl3 at a temperature of 0 °C. After the mixture was reacted at room temperature for several hours, an extraction process was performed on it using CH2Cl2 to obtain an organic layer, and water was removed from the organic layer using MgSO4. The reaction product was concentrated under reduced pressure and purified by column chromatography under the condition of a volume ratio of CH2Cl2:hexane = 2:8 to obtain 3.5 g of Intermediate 1-2 as a light yellow solid (yield: 37%).
[0679] (3) Preparation Example 3: Synthesis of Intermediate 1-3
[0680]
[0681] Intermediate 1-2 (3.0 g, 0.005 mol), 2-bromo-4-(tert-butyl)pyridine (1.0 g, 0.005 mol), copper(I) iodide (0.25 g, 0.001 mol), 1-methyl-1H-imidazole (0.38 g, 0.005 mol) and lithium tert-butoxide (0.62 g, 0.008 mol) were added to 30 mL of anhydrous toluene, and the mixture was heated under reflux in an inert gas atmosphere for 18 hours. The resulting product was washed with ethyl acetate, H2O and NH4OH, and an extraction process was performed on it using CH2Cl2 to obtain an organic layer. The filtrate was purified using a silica gel filter, and the solvent was removed under reduced pressure to obtain 3.03 g of Intermediate 1-3. (Yield: 82%)
[0682] (4) Preparation Example 4: Synthesis of Intermediate 1-4
[0683]
[0684] Intermediate 1-3 (3 g, 0.004 mol), picolinic acid (0.26 g, 0.002 mol), copper(I) iodide (0.16 g, 0.001 mol), and tripotassium phosphate (1.79 g, 0.008 mol) were added to and dissolved in 50 mL of anhydrous DMSO, and an inert gas was used. 3-Chlorophenol (0.6 g, 0.005 mol) was added and the reaction was carried out at a temperature of 145 °C for 18 hours. After the reaction was terminated, the reaction product was cooled and H2O was added thereto to form a precipitate. The precipitate was filtered through a filter, dissolved in CH2Cl2, washed with brine, and the moisture was removed from the organic layer by adding MgSO4. The resulting product was concentrated under reduced pressure and purified by column chromatography under the condition of a volume ratio of CH2Cl2:hexane = 2:1 to obtain 2.36 g of white solid Intermediate 1-4 (yield: 73%).
[0685] (5) Preparation Example 5: Synthesis of Intermediate 1-5
[0686]
[0687] Intermediate 1-4 (2.3 g, 0.003 mol), N1-([1,1':3',1"-terphenyl]-2′-yl)benzene-1,2-diamine hydrochloride (1.13 g, 0.003 mol), [PdCl(C3H5)]2 (0.03 g, 0.1 mmol), di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (0.13 g, 0.4 mmol), and sodium tert-butoxide (1.0 g, 0.011 mol) were added to and dissolved in 40 mL of anhydrous toluene, and the mixture was heated under reflux in an inert gas atmosphere for 18 hours. The solvent was removed under reduced pressure, and the resulting product was purified by column chromatography under the condition of a volume ratio of CH2Cl2:hexane = 4:1 to obtain 2.56 g of white solid Intermediate 1-5 (yield: 80%).
[0688] (6) Preparation Example 6: Synthesis of Intermediate 1-6
[0689]
[0690] Intermediate 1-5 (2.5 g, 0.003 mol) was added to and dissolved in 35 mL of triethoxymethane, and HCl (0.1 g, 0.003 mol) was added to carry out the reaction at a temperature of 80 °C for 18 hours. The solvent was removed from the reaction product under reduced pressure to obtain 2.5 g of Intermediate 1-6. (Yield: 96%)
[0691] (7) Preparation Example 7: Synthesis of Compound 1
[0692]
[0693] Intermediate 1-6 (2.5 g, 0.002 mol) and silver(I) mono-μ-oxo-bis[silver(III)] (0.26 g, 0.001 mol) were added to and dissolved in 20 mL of 1,2-dichloroethane and reacted at room temperature for 18 hours. After removing the solvent from the reaction product under reduced pressure, 20 mL of 1,2-chlorobenzene and Pt(COD)Cl2 (0.85 g, 0.023 mol) were added, and the resulting mixture was heated under reflux for 3 days. After removing the solvent under reduced pressure, the reaction product was purified by column chromatography under the condition of a volume ratio of CH2Cl2:hexane = 2:1 to obtain 1.67 g of white solid Compound 1 (yield: 59%).
[0694] For the compound synthesized according to Synthesis Example 1 1 1H NMR and MS / FAB are shown in Table 1. In addition to the compounds shown in Table 1, those skilled in the art can easily identify the synthesis methods of other compounds by referring to the synthesis route and raw materials.
[0695] [Table 1]
[0696]
[0697] [Example]
[0698] Example 1
[0699] As the anode, a glass substrate (product of Corning Inc.) with 15 Ω / cm 2 ITO formed thereon was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, washed with ozone by ultraviolet irradiation for 30 minutes, and mounted on a vacuum deposition apparatus.
[0700] Compound HT3 was vacuum deposited on the anode to form a hole transport layer with a thickness of and Compound HT40 was vacuum deposited on the hole transport layer to form an emission assisting layer with a thickness of
[0701] Compound H125, Compound H126, and Compound 1 (dopant) were vacuum deposited on the emission assisting layer in a weight ratio of 45:45:10 to form an emission layer with a thickness of
[0702] Compound ET37 was vacuum deposited on the emission layer to form a buffer layer with a thickness of and Compound ET46 and Liq were vacuum deposited on the buffer layer in a weight ratio of 5:5 to form a layer with a thickness of An electron transport layer with a thickness of. Yb is vacuum-deposited on the electron transport layer to form an electron injection layer with a thickness of And Ag and Mg are vacuum-deposited thereon in a weight ratio of 5:5 to form a cathode with a thickness of Thereby manufacturing an organic light-emitting device.
[0703]
[0704]
[0705] Examples 2 to 8 and Comparative Examples 1 and 2
[0706] An organic light-emitting device is manufactured in substantially the same manner as in Example 1, except that when forming the emission layer, the corresponding compound shown in Table 2 is used as a dopant.
[0707] Evaluation Example 1: Evaluation of the characteristics of the organic light-emitting device
[0708] By using Keithley MU 236 and a luminance meter CS-2000 to measure the driving voltage of the organic light-emitting devices manufactured according to Examples 1 to 8 and Comparative Examples 1 and 2 at 10 mA / cm 2 And the maximum emission wavelength and lifetime (T 2 ) at 1,000 cd / m 90 The results are shown in Table 2. In Table 2, the relative lifetime (T 90 , %) is a measure of the time (hr) taken for the luminance to reach 90% of the initial luminance relative to Comparative Example 1.
[0709] [Table 2]
[0710]
[0711]
[0712] Referring to Table 2 confirms that the organic light-emitting devices of Examples 1 to 8 have a lower driving voltage and significantly better lifetime compared to the organic light-emitting devices of Comparative Examples 1 and 2.
[0713] An organic light-emitting device including an organometallic compound can have a low driving voltage and a long lifetime. High-quality electronic devices and consumer products can be manufactured by using the organic light-emitting device.
[0714] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some instances, as will be apparent to those of ordinary skill in the art, features, characteristics, and / or elements described in connection with an embodiment may be used singly or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless specifically indicated otherwise. Accordingly, those of ordinary skill in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.
Claims
1. An organometallic compound represented by Formula 1: Wherein in Formula 1, M1 is platinum, palladium, copper, silver, gold, rhodium, iridium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, A 10 is each an unsubstituted or at least one R 10 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group, A 20 each being unsubstituted or substituted by at least one R 20 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group, A 30 each being unsubstituted or substituted by at least one R 30 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group, A 40 to A 42 each independently is an unsubstituted or at least one R 40 substituted C5-C 60 carbocyclic group or C1-C 60 heterocyclic group, A 43 and A 44 each independently is an unsubstituted or at least one R 40 -substituted 5-membered carbocyclic group or 5-membered heterocyclic group, Y 10 、Y 20 、Y 30 and Y 40 are each independently C or N, T1 to T4 are each independently a chemical bond, L 11 to L 14 each independently represents a 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)-*' or *-Ge(R1)(R2)-*', a11 to a14 are each independently 0, 1, 2, 3, 4 or 5, R1, R2, R 10 , R 20 , R 30 and R 40 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 10 cycloalkyl, unsubstituted or substituted by at least one R 10a substituted C1-C 10 heterocycloalkyl, unsubstituted or substituted by at least one R 10a substituted C3-C 10 cycloalkenyl, unsubstituted or substituted by at least one R 10a substituted C1-C 10 heterocycloalkenyl, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryl, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroaryl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroaryloxy, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroarylthio, unsubstituted or substituted by at least one R 10a substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted by at least one R 10a substituted monovalent non-aromatic fused heteropolycyclic group, -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) or -P(=S)(Q1)(Q2), R1, R2, R 10 , R 20 , R 30 and R 40 in which two or more adjacent groups are optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C5-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each unsubstituted or substituted with the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 )、-P(=S)(Q 11 )(Q 12 ) or any combination thereof; each unsubstituted or substituted with the following C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group or C1-C 60 heteroarylthio group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, C1-C 60 heteroaryloxy group, C1-C 60 heteroarylthio group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 )、-P(=S)(Q 21 )(Q 22 ) or any combination thereof; or -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 ) or -P(=S)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amidino; hydrazino; hydrazono; C1-C 60 alkyl; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; or a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group, each of which is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof.
2. The organometallic compound according to claim 1, wherein M1 is Pt, Pd, Cu, Ag or Au.
3. The organometallic compound according to claim 1, wherein A 10 , A 20 , A 30 and A 40 to A 42 are each independently a group represented by one of Formula 2-1 to Formula 2-43: Wherein in Formulas 2-1 to 2-43, X 21 to X 23 each independently is C(Z 24 ) or C-*, X 21 to X 23 at least two of which are each C-*, X 24 is N-*, X 25 and X 26 each independently is C(Z 24 ), C-*, C(Z 24 )(Z 25 ), or C(Z 24 )-*, X 25 and X 26 at least one of which is C-* or C(Z 24 )-*, X 27 and X 28 each independently is N, N(Z 25 ) or N-*, X 29 is C(Z 24 ), C-*, C(Z 24 )(Z 25 ), or C(Z 24 )-*, Among them, for X 27 to X 29 : X 27 and X 28 one of which is N-*, and X 29 is C-* or C(Z 24 )-*; or X 27 and X 28 are each N-*, and X 29 is C(Z 24 ) or C(Z 24 )(Z 25 ), Z 21 to Z 25 each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthryl, triphenylene, pyridyl, pyrimidinyl, carbazolyl or triazinyl, c21 is 1, 2 or 3, c22 is 1, 2, 3, 4 or 5, c23 is 1, 2, 3 or 4, c24 is 1 or 2, and * indicates the binding site to the adjacent atom.
4. The organometallic compound according to claim 1, wherein L 11 to L 14 are each independently a single bond, *-O-*', *-S-*', *-N(R1)-*', *-C(R1)(R2)-*', *-Si(R1)(R2)-*' or *-B(R1)-*'.
5. The organometallic compound according to claim 1, wherein a11 is 0.
6. The organometallic compound according to claim 1, wherein R1, R2, R 10 , R 20 , R 30 and R 40 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl or C1-C 20 alkoxy; C1-C each independently substituted by deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof 20 alkyl or C1-C 20 alkoxy; or A group represented by one of Formulas 5-1 to 5-26 and Formulas 6-1 to 6-55, and R1, R2, R 10 , R 20 , R 30 and R 40 Two or more adjacent groups among them are optionally bonded to each other to form: cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl; or cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, fluorenyl or carbazolyl each independently substituted by deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl or any combination thereof: Wherein in Formulas 5-1 to 5-26 and Formulas 6-1 to 6-55, Y 31 and Y 32 each independently is O, S, C(Z 33 )(Z 34 ), N(Z 33 ), or Si(Z 33 )(Z 34 ), Z 31 to Z 34 each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthrenyl, anthracenyl, triphenylene, pyridyl, pyrimidinyl, carbazolyl or triazinyl, e2 is 1 or 2, e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, e5 is an integer selected from 1 to 5, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, e9 is an integer selected from 1 to 9, and * indicates the binding site to the adjacent atom.
7. The organometallic compound according to claim 1, wherein the organometallic compound is represented by Formula 11: Wherein in Formula 11, M1, A 10 , A 20 , A 30 , Y 10 , Y 20 , Y 30 , Y 40 , T1 to T4, L 11 to L 14 and a11 to a14 are each the same as defined in Formula 1, One of X1 and X2 is a single bond, The other of X1 and X2 is O, S, Se, N(R 52 ), or C(R 52 )(R 53 ), One of X3 and X4 is a single bond, The other of X3 and X4 is O, S, Se, N(R 54 ), or C(R 54 )(R 55 ), Y 41 is C(R 41 ), C or N, Y 42 is C(R 42 ) or N, Y 43 is C(R 43 ) or N, Y 44 is C(R 44 ) or N, Y 45 is C(R 45 ) or N, Y 46 is C(R 46 ) or N, Y 47 is C(R 47 ) or N, Y 48 is C(R 48 ) or N, Y 49 is C(R 49 ) or N, Y 50 is C(R 50 ) or N, Y 51 is C(R 51 ) or N, and R 41 to R 55 each independently is the same as that defined by R in Reference Formula 1 40 as defined.
8. The organometallic compound according to claim 1, wherein the organometallic compound is represented by one of Formulas 21 to 28: Wherein in Formulas 21 to 28, M1, T1 to T4, and L 12 each being the same as defined in Formula 1 X1 and X2 are each independently O, S, Se, N(R 52 ), or C(R 52 )(R 53 ), X3 and X4 are each independently O, S, Se, N(R 54 ), or C(R 54 )(R 55 ), Y 11 is C(R 11 ), or N, Y 12 is C(R 12 ) or N, Y 13 is C(R 13 ) or N, Y 14 is C(R 14 ) or N, Y 22 is C(R 22 ) or N, Y 23 is C(R 23 ) or N, Y 24 is C(R 24 ) or N, Y 25 is C(R 25 ) or N, Y 26 is C(R 26 ) or N, Y 27 is C(R 27 ) or N, Y 31 is C(R 31 ) or N, Y 32 is C(R 32 ), or N, Y 33 is C(R 33 ) or N, Y 42 is C(R 42 ) or N, Y 43 is C(R 43 ) or N, Y 44 is C(R 44 ) or N, Y 45 is C(R 45 ) or N, Y 46 is C(R 46 ) or N, Y 47 is C(R 47 ) or N, Y 48 is C(R 48 ) or N, Y 49 is C(R 49 ) or N, Y 50 is C(R 50 ) or N, Y 51 is C(R 51 ) or N, R 11 to R 14 each independently is the same as that defined by R in Reference Formula 1 10 as defined R 21 to R 27 each independently is the same as that defined by R in Reference Formula 1 20 as defined R 31 to R 33 each independently is the same as defined for R in Reference Formula 1, and 30 and R 42 to R 55 each independently is the same as defined for R in Reference Formula 1 40 as defined.
9. The organometallic compound according to claim 1, wherein the organometallic compound is electrically neutral.
10. The organometallic compound according to claim 1, wherein the organometallic compound is one of Compounds 1 to 192:
11. An organic light-emitting device, comprising: A first electrode; A second electrode facing the first electrode; A sandwich layer between the first electrode and the second electrode and including an emission layer; And The organometallic compound according to any one of claims 1 to 10.
12. The organic light-emitting device according to claim 11, wherein The first electrode is an anode, The second electrode is a cathode, The sandwich layer further includes: A hole transport region between the first electrode and the emission layer; And An electron transport region between the emission layer and the second electrode, The hole transport region includes at least one of a hole injection layer, a hole transport layer, an emission auxiliary layer and an electron blocking layer, and The electron transport region includes at least one of a buffer layer, a hole blocking layer, an electron transport layer and an electron injection layer.
13. The organic light-emitting device according to claim 11, wherein the emitting layer comprises the organometallic compound.
14. The organic light-emitting device according to claim 13, wherein the emitting layer comprises a host and a dopant, and the dopant comprises the organometallic compound.
15. The organic light-emitting device according to claim 13, wherein the emitting layer emits blue light or green light each having a maximum emission wavelength in the range of 400 nm to 580 nm.
16. The organic light-emitting device according to claim 14, wherein the host comprises a first host compound and a second host compound, the first host compound is a hole-transporting host, and the second host compound is an electron-transporting host.
17. An electronic device comprising the organic light-emitting device according to any one of claims 11 to 16.
18. The electronic device according to claim 17, further comprising: a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and the first electrode of the organic light-emitting device is electrically connected to at least one of the source electrode and the drain electrode.
19. A consumer product comprising the organic light-emitting device according to any one of claims 11 to 16.
20. The consumer product according to claim 19, wherein the consumer product is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
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KR1020240015182A