Light-emitting device including organometallic compound, electronic device and electronic equipment including light-emitting device, and organometallic compound
By using organometallic compounds in the interlayer and emission layer of the light emitting device, the shortcomings of the existing light emitting devices in terms of viewing angle width, contrast, response time and driving voltage are solved, and a high-performance light emitting effect is achieved.
Patent Information
- Application Number
- CN202411527398.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-31
- Filing Date
- 2024-10-30
- Publication Date
- 2025-05-02
AI Technical Summary
The existing light emitting devices have shortcomings in viewing angle width, contrast, response time and driving voltage, and it is difficult to meet the needs of high performance.
The light emitting device including an organometallic compound is designed using a first electrode, a second electrode, an interlayer and an emission layer, which contains the organometallic compound represented by Formula 1, the emission layer may include a body and a dopant, and the dopant also contains the organometallic compound.
A wide viewing angle, high contrast and short response time are achieved, improving the overall performance of the luminous device, especially in terms of brightness, driving voltage and response speed.
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Figure CN119912497A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0148439 filed in the Korean Intellectual Property Office on October 31, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] Embodiments relate to a light-emitting device including an organic metal compound, electronic equipment and electronic devices including the light-emitting device, and the organic metal compound. Background Art
[0004] The light-emitting device is a self-emissive device having a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] In the light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are arranged on the first electrode in sequence. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.
[0006] It is to be understood that this background technology section is intended, in part, to provide a useful background for understanding the technology. However, this background technology section may also include ideas, concepts, or cognitions that were not part of the known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention
[0007] Embodiments provide a light emitting device including an organic metal compound, an electronic device and an electronic equipment including the light emitting device, and the organic metal compound.
[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments presented in the disclosure.
[0009] An embodiment provides a light emitting device, which may include:
[0010] The first electrode,
[0011] a second electrode facing the first electrode,
[0012] an interlayer between the first electrode and the second electrode and including an emitting layer, and
[0013] An organometallic compound represented by Formula 1:
[0014] [Formula 1]
[0015]
[0016] In formula 1,
[0017] M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm),
[0018] X 1 Can be C,
[0019] X 1 The bond between and M can be a coordination bond,
[0020] X 2 To X 4 can be independently C or N,
[0021] Cyclo 1 CY 2 CY 31 CY 32 and CY 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0022] L 1 To L 3 can be independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R1b )-*', where * and *' each indicate a bonding site to an adjacent atom,
[0023] n1 to n3 may each independently be an integer selected from 1 to 10,
[0024] R 1 , R 11 , R 2 , R 31 , R 32 , R 4 , R 1a and R 1b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1)、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0025] a1, a2, a31, a32 and a4 may each independently be an integer selected from 1 to 20,
[0026] R with quantity a1 1 , R 11 , the number of R is a2 2 , the number of R is a31 31 , the number of R is a32 32 , R with quantity a4 4 , R 1a and R 1b Two or more adjacent groups in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0027] R with quantity a1 1 Two adjacent groups in; the number of R is a2 2 Two adjacent groups in; the number of R is a31 31 Two adjacent groups in; the number of R is a32 32 Two adjacent groups in; or a4 number of R 4 Two adjacent groups in may optionally be bonded to each other to form a group represented by Formula 1A, and
[0028] The organometallic compound represented by Formula 1 may include at least one group represented by Formula 1A:
[0029] [Formula 1A]
[0030]
[0031] In Formula 1A,
[0032] X 51 Can be C(R 51 ) or N,
[0033] X 52 Can be C(R 52 ) or N,
[0034] X 53 Can be C(R 53 ) or N,
[0035] X 54 Can be C(R 54 ) or N,
[0036] X 55 Can be C(R 55 ) or N,
[0037] X 56 Can be C(R 56 ) or N,
[0038] X 57 Can be C(R 57 ) or N,
[0039] X 58 Can be C(R 58 ) or N,
[0040] R 51 To R 58 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1)(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0041] * and *' each indicate a bonding site to an adjacent atom,
[0042] R 10a Can be:
[0043] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0044] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0045] Each unsubstituted or substituted C3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0046] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32)、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0047] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0048] In an embodiment, the emission layer may include a host and a dopant; and the dopant may include an organic metal compound.
[0049] In an embodiment, the light emitting device may further include a nitrogen-containing C 1 -C 60 A second compound of a heterocyclic group, a third compound comprising a group represented by Formula 3 (which will be explained herein), a fourth compound which may be a delayed fluorescence compound, or any combination thereof, wherein the organic metal compound, the second compound, the third compound and the fourth compound may be different from each other.
[0050] In an embodiment, the second compound may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof; and the fourth compound may include at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0051] In an embodiment, the emission layer may include: an organic metal compound; and a second compound, a third compound, a fourth compound, or any combination thereof; and the emission layer may emit blue light.
[0052] Embodiments provide electronic devices that may include a light emitting device.
[0053] 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 light emitting device may be electrically connected to at least one of the source electrode and the drain electrode.
[0054] 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.
[0055] Embodiments provide electronic equipment that may include a light emitting device.
[0056] In an embodiment, the electronic device 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 retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0057] Embodiments provide an organometallic compound that may be represented by Formula 1, which is explained herein.
[0058] In an embodiment, in Formula 1, M may be platinum (Pt), palladium (Pd), or gold (Au).
[0059] In an embodiment, in Formula 1, X 2 and X 3 Can be C; X 4 Can be N; X 4 The bond between X and M may be a coordination bond; and 2 The key between M and X 3 The bonds between M and M may each be covalent bonds.
[0060] In an embodiment, in Formula 1, ring CY 1 CY 2 CY 31 CY 32 and CY 4 The phenyl group may be independently phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazole yl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilanyl, dibenzothiasilanyl, dibenzodihydroazasilanyl, dibenzodihydrodihydrodisilacyclohexanyl, dibenzodihydrosilanyl, dibenzodioxanyl, dibenzooxathiacyclohexanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiacyclohexanyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl.
[0061] In an embodiment, in Formula 1, L 1 and L 3 Each of them can be a single bond; L 2 It can be *-O-*' or *-S-*'; and n2 can be 1.
[0062] In an embodiment, in Formula 1, R 1 , R 11 , R 2 , R 31 , R 32 and R 4 Can be independently:
[0063] Hydrogen, deuterium, -F, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0064] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -CD 3 、-CD 2H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl or any combination thereof;
[0065] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof; or
[0066] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -N(Q1 )(Q 2 ),and
[0067] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0068] In an embodiment, in Formula 1,
[0069] Depend on The moiety represented by may be a moiety represented by one of Formula CY1(1) to Formula CY1(11), which are explained herein,
[0070] Depend on The moiety represented by may be a moiety represented by one of Formula CY2(1) to Formula CY2(13), which are explained herein,
[0071] Depend on The moiety represented by may be a moiety represented by one of Formula CY31(1) to Formula CY31(6), which are explained herein,
[0072] Depend on The moiety represented by may be a moiety represented by one of Formula CY32(1) to Formula CY32(16), which are explained herein, and
[0073] Depend on The moiety represented may be a moiety represented by one of Formula CY4(1) to Formula CY4(29), which are explained herein.
[0074] In an embodiment, in Formula 1A, X 51 Can be C(R 51 ), X 52 Can be C(R 52), X 53 Can be C(R 53 ), X 54 Can be C(R 54 ), X 55 Can be C(R 55 ), X 56 Can be C(R 56 ), X 57 Can be C(R 57 ), and X 58 Can be C(R 58 ).
[0075] In an embodiment, the organometallic compound may be represented by Formula 1-1, which is explained herein.
[0076] In an embodiment, the organometallic compound satisfies at least one of Conditions 1 to 12, which are explained herein.
[0077] It is to be understood that the above embodiments have been described in a generic and illustrative sense only and not for purposes of limitation, and that the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0078] The attached drawings are included to provide a further understanding of the embodiments, and are incorporated into and constitute a part of this specification. The drawings illustrate the embodiments of the present disclosure and its principles. The above and other aspects and features of the present disclosure will be more apparent by describing its embodiments in detail with reference to the attached drawings, in which:
[0079] Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;
[0080] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0081] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0082] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to an embodiment;
[0083] Figure 5 is a schematic perspective view of the exterior of a vehicle as an electronic device including a light emitting device according to an embodiment; and
[0084] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0085] The present disclosure will now be described more fully hereinafter with reference to the attached drawings in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as being limited to the embodiments set forth herein. Rather, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the scope of the present disclosure to those skilled in the art.
[0086] In the drawings, the size, ratio, and dimensions (eg, thickness) of elements may be exaggerated for ease of description and for clarity. Like reference numerals and reference characters refer to like elements throughout.
[0087] In the specification, 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 may be directly on, directly connected to or directly coupled to the other element (or region, layer, portion, etc.), or one or more intervening elements may be present 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 may directly cover the other element (or region, layer, portion, etc.), or one or more intervening elements may be present between them.
[0088] In the specification, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without another element (such as an adhesive element) between them.
[0089] As used herein, expressions used in the singular such as “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0090] 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" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a conjunctive sense or a disjunctive sense and may be understood to be equivalent to "and / or".
[0091] 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 the purposes of its meaning and interpretation. For example, "at least one of A, B, and C" may 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 does not modify the individual elements of the list.
[0092] It will be understood that although the terms first, second, etc. may be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teachings of the present disclosure, the first element may be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element may be referred to as the first element.
[0093] For ease of description, spatially relative terms such as "below," "under," "down," "above," or "on" may be used herein to describe the relationship between one element or component and another element or component as illustrated in the accompanying drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the accompanying drawings. For example, in the case where the device illustrated in the accompanying drawings is turned over, a device that is "below" or "below" another device may be placed "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 therefore the spatially relative terms may be interpreted differently depending on the orientation.
[0094] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation of the stated value determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the stated quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the stated value, or within ±20%, ±10%, or ±5% of the stated value.
[0095] It should be understood that the terms “comprises,” “comprising,” “include,” “including,” “have,” “having,” “contains,” and “containing” and the like are intended to indicate the presence of the recited features, integers, steps, operations, elements, components, or combinations 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 combinations thereof.
[0096] Unless otherwise defined or implied herein, all terms (including technical terms and scientific terms) used have the same meaning as those commonly understood by those skilled in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and should not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.
[0097] An embodiment provides a light emitting device, which may include:
[0098] a first electrode;
[0099] a second electrode facing the first electrode;
[0100] an interlayer between the first electrode and the second electrode and including an emissive layer; and
[0101] An organometallic compound represented by Formula 1:
[0102] [Formula 1]
[0103]
[0104] The details about Formula 1 are the same as those described herein.
[0105] In an embodiment,
[0106] The first electrode of the light emitting device may be an anode,
[0107] The second electrode of the light emitting device may be a cathode,
[0108] The interlayer may further include a hole transport region disposed between the first electrode and the emissive layer and an electron transport region disposed between the emissive layer and the second electrode,
[0109] 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, and
[0110] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0111] In an embodiment, an interlayer of a light-emitting device may include an organic metal compound represented by Formula 1.
[0112] In an embodiment, an emission layer of a light emitting device may include the organic metal compound represented by Formula 1.
[0113] In an embodiment, the emission layer of the light emitting device may include a dopant and a host, and the dopant may include an organic metal compound represented by Formula 1. For example, the organic metal compound represented by Formula 1 may be used as a dopant. For example, the emission layer may emit blue light. The blue light may have a maximum emission wavelength in the range of, for example, about 430 nm to about 480 nm.
[0114] In embodiments, the electron transport region of the light emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In embodiments, the hole blocking layer may contact (eg, directly contact) the emission layer.
[0115] In an embodiment, the light emitting device may further include a nitrogen-containing C 1 -C 60 a second compound containing a heterocyclic group, a third compound containing a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence (eg, a delayed fluorescence compound), or any combination thereof, and
[0116] The organometallic compound, the second compound, the third compound and the fourth compound in the light-emitting device may be different from each other:
[0117] [Formula 3]
[0118]
[0119] In formula 3,
[0120] Cyclo 71 and CY 72 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group,
[0121] X 71 can be: a single bond; or a linking group comprising O, S, N, B, C, Si or any combination thereof, and
[0122] * indicates a bonding site to any atom in the remaining part other than the group represented by Formula 3 of the third compound.
[0123] In an embodiment, the organometallic compound represented by Formula 1 may include at least one deuterium.
[0124] In an embodiment, the second to fourth compounds may each independently include at least one deuterium.
[0125] In an embodiment, the second compound may include at least one silicon.
[0126] In an embodiment, the third compound may include at least one silicon.
[0127] In an embodiment, the light emitting device may further include a second compound and a third compound in addition to the organometallic compound represented by Formula 1, and at least one of the second compound and the third compound may include at least one deuterium, at least one silicon, or any combination thereof.
[0128] In an embodiment, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound. At least one of the organometallic compound represented by Formula 1 and the second compound may include at least one deuterium. For example, in addition to the organometallic compound represented by Formula 1 and the second compound, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof.
[0129] In an embodiment, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound. At least one of the organometallic compound represented by Formula 1 and the third compound may include at least one deuterium. For example, in addition to the organometallic compound represented by Formula 1 and the third compound, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a fourth compound, or any combination thereof.
[0130] In an embodiment, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., an emission layer in a light-emitting device) may further include a fourth compound. At least one of the organometallic compound represented by Formula 1 and the fourth compound may include at least one deuterium. The fourth compound may be used to improve the color purity, luminous efficiency, and life characteristics of the light-emitting device. For example, in addition to the organometallic compound represented by Formula 1 and the fourth compound, the light-emitting device (e.g., an emission layer in a light-emitting device) may further include a second compound, a third compound, or any combination thereof.
[0131] In an embodiment, in addition to the organometallic compound represented by Formula 1, the light-emitting device (e.g., an emission layer in the light-emitting device) may further include a second compound and a third compound. The second compound and the third compound may form an excited complex. At least one of the organometallic compound represented by Formula 1, the second compound, and the third compound may include at least one deuterium.
[0132] In an embodiment, an emission layer of a light emitting device may include: the organic metal compound represented by Formula 1; and the second compound, the third compound, the fourth compound, or any combination thereof, and the emission layer may emit blue light.
[0133] In an embodiment, the blue light may have a maximum emission wavelength in the range of about 430nm to about 480nm. For example, the blue light may have a maximum emission wavelength in the range of about 430nm to about 475nm. For example, the blue light may have a maximum emission wavelength in the range of about 440nm to about 475nm. For example, the blue light may have a maximum emission wavelength in the range of about 450nm to about 475nm. For example, the blue light may have a maximum emission wavelength in the range of about 430nm to about 470nm. For example, the blue light may have a maximum emission wavelength in the range of about 440nm to about 470nm. For example, the blue light may have a maximum emission wavelength in the range of about 450nm to about 470nm. For example, the blue light may have a maximum emission wavelength in the range of about 430nm to about 465nm. For example, the blue light may have a maximum emission wavelength in the range of about 440nm to about 465nm. For example, the blue light may have a maximum emission wavelength in the range of about 450nm to about 465nm. For example, the blue light may have a maximum emission wavelength in the range of about 430 nm to about 460 nm. For example, the blue light may have a maximum emission wavelength in the range of about 440 nm to about 460 nm. For example, the blue light may have a maximum emission wavelength in the range of about 450 nm to about 460 nm.
[0134] In an embodiment, the second compound may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0135] In an embodiment, the third compound may not include CBP or mCBP:
[0136]
[0137] In an embodiment, the fourth compound may be a compound in which the difference between the triplet energy level (eV) and the singlet energy level (eV) may be in the range of about 0 eV to about 0.5 eV (or in the range of about 0 eV to about 0.3 eV).
[0138] In an embodiment, the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-constituting atoms.
[0139] In an embodiment, the fourth compound may be a C-containing 8 -C 60 A polycyclic group compound in which two or more cyclic groups are fused while sharing boron (B).
[0140] In an embodiment, the fourth compound may include a ring in which at least one third ring is fused to at least one fourth ring,
[0141] The third ring can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and
[0142] The fourth ring may be 1,2-azaboraphenyl, 1,3-azaboraphenyl, 1,4-azaboraphenyl, 1,2-dihydro-1,2-azaboraphenyl, 1,4-oxaboraphenyl, 1,4-thiaboraphenyl or 1,4-dihydroboraphenyl.
[0143] In an embodiment, the third compound may not include the compound represented by Formula 3-1 described herein.
[0144] In an embodiment, the second compound may include a compound represented by Formula 2:
[0145] [Formula 2]
[0146]
[0147] In formula 2,
[0148] L 51 To L 53 may be independently a single bond, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0149] b51 to b53 may each independently be an integer selected from 1 to 5,
[0150] X 54 Can be N or C(R 54 ),
[0151] X 55 Can be N or C(R 55 ),
[0152] X 56 Can be N or C(R 56 ),and
[0153] X 54 To X 56 At least one of may each be N, and
[0154] R 51 To R 56 and R10a Each may be the same as described herein.
[0155] In an embodiment, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0156] [Formula 3-1]
[0157]
[0158] [Formula 3-2]
[0159]
[0160] [Formula 3-3]
[0161]
[0162] [Formula 3-4]
[0163]
[0164] [Formula 3-5]
[0165]
[0166] In Formula 3-1 to Formula 3-5,
[0167] Cyclo 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 Cyclic group or pyridyl group, X 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a )(R 82b ),
[0168] X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0169] X 84 Can be O, S, N[(L 84) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0170] X 85 Can be C or Si,
[0171] L 81 To L 85 can be independently a single bond, *-C(Q 4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a Substituted pyridyl, wherein Q 4 and Q 5 Each independently and with reference Q 1 Same as described,
[0172] b81 to b85 may each independently be an integer selected from 1 to 5,
[0173] R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b each being the same as described herein,
[0174] a71 to a74 may each independently be an integer selected from 0 to 20, and
[0175] R 10a May be the same as described herein.
[0176] In an embodiment, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0177] [Formula 502]
[0178]
[0179] [Formula 503]
[0180]
[0181] In equation 502 and equation 503,
[0182] Ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0183] Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0184] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0185] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0186] Y 508 Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0187] Y 51 and Y 52 may be each independently B, P(=O) or S(=O),
[0188] R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R507a , R 507b , R 508a and R 508b each being the same as described herein, and
[0189] a501 to a504 may each independently be an integer selected from 0 to 20.
[0190] In an embodiment, the light emitting device may satisfy at least one of conditions A to D:
[0191] [Condition A]
[0192] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound is greater than the LUMO energy level (eV) of the organometallic compound represented by Formula 1;
[0193] [Condition B]
[0194] The LUMO energy level (eV) of the organometallic compound represented by Formula 1> the LUMO energy level (eV) of the second compound;
[0195] [Condition C]
[0196] The highest occupied molecular orbital (HOMO) energy level (eV) of the organometallic compound represented by Formula 1 is greater than the HOMO energy level (eV) of the third compound; and
[0197] [Condition D]
[0198] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.
[0199] The HOMO energy level and the LUMO energy level of each of the organometallic compound represented by Formula 1, the second compound, and the third compound may each be a negative value, and may be measured according to a method of the related art.
[0200] In an embodiment, the absolute value of the difference between the LUMO energy level of the organic metal compound represented by Formula 1 and the LUMO energy level of the second compound may be in the range of about 0.1 eV to about 1.0 eV; or the absolute value of the difference between the LUMO energy level of the organic metal compound represented by Formula 1 and the LUMO energy level of the third compound may be in the range of about 0.1 eV to about 1.0 eV, or the absolute value of the difference between the HOMO energy level of the organic metal compound represented by Formula 1 and the HOMO energy level of the second compound may be equal to or less than about 1.25 eV (for example, in the range of 0.2 eV to about 1.25 eV) or the absolute value of the difference between the HOMO energy level of the organic metal compound represented by Formula 1 and the HOMO energy level of the third compound may be equal to or less than about 1.25 eV (for example, in the range of about 0.2 eV to about 1.25 eV).
[0201] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions as described above, a balance between holes and electrons injected into the emission layer can be achieved.
[0202] The light emitting device may have the structure of the first embodiment or the second embodiment.
[0203] [First embodiment]
[0204] According to the first embodiment, the organic metal compound represented by Formula 1 may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host, the organic metal compound represented by Formula 1 may be different from the host, and the emission layer may emit phosphorescence or fluorescence emitted from the organic metal compound represented by Formula 1. For example, according to the first embodiment, the organic metal compound represented by Formula 1 may be a dopant or an emitter. In an embodiment, the organic metal compound represented by Formula 1 may be a phosphorescent dopant or a phosphorescent emitter.
[0205] Phosphorescence or fluorescence emitted from the organometallic compound represented by Formula 1 may be blue light.
[0206] The emission layer may further include an auxiliary dopant. The auxiliary dopant may improve the light emission efficiency of the organometallic compound represented by Formula 1 (which may be a dopant or an emitter) by efficiently transferring to the organometallic compound represented by Formula 1.
[0207] The auxiliary dopant may be different from the organometallic compound represented by Formula 1 and the host.
[0208] In an embodiment, the auxiliary dopant may be a compound emitting delayed fluorescence.
[0209] In an implementation, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0210] [Second embodiment]
[0211] According to a second embodiment, the organic metal compound represented by Formula 1 may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host and a dopant, the organic metal compound represented by Formula 1, the host and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
[0212] In an embodiment, the organometallic compound represented by Formula 1 in the second embodiment may not be used as a dopant but may be used as an auxiliary dopant that transfers energy to a dopant (or an emitter).
[0213] In an embodiment, the organometallic compound represented by Formula 1 in the second embodiment may be used as an emitter, and may also be used as an auxiliary dopant that transfers energy to a dopant (or emitter).
[0214] In an embodiment, phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (eg, blue delayed fluorescence).
[0215] The dopant (or emitter) in the second embodiment may be any phosphorescent dopant material (e.g., an organic metal compound represented by Formula 1 as described herein, an organic metal compound represented by Formula 401 as described herein, or any combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501 as described herein, a compound represented by Formula 502 as described herein, a compound represented by Formula 503 as described herein, or any combination thereof).
[0216] In the first and second embodiments, the blue light may have a maximum emission wavelength in the range of about 390nm to about 500nm. For example, the blue light in the first and second embodiments may be a blue light having a maximum emission wavelength in the range of about 410nm to about 490nm. For example, the blue light in the first and second embodiments may be a blue light having a maximum emission wavelength in the range of about 430nm to about 480nm. For example, the blue light in the first and second embodiments may be a blue light having a maximum emission wavelength in the range of about 440nm to about 475nm. For example, the blue light in the first and second embodiments may be a blue light having a maximum emission wavelength in the range of about 455nm to about 470nm.
[0217] The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503 as described herein.
[0218] The host in the first and second embodiments may be any host material (e.g., a compound represented by Formula 301 as described herein, a compound represented by Formula 301-1 as described herein, a compound represented by Formula 301-2 as described herein, or any combination thereof).
[0219] In an embodiment, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
[0220] In an embodiment, the light emitting device may further include a capping layer disposed outside the first electrode and / or outside the second electrode.
[0221] In an embodiment, the light emitting device may further include at least one of a first capping layer disposed outside the first electrode and a second capping layer disposed outside the second electrode, and the organic metal compound represented by Formula 1 may be included in at least one of the first capping layer and the second capping layer. Further details about the first capping layer and / or the second capping layer are the same as described herein.
[0222] In an embodiment, the light emitting device may include:
[0223] A first capping layer disposed outside the first electrode and including an organic metal compound represented by Formula 1;
[0224] a second capping layer disposed outside the second electrode and including an organic metal compound represented by Formula 1; or
[0225] A first capping layer and a second capping layer.
[0226] The expression “(the interlayer and / or the capping layer) includes the organic metal compound represented by Formula 1” as used herein may be understood as “(the interlayer and / or the capping layer) may include one organic metal compound represented by Formula 1 or two or more different kinds of organic metal compounds each represented by Formula 1”.
[0227] In an embodiment, the interlayer and / or the capping layer may include only Compound 1 as an organic metal compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include Compound 1 and Compound 2 as organic metal compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both be present in the emission layer), or Compound 1 and Compound 2 may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0228] The term "interlayer" as used herein refers to a single layer and / or multiple layers between a first electrode and a second electrode of a light emitting device.
[0229] Another embodiment provides an electronic device, which may include a light emitting device. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. The electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. Further details about the electronic device are the same as described herein.
[0230] Another embodiment provides an electronic device, which may include a light emitting device.
[0231] In an embodiment, the electronic device 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 retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0232] Another embodiment provides an organometallic compound that may be represented by Formula 1. Details regarding Formula 1 are the same as described herein.
[0233] The synthesis method of the organometallic compound represented by Formula 1 can be identified by one of ordinary skill in the art by referring to the Synthesis Examples and / or Examples provided below.
[0234] [Description of Formula 1 and Formula 1A]
[0235] [Formula 1]
[0236]
[0237] In Formula 1, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
[0238] In an embodiment, M may be Pt, Pd, or Au.
[0239] In an embodiment, M may be Pt.
[0240] In formula 1, X 1 Can be C, and X 1 The bond between M and R may be a coordinate bond.
[0241] In an embodiment, X 1 It may be C of the carbene portion.
[0242] In formula 1, X 2 To X 4 They may each independently be C or N.
[0243] In an embodiment, X 2 and X 3 can each be C, and
[0244] X4 Can be N.
[0245] In an embodiment, X 2 The key between X and M 3 and the key between M, and X 4 One of the bonds between and M may each be a coordinate bond, and the other two bonds may each be a covalent bond.
[0246] In an embodiment, X 4 The bond between and M may be a coordination bond, and
[0247] X 2 The key between M and X 3 The bonds between M and M may each be covalent bonds.
[0248] In an embodiment, X 2 and X 3 can each be C, and X 4 Can be N,
[0249] X 4 The bond between and M may be a coordination bond, and
[0250] X 2 The key between M and X 3 The bonds between M and M may each be covalent bonds.
[0251] In Formula 1, ring CY 1 CY 2 CY 31 CY 32 and CY 4 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group.
[0252] In an embodiment, cyclo CY 1 CY 2 CY 31 CY 32 and CY 4 Can be independently:
[0253] Phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazole 1-4-nitro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1,1-dihydro-1
[0254] In an embodiment, cyclo CY 1 It may be imidazolyl, triazolyl, benzimidazolyl, naphthoimidazolyl or imidazopyridinyl.
[0255] In an embodiment, cyclo CY 2 It can be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzocarbazolyl, benzofluorenyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzocarbazolyl, dibenzofluorenyl, dinaphthothiophenyl, azadibenzofuranyl 1-4-nitro-1,1-di-1-nitro-2-nitro-3-ol, 1-nitro-1-oxo-2-nitro-4-ol, 1-nitro-1-oxo ...3-ol, 1-nitro-1-oxo-2-nitro-3-ol, 1-nitro-1-oxo-2-nitro-3-ol, 1-nitro-1
[0256] In an embodiment, cyclo CY 2 It may be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl or dibenzosilyl.
[0257] In an embodiment, cyclo CY 31 and CY 32 Can be independently:
[0258] phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl or dibenzosilyl.
[0259] In an embodiment, cyclic CY 4 Can be nitrogen-containing C 1 -C 60 Heterocyclic group.
[0260] In an embodiment, cyclic CY 4 It may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, benzopyrazolyl, benzimidazolyl or benzothiazolyl.
[0261] In formula 1, L 1 To L 3 can be independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*'、*-S-*'、*-S(=O)-*'、*-S(=O) 2 -*'or*-Ge(R 1a )(R 1b )-*', where * and *' each indicate a bonding site to an adjacent atom.
[0262] In Formula 1, n1 to n3 respectively indicate L 1 Quantity to L 3 The number of L1 to L2 is 2 or more, and n1 to n3 may each independently be an integer selected from 1 to 10. When n1 is 2 or more, two or more L 1 may be the same as or different from each other. When n2 is 2 or greater, two or more L 2 may be the same as or different from each other, and when n3 is 2 or greater, two or more L 3 Can be the same as or different from each other.
[0263] In formula 1, R 1a and R 1b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ).
[0264] R 10a and Q 1 To Q 3 Each is the same as described herein.
[0265] In an embodiment, L1 and L 3 Each may be a single bond.
[0266] In an embodiment, L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0267] In an embodiment, L 1 and L 3 can each be a single bond, and
[0268] L 2 It can be *-O-*' or *-S-*', and n2 can be 1.
[0269] In an embodiment, R 1a and R 1b Can be independently:
[0270] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0271] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
[0272] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl oxazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32)、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0273] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0274] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0275] In formula 1, R 1 , R 11 , R 2 , R 31 , R 32 and R 4can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ).
[0276] R 10a and Q 1 To Q 3 Each is the same as described herein.
[0277] In Formula 1, a1, a2, a31, a32 and a4 respectively indicate R 1 The number of2 The number of 31 The number of 32 The number and R 4 , and a1, a2, a31, a32 and a4 may each independently be an integer selected from 1 to 20. When a1 is 2 or more, two or more R 1 may be the same as or different from each other. When a2 is 2 or greater, two or more R 2 may be the same as or different from each other. When a31 is 2 or greater, two or more R 31 may be the same as or different from each other. When a32 is 2 or greater, two or more R 32 may be the same as or different from each other, and when a4 is 2 or greater, two or more R 4 Can be the same as or different from each other.
[0278] In an embodiment, R 1 , R 11 , R 2 , R 31 , R 32 and R 4 Can be independently:
[0279] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0280] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
[0281] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl oxazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0282] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0283] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0284] In an embodiment, R 1 , R 11 , R 2 , R 31 , R 32 and R 4 Can be independently:
[0285] Hydrogen, deuterium, -F, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0286] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl or any combination thereof;
[0287] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31)(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof; or
[0288] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -N(Q 1 )(Q 2 ),and
[0289] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0290] In an embodiment, R 1 , R 11 , R 2 , R 31 , R 32 and R 4 Can be independently:
[0291] Hydrogen, deuterium or C 1 -C 20 alkyl;
[0292] C replaced by 1 -C 20 Alkyl: deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, or any combination thereof;
[0293] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl or naphthyl: deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 ) or any combination thereof; or
[0294] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0295] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; either unsubstituted or substituted with deuterium, C 1 -C 60 C substituted with alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic group.
[0296] In an embodiment, in Formula 1, The moiety represented by may be a moiety represented by one of formula CY1(1) to formula CY1(11):
[0297]
[0298] In formula CY1(1) to formula CY1(11),
[0299] R 11 To R 17 Can be independently combined with reference R in formula 1 1 The same as defined above, * indicates the bonding site with M in Formula 1, and
[0300] *' indicates the same as L in Formula 1 1 bonding site.
[0301] In an embodiment, in Formula 1, The moiety represented by may be a moiety represented by one of Formula CY2(1) to Formula CY2(13):
[0302]
[0303]
[0304] In formula CY2(1) to formula CY2(13),
[0305] T 21 Can be B(Y 21 )、C(Y 21 )(Y 22 )、N(Y 21 ), O, S or Si(Y 21 )(Y 22 ),
[0306] T 22 Can be C(Y 21 ), N or Si(Y 21 ),
[0307] R 21 To R 26 , Y 21 and Y 22 Can be independently combined with reference R in formula 1 2 The same as limited,
[0308] * indicates the bonding site with M in Formula 1,
[0309] *' indicates the same as L in formula 1 1 The bonding sites of
[0310] *" indicates the same as L in Formula 1 2 bonding site.
[0311] In an embodiment, in Formula 1, The portion represented by may be a portion represented by one of Formula CY31(1) to Formula CY31(6):
[0312]
[0313] In formula CY31(1) to formula CY31(6),
[0314] T 31 Can be C(Y 311 )(Y 312 )、N(Y 311 ), O, S or Si(Y 311 )(Y 312 ),
[0315] R 311 To R 314 , Y 311 and Y 312 Can be independently combined with reference R in formula 1 31 The same as limited,
[0316] * indicates the bonding site with M in Formula 1,
[0317] *" indicates the same as L in Formula 1 2 The bonding site of
[0318] * 2 indicates the bonding site to N in Formula 1, and
[0319] * 3 Indicates the ring CY in formula 1 32 bonding site.
[0320] In an embodiment, in Formula 1, The portion represented by may be a portion represented by one of Formula CY32(1) to Formula CY32(16):
[0321]
[0322]
[0323] In formula CY32(1) to formula CY32(16),
[0324] T 32 Can be C(Y 321 )(Y 322 )、N(Y 321 ), O, S or Si(Y 321 )(Y 322 ),
[0325] R 321 To R 328 , Y 321 and Y 322 Can be independently combined with reference R in formula 1 32 The same as limited,
[0326] *2 indicates the bonding site to N in Formula 1, and
[0327] * 3 Indicates the ring CY in formula 1 31 bonding site.
[0328] In an embodiment, in Formula 1, The moiety represented by may be a moiety represented by one of Formula CY4(1) to Formula CY4(29):
[0329]
[0330]
[0331] In formula CY4(1) to formula CY4(29),
[0332] R 41 To R 47 Can be independently combined with reference R in formula 1 4 The same as defined above, * indicates the bonding site with M in Formula 1, and
[0333] *"' indicates the same as L in Formula 1 3 bonding site.
[0334] R with quantity a1 1 , R 11 , the number of R is a2 2 , the number of R is a31 31 , the number of R is a32 32 , R with quantity a4 4 , R 1a and R 1b Two or more adjacent groups in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and
[0335] R 10a May be the same as described herein.
[0336] In formula 1, the number of R is a1 1 Two adjacent groups in; the number of R is a2 2 Two adjacent groups in; the number of R is a31 31 Two adjacent groups in; the number of R is a32 32 Two adjacent groups in; or a4 number of R4 Two adjacent groups in may be optionally bonded to each other to form a group represented by Formula 1A.
[0337] In an embodiment, the organometallic compound represented by Formula 1 may include at least one group represented by Formula 1A:
[0338] [Formula 1A]
[0339]
[0340] In Formula 1A, X 51 Can be C(R 51 ) or N, X 52 Can be C(R 52 ) or N, X 53 Can be C(R 53 ) or N, X 54 Can be C(R 54 ) or N, X 55 Can be C(R 55 ) or N, X 56 Can be C(R 56 ) or N, X 57 Can be C(R 57 ) or N, and X 58 Can be C(R 58 ) or N.
[0341] In Formula 1A, R 51 To R 58 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0342] R 10a and Q 1 To Q 3 Each is the same as described herein.
[0343] In an embodiment, X 51 Can be C(R 51 ), X 52 Can be C(R 52 ), X 53 Can be C(R 53 ), X 54 Can be C(R 54 ), X 55 Can be C(R 55 ), X 56 Can be C(R 56 ), X 57 Can be C(R 57 ), and X 58 Can be C(R 58 ).
[0344] In an embodiment, R 51 To R 58 Can be independently:
[0345] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0346] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
[0347] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl oxazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorolyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0348] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0349] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0350] In an embodiment, R 51 To R 58 Can be independently:
[0351] Hydrogen, deuterium, -F, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0352] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl or any combination thereof;
[0353] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, -CD 3 、-CD 2 H.-CDH2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof; or
[0354] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -N(Q 1 )(Q 2 ),and
[0355] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C60 Heterocyclic group.
[0356] In an embodiment, R 51 To R 58 Can be independently:
[0357] Hydrogen, deuterium or C 1 -C 20 alkyl;
[0358] C replaced by 1 -C 20 Alkyl: deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, or any combination thereof;
[0359] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl or naphthyl: deuterium, -CD 3 、-CD 2 H.-CDH 2 , C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 ) or any combination thereof; or
[0360] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0361] Q 1 To Q 3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60Alkynyl; either unsubstituted or substituted with deuterium, C 1 -C 60 C substituted with alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic group.
[0362] In Formula 1A, * and *' each indicate a bonding site to an adjacent atom.
[0363] In an embodiment, the organometallic compound represented by Formula 1 may be represented by Formula 1-1:
[0364] [Formula 1-1]
[0365]
[0366] In formula 1-1,
[0367] M and R 11 may each be the same as defined in Formula 1,
[0368] L 2 Can be *-O-*' or *-S-*',
[0369] X 12 Can be C(R 12 ) or N,
[0370] X 13 Can be C(R 13 ) or N,
[0371] X 14 Can be C(R 14 ) or N,
[0372] X 15 Can be C(R 15 ) or N,
[0373] X 21 Can be C(R 21 ) or N,
[0374] X 22 Can be C(R 22 ) or N,
[0375] X 23 Can be C(R 23 ) or N,
[0376] X 311 Can be C(R 311 ) or N,
[0377] X 312 Can be C(R 312 ) or N,
[0378] X 321 Can be C(R 321 ) or N,
[0379] X 322 Can be C(R 322 ) or N,
[0380] X 323 Can be C(R 323 ) or N,
[0381] X 324 Can be C(R 324 ) or N,
[0382] X 41 Can be C(R 41 ) or N,
[0383] X 42 Can be C(R 42 ) or N,
[0384] X 43 Can be C(R 43 ) or N,
[0385] X 44 Can be C(R 44 ) or N,
[0386] R 12 To R 15 Can be independently combined with reference R in formula 1 1 The same as limited,
[0387] R 21 To R 23 Can be independently combined with reference R in formula 1 2 The same as limited,
[0388] R 311 and R 312 Can be independently combined with reference R in formula 1 31 The same as limited,
[0389] R 321 To R 324 Can be independently combined with reference R in formula 1 32 The same as defined, and
[0390] R 41 To R 44 Can be independently combined with reference R in formula 1 4 Same as defined.
[0391] In an embodiment, the organometallic compound represented by Formula 1-1 may satisfy at least one of Conditions 1 to 12:
[0392] [Condition 1]
[0393] X 12 C(R 12 ), X 13 C(R 13 ), and R 12 and R 13 bonded to each other to form a group represented by Formula 1A;
[0394] [Condition 2]
[0395] X 13 C(R 13 ), X 14 C(R 14 ), and R 13 and R 14 bonded to each other to form a group represented by Formula 1A;
[0396] [Condition 3]
[0397] X 14 C(R 14 ), X 15 C(R 15 ), and R 14 and R 15 bonded to each other to form a group represented by Formula 1A;
[0398] [Condition 4]
[0399] X 21 C(R 21 ), X 22 C(R 22 ), and R 21 and R 22 bonded to each other to form a group represented by Formula 1A;
[0400] [Condition 5]
[0401] X 22 C(R 22 ), X 23 C(R 23 ), and R 22 and R 23 bonded to each other to form a group represented by Formula 1A;
[0402] [Condition 6]
[0403] X 311 C(R 311 ), X 312 C(R 312 ), and R 311 and R312 bonded to each other to form a group represented by Formula 1A;
[0404] [Condition 7]
[0405] X 321 C(R 321 ), X 322 C(R 322 ), and R 321 and R 322 bonded to each other to form a group represented by Formula 1A;
[0406] [Condition 8]
[0407] X 322 C(R 322 ), X 323 C(R 323 ), and R 322 and R 323 bonded to each other to form a group represented by Formula 1A;
[0408] [Condition 9]
[0409] X 323 C(R 323 ), X 324 C(R 324 ), and R 323 and R 324 bonded to each other to form a group represented by Formula 1A;
[0410] [Condition 10]
[0411] X 41 C(R 41 ), X 42 C(R 42 ), and R 41 and R 42 bonded to each other to form a group represented by Formula 1A;
[0412] [Condition 11]
[0413] X 42 C(R 42 ), X 43 C(R 43 ), and R 42 and R 43 bonded to each other to form a group represented by Formula 1A;
[0414] [Condition 12]
[0415] X 43 C(R 43 ), X 44 C(R44 ), and R 43 and R 44 are bonded to each other to form a group represented by Formula 1A.
[0416] Unless otherwise specified, in Formula 1 and Formula 1A, R 10a Can be:
[0417] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0418] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0419] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0420] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0421] Unless otherwise specified, in Formula 1 and Formula 1A, Q 1 To Q3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0422] The organic metal compound represented by Formula 1 may include at least one group represented by Formula 1A, and the group represented by Formula 1A may cause a steric protection effect in the molecule. Accordingly, by using the organic metal compound represented by Formula 1, a light-emitting device (e.g., an organic light-emitting device) having a reduced driving voltage, improved color purity and luminous efficiency, and increased lifespan may be implemented.
[0423] [Description of Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503]
[0424] [Formula 2]
[0425]
[0426] In formula 2, L 51 To L 53 may be independently a single bond, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0427] In Formula 2, b51 to b53 respectively indicate L 51 Quantity to L 53 The number of L, and b51 to b53 may each independently be an integer selected from 1 to 5. When b51 is 2 or more, two or more L 51 may be the same or different from each other. When b52 is 2 or greater, two or more L 52 may be the same as or different from each other, and when b53 is 2 or greater, two or more L 53 In an embodiment, b51 to b53 may be 1 or 2, respectively.
[0428] In an embodiment, in Formula 2, L 51 To L 53 Can be independently:
[0429] a single key; or
[0430] phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl , oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilanyl, dibenzothiasilanyl, dibenzodihydroazasilanyl, dibenzodihydrodihydrodisilacyclohexanyl, dibenzodihydrosilanyl, dibenzodioxanyl, dibenzothiasilanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiacyclohexanyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -O(Q 31 )、-S(Q31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, and
[0431] Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0432] In an embodiment, in Formula 2, L 51 With R 51 The key between 52 With R 52 The key between 53 With R 53 A bond between two or more L 51 A bond between two or more L 52 A bond between two or more L 53 The key between 51 With X 54 and X 55 The bonds between carbons, L 52 With X 54 and X 56 The bonds between the carbons, and L 53 With X 55 and X 56 The bonds between the carbon atoms in between may each be a "carbon-carbon single bond".
[0433] In formula 2, X 54 Can be N or C(R 54 ), X 55 Can be N or C(R 55 ), X 56 Can be N or C(R 56 ), and X 54 To X 56At least one of may be N. In Formula 2, R 54 To R 56 Each may be the same as described herein. For example, X 54 To X 56 Two or three of them can each be N.
[0434] In formula 2, R 51 To R 56 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each is the same as described herein.
[0435] In an embodiment, in Formula 2, R 51 To R 56 Can be independently:
[0436] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0437] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
[0438] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzo furanyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0439] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0440] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0441] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0442] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0443] [Formula 91]
[0444]
[0445] In formula 91,
[0446] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group,
[0447] X 91 Can be single bond, O, S, N(R 91 )、B(R 91 )、C(R 91a )(R 91b ) or Si(R 91a )(R 91b ),
[0448] R 91 , R 91a and R 91b Can be compared with reference R 82 , R 82a and R 82b Same as described,
[0449] R 10a may be the same as described herein, and
[0450] *Indicates bonding sites to neighboring atoms.
[0451] In an embodiment, in Formula 91,
[0452] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a substituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, and
[0453] R91 , R 91a and R 91b Can be independently:
[0454] Hydrogen or C 1 -C 10 Alkyl; or
[0455] phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0456] In an embodiment, in Formula 2, *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented by may each be other than phenyl.
[0457] In an embodiment, in Formula 2, *-(L 51 ) b51 -R 51 The groups represented by *-(L 52 ) b52 -R 52 The groups represented may be the same as each other.
[0458] In an embodiment, in Formula 2, *-(L 51 ) b51 -R 51 The group represented by *-(L 52 ) b52 -R 52 The groups represented may be different from each other.
[0459] In an embodiment, in Formula 2, b51 and b52 may each independently be 1, 2 or 3; and L 51 and L 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0460] In an embodiment, in Formula 2, R 51 and R 52 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0461] Q 1 To Q 3 can be each independently unsubstituted or substituted with deuterium, -F, cyano, methyl, C 1 -C 60 Alkyl, C 1 -C 60 C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0462] In an embodiment, in Formula 2,
[0463] By *-(L 51 ) b51 -R 51 The group represented by may be a group represented by one of the formulas CY51-1 to CY51-26, and / or
[0464] By *-(L 52 ) b52 -R 52 The group represented by may be a group represented by one of the formulas CY52-1 to CY52-26, and / or
[0465] By *-(L 53 ) b53 -R 53 The group represented by may be a group represented by one of the formulas CY53-1 to CY53-27, -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ):
[0466]
[0467]
[0468]
[0469] In formula CY51-1 to formula CY51-26, formula CY52-1 to formula CY52-26 and formula CY53-1 to formula CY53-27,
[0470] Y 63 Can be single bond, O, S, N(R 63 )、B(R 63 )、C(R 63a )(R 63b ) or Si(R 63a )(R 63b ),
[0471] Y 64 Can be single bond, O, S, N(R 64 )、B(R 64 )、C(R 64a )(R 64b ) or Si(R 64a )(R 64b ),
[0472] Y 67 Can be single bond, O, S, N(R 67 )、B(R 67 )、C(R 67a )(R 67b ) or Si(R 67a )(R 67b ),
[0473] Y 68 Can be single bond, O, S, N(R 68 )、B(R 68 )、C(R 68a )(R 68b ) or Si(R 68a )(R 68b ),
[0474] Y in formula CY51-16 and formula CY51-17 63 and Y 64 They may not all be single bonds at the same time.
[0475] Y in formula CY52-16 and formula CY52-17 67 and Y 68 They may not all be single bonds at the same time.
[0476] R 51 To R51e , R 61 To R 64 , R 63a , R 63b , R 64a and R 64b Can be independently compared with reference R 51 Same as described, except that R 51 To R 51e Each of them may not be hydrogen,
[0477] R 52 To R 52e , R 65 To R 68 , R 67a , R 67b , R 68a and R 68b Can be independently compared with reference R 52 Same as described, except that R 52 To R 52e Each of them may not be hydrogen,
[0478] R 53 To R 53e , R 69a and R 69b Can be independently compared with reference R 53 Same as described, except that R 53 To R 53e may each be other than hydrogen, and
[0479] *Indicates bonding sites to neighboring atoms.
[0480] In an embodiment,
[0481] In Formula CY51-1 to Formula CY51-26 and Formula CY52-1 to Formula CY52-26, R 51 To R 51e and R 52 To R 52e Can be independently:
[0482] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzo furanyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoline oxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl or any combination thereof; or
[0483] -C(Q 1 )(Q 2 )(Q 3 ) or -Si(Q 1 )(Q 2 )(Q 3 ),and
[0484] Q 1 To Q3 may be each independently phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0485] In formula CY51-16 and formula CY51-17, Y 63 Can be O or S and Y 64 Can be Si(R 64a )(R 64b ), or Y 63 Can be Si(R 63a )(R 63b ) and Y 64 can be O or S, and
[0486] In formula CY52-16 and formula CY52-17, Y 67 Can be O or S and Y 68 Can be Si(R 68a )(R 68b ), or Y 67 Can be Si(R 67a )(R 67b ) and Y 68 Can be O or S.
[0487] [Formula 3]
[0488]
[0489] In Formula 3, ring CY 71 and CY 72 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridyl group.
[0490] In formula 3, X 71 It can be: a single bond; or a linking group including O, S, N, B, C, Si or any combination thereof.
[0491] In Formula 3, * indicates a bonding site to any atom in the remaining portion other than the group represented by Formula 3 of the third compound.
[0492] [Formula 3-1]
[0493]
[0494] [Formula 3-2]
[0495]
[0496] [Formula 3-3]
[0497]
[0498] [Formula 3-4]
[0499]
[0500] [Formula 3-5]
[0501]
[0502] In Formula 3-1 to Formula 3-5, ring CY 71 To Ring CY 74 can be independently π-electron-rich C 3 -C 60 A cyclic group or a pyridyl group.
[0503] In Formula 3-1 to Formula 3-5, X 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a )(R 82b ).
[0504] In Formula 3-1 to Formula 3-5, X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ).
[0505] In Formula 3-1 to Formula 3-5, X 84 Can be O, S, N[(L 84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ).
[0506] In Formula 3-1 to Formula 3-5, X 85 Can be C or Si.
[0507] In Formula 3-1 to Formula 3-5, L 81 To L 85 can be independently a single bond, *-C(Q4 )(Q 5 )-*'、*-Si(Q 4 )(Q 5 )-*', unsubstituted or replaced by at least one R 10a Substituted π-electron-rich C 3 -C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a substituted pyridyl, and
[0508] Q 4 and Q 5 Can be independently compared with reference Q 1 Same as described.
[0509] In Formulae 3-1 to 3-5, b81 to b85 may each independently be an integer selected from 1 to 5.
[0510] In Formula 3-1 to Formula 3-5, R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b Each may be the same as described herein.
[0511] In Formula 3-1 to Formula 3-5, a71 to a74 respectively indicate R 71 The number of R 74 , and a71 to a74 may each independently be an integer selected from 0 to 20. When a71 is 2 or more, two or more R 71 may be the same as or different from each other. When a72 is 2 or greater, two or more R 72 may be the same as or different from each other. When a73 is 2 or greater, two or more R 73 may be the same as or different from each other, and when a74 is 2 or greater, two or more R 74 In an embodiment, a71 to a74 may each independently be an integer selected from 0 to 8.
[0512] In Formula 3-1 to Formula 3-5, R 10a May be the same as described herein.
[0513] In an embodiment, in Formula 3-1 to Formula 3-5, L 81 To L 85 Can be independently:
[0514] single bond;
[0515] *-C(Q 4 )(Q 5 )-*' or *-Si(Q 4 )(Q 5 )-*';or
[0516] phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, 1,2-triphenylenyl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirolyl, dibenzothirolyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl or benzothiadiazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, dimethyldibenzosilyl, diphenyldibenzosilyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, and
[0517] Q 4 , Q 5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C 1 -C20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0518] In an embodiment, in Formula 3-1 and Formula 3-2, The moiety represented by may be a moiety represented by one of Formula CY71-1(1) to Formula CY71-1(8), and / or
[0519] In formula 3-1 and formula 3-3, The moiety represented by may be a moiety represented by one of Formula CY71-2(1) to Formula CY71-2(8), and / or
[0520] In formula 3-2 and formula 3-4, The moiety represented by may be a moiety represented by one of Formula CY71-3(1) to Formula CY71-3(32), and / or
[0521] In formula 3-3 to formula 3-5, The moiety represented by may be a moiety represented by one of Formula CY71-4(1) to Formula CY71-4(32), and / or
[0522] In formula 3-5, The moiety represented by may be a moiety represented by one of Formula CY71-5(1) to Formula CY71-5(8):
[0523]
[0524]
[0525]
[0526]
[0527] In formula CY71-1(1) to formula CY71-1(8), formula CY71-2(1) to formula CY71-2(8), formula CY71-3(1) to formula CY71-3(32), formula CY71-4(1) to formula CY71-4(32) and formula CY71-5(1) to formula CY71-5(8),
[0528] X 82 To X 85 , L 81 ,b81,R 81 and R 85 may be the same as described in this article, respectively,
[0529] X 86Can be single bond, O, S, N(R 86 )、B(R 86 )、C(R 86a )(R 86b ) or Si(R 86a )(R 86b ),
[0530] X 87 Can be single bond, O, S, N(R 87 )、B(R 87 )、C(R 87a )(R 87b ) or Si(R 87a )(R 87b ),
[0531] In Formula CY71-1(2) to Formula CY71-1(4), Formula CY71-4(2) to Formula CY71-4(4), Formula CY71-4(10) to Formula CY71-4(12), Formula CY71-4(18) to Formula CY71-4(20), and Formula CY71-4(26) to Formula CY71-4(28), X 86 and X 87 They may not all be single bonds at the same time.
[0532] X 88 Can be single bond, O, S, N(R 88 )、B(R 88 )、C(R 88a )(R 88b ) or Si(R 88a )(R 88b ),
[0533] X 89 Can be single bond, O, S, N(R 89 )、B(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0534] In Formulas CY71-2(2) to CY71-2(4), CY71-3(2) to CY71-3(4), CY71-3(10) to CY71-3(12), CY71-3(18) to CY71-3(20), CY71-3(26) to CY71-3(28), and CY71-5(2) to CY71-5(4), X 88 and X 89 may not each be a single bond at the same time, and
[0535] R86 To R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b Can be independently compared with reference R 81 Same as described.
[0536] [Formula 502]
[0537]
[0538] [Formula 503]
[0539]
[0540] In Formula 502 and Formula 503, ring A 501 To Ring A 504 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0541] In equations 502 and 503, Y 505 Can be O, S, N (R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ).
[0542] In equations 502 and 503, Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ).
[0543] In equations 502 and 503, Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ).
[0544] In equations 502 and 503, Y 508Can be O, S, N (R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ).
[0545] In equations 502 and 503, Y 51 and Y 52 They may each independently be B, P(═O) or S(═O).
[0546] In equations 502 and 503, R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b Each may be the same as described herein.
[0547] In equations 502 and 503, a501 to a504 respectively indicate R 501 The number of R 504 , and a501 to a504 may each independently be an integer selected from 0 to 20. When a501 is 2 or more, two or more R 501 may be the same or different from each other. When a502 is 2 or greater, two or more R 502 may be the same or different from each other. When a503 is 2 or greater, two or more R 503 may be the same as or different from each other, and when a504 is 2 or greater, two or more R 504 In an embodiment, a501 to a504 may each independently be an integer selected from 0 to 8.
[0548] In the specification, in Formula 2, Formula 3-1 to Formula 3-5, Formula 502 and Formula 503, R 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ). Q 1 To Q 3 Each may be the same as described herein.
[0549] In an embodiment, R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502, and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b , and R 10a Can be independently:
[0550] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0551] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
[0552] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzo furanyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0553] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0554] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0555] -CH 3 、-CD 3 、-CD2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0556] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C 1 -C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0557] In an embodiment, R in Formula 1 1 , R 11 , R 2 , R 31 , R 32 and R 4 And R in Formula 1A 51 To R 58 ; R in Formula 2, Formula 3-1 to Formula 3-5, Formula 502 and Formula 503 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , R 84b , R 500a , R 500b , R 501 To R 508 , R 505a , R 505b , R 506a , R 506b, R 507a , R 507b , R 508a and R 508b ; and R 10a Can be independently:
[0558] Hydrogen, deuterium, -F, cyano, nitro, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H or -CFH 2 ;
[0559] A group represented by one of Formula 9-1 to Formula 9-19; or
[0560] A group represented by one of the formulas 10-1 to 10-246, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 ) or -P(=O)(Q 1 )(Q 2 )(where Q 1 To Q 3 may each be the same as described herein):
[0561]
[0562]
[0563]
[0564]
[0565]
[0566]
[0567] In Formulae 9-1 to 9-19 and 10-1 to 10-246, * indicates a bonding site to an adjacent atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group.
[0568] [Examples of Compounds]
[0569] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compound 1 to Compound 52:
[0570]
[0571]
[0572]
[0573] [ Figure 1 Description]
[0574] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110 , an interlayer 130 , and a second electrode 150 .
[0575] In the following, reference will be made to Figure 1 A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to an embodiment are described.
[0576] [First electrode 110]
[0577] exist Figure 1 In the embodiment, a substrate may be further 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 plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0578] The first electrode 110 may be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.
[0579] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), 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 used to form 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.
[0580] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.
[0581] [Interlayer 130]
[0582] The interlayer 130 is disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0583] 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 .
[0584] In addition to various organic materials, the interlayer 130 may further include metal-containing compounds (such as organic metal compounds) or inorganic materials (such as quantum dots), etc.
[0585] 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 disposed between the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer, the light emitting device 10 may be a tandem light emitting device.
[0586] [Hole Transport Region in Interlayer 130]
[0587] The hole transport region may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multilayer structure including a plurality of layers including different materials.
[0588] 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.
[0589] In an embodiment, the hole transport region may have a multi-layer structure, which includes a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the layers of each structure may be stacked in the order described in their respective descriptions starting from the first electrode 110, but the structure of the hole transport region is not limited thereto.
[0590] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0591] [Formula 201]
[0592]
[0593] [Formula 202]
[0594]
[0595] In equation 201 and equation 202,
[0596] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0597] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0598] xa1 to xa4 may each independently be an integer selected from 0 to 5,
[0599] xa5 may be an integer selected from 1 to 10,
[0600] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0601] R 201 and R 202 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C8 -C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16, etc.),
[0602] R 203 and R 204 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 polycyclic groups, and
[0603] na1 may be an integer selected from 1 to 4.
[0604] 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 CY217:
[0605]
[0606] In formula CY201 to formula CY217, R 10b and R 10c Can be independently compared with reference R 10a Same as described, CY 201 To Ring CY 204 Can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.
[0607] In an embodiment, in Formula CY201 to Formula CY217, ring CY 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.
[0608] 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.
[0609] 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.
[0610] In an embodiment, in Formula 201, xa1 may be 1, R 201 may be a group represented by one of the formulas CY201 to CY203, xa2 may be 0, and R 202 It may be a group represented by one of Formula CY204 to Formula CY207.
[0611] 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 CY203.
[0612] 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 CY203, and may each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0613] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include a group represented by one of Formulas CY201 to CY217.
[0614] 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"-tri(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:
[0615]
[0616]
[0617]
[0618]
[0619]
[0620] The thickness of the hole transport region may be 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 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 to about When the thickness of the hole transport region, the hole injection layer and the hole transport layer is within the above range, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0621] The emission auxiliary layer can increase the luminous efficiency by compensating the optical resonance distance according to the wavelength of 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 material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0622] [p-dopant]
[0623] In addition to the above materials, the hole transport region may further include a charge generation material for improving conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (eg, in the form of a single layer composed of the charge generation material).
[0624] The charge generating material may be, for example, a p-dopant.
[0625] In an embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level less than or equal to about −3.5 eV.
[0626] In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0627] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
[0628] Examples of the cyano group-containing compound may include HAT-CN and a compound represented by Formula 221, and the like:
[0629]
[0630] [Formula 221]
[0631]
[0632] In formula 221,
[0633] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 a heterocyclic group, and
[0634] R 221 To R 223 At least one of them may be independently C each substituted by 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0635] In a compound including an element EL1 and an element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0636] 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.); late 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.), etc.
[0637] Examples of metalloids may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
[0638] Examples of non-metal may include oxygen (O) and halogen (eg, F, Cl, Br, I, etc.), and the like.
[0639] 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.
[0640] Examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and rhenium oxides (e.g., ReO 3 etc.
[0641] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.
[0642] 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, CsI, and the like.
[0643] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and BaI 2 wait.
[0644] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 , TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 , PtCl 2 , PtBr 2 , PtI 2 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.), etc.
[0645] Examples of late transition metal halides may include zinc halides (eg, ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and tin halides (e.g., SnI 2 etc.
[0646] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 、YbCl、YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and SmI 3 wait.
[0647] Examples of metalloid halides may include antimony halides (eg, SbCl 5 etc.
[0648] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2Te, CuTe, Ag 2 Te, AgTe, Au 2 Te, etc.), late 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.), etc.
[0649] [Emitting layer in interlayer 130]
[0650] When the light-emitting device 10 is a full-color 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 the sub-pixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light. In an embodiment, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0651] In an embodiment, the emission layer may include a host and a dopant (or emitter). In an embodiment, in addition to the host and the dopant (or emitter), the emission layer may further include an auxiliary dopant that promotes energy transfer to the dopant (or emitter). When the emission layer includes a dopant (or emitter) and an auxiliary dopant, the dopant (or emitter) and the auxiliary dopant may be different from each other.
[0652] The organometallic compound represented by Formula 1 described herein may be used as a dopant (or emitter), or may be used as an auxiliary dopant.
[0653] The amount (weight) of the dopant (or emitter) in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0654] The emission layer may include an organic metal compound represented by Formula 1. Based on 100 parts by weight of the emission layer, the amount (weight) of the organic metal compound represented by Formula 1 in the emission layer may be in the range of about 0.01 parts by weight to about 30 parts by weight. For example, based on 100 parts by weight of the emission layer, the amount (weight) of the organic metal compound represented by Formula 1 in the emission layer may be in the range of about 0.1 parts by weight to about 20 parts by weight. For example, based on 100 parts by weight of the emission layer, the amount (weight) of the organic metal compound represented by Formula 1 in the emission layer may be in the range of about 0.1 parts by weight to about 15 parts by weight.
[0655] In an embodiment, the emissive layer may include quantum dots.
[0656] In an embodiment, the emission layer may include a delayed fluorescent material (compound). The delayed fluorescent material may be used as a host or as a dopant in the emission layer.
[0657] The thickness of the emission layer can be about to about For example, the thickness of the emission layer may be in the range of about to about When the thickness of the emission layer is within the above range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0658] [main body]
[0659] The host in the emissive layer can include the second compound or the third compound described herein, or any combination thereof.
[0660] In an embodiment, the host may include a compound represented by Formula 301:
[0661] [Formula 301]
[0662] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0663] In formula 301,
[0664] Ar 301 and L 301 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0665] xb11 can be 1, 2 or 3,
[0666] xb1 may be an integer selected from 0 to 5,
[0667] R 301 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -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 C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0668] xb21 may be an integer selected from 1 to 5, and
[0669] Q 301 To Q 303 Can be independently compared with reference Q 1 Same as described.
[0670] 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.
[0671] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0672] [Formula 301-1]
[0673]
[0674] [Formula 301-2]
[0675]
[0676] In Formula 301-1 and Formula 301-2,
[0677] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0678] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0679] xb22 and xb23 can each independently be 0, 1 or 2,
[0680] L 301 , xb1 and R 301 may each be the same as described herein,
[0681] L 302 To L 304 Can be independently compared with reference L 301 Same as described,
[0682] xb2 to xb4 may each independently be the same as described with reference to xb1, and
[0683] R 302 To R 305 and R 311 To R 314 Can be independently compared with reference R 301 Same as described.
[0684] In an embodiment, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0685] In an embodiment, the host may include one of Compounds H1 to H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(9-carbazolyl)benzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), or any combination thereof:
[0686]
[0687]
[0688]
[0689]
[0690]
[0691]
[0692]
[0693] In an embodiment, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0694] The body may have various modifications. For example, the body may include only one type of compound, or may include two or more types of different compounds.
[0695] [Phosphorescent dopant]
[0696] The emission layer may include the organometallic compound represented by Formula 1 described herein as a phosphorescent dopant.
[0697] In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 as described herein, and the organometallic compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0698] The phosphorescent dopant may include at least one transition metal as a central metal.
[0699] 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.
[0700] The phosphorescent dopant may be electrically neutral.
[0701] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0702] [Formula 401]
[0703] M(L 401 ) xc1 (L 402 ) xc2 .
[0704] In formula 401,
[0705] M may 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)),
[0706] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,
[0707] [Formula 402]
[0708]
[0709] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,
[0710] In formula 402,
[0711] X 401 and X 402 can be independently N or C,
[0712] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0713] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',
[0714] X 403 and X 404 can be independently 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 ),
[0715] Q 411 To Q 414 Can be independently compared with reference Q 1 Same as described,
[0716] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -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 ),
[0717] Q 401 To Q 403 Can be independently compared with reference Q 1 Same as described,
[0718] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0719] * and *' in Formula 402 each indicate a bonding site to M in Formula 401.
[0720] In an embodiment, in formula 402, X 401 may be nitrogen and X 402 Can be carbon, or X 401 and X 402 Each of may be nitrogen.
[0721] In an embodiment, when xc1 in Formula 401 is 2 or greater, two or more L 401 The two rings A 401 Optionally, T as a linker 402 connected to each other, and two or more L 401The two rings A 402 Optionally, T as a linker 403 are connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). For example, T 402 and T 403 Can be independently compared with reference T 401 Same as described.
[0722] In formula 401, L 402 Can be an organic ligand. In an embodiment, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0723] The phosphorescent dopant may include, for example, one of Compound PD1 to Compound PD39 or any combination thereof:
[0724]
[0725]
[0726]
[0727] [Fluorescent dopant]
[0728] When the emission layer includes the organometallic compound represented by Formula 1 described herein, and the organometallic compound represented by Formula 1 is used as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0729] In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 described herein, and the organometallic compound represented by Formula 1 is used as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0730] The fluorescent dopant and the auxiliary dopant may each independently include an aromatic amine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0731] In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
[0732] [Formula 501]
[0733]
[0734] In formula 501,
[0735] Ar 501 , L 501 To L 503 , R501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0736] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0737] xd4 can be 1, 2, 3, 4, 5 or 6.
[0738] In an embodiment, in Formula 501, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed to each other (for example, anthracenyl, 1,2-triphenylenyl, pyrenyl, etc.).
[0739] In an embodiment, in Formula 501, xd4 in Formula 501 may be 2.
[0740] In an embodiment, the fluorescent dopant and the auxiliary dopant may each include one of Compound FD1 to Compound FD37, DPVBi, DPAVBi, or any combination thereof:
[0741]
[0742]
[0743]
[0744]
[0745] [Delayed fluorescence material]
[0746] The emission layer may include a delayed fluorescent material (compound).
[0747] The delayed fluorescence material described herein may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0748] The delayed fluorescent material may include, for example, the fourth compound described herein.
[0749] The delayed fluorescent material included in the emission layer may serve as a host or as a dopant depending on the types of other materials included in the emission layer.
[0750] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be in the range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and therefore, the light emitting device 10 may have improved luminous efficiency.
[0751] In an embodiment, the delayed fluorescent material may include: at least one electron donor (eg, a π-electron-rich C 3 -C 60 Cyclic groups, such as carbazolyl, etc.) and at least one electron acceptor (e.g., sulfoxide, cyano, π-electron-deficient nitrogen-containing C 1 -C 60 heterocyclic group, etc.); or a C in which two or more cyclic groups are fused while sharing boron (B); 8 -C 60 Materials with polycyclic groups, etc.
[0752] Examples of the delayed fluorescent material may include at least one of Compound DF1 to Compound DF14:
[0753]
[0754]
[0755] [Quantum dot]
[0756] The emissive layer may include quantum dots.
[0757] In the specification, the quantum dot may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
[0758] The diameter of the quantum dots may, for example, be in the range of about 1 nm to about 10 nm.
[0759] The quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any process similar thereto.
[0760] The wet chemical process is a method including mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. When the quantum dot particle crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal and controls the growth of the quantum dot particle crystal, so that the growth of the quantum dot particle crystal can be controlled by a process that is lower in cost and easier to perform than a vapor deposition method such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0761] 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.
[0762] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, etc.; or any combination thereof.
[0763] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb, etc.; or any combination thereof. In an embodiment, the III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
[0764] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and InTe, etc.; ternary compounds, such as InGaS 3 and InGaSe 3 etc.; or any combination thereof.
[0765] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and AgAlO 2 etc.; or any combination thereof.
[0766] Examples of Group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe and PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe and SnPbSTe; or any combination thereof.
[0767] Examples of Group IV elements or compounds may include: single element materials such as Si and Ge, etc.; binary compounds such as SiC and SiGe, etc.; or any combination thereof.
[0768] Each element included in the multi-element compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particle at a uniform concentration or at a non-uniform concentration.
[0769] In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell dual structure. In an embodiment, in the case where the quantum dot has a core-shell dual structure, the material included in the core and the material included in the shell may be different from each other.
[0770] The shell of the quantum dot 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 dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, wherein the concentration of the material present in the shell decreases toward the center of the core.
[0771] Examples of the shell of the quantum dot may include metal oxides, metalloid oxides or 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 SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and NiO, etc.; ternary compounds, such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and CoMn 2 O 4 etc.; or any combination thereof.
[0772] 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. Examples of 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.
[0773] The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 45 nm. For example, the quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 40 nm. For example, the quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 30 nm. When the FWHM of the emission wavelength spectrum of the quantum dot is within these ranges, the quantum dot may have improved color purity or improved color reproducibility. The light emitted by the quantum dot may be emitted in all directions, so that the wide viewing angle may be improved.
[0774] In embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, or the like.
[0775] Because the energy 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, a light-emitting device that emits light of various wavelength bands can be implemented. In detail, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In an embodiment, the size of the quantum dots can be configured to emit white light through a combination of light of various colors.
[0776] [Electron Transport Region in Interlayer 130]
[0777] The electron transport region may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multilayer structure including a plurality of layers including different materials.
[0778] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0779] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked in their respective described order starting from the emission layer, but the structure of the electron transport region is not limited thereto.
[0780] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group.
[0781] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[0782] [Formula 601]
[0783] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0784] In formula 601,
[0785] Ar 601 and L 601may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0786] xe11 can be 1, 2 or 3,
[0787] xe1 can be 0, 1, 2, 3, 4 or 5,
[0788] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -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 ),
[0789] Q 601 To Q 603 Can be independently compared with reference Q 1 Same as described,
[0790] xe21 can be 1, 2, 3, 4, or 5, and
[0791] Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Heterocyclic group.
[0792] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 Can be connected to each other via a single bond.
[0793] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0794] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0795] [Formula 601-1]
[0796]
[0797] In formula 601-1,
[0798] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and X 614 To X 616 At least one of them may each be N,
[0799] L 611 To L 613 Can be independently compared with reference L 601 Same as described,
[0800] xe611 to xe613 can each independently be the same as described with reference to xe1,
[0801] R 611 To R 613 Can be independently compared with reference R 601 Same as described, and
[0802] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0803] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0804] In an embodiment, the electron transport region may include: one of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, TAZ, NTAZ or any combination thereof:
[0805]
[0806]
[0807]
[0808] The thickness of the electron transport region can be about to about For example, the thickness of the electron transport region may 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 may be independently 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 may be independently about to about For example, the thickness of the electron transport layer may 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 the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0809] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the above-mentioned materials.
[0810] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions.
[0811] Ligands coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex may 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.
[0812] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1(Liq) or compound ET-D2:
[0813]
[0814] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
[0815] The electron injection layer may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multilayer structure including multiple layers containing different materials.
[0816] 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.
[0817] Examples of alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0818] Examples of alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.
[0819] Examples of alkali metal compounds may include: alkali metal oxides, such as Li 2 O, Cs 2 O, and K 2 O, etc.; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and RbI, etc.; or any combination thereof. Alkaline earth metal compounds 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), and Ba x Ca1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal compound may include YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3 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, La 2 Te 3 , Ce 2 Te 3 , Pr 2 Te 3 , Nd 2 Te 3 , Pm 2 Te 3 , Sm 2 Te 3 , Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 , Dy 2 Te 3 , Ho 2 Te 3 , Er 2 Te 3 , Tm 2 Te 3 , Yb 2 Te 3 and Lu 2 Te 3 etc.
[0820] Examples of alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include: one of metal ions of an alkali metal, an alkaline earth metal, or a rare earth metal, and a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0821] In an embodiment, 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).
[0822] In an embodiment, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide), 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. For example, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, a LiF:Yb co-deposition layer, and the like.
[0823] 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.
[0824] The thickness of the electron injection layer can be about to about For example, the thickness of the electron injection layer may be about to about When the thickness of the electron injection layer is within the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0825] [Second electrode 150]
[0826] The second electrode 150 may be disposed on the interlayer 130 having the structure as described above. The second electrode 150 may be a cathode as an electron injection electrode, and as a material for forming the second electrode 150, metals, alloys, conductive compounds, or any combination thereof each having a low work function may be used.
[0827] 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.
[0828] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0829] [Capping layer]
[0830] The first capping layer may be arranged outside the first electrode 110 and / or the second capping layer may be arranged outside the second electrode 150. In detail, the 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 sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are sequentially stacked in the stated 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 may be sequentially stacked in the stated order.
[0831] The light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the first electrode 110 which can be a semi-transmissive electrode or a transmissive electrode and through the first capping layer. The light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the second electrode 150 which can be a semi-transmissive electrode or a transmissive electrode and through the second capping layer.
[0832] The first capping layer and the second capping layer can increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0833] Each of the first capping layer and the second capping layer may include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).
[0834] 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.
[0835] At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine-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 amine-containing compound may be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0836] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine-containing compound.
[0837] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0838] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0839]
[0840] [membrane]
[0841] The organometallic compound represented by Formula 1 may be included in various films. Accordingly, another embodiment provides a film that may include the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or 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, a quantum dot content layer, etc.), a light blocking member (e.g., a light reflection layer, a light absorption layer, etc.) or a protective member (e.g., an insulating layer, a dielectric layer, etc.), etc.
[0842] [Electronic equipment]
[0843] The light emitting device may be included in various electronic devices. In an embodiment, the electronic device including the light emitting device may be a light emitting device or an authentication device, etc.
[0844] In addition to the light-emitting device, the electronic device (e.g., 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 arranged in at least one direction of travel of the light emitted from the light-emitting device. In an embodiment, the light emitted from the light-emitting device may be blue light, green light, or white light. The light-emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots.
[0845] 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.
[0846] A pixel defining layer may be disposed between the plurality of sub-pixels to define each sub-pixel.
[0847] The color filter may further include a plurality of color filter regions and a plurality of light shielding patterns arranged between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a plurality of light shielding patterns arranged between the plurality of color conversion regions.
[0848] 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. For example, 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. For example, the color filter region (or color conversion region) may include quantum dots. For example, 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 as described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0849] In an embodiment, the 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 this regard, the first first color light, the second first color light, and the third first color light may have different maximum emission wavelengths from each other. For example, 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.
[0850] In addition to the 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 light emitting device.
[0851] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0852] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
[0853] The electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light emitting device. The sealing portion may allow light from the light emitting device to be extracted to the outside, and may simultaneously prevent ambient air and moisture from penetrating into the 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 of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0854] Depending on the purpose of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may be further arranged on the sealing portion. Examples of the functional layer may include a touch screen layer and 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. 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., a fingertip, a pupil, etc.).
[0855] In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.
[0856] The electronic device can be applied to various displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring tools, instruments (e.g., instruments for vehicles, aircraft, and ships), or projectors, etc.
[0857] [Electronic equipment]
[0858] Light emitting devices may be included in various electronic devices.
[0859] In an embodiment, the electronic equipment including the light emitting device 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 retractable display, a laser printer, a telephone, a mobile phone, a tablet computer, a tablet mobile phone computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays spliced together, a theater screen, a stadium screen, a light therapy device or a sign.
[0860] The light emitting device may have excellent light emitting efficiency and a long lifespan, and thus electronic equipment including the light emitting device may have characteristics such as high brightness, high resolution, and low power consumption.
[0861] [ Figure 2 and Figure 3 Description]
[0862] Figure 2 is a schematic cross-sectional view of a light emitting device as an example of an electronic device according to an embodiment.
[0863] Figure 2 The light emitting apparatus includes a substrate 100, a thin film transistor (TFT), a light emitting device, and a packaging portion 300 sealing the light emitting device.
[0864] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0865] 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.
[0866] 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.
[0867] A 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 .
[0868] 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 and between the gate electrode 240 and the drain electrode 270 to insulate each other.
[0869] Source electrode 260 and drain electrode 270 may be disposed on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may contact exposed portions of the source and drain regions of active layer 220, respectively.
[0870] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0871] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be disposed to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed portion of the drain electrode 270.
[0872] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a selected 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 layer 290 may be a polyimide-based organic film or a polyacrylic organic film. Figure 2 Although not shown in the figure, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.
[0873] The second electrode 150 may be disposed on the interlayer 130, and the second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
[0874] The encapsulation part 300 may be disposed on the second capping layer 170. The encapsulation part 300 may be disposed on the light emitting device to protect the light emitting device from moisture or oxygen. The encapsulation 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 comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyaromatic ester, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE)), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0875] Figure 3 is a schematic cross-sectional view of a light emitting device as an example of an electronic device according to another embodiment.
[0876] Figure 3 Light emitting devices and Figure 2 The light emitting device of is substantially the same, except that the light shielding pattern 500 and the functional area 400 are additionally arranged on the encapsulation portion 300. The functional area 400 may be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. In an embodiment, Figure 3 The light-emitting device included in the light-emitting apparatus may be a series light-emitting device.
[0877] [ Figure 4 Description]
[0878] Figure 4is a schematic perspective view of an electronic device 1 including a light emitting device according to an embodiment.
[0879] The electronic device 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 personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigation device, an ultra mobile PC (UMPC)), but also various products (such as a TV, a laptop computer, a monitor, a billboard, or an Internet of Things (IOT) device). The electronic device 1 may be such a product as described above or a part thereof.
[0880] In an embodiment, the electronic device 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.
[0881] For example, the electronic device 1 may be a dashboard of a vehicle, a center console of a vehicle, a central information display arranged on the dashboard of a vehicle, an interior rearview mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display arranged on the backrest of a front seat, a head-up display (HUD) installed in front of the vehicle or projected on the front windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For convenience of explanation, Figure 4 An embodiment is explained in which the electronic device 1 is a smart phone.
[0882] The electronic device 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 pixel array arranged in the display area DA.
[0883] The non-display area NDA is an area where an image is not displayed, and may surround the display area DA. A driver for providing an electrical signal or power to a display element arranged in the display area DA may be arranged in the non-display area NDA. A pad to which an electronic element or a printed circuit substrate may be electrically connected may be arranged in the non-display area NDA.
[0884] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction. In another embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In yet another embodiment, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0885] [ Figure 5 and FIG. 6A to FIG. 6C Description]
[0886] Figure 5 is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to an embodiment. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of vehicle 1000 according to an embodiment.
[0887] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to various devices for moving an object to be transported (such as a person, object, or animal) from a starting point to a destination point. Examples of the vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on an ocean or river, or an airplane flying in the air using air action, etc.
[0888] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a given direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0889] The vehicle 1000 may include a body having an interior and an exterior, and a chassis as a part other than the body in which mechanical equipment required for driving is installed. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear left and right wheels, etc.
[0890] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , an instrument panel 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0891] The side window glass 1100 and the front window glass 1200 may be divided by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0892] The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed in a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the instrument panel 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0893] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. The virtual straight line L connecting the side window glass 1100 may extend in the x-axis direction or in a direction opposite to the x-axis direction. The virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or in a direction opposite to the x-axis direction.
[0894] The front window glass 1200 may be mounted on the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0895] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In an embodiment, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be arranged on the outer side of the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be arranged on the outer side of the second side window glass 1120.
[0896] Instrument panel 1400 may be arranged in front of the steering wheel. Instrument panel 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a driving record system, an automatic shift selector indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0897] The center console 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The center console 1500 may be arranged at one side of the instrument panel 1400 .
[0898] The passenger seat instrument panel 1600 may be spaced apart from the instrument panel 1400, and the center console 1500 is disposed between the passenger seat instrument panel 1600 and the instrument panel 1400. In an embodiment, the instrument panel 1400 may be disposed to correspond to a driver's seat (not shown), and the passenger seat instrument panel 1600 may be disposed to correspond to a passenger seat (not shown). In an embodiment, the instrument panel 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0899] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged in at least one of the instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0900] The display device 2 may include an organic light-emitting display device, an inorganic light-emitting display device, or a quantum dot display device, etc. Hereinafter, as the display device 2 according to an embodiment of the present disclosure, an organic light-emitting display device including a light-emitting device according to the present disclosure will be described as an example, but various types of display devices as described herein may be used as embodiments.
[0901] refer to Fig. 6A , the display device 2 may be arranged in the center console 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information about audio settings, video settings, or vehicle settings.
[0902] refer to Figure 6B , the display device 2 may be arranged in the instrument panel 1400. When the display device 2 is arranged in the instrument panel 1400, the instrument panel 1400 may display driving information and the like through the display device 2. For example, the instrument panel 1400 may digitally implement driving information. The instrument panel 1400 may digitally display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and various warning lights or icons may be displayed through digital signals.
[0903] refer to Figure 6C , the display device 2 may be arranged in the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or may be arranged on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display an image related to the information displayed on the instrument panel 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 may display information different from the information displayed on the instrument panel 1400 and / or different from the information displayed on the center console 1500.
[0904] [Manufacturing method]
[0905] 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, etc.
[0906] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a temperature of about 100° C. to about 500° C., or at a temperature of about 100° C. to about 500° C. -8 To about 10 -3 Torr range and under vacuum at about to about The deposition rate is carried out at a range of , depending on the material to be included in the layer to be formed and the structure of the layer to be formed.
[0907] [Definition of terms]
[0908] As used herein, the term "C 3 -C 60 The term "carbocyclic group" may be a cyclic group consisting of carbon atoms as the only ring-forming atoms and having 3 to 60 carbon atoms, and as used herein, 1 -C 60 The "heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and further having at least one hetero atom as a ring-constituting atom in addition to the carbon atoms. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups 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. 1 -C 60 The number of carbon atoms forming the ring of the heterocyclic group may be 3 to 61.
[0909] As used herein, the term "cyclic group" may be C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0910] As used herein, the term "π-electron-rich C 3 -C 60 The "cyclic group" may have 3 to 60 carbon atoms and may not include a cyclic group having *-N=*' as a ring-forming portion, and the term "π-electron-deficient nitrogen-containing C 1 -C 60 The "heterocyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming portion.
[0911] In an embodiment,
[0912] C 3 -C 60The carbocyclic group may be a T1 group, or a group in which two or more T1 groups are fused to each other (e.g., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylene group, a peryl group, a pentaphenanthrenyl group, a heptalenyl group, a tetracenyl group, a phenanthrenyl group, a hexacenyl group, a pentacene group, a rubinyl group, a coronet group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, or an indenoanthryl group),
[0913] C 1 -C 60 The 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., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothioyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothioyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranoyl group, a benzonaphthothiophenyl group, a benzonaphthothioyl group, a benzofuranodibenzofuranodibenzothiophenyl group, a ... phenyl, benzothiophene and dibenzothiophene, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl quinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0914] Pi-electron-rich C 3 -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., C 3 -C 60carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothiophenyldibenzothiophenyl, etc.),
[0915] π-electron-deficient nitrogen-containing C 1 -C 60 The heterocyclic 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, yl, benzoisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0916] wherein the T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,
[0917] The T2 group can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiarolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,
[0918] The T3 group may be a furyl group, a thienyl group, a 1H-pyrrolyl group, a thiole group or a borocyclopentadienyl group, and
[0919] The T4 group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0920] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The "heterocyclic group" may each be a monovalent group or a polyvalent group fused (e.g., bonded together) to a cyclic group according to the structure of the formula using the corresponding term. For example, "phenyl" may be benzo, phenyl or phenylene, etc., which can be easily understood by ordinary technicians in the art based on the structure of the formula including "phenyl".
[0921] Unit Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 An example of a heterocyclic group is C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 An example of a heterocyclic group is C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0922] As used herein, the term "C 1 -C 60 The “alkyl group” may be a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, 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, tert-decyl, and the like. As used herein, the term “C 2-4-1” may be any of a plurality of groups. 1 -C 60 The "alkylene" may be 1 -C 60 An alkyl group is a divalent group having the same structure.
[0923] As used herein, the term "C 2 -C 60 The "alkenyl" may be 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end, and examples thereof may include vinyl, propenyl, or butenyl, etc. As used herein, the term “C 2 -C 60 "Alkenylene" can be 2 -C 60 Alkenyl groups have divalent groups of the same structure.
[0924] As used herein, the term "C 2 -C 60 "Alkynyl" may be 2 -C60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end, and examples thereof may include ethynyl and propynyl, etc. As used herein, the term “C 2 -C 60 The "alkynylene group" may be 2 -C 60 Alkynyl groups are divalent groups with the same structure.
[0925] As used herein, the term "C 1 -C 60 "Alkoxy" may be -O(A 101 )(where A 101 Can be C 1 -C 60 The monovalent group represented by an alkyl group may include a methoxy group, an ethoxy group, an isopropoxy group, and the like.
[0926] As used herein, the term "C 3 -C 10 The term "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 or bicyclo[2.2.2]octyl, and the like. As used herein, the term "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 or bicyclo[2.2.2 3 -C 10 The cycloalkylene group may be 3 -C 10 The cycloalkyl group has a divalent group of the same structure.
[0927] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein may be a monovalent cyclic group of 1 to 10 carbon atoms further including at least one hetero atom as a ring-forming atom in addition to carbon atoms, and examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothienyl, and the like. 1 -C 10 The heterocycloalkylene group may be 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.
[0928] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof are cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. 3 -C10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group of the same structure.
[0929] As used herein, the term "C 1 -C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group of 1 to 10 carbon atoms which further includes at least one heteroatom as a ring-constituting atom in addition to carbon atoms and has at least one double bond in its ring structure. 1 -C 10 Examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term “C 1 -C 10 The heterocycloalkenylene group may be 1 -C 10 The heterocycloalkenyl group has a divalent group of the same structure.
[0930] As used herein, the term "C 6 -C 60 The term "aryl" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 The "arylene group" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, and ovalenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the respective rings may be fused to each other.
[0931] As used herein, the term "C 1 -C 60 The term "heteroaryl" as used herein may be a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 The "heteroarylene group" may be a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the respective rings may be fused to each other.
[0932] The term "monovalent non-aromatic fused polycyclic group" as used herein may be a monovalent group having two or more rings fused to each other, only carbon atoms as ring atoms, and no aromaticity in its entire molecular structure (e.g., having 8 to 60 carbon atoms). Examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenoanthryl, and the like. The term "divalent non-aromatic fused polycyclic group" as used herein may be a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
[0933] The term “monovalent non-aromatic fused heteropolycyclic group” as used herein may be a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings fused to each other, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may be a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0934] As used herein, the term "C 6 -C60 "Aryloxy" may be -O(A 102 )(where A 102 Can be C 6 -C 60 aryl) and as used herein, the term "C 6 -C 60 The "arylthio" group may be -S(A 103 )(where A 103 Can be C 6 -C 60 A group represented by an aryl group.
[0935] As used herein, the term "C 7 -C 60 The "aralkyl" may be -(A 104 )(A 105 )(where A 104 Can be C 1 -C 54 Alkylene, and A 105 Can be C 6 -C 59 aryl) and as used herein, the term "C 2 -C 60 The heteroarylalkyl group may be -(A 106 )(A 107 )(where A 106 Can be C 1 -C 59 Alkylene, and A 107 Can be C 1 -C 59 A group represented by a heteroaryl group.
[0936] In the specification, the group "R 10a " can be:
[0937] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0938] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6-C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0939] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0940] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0941] In the manual, Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0942] The term "heteroatom" as used herein may be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0943] The term “transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), or gold (Au), among others.
[0944] In the specification, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, the term "tert-Bu" or "Bu t ” each refers to a tert-butyl group, and the term “OMe” refers to a methoxy group.
[0945] As used herein, the term "biphenyl" may be a "phenyl group substituted with a phenyl group". For example, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0946] The term "terphenyl" as used herein may be a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0947] Unless otherwise defined, the symbols used herein are *, *', *", *'', * 2 and* 3 Each refers to a bonding site to an adjacent atom in the corresponding formula or moiety.
[0948] 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 may be interpreted in a broader sense than the three axes in the aforementioned orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may be axes that are orthogonal to each other, or may be axes that are not orthogonal to each other in different directions.
[0949] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in detail with reference to Synthesis Examples and Examples. The phrase "using B instead of A" used in describing Synthesis Examples means using B instead of A in the same molar equivalent.
[0950] [Example]
[0951] Synthesis Example 1: Synthesis of Compound 2
[0952]
[0953] Synthesis of intermediate 2-1
[0954] 2-Bromo-3-nitro-9,10-dihydro-9,10-[1,2]benzanthracene (2 eq), 2-methylpropane-2-amine (1 eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (0.10 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (0.05eq) and sodium tert-butoxide (NaOtBu) (3eq) were dissolved in toluene, stirred at 110° C. for 24 hours (overnight), and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using dichloromethane (MC) and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane), thereby synthesizing intermediate 2-1 (yield: 77%).
[0955] Synthesis of intermediate 2-2
[0956] Intermediate 2-1 (1 eq) and tin (5 eq) were dissolved in ethanol (EtOH) and stirred. After adding hydrogen chloride (12 M), the resulting reaction mixture was stirred at 80 ° C for 6 hours and cooled to room temperature. The reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 2-2 (yield: 80%).
[0957] Synthesis of intermediate 2-3
[0958] Intermediate 2-2 (1 eq), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1 eq), Pd 2 (dba) 3 (0.05eq), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (XPhos) (0.10eq) and NaOtBu (2eq) were dissolved in toluene (0.1M), stirred at 110°C for 2 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 2-3 (yield: 75%).
[0959] Synthesis of intermediate 2-4
[0960] Intermediate 2-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% deuterium chloride (DCl) (1.5 eq) was added thereto. The resulting reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove triethyl orthoformate therefrom. The reaction mixture was subjected to three extraction processes using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: methanol), thereby synthesizing intermediate 2-4 (yield: 84%).
[0961] Synthesis of compound 2
[0962] The intermediate 2-(1 eq), potassium chloroplatinite(II) (K 2 PtCl 4 ) (1.1eq) and 2,6-lutidine (4.0eq) were dissolved in 1,2-dichlorobenzene (o-DCB) (0.05M), stirred at 120°C for 18 hours under nitrogen, and cooled to room temperature. The resulting reaction mixture was concentrated to remove 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to three extraction processes using dichloromethane and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize compound 2 (yield: 50%).
[0963] ESI-LCMS:[M]+:C 52 H 43 N 4 OPt,934.3
[0964] Synthesis Example 2: Synthesis of Compound 16
[0965]
[0966] Synthesis of intermediate 16-1
[0967] 1-Bromo-2-nitrobenzene (2 eq), aniline (1 eq), SPhos (0.10 eq), Pd 2 (dba) 3 (0.05eq) and NaOtBu (3eq) were dissolved in toluene, stirred at 110°C for 24 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 16-1 (yield: 84%).
[0968] Synthesis of intermediate 16-2
[0969] Intermediate 16-1 (1 eq) and tin (5 eq) were dissolved in EtOH and stirred. After adding hydrogen chloride (12 M), the resulting reaction mixture was stirred at 80 ° C for 6 hours and cooled to room temperature. The reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 16-2 (yield: 82%).
[0970] Synthesis of intermediate 16-3
[0971] Intermediate 16-2 (1 eq), (9s,10s)-12-(2-(3-bromophenoxy)-9H-carbazole-9-yl)-9,10-dihydro-9,10-[3,4]pyridoanthracene (1 eq), Pd 2 (dba) 3 (0.05eq), XPhos (0.10eq) and NaOtBu (2eq) were dissolved in toluene (0.1M), stirred at 110°C for 2 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 16-3 (yield: 75%).
[0972] Synthesis of intermediate 16-4
[0973] Intermediate 16-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCl (1.5 eq) was added thereto. The resulting reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove triethyl orthoformate therefrom. The reaction mixture was subjected to three extraction processes using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: methanol), thereby synthesizing intermediate 16-4 (yield: 81%).
[0974] Synthesis of compound 16
[0975] Intermediate 16-4 (1 eq), potassium chloroplatinite (II) acid (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120 ° C for 18 hours under nitrogen, and cooled to room temperature. The resulting reaction mixture was concentrated to remove 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to three extraction processes using dichloromethane and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize compound 16 (yield: 51%).
[0976] ESI-LCMS:[M]+:C 50 H 31 N 4 OPt,898.2
[0977] Synthesis Example 3: Synthesis of Compound 38
[0978]
[0979] Synthesis of Intermediate 38-1
[0980] 1-Bromo-2-nitrobenzene (2 eq), [1,1':3',1"-terphenyl]-2,2",3,3",4,4",5,5",6,6"-d 10 -2'-amine (1 eq), SPhos (0.10 eq), Pd 2 (dba) 3 (0.05eq) and NaOtBu (3eq) were dissolved in toluene, stirred at 110°C for 24 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 38-1 (yield: 82%).
[0981] Synthesis of Intermediate 38-2
[0982] Intermediate 38-1 (1 eq) and tin (5 eq) were dissolved in EtOH and stirred. After adding hydrogen chloride (12 M), the resulting reaction mixture was stirred at 80 ° C for 6 hours and cooled to room temperature. The reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 38-2 (yield: 81%).
[0983] Synthesis of intermediate 38-3
[0984] Intermediate 38-2 (1 eq), 7-(3-bromophenoxy)-5-(4-(tert-butyl)pyridin-2-yl)-8,13-dihydro-5H-8,13-[1,2]benzanthracene[2,3-c]carbazole-9,10,11,12,16,17,18,19-d 8 (1eq), Pd 2 (dba) 3(0.05eq), XPhos (0.10eq) and NaOtBu (2eq) were dissolved in toluene (0.1M), stirred at 110°C for 2 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 38-3 (yield: 73%).
[0985] Synthesis of intermediate 38-4
[0986] Intermediate 38-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCl (1.5 eq) was added thereto. The resulting reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove triethyl orthoformate therefrom. The reaction mixture was subjected to three extraction processes using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: methanol), thereby synthesizing intermediate 38-4 (yield: 77%).
[0987] Synthesis of compound 38
[0988] Intermediate 38-4 (1 eq), potassium chloroplatinite (II) acid (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120 ° C for 18 hours under nitrogen, and cooled to room temperature. The resulting reaction mixture was concentrated to remove 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to three extraction processes using dichloromethane and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize compound 38 (yield: 49%).
[0989] ESI-LCMS:[M]+:C 66 H 29 D 18 N 4 OPt, 1124.5
[0990] Synthesis Example 4: Synthesis of Compound 47
[0991]
[0992] Synthesis of Intermediate 47-1
[0993] 1-Bromo-2-nitrobenzene (2 eq), methane-d 3 -amine (1 eq), SPhos (0.10 eq), Pd 2 (dba) 3(0.05eq) and NaOtBu (3eq) were dissolved in toluene, stirred at 110°C for 24 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 47-1 (yield: 83%).
[0994] Synthesis of Intermediate 47-2
[0995] Intermediate 47-1 (1 eq) and tin (5 eq) were dissolved in EtOH and stirred. After adding hydrogen chloride (12 M), the resulting reaction mixture was stirred at 80 ° C for 6 hours and cooled to room temperature. The reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 47-2 (yield: 82%).
[0996] Synthesis of Intermediate 47-3
[0997] Intermediate 47-2 (1 eq), 2-((4-bromo-9,10-dihydro-9,10-[1,2]benzanthracene-2-yl)oxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1 eq), Pd 2 (dba) 3 (0.05eq), XPhos (0.10eq) and NaOtBu (2eq) were dissolved in toluene (0.1M), stirred at 110°C for 2 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 47-3 (yield: 74%).
[0998] Synthesis of Intermediate 47-4
[0999] Intermediate 47-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCl (1.5 eq) was added thereto. The resulting reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove triethyl orthoformate therefrom. The reaction mixture was subjected to three extraction processes using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: methanol), thereby synthesizing intermediate 47-4 (yield: 78%).
[1000] Compound 47
[1001] Intermediate 47-4 (1 eq), potassium chloroplatinite (II) acid (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120 ° C for 18 hours under nitrogen, and cooled to room temperature. The resulting reaction mixture was concentrated to remove 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to three extraction processes using dichloromethane and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize compound 47 (yield: 50%).
[1002] ESI-LCMS:[M]+:C 49 H 34 D 3 N 4 OPt,895.3
[1003] Synthesis Example 5: Synthesis of Compound 49
[1004]
[1005] Synthesis of Intermediate 49-1
[1006] 1-Bromo-2-nitrobenzene (2 eq), 9,10-dihydro-9,10-[1,2]benzanthracene-1-amine (1 eq), SPhos (0.10 eq), Pd 2 (dba) 3 (0.05eq) and NaOtBu (3eq) were dissolved in toluene, stirred at 110°C for 24 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 49-1 (yield: 79%).
[1007] Synthesis of Intermediate 49-2
[1008] Intermediate 49-1 (1 eq) and tin (5 eq) were dissolved in EtOH and stirred. After adding hydrogen chloride (12 M), the resulting reaction mixture was stirred at 80 ° C for 6 hours and cooled to room temperature. The reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 49-2 (yield: 80%).
[1009] Synthesis of Intermediate 49-3
[1010] Intermediate 49-2 (1 eq), (7r,12r)-3-(3-bromophenoxy)-5-(4-(tert-butyl)pyridin-2-yl)-7,12-dihydro-5H-7,12-[1,2]benzonaphtho[2,3-b]carbazole (1 eq), Pd 2 (dba) 3 (0.05eq), XPhos (0.10eq) and NaOtBu (2eq) were dissolved in toluene (0.1M), stirred at 110°C for 2 hours, and cooled to room temperature. The resulting reaction mixture was distilled under a reduced pressure of 8 mbar to remove the solvent therefrom, and three extraction processes were performed using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize intermediate 49-3 (yield: 72%).
[1011] Synthesis of Intermediate 49-4
[1012] Intermediate 49-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCl (1.5 eq) was added thereto. The resulting reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove triethyl orthoformate therefrom. The reaction mixture was subjected to three extraction processes using MC and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: methanol), thereby synthesizing intermediate 49-4 (yield: 75%).
[1013] Synthesis of compound 49
[1014] Intermediate 49-4 (1 eq), potassium chloroplatinite (II) acid (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120 ° C for 18 hours under nitrogen, and cooled to room temperature. The resulting reaction mixture was concentrated to remove 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to three extraction processes using dichloromethane and water. The resulting organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC: hexane) to synthesize compound 49 (yield: 50%).
[1015] ESI-LCMS:[M]+:C 68 H 47 N 4 OPt, 1130.4
[1016] MS / FAB of the compounds synthesized according to the Synthesis Examples are shown in Table 1. Synthesis methods of compounds other than the compounds synthesized in the Synthesis Examples can be easily recognized by those skilled in the art by referring to the synthesis routes and raw materials.
[1017] [Table 1]
[1018]
[1019] Evaluation Example 1
[1020] The HOMO energy level (E) of each of Compounds 2, 16, 38, 47, 49 and CE1 to CE5 was evaluated using a density functional theory (DFT) method with a Gaussian program with structure optimization at the B3LYP / 6-311G (d, p) level. HOMO ), LUMO energy level (E LUMO ), HOMO-LUMO band gap energy (E g ), T 1 Energy levels (nm) and triplet metal and ligand charge transfer states ( 3 The presence rate (%) of MLCT) was measured, and the results are shown in Table 2. 1 The energy level can be expressed using the formula Convert eV to nm (wavelength).
[1021] [Table 2]
[1022]
[1023]
[1024]
[1025] Example 1
[1026] As an anode, a 15Ω / cm 2 A glass substrate of ITO (product of Corning Incorporated) was cut into a size of 50 mm×50 mm×0.7 mm, cleaned by ultrasonic treatment with isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet light and exposed to ozone for 30 minutes, and mounted on a vacuum deposition apparatus.
[1027] 2-TNAT was vacuum deposited on the anode to form a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) was vacuum deposited on the hole injection layer to form a hole injection layer having a thickness of Thickness of hole transport layer.
[1028] Compound 2, compound DFD29, compound HTH29 and compound ETH2 are vacuum deposited on the hole transport layer to form a In this regard, the amount of compound 2 is 13 parts by weight based on 100 parts by weight of the emission layer, and the amount of compound DFD29 is 0.4 parts by weight based on 100 parts by weight of the emission layer. The weight ratio of compound HTH29 to compound ETH2 is 6.5:3.5.
[1029] Compound HBL-1 was vacuum deposited on the emission layer to form a Thickness of hole blocking layer.
[1030] CNNPTRZ and Liq were vacuum deposited on the hole blocking layer to form a In this regard, the weight ratio of CNNPTRZ to Liq is 4:6.
[1031] Yb is vacuum deposited on the electron transport layer to form a The thickness of the electron injection layer.
[1032] Mg is vacuum deposited on the electron injection layer to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[1033]
[1034]
[1035] Examples 2 to 5 and Comparative Examples 1 to 5
[1036] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compound used in forming the emission layer was changed as shown in Table 3.
[1037] Evaluation Example 1
[1038] The brightness of each of the organic light-emitting devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 5 was measured at 1,000 cd / m using a Keithley MU 236 and a luminance meter PR650. 2 The driving voltage (V), luminous efficiency (cd / A), maximum emission wavelength (nm) and lifespan (T95) under the conditions of 100 nm and 100 nm were measured, and the results are shown in Table 3. In this regard, the lifespan (T95) is a measure of the time (hr) taken until the luminance drops to 95% of the initial luminance, and the lifespan ratio represents the ratio (%) of the lifespan of each example relative to the lifespan (T95) of Comparative Example 1 which is 100.
[1039] [Table 3]
[1040]
[1041] According to Table 3, it is confirmed that the organic light-emitting devices according to Examples 1 to 5 emit blue light and have more excellent driving voltage, luminous efficiency, and lifespan than the organic light-emitting devices according to Comparative Examples 1 to 5.
[1042] According to embodiments, by using the organometallic compound represented by Formula 1, a light emitting device having reduced driving voltage, improved color purity and luminous efficiency, and increased lifespan, and high-quality electronic devices and electronic equipment including the light emitting device may be manufactured.
[1043] 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 cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described in conjunction with embodiments may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments, unless specifically indicated otherwise. Accordingly, one 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 as set forth in the claims.
Claims
1. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emitting layer; as well as An organometallic compound represented by Formula 1: Formula 1 In formula 1, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 is C, The bond between X1 and M is a coordination bond. X2 to X4 are each independently C or N, CycloCY1, CycloCY2, CycloCY 31 CY 32 and ring CY4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1 to L3 are each independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', where * and *' each indicate a bonding site to an adjacent atom, n1 to n3 are each independently an integer selected from 1 to 10, R1, R 11 , R2, R 31 , R 32 , R4, R 1a and R 1b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), a1, a2, a31, a32 and a4 are each independently an integer selected from 1 to 20, The number of R1 and R is a1 11 , R2 with quantity a2, R with quantity a31 31 , the number of R is a32 32 , R4 with quantity a4, R 1a and R 1b Two or more adjacent groups in the group are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Two adjacent groups in R1 with a number of a1; two adjacent groups in R2 with a number of a2; and a31 31 Two adjacent groups in; the number of R is a32 32 or two adjacent groups in R4 of which the number is a4 are optionally bonded to each other to form a group represented by Formula 1A, and The organometallic compound represented by Formula 1 includes at least one group represented by Formula 1A: Formula 1A Wherein in Formula 1A, X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, X 54 C(R 54 ) or N, X 55 C(R 55 ) or N, X 56 C(R 56 ) or N, X 57 C(R 57 ) or N, X 58 C(R 58 ) or N, R 51 To R 58 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), * and *' each indicate a bonding site to an adjacent atom, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; 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 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C4 substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.
2. The light emitting device according to claim 1, wherein: The emission layer includes a host and a dopant, and The dopant includes the organometallic compound.
3. The light emitting device according to claim 1, further comprising: Contains at least one nitrogen-containing C1-C 60 A second compound comprising a heterocyclic group, a third compound comprising a group represented by Formula 3, a fourth compound being a delayed fluorescence compound, or any combination thereof, wherein: The organometallic compound, the second compound, the third compound, and the fourth compound are different from each other; Formula 3 In Formula 3, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 Cyclic group or pyridyl group, X 71 is: a single bond; or a linking group comprising O, S, N, B, C, Si or any combination thereof, and * indicates a bonding site to an atom in the remaining part other than the group represented by Formula 3 of the third compound.
4. The light emitting device according to claim 3, wherein: The second compound comprises a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group or any combination thereof, and The fourth compound includes at least one cyclic group including boron and nitrogen as ring-forming atoms.
5. The light emitting device according to claim 3, wherein: The transmitting layer comprises: the organometallic compound; and The second compound, the third compound, the fourth compound, or any combination thereof, and the emission layer emits blue light. 6 . An electronic device comprising the light emitting device according to claim 1 .
7. The electronic device according to claim 6, further comprising: A thin film transistor, wherein: The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically connected to at least one of the source electrode and the drain electrode.
8. The electronic device according to claim 6, further comprising: Color filters, color conversion layers, touch screen layers, polarizing layers, or any combination thereof.
9. An electronic device comprising the light emitting device according to any one of claims 1 to 5.
10. The electronic device according to claim 9, wherein: The electronic device 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 retractable display, a laser printer, a phone, a mobile phone, a tablet computer, a phablet, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays spliced together, a theater screen, a stadium screen, a light therapy device or a sign.
11. An organometallic compound represented by Formula 1: Formula 1 In formula 1, M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 is C, The bond between X1 and M is a coordination bond. X2 to X4 are each independently C or N, CycloCY1, CycloCY2, CycloCY 31 CY 32 and ring CY4 are each independently C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group, L1 to L3 are each independently a single bond, *-C(R 1a )(R 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Al(R 1a )-*、*-Si(R 1a )(R 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', where * and *' each indicate a bonding site to an adjacent atom, n1 to n3 are each independently an integer selected from 1 to 10, R1, R 11 , R2, R 31 , R 32 , R4, R 1a and R 1b Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), a1, a2, a31, a32 and a4 are each independently an integer selected from 1 to 20, The number of R1 and R is a1 11 , R2 with quantity a2, R with quantity a31 31 , the number of R is a32 32 , R4 with quantity a4, R 1a and R 1b Two or more adjacent groups in the group are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Two adjacent groups in R1 with a number of a1; two adjacent groups in R2 with a number of a2; and a31 31 Two adjacent groups in; the number of R is a32 32 or two adjacent groups in R4 of which the number is a4 are optionally bonded to each other to form a group represented by Formula 1A, and The organometallic compound represented by Formula 1 includes at least one group represented by Formula 1A, Formula 1A Wherein in Formula 1A, X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, X 54 C(R 54 ) or N, X 55 C(R 55 ) or N, X 56 C(R 56 ) or N, X 57 C(R 57 ) or N, X 58 C(R 58 ) or N, R 51 To R 58 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced 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 C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1) or -P(═O)(Q1)(Q2), * and *' each indicate a bonding site to an adjacent atom, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; 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 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C4 substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.
12. The organometallic compound according to claim 11, wherein M is platinum, palladium or gold.
13. The organometallic compound according to claim 11, wherein: X2 and X3 are each C, X4 is N, The bond between X4 and M is a coordination bond, and The bond between X2 and M and the bond between X3 and M are each covalent bonds.
14. The organometallic compound according to claim 11, wherein: CycloCY1, CycloCY2, CycloCY 31 CY 32 and Ring CY4 are each independently phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, cyclopentadienyl, furanyl, thienyl, thirol, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothirol, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxaz ... oxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilanyl, dibenzothiasilanyl, dibenzodihydroazasilanyl, dibenzodihydrodihydrodisilacyclohexanyl, dibenzodihydrosilanyl, dibenzodioxanyl, dibenzooxathiacyclohexanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiacyclohexanyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridinyl or dibenzodihydropyrazinyl.
15. The organometallic compound according to claim 11, wherein: L1 and L3 are each a single bond, L2 is *-O-*' or *-S-*', and n2 is 1.
16. The organometallic compound according to claim 11, wherein: R1, R 11 , R2, R 31 , R 32 and R4 are each independently: Hydrogen, Deuterium, -F, C1-C 20 Alkyl or C1-C 20 Alkoxy; C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl or any combination thereof; each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) or any combination thereof; or -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted by deuterium, -F, C1-C 60 Alkyl, C1-C 60 C3-C4 substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
17. The organometallic compound according to claim 11, wherein in Formula 1, Depend on The part represented by is a part represented by one of the formulas CY1(1) to CY1(11), Depend on The portion represented by is a portion represented by one of formula CY2(1) to formula CY2(13), Depend on The portion represented by is a portion represented by one of the formulas CY31(1) to CY31(6), Depend on The portion represented by is a portion represented by one of Formula CY32(1) to Formula CY32(16), and Depend on The portion represented by is a portion represented by one of Formula CY4(1) to Formula CY4(29): Among them, in Formulas CY1(1) to CY1(11), CY2(1) to CY2(13), CY31(1) to CY31(6), CY32(1) to CY32(16) and CY4(1) to CY4(29), T 21 is B(Y 21 ), C(Y 21 )(Y 22 ), N(Y 21 ), O, S or Si(Y 21 )(Y 22 ), T 22 is C(Y 21 ), N or Si(Y 21 ), T 31 is C(Y 311 )(Y 312 ), N(Y 311 ), O, S or Si(Y 311 )(Y 312 ), T 32 is C(Y 321 )(Y 322 ), N(Y 321 ), O, S or Si(Y 321 )(Y 322 ), R 11 To R 17 Each is independently the same as defined with reference to R1 in Formula 1, R 21 To R 26 , Y 21 and Y 22 Each is independently the same as defined with reference to R2 in Formula 1, R 311 To R 314 , Y 311 and Y 312 Each independently corresponds to R in Formula 1 31 The same as limited, R 321 To R 328 , Y 321 and Y 322 Each independently corresponds to R in Formula 1 32 The same as limited, R 41 To R 47 Each is independently the same as defined with reference to R4 in Formula 1, * indicates the bonding site with M in Formula 1, *' indicates the bonding site with L1 in Formula 1, *" indicates the bonding site with L2 in Formula 1, *"' indicates the bonding site with L3 in Formula 1, * 2 indicates the bonding site to N in Formula 1, and * 3 Indicates the ring CY in formula 1 31 Or CY 32 bonding site.
18. The organometallic compound according to claim 11, wherein: X 51 C(R 51 ), X 52 C(R 52 ), X 53 C(R 53 ), X 54 C(R 54 ), X 55 C(R 55 ), X 56 C(R 56 ), X 57 C(R 57 ),and X 58 C(R 58 ).
19. The organometallic compound according to claim 11, wherein the organometallic compound is represented by Formula 1-1: Formula 1-1 In formula 1-1, M and R 11 Each is defined as Formula 1, L2 is *-O-*' or *-S-*', X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, X 14 C(R 14 ) or N, X 15 C(R 15 ) or N, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, X 23 C(R 23 ) or N, X 311 C(R 311 ) or N, X 312 C(R 312 ) or N, X 321 C(R 321 ) or N, X 322 C(R 322 ) or N, X 323 C(R 323 ) or N, X 324 C(R 324 ) or N, X 41 C(R 41 ) or N, X 42 C(R 42 ) or N, X 43 C(R 43 ) or N, X 44 C(R 44 ) or N, R 12 To R 15 Each is independently the same as defined with reference to R1 in Formula 1, R 21 To R 23 Each is independently the same as defined with reference to R2 in Formula 1, R 311 and R 312 Each independently corresponds to R in Formula 1 31 The same as limited, R 321 To R 324 Each independently corresponds to R in Formula 1 32 The same as defined, and R 41 To R 44 Each is independently the same as defined with reference to R4 in Formula 1.
20. The organometallic compound according to claim 19, wherein the organometallic compound satisfies at least one of conditions 1 to 12: Condition 1 X 12 C(R 12 ), X 13 C(R 13 ), and R 12 and R 13 bonded to each other to form the group represented by Formula 1A; Condition 2 X 13 C(R 13 ), X 14 C(R 14 ), and R 13 and R 14 bonded to each other to form the group represented by Formula 1A; Condition 3 X 14 C(R 14 ), X 15 C(R 15 ), and R 14 and R 15 bonded to each other to form the group represented by Formula 1A; Condition 4 X 21 C(R 21 ), X 22 C(R 22 ), and R 21 and R 22 bonded to each other to form the group represented by Formula 1A; Condition 5 X 22 C(R 22 ), X 23 C(R 23 ), and R 22 and R 23 bonded to each other to form the group represented by Formula 1A; Condition 6 X 311 C(R 311 ), X 312 C(R 312 ), and R 311 and R 312 bonded to each other to form the group represented by Formula 1A; Condition 7 X 321 C(R 321 ), X 322 C(R 322 ), and R 321 and R 322 bonded to each other to form the group represented by Formula 1A; Condition 8 X 322 C(R 322 ), X 323 C(R 323 ), and R 322 and R 323 bonded to each other to form the group represented by Formula 1A; Condition 9 X 323 C(R 323 ), X 324 C(R 324 ), and R 323 and R 324 bonded to each other to form the group represented by Formula 1A; Condition 10 X 41 C(R 41 ), X 42 C(R 42 ), and R 41 and R 42 bonded to each other to form the group represented by Formula 1A; Condition 11 X 42 C(R 42 ), X 43 C(R 43 ), and R 42 and R 43 bonded to each other to form the group represented by Formula 1A; Condition 12 X 43 C(R 43 ), X 44 C(R 44 ), and R 43 and R 44 are bonded to each other to form the group represented by Formula 1A.
Citation Information
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