Organic light emitting element
Patent Information
- Application Number
- CN202211376687.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-11-10
- Filing Date
- 2022-11-04
- Publication Date
- 2026-10-27
- Estimated Expiration
- 2042-11-04
AI Technical Summary
[0037]应理解,前述一般性描述和以下详细描述二者均为示例性和说明性的,并且旨在提供对如所要求保护的发明构思的进一步说明。
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Figure CN116113298B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority to Korean Patent Application No. 10-2021-0154311, filed on November 10, 2021, which is incorporated herein by reference for all purposes, as if fully set forth herein. Technical Field
[0003] The embodiments disclosed herein relate to organic light-emitting elements. Background Technology
[0004] Organic light emission generally refers to the phenomenon of converting electrical energy into light energy through organic materials. An organic light-emitting element (OLED) is a light-emitting element that utilizes the organic light emission phenomenon. The OLED typically includes an anode, a cathode, and a layer of organic material disposed therebetween.
[0005] The organic material layer may have a multilayer structure composed of different materials to improve the efficiency and stability of the organic light-emitting element, and may include a light-emitting layer (also known as an emissive material layer (EML)).
[0006] For organic light-emitting diodes (OLEDs), lifetime and efficiency are the most critical issues. Efficiency, lifetime, and driving voltage are interrelated. If efficiency is increased, the driving voltage is relatively reduced, which decreases the crystallization of organic materials during driving through Joule heating, thus leading to an increase in lifetime.
[0007] The emissive layer (EML) plays a crucial role in enhancing the luminescence characteristics and increasing the lifetime of organic light-emitting elements (OLEDs). In particular, to achieve high efficiency, the host material of the EML must possess high triplet energy levels and exhibit material stability. Summary of the Invention
[0008] Therefore, embodiments of this disclosure relate to organic light-emitting elements that substantially eliminate one or more problems caused by limitations and disadvantages in the relevant field.
[0009] For organic light-emitting elements (OLEDs) to fully exhibit their superior characteristics, the materials constituting the organic material layer should be stable and possess excellent efficiency. Because phosphorescent OLEDs have a hole mobility greater than electron mobility and a long triplet lifetime in the emitting layer, the excitons formed in the emitting layer are distributed over a wide area, potentially reducing luminescence. Therefore, the inventors of this disclosure have invented an OLED that can possess excellent efficiency or a long lifetime.
[0010] One aspect of this disclosure provides an organic light-emitting element with high efficiency or long lifespan.
[0011] Other features and aspects will be set forth in the following description and will be apparent in part from the description or may be learned by practice of the inventive concept provided herein. Other features and aspects of the inventive concept may be realized and obtained by means of structures particularly pointed out in the draft specification, or which may be derived therefrom, the claims, and the drawings.
[0012] In order to achieve these and other aspects of the inventive concept embodied and broadly described herein, the organic light-emitting element includes a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode.
[0013] The organic material layer contains compounds represented by the following chemical formula 1:
[0014] [Chemical Formula 1]
[0015]
[0016] In chemical formula 1, A is chemical formula a, B is chemical formula b, and L is one of the following: direct bond, chemical formula L-1, chemical formula L-2, and chemical formula L-3.
[0017] [Chemical formula a]
[0018]
[0019] [Chemical formula L-1]
[0020]
[0021] [Chemical formula L-2]
[0022]
[0023] [Chemical formula L-3]
[0024]
[0025] [Chemical formula b]
[0026]
[0027] In chemical formula a,
[0028] X1, X2, X3, and X4 are selected from N, S, O, and R. 16 i) If X1 is N, then X2 is selected from O and S and together with X1 forms a pentagonal ring, and X3 and X4 are R. 16 ii) If X2 is N, then X1 or X3 is selected from O and S and forms a pentagonal ring together with X2; X1, X3, and X4 that do not form a pentagonal ring are R. 16iii) If X3 is N, then X2 or X4 is selected from O and S and forms a pentagonal ring together with X3. X1, X2, and X4, which do not form a pentagonal ring, are R. 16 , and iv) if X4 is N, then X3 is selected from O and S and together with X4 forms a pentagonal ring, and X1 and X2 are R. 16 ,
[0029] R1, R2, and R3 are each independently selected from hydrogen; C1 to C 20 Alkyl; C3 to C 30 cycloalkyl; C1 to C 20 Alkyl group; C6 to C 60 Aryloxy group; C1 to C 20 Alkyl thio; C6 to C 60 Arylthio; C1 to C 20 alkylsulfonyl; C6 to C 60 Arylsulfonyl; C6 to C 60 aryl; fluorenyl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group,
[0030] R4, R5, R6, R7 and R 16 Each is independently hydrogen or C6 to C 60 Aryl group, and one of R4, R5, R6, and R7 is a direct bond connected to L.
[0031] In chemical formulas L-1 to L-3,
[0032] R8 to R in chemical formula L-1 16 R8 to R in chemical formula L-2 15 and R8 to R in chemical formula L-3 15 One of them is a direct bond connected to A of Formula 1, another is a direct bond connected to B of Formula 1, and the remainder, which are not direct bonds connected to A or B, are each independently selected from hydrogen; cyano; halogen; C1 to C2. 20 Alkyl; C3 to C 30 cycloalkyl; C1 to C 20 Alkyl group; C6 to C 60 Aryloxy group; C1 to C 20 Alkyl thio; C6 to C 60 Arylthio; C1 to C 20 alkylsulfonyl; C6 to C 60 arylsulfonyl; silyl; C6 to C 60 arylphosphine group; phosphine oxide group; C6 to C 60 aryl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group,
[0033] In chemical formula b,
[0034] Z is a direct bond or a C6 to C6 bond connected to L in chemical formula 1. 20 Aryl, R 17 and R 18 Each was independently selected from C6 to C 60 aryl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups, and
[0035] The alkyl group, the cycloalkyl group, the alkoxy group, the aryloxy group, the alkylthio group, the arylthio group, the alkylsulfonyl group, the arylsulfonyl group, the fluorenyl group, the aryl group, the heterocyclic group, the silyl group, and the arylphosphinyl group are each optionally further substituted by one or more substituents selected from the following: halogen groups; C1 to C2. 20 Alkyl; C2 to C 20 Alkenyl; C2 to C 20 Alkyne group; fluorene group; C6 to C 20 Aryl groups; and C2 to C 20 Heterocyclic group.
[0036] According to embodiments of this disclosure, organic light-emitting elements with high efficiency or long lifespan can be provided.
[0037] It should be understood that both the foregoing general description and the following detailed description are exemplary and illustrative, and are intended to provide further explanation of the inventive concept as claimed. Attached Figure Description
[0038] The accompanying drawings, included to provide a further understanding of this disclosure and incorporated into and constituting a part of this application, illustrate embodiments of the disclosure and, together with the specification, serve to illustrate the various principles of the disclosure. In the drawings:
[0039] Figure 1 and Figure 2 A view of an organic light-emitting element according to an embodiment of the present disclosure is shown schematically;
[0040] Figure 3 A view of an organic light-emitting element according to an embodiment of the present disclosure is shown schematically; and
[0041] Figure 4 A view of an organic light-emitting element according to an embodiment of the present disclosure is shown schematically. Detailed Implementation
[0042] In the following description of embodiments or implementations of this disclosure, reference will be made to accompanying drawings that illustrate specific embodiments or implementations by way of example, and in which the same reference numerals and symbols may be used to designate the same or similar components even in drawings shown differently from each other. Furthermore, in the following description of embodiments or implementations of this disclosure, descriptions of well-known functions and components incorporated herein may be omitted where such detailed descriptions would obscure the subject matter of some embodiments of this disclosure. Terms used herein, such as “comprising,” “having,” “including,” “constituting,” “made of,” and “formed by,” are generally intended to allow for the addition of additional components unless used with the term “only.” As used herein, the singular forms are intended to include the plural forms unless the context clearly indicates otherwise.
[0043] Terms such as “first,” “second,” “A,” “B,” “(A),” or “(B)” may be used herein to describe elements of this disclosure. Each of these terms is not used to define the nature, order, sequence, or number of elements, but only to distinguish the corresponding element from other elements.
[0044] When referring to the first element as "connected or coupled to," "contacting or covering," etc., as a second element, it should be interpreted as meaning that not only can the first element be "directly connected or coupled to" or "directly contacting or covering" the second element, but the third element can also be "between" the first and second elements, or the first and second elements can be "connected or coupled," "contacting or covering" each other via a fourth element. Here, the second element can be included in at least one of two or more elements that are "connected or coupled," "contacting or covering" each other.
[0045] Unless used together with the terms “directly” or “immediately”, these terms may be used to describe discontinuous or non-sequential processes or operations when using time-related terms such as “after,” “following,” “next,” “before,” etc., to describe the process or operation of an element or configuration, or the flow or steps in an operating method, processing method, or manufacturing method.
[0046] Furthermore, when referring to any size, relative size, etc., it should be assumed that the numerical value of an element or feature, or corresponding information (e.g., level, range, etc.), even without a specific description, includes tolerances or error ranges that may be caused by various factors (e.g., process parameters, internal or external influences, noise, etc.). Additionally, the term "can / may" fully encompasses all the meanings of the term "able to".
[0047] The various embodiments of this disclosure will be described in detail below with reference to the accompanying drawings.
[0048] As used herein, unless otherwise stated, the term "halogenated" or "halogen" includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), etc.
[0049] As used herein, unless otherwise stated, the term "alkyl" or "alkyl group" may mean a group having 1 to 60, 1 to 20, or 1 to 6 carbon atoms connected by single bonds and including a saturated aliphatic functional group of a straight-chain alkyl, a branched alkyl, a cycloalkyl (alicyclic group), an alkyl-substituted cycloalkyl, or a cycloalkyl-substituted alkyl.
[0050] As used herein, unless otherwise stated, the term "halogenated alkyl" or "halogenated alkyl" may mean an alkyl group that has been substituted with a halogen.
[0051] As used herein, unless otherwise stated, the terms "alkenyl" or "alkynyl" may have double or triple bonds, respectively, and may include straight-chain or branched groups and have 2 to 60, 2 to 20, or 2 to 6 carbon atoms.
[0052] As used herein, unless otherwise stated, the term "cycloalkyl" can refer to an alkyl group that forms a ring having 3 to 60, 3 to 20, or 3 to 8 carbon atoms.
[0053] As used herein, unless otherwise stated, the term "alkoxy" or "alkyloxy" refers to an alkyl group in which an oxygen group is bonded and may have 1 to 60 carbon atoms.
[0054] As used herein, unless otherwise stated, the term "alkenyloxy group" or "alkenyloxy group" refers to an alkenyl group in which an oxygen group is attached and which may have 2 to 60 carbon atoms.
[0055] As used herein, unless otherwise specified, the terms "aryl" or "arylene" can each have 6 to 60 carbon atoms, but are not limited thereto. In this disclosure, aryl or arylene can include monocyclic, cyclic aggregates, fused polycyclic systems, spirocyclic compounds, etc. For example, aryl includes, but is not limited to, phenyl, biphenyl, naphthyl, anthracene, indene, phenanthrene, triphenylene, pyrene, etc. base, Naphthyl, tetraphenyl or fluoranthracene. Naphthyl may include 1-naphthyl and 2-naphthyl, and anthracene may include 1-anthrayl, 2-anthrayl and 9-anthrayl.
[0056] In this disclosure, unless otherwise stated, the terms "fluorenyl" or "fluoreneyl" may refer to a monovalent or divalent functional group of fluorene, respectively. "Fluorenyl" or "fluoreneyl" may mean a substituted fluorenyl or a substituted fluoreneyl group. "Substituted fluorenyl" or "substituted fluoreneyl" may refer to a substituted monovalent or divalent functional group of fluorene. "Substituted fluorene" may mean that at least one of the following substituents R, R', R" and R"' is a functional group other than hydrogen. This may include cases where R and R' are bonded to each other to form a spirocyclic compound together with the carbon atoms they are bonded to.
[0057]
[0058] As used herein, the term "spirocyclic compound" has a spiro union, and the spiro union refers to the junction of two rings that share only one atom. In this case, the atom shared by the two rings can be referred to as a "spiro atom".
[0059] As used herein, the term "heterocyclic group" may include not only aromatic rings such as "heteroaryl" or "hybridoaryl," but also non-aromatic rings, and unless otherwise stated, refers to a ring having 2 to 50 carbon atoms and one or more heteroatoms, but is not limited thereto. As used herein, unless otherwise stated, the term "heteroatom" refers to N, O, S, P, or Si, and a heterocyclic group may mean a monocyclic group, a ring aggregate, a fused polycyclic system, or a spirocyclic compound containing a heteroatom.
[0060] "Heterocyclic group" can include a ring of SO2 that replaces carbon to form a ring. For example, "heterocyclic group" can include the following compounds.
[0061]
[0062] As used herein, the term "ring" can include monocyclic and polycyclic rings, can include hydrocarbon rings and heterocycles containing at least one heteroatom, or can include aromatic and non-aromatic rings.
[0063] As used herein, the term "polycyclic" can include cyclic aggregates, fused polycyclic systems and spirocyclic compounds, can include aromatic compounds and non-aromatic compounds, or can include heterocycles containing at least one heteroatom and hydrocarbon rings.
[0064] As used herein, the term "aliphatic ring group" refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and may include monocyclic, cyclic aggregates, fused polycyclic systems and spirocyclic compounds, and unless otherwise stated, may mean a ring having 3 to 60 carbon atoms. For example, the fusion of benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, also corresponds to an aliphatic ring.
[0065] As used herein, the term "alkylsilyl" can refer to a monovalent substituent in which three alkyl groups are bonded to a Si atom.
[0066] As used herein, the term "arylsilyl" can refer to a monovalent substituent in which three aryl groups are bonded to Si atoms.
[0067] As used herein, the term "alkylarylsilyl" can refer to a monovalent substituent in which one alkyl group and two aryl groups are bonded to a Si atom, or in which two alkyl groups and one aryl group are bonded to a Si atom.
[0068] As used herein, the term "cyclic assembly" refers to a system of two or more rings (single-ring or fused-ring systems) directly connected to each other by single or double bonds. For example, in the case of aryl groups, biphenyl or terphenyl groups can be cyclic assemblies, but are not limited thereto.
[0069] As used herein, the term "fused polycyclic system" refers to a type of fused ring that shares at least two atoms. For example, in the case of aryl, naphthyl, phenanthryl, or fluorenyl can be fused polycyclic systems, but are not limited to these.
[0070] When prefixes are named sequentially, they can indicate that substituents are listed in the order specified first. For example, arylalkoxy can indicate an aryl-substituted alkoxy group, alkoxycarbonyl can indicate an alkoxy-substituted carbonyl group, and arylcarbonylalkenyl can indicate an arylcarbonyl-substituted alkenyl group. An arylcarbonyl group can be an aryl-substituted carbonyl group.
[0071] Unless otherwise expressly stated, in the terms “substituted” or “unsubstituted” as used herein, “substituted” may mean substituted with one or more substituents selected from: halogen; amino; nitrile; nitro; C1 to C2. 20 Alkyl; C1 to C 20 Alkoxy; C1 to C 20 Alkylamine group; C1 to C 20 Alkylthiophene group; C6 to C 20 Arylthiophene group; C2 to C 20 Alkenyl; C2 to C 20 alkynyl group; C3 to C 20 cycloalkyl; C6 to C 20 Aryl; C8 to C 20 arylalyl; silyl; boronyl; germanyl; and C2 to C3 groups comprising at least one heteroatom selected from O, N, S, Si, and P. 20 Heterocyclic groups, but not limited to the substituents described above.
[0072] In this disclosure, the “functional group names” corresponding to aryl, arylene, and heterocyclic groups, provided as examples of symbols and their substituents, can be described as “names of functional groups reflecting valence states”, but can also be described as “names of the parent compound.” For example, in the case of “phenanthrene” for a type of aryl, its name can be specified as “phenanthrene (group)” as a definite group, such as a monovalent group, and “arypheneyl (group)” as a divalent group, but can also be specified as “phenanthrene” as the name of the parent compound, regardless of valence state. Similarly, pyrimidine can be specified as “pyrimidine” regardless of valence state, or can be specified as a monovalent pyrimidinyl (group) and a divalent pyrimidinyl (group). Therefore, in this disclosure, when the type of substituent is specified by the name of the parent compound, it can mean an n-valent “group” formed by the separation of hydrogen atoms bonded to carbon atoms and / or heteroatoms of the parent compound.
[0073] Furthermore, unless explicitly stated otherwise, the formulas used in this disclosure may be applied in the same manner as those defined by the substituents in the following formulas.
[0074]
[0075] When a is 0, it means that the substituent R 1 The absence of hydrogen atoms means that the hydrogen atoms are bonded to each of the carbon atoms forming the benzene ring. In this case, a chemical formula or chemical compound can be specified without indicating the hydrogen atoms bonded to the carbon atoms. Furthermore, when a is 1, a substituent R... 1 It bonds to any of the carbon atoms forming the benzene ring, and when a is 2 or 3, it can bond as follows. When a is an integer from 4 to 6, it bonds to the carbon atoms of the benzene ring in a similar manner, and when a is an integer of 2 or greater, R 1 They can be the same or different.
[0076]
[0077] In this disclosure, when substituents are bonded to each other to form a ring, it can mean that adjacent groups are bonded to each other to form a monocyclic or fused polycyclic ring, and the monocyclic or fused polycyclic ring can include a heterocyclic ring containing at least one heteroatom and a hydrocarbon ring, and can include aromatic rings and non-aromatic rings.
[0078] In this disclosure, an organic light-emitting element may mean an assembly between an anode and a cathode, or an organic light-emitting diode comprising an anode, a cathode, and an assembly positioned therebetween.
[0079] In some cases, in this disclosure, an organic light-emitting element may mean an organic light-emitting diode and a panel including therethe, or an electronic device including said panel and circuitry. The electronic device may include, for example, a display device, a light-emitting device, a solar cell, a portable or mobile terminal (e.g., a smartphone, tablet computer, PDA, electronic dictionary, or PMP), a navigation terminal, a gaming device, various TVs, and various computer monitors, but is not limited thereto, and may include any type of device including said components.
[0080] Figure 1 A view of an organic light-emitting element according to an embodiment of the present disclosure is shown schematically.
[0081] An organic light-emitting element 100 according to an embodiment of the present disclosure includes a first electrode 110, a second electrode 120, and an organic material layer 130 positioned between the first electrode 110 and the second electrode 120.
[0082] For example, the first electrode 110 can be an anode electrode, and the second electrode 120 can be a cathode electrode.
[0083] For example, the first electrode 110 can be a transparent electrode, and the second electrode 120 can be a reflective electrode. In another example, the first electrode 110 can be a reflective electrode, and the second electrode 120 can be a transparent electrode.
[0084] The organic material layer 130 is a layer located between the first electrode 110 and the second electrode 120 and contains organic material, and may be composed of a plurality of layers.
[0085] The organic material layer 130 contains a compound represented by chemical formula 1. The compound represented by chemical formula 1 is described in detail below.
[0086] The organic material layer 130 may include a light-emitting layer. The organic material layer 130 may also include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
[0087] For example, the organic material layer 130 may include a hole injection layer positioned on the first electrode 110, a hole transport layer positioned on the hole injection layer, a light-emitting layer positioned on the hole transport layer, an electron transport layer positioned on the light-emitting layer, and an electron injection layer positioned on the electron transport layer. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode.
[0088] The light-emitting layer is a layer in which light is emitted when holes and electrons transferred from the first electrode 110 and the second electrode 120 meet, and may contain, for example, a host material and dopants.
[0089] The luminescent layer may contain the compound represented by Chemical Formula 1. The compound represented by Chemical Formula 1 may be the host compound of the luminescent layer. For example, the compound represented by Chemical Formula 1 may be the phosphorescent host compound of the luminescent layer.
[0090] The luminescent layer may also contain a host compound different from the compound represented by Chemical Formula 1 described above. There are no particular limitations on the type of host compound that may be additionally included, and known host compounds may be used.
[0091] Figure 2 A view of an organic light-emitting element according to an embodiment of the present disclosure is shown schematically.
[0092] An organic light-emitting element 200 according to an embodiment of the present disclosure includes a first electrode 110, a second electrode 120, and an organic material layer 130 positioned between the first electrode 110 and the second electrode 120.
[0093] For example, the first electrode 110 can be an anode electrode, and the second electrode 120 can be a cathode electrode.
[0094] For example, the first electrode 110 can be a transparent electrode, and the second electrode 120 can be a reflective electrode. In another example, the first electrode 110 can be a reflective electrode, and the second electrode 120 can be a transparent electrode.
[0095] The organic material layer 130 is a layer located between the first electrode 110 and the second electrode 120 and contains organic material, and may be composed of a plurality of layers.
[0096] The organic material layer 130 contains a compound represented by chemical formula 1. The compound represented by chemical formula 1 is described in detail below.
[0097] The organic material layer 130 may include a hole injection layer 231 positioned on the first electrode 110, a hole transport layer 232 positioned on the hole injection layer 231, a light-emitting layer 233 positioned on the hole transport layer 232, an electron transport layer 234 positioned on the light-emitting layer 233, and an electron injection layer 235 positioned on the electron transport layer 234. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode. The organic material layer 130 may not include... Figure 2 Some of the layers shown may include additional functional layers, such as light-emitting auxiliary layers.
[0098] The light-emitting layer 233 may contain the compound represented by chemical formula 1.
[0099] The luminescent layer 233 may comprise a host compound 2331 and a dopant 2332. The host compound 2331 may be the compound represented by Chemical Formula 1 described above. The host compound 2331 may also comprise another compound different from the compound represented by Chemical Formula 1 described above. For example, the host compound 2331 may comprise a compound represented by Chemical Formula 1 and a biscarbazole-based compound.
[0100] There are no particular restrictions on the type of dopant 2332. For example, dopant 2332 can be a green phosphorescent dopant. For example, dopant 2332 can be a metal complex, such as a metal complex of iridium.
[0101] Figure 3 A view of an organic light-emitting element according to an embodiment of the present disclosure is shown for illustrative purposes.
[0102] Reference Figure 3 The organic material layer 130 includes a first stack 331, a second stack 332, and a charge generation layer 333 positioned between the first stack 331 and the second stack 332.
[0103] The organic light-emitting element 300 can be a series-connected organic light-emitting element comprising a plurality of stacked bodies, each of which includes a light-emitting layer. The plurality of light-emitting layers can be formed of the same material or different materials. The first stack 331 may include a first light-emitting layer 3313. The second stack 332 may include a second light-emitting layer 3323. The first light-emitting layer 3313 and the second light-emitting layer 3323 can be formed of the same material or different materials.
[0104] The first stack 331 may include a first light-emitting layer 3313. The first light-emitting layer 3313 may include, for example, a first host compound 33131 and a first dopant 33132.
[0105] The first stack 331 may further include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
[0106] For example, the first stack 331 may include a first hole injection layer 3311 positioned on the first electrode 110, a first hole transport layer 3312 positioned on the first hole injection layer 3311, a first light-emitting layer 3313 positioned on the first hole transport layer 3312, a first electron transport layer 3314 positioned on the first light-emitting layer 3313, and a first electron injection layer 3315 positioned on the first electron transport layer 3314. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode. The first stack 331 may not include... Figure 3 Some of the layers shown may include additional functional layers, such as light-emitting auxiliary layers.
[0107] The first light-emitting layer 3313 may contain the compound represented by chemical formula 1.
[0108] The first luminescent layer 3313 may comprise a first host compound 33131 and a first dopant 33132. The first host compound 33131 may be the compound represented by Chemical Formula 1 described above. The first host compound 33131 may also comprise another compound different from the compound represented by Chemical Formula 1 described above. For example, the first host compound 33131 may comprise the compound represented by Chemical Formula 1 and a biscarbazole-based compound.
[0109] There are no particular restrictions on the type of the first dopant 33132. For example, the first dopant 33132 can be a green phosphorescent dopant. For example, the first dopant 33132 can be a metal complex, such as a metal complex of iridium.
[0110] The second stack 332 may include a second light-emitting layer 3323. The second light-emitting layer 3323 may contain, for example, a second host compound and a second dopant.
[0111] The second stack 332 may further include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
[0112] For example, the second stack 332 may include a second hole injection layer 3321 positioned on the first electrode 110, a second hole transport layer 3322 positioned on the second hole injection layer 3321, a second light-emitting layer 3323 positioned on the second hole transport layer 3322, a second electron transport layer 3324 positioned on the second light-emitting layer 3323, and a second electron injection layer 3325 positioned on the second electron transport layer 3324. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode. The second stack 332 may not include... Figure 3 Some of the layers shown may include additional functional layers, such as light-emitting auxiliary layers.
[0113] The second light-emitting layer 3323 can emit light of the same or different color as the light emitted by the first light-emitting layer 3313. In this disclosure, the light-emitting layer emitting light of the same color means that the light-emitting layer not only emits light of the same color coordinates, but also emits light of colors similar to each other that are classified as pixels of the same color in the technical field of this disclosure.
[0114] The second luminescent layer 3323 may contain a second host compound and a second dopant.
[0115] There are no particular restrictions on the type of the second host compound. The second host compound may be the same as or different from the first host compound 33131.
[0116] There are no particular restrictions on the type of the second dopant. The second dopant may be the same as or different from the first dopant 33132.
[0117] In embodiments of this disclosure, the second light-emitting layer 3323 may emit light of the same color as that emitted by the first light-emitting layer 3313. In the above embodiments, the second light-emitting layer 3323 may comprise the compound represented by Chemical Formula 1.
[0118] In embodiments where the first light-emitting layer 3313 and the second light-emitting layer 3323 emit light of the same color, the second host compound may be the compound represented by Chemical Formula 1 described above. The second host compound may also include another compound different from the compound represented by Chemical Formula 1. For example, the second host compound may include the compound represented by Chemical Formula 1 and a biscarbazole-based compound.
[0119] In embodiments where the first light-emitting layer 3313 and the second light-emitting layer 3323 emit light of the same color, the type of the second dopant is not particularly limited and can be the same as the first dopant 33132. For example, the second dopant can be a green phosphorescent dopant. For example, the second dopant can be a metal complex, such as a metal complex of iridium.
[0120] The charge generation layer 333 can be formed between a plurality of light-emitting layers to facilitate charge distribution, thereby improving the current efficiency of the light-emitting layers. Therefore, the charge generation layer 333 is positioned between a first stack 331 including a first light-emitting layer 3313 and a second stack 332 including a second light-emitting layer 3323.
[0121] The charge generation layer 333 may include a p-type charge generation layer and an n-type charge generation layer to facilitate charge distribution. When the first electrode 110 is an anode electrode and the second electrode 120 is a cathode electrode, the p-type charge generation layer may be positioned on one side of the cathode electrode, and the n-type charge generation layer may be positioned on one side of the anode electrode.
[0122] Although Figure 3 A series-connected organic light-emitting element comprising two stacked bodies is shown, but embodiments of this disclosure are not limited thereto, and may include series-connected organic light-emitting elements comprising two or more stacked bodies. When the organic light-emitting element 300 includes additional stacked bodies, an additional charge-generating layer may be positioned between the additional stacked bodies and the adjacent first stacked body 331 or second stacked body 332.
[0123] Figure 4A view of an organic light-emitting element according to an embodiment of the present disclosure is shown schematically.
[0124] Reference Figure 4 The organic material layer 130 includes a first stack 431, a second stack 432, a third stack 433, a first charge-generating layer 434 positioned between the first stack 431 and the second stack 432, and a second charge-generating layer 435 positioned between the first stack 431 and the third stack 433. Figure 4 In the embodiment shown, the first stack 431 is positioned between the second stack 432 and the third stack 433, but embodiments of the present disclosure that include three stacks are not limited to this structure, and the positions of the first stack 431, the second stack 432 and the third stack 433 may be interchanged.
[0125] The organic light-emitting element 400 can be a series-connected organic light-emitting element comprising a plurality of stacked bodies, each of which includes a light-emitting layer. The plurality of light-emitting layers can be formed of the same material or different materials.
[0126] The first stack 431 may include a first light-emitting layer 4313. The first light-emitting layer 4313 may include, for example, a first host compound 43131 and a first dopant 43132.
[0127] The first stack 431 may further include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
[0128] For example, the first stack 431 may include a first hole injection layer 4311 positioned on the first electrode 110, a first hole transport layer 4312 positioned on the first hole injection layer 4311, a first light-emitting layer 4313 positioned on the first hole transport layer 4312, a first electron transport layer 4314 positioned on the first light-emitting layer 4313, and a first electron injection layer 4315 positioned on the first electron transport layer 4314. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode. The first stack 431 may not include... Figure 4 Some of the layers shown may include additional functional layers, such as light-emitting auxiliary layers.
[0129] The first luminescent layer 4313 may contain the compound represented by chemical formula 1.
[0130] The first luminescent layer 4313 may comprise a first host compound 43131 and a first dopant 43132. The first host compound 43131 may be the compound represented by Chemical Formula 1 described above. The first host compound 43131 may also comprise another compound different from the compound represented by Chemical Formula 1 described above. For example, the first host compound 43131 may comprise the compound represented by Chemical Formula 1 and a biscarbazole-based compound.
[0131] There are no particular restrictions on the type of the first dopant 43132. For example, the first dopant 43132 can be a green phosphorescent dopant. For example, the first dopant 43132 can be a metal complex, such as a metal complex of iridium.
[0132] The second stack 432 may include a second light-emitting layer 4323. The second light-emitting layer 4323 may include, for example, a second host compound and a second dopant.
[0133] The second stack 432 may further include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
[0134] For example, the second stack 432 may include a second hole injection layer 4321 positioned on the first electrode 110, a second hole transport layer 4322 positioned on the second hole injection layer 4321, a second light-emitting layer 4323 positioned on the second hole transport layer 4322, a second electron transport layer 4324 positioned on the second light-emitting layer 4323, and a second electron injection layer 4325 positioned on the second electron transport layer 4324. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode. The second stack 432 may not include... Figure 4 Some of the layers shown may include additional functional layers, such as light-emitting auxiliary layers.
[0135] The second light-emitting layer 4323 can emit light of the same color or a different color as the light emitted by the first light-emitting layer 4313.
[0136] The second luminescent layer 4323 may contain a second host compound and a second dopant.
[0137] There are no particular restrictions on the type of the second host compound. The second host compound may be the same as or different from the first host compound 43131.
[0138] There are no particular restrictions on the type of the second dopant. The second dopant may be the same as or different from the first dopant 43132.
[0139] In embodiments of this disclosure, the second light-emitting layer 4323 may emit light of the same color as that emitted by the first light-emitting layer 4313. In the above embodiments, the second light-emitting layer 4323 may comprise the compound represented by Chemical Formula 1.
[0140] In embodiments where the first light-emitting layer 4313 and the second light-emitting layer 4323 emit light of the same color, the second host compound may be the compound represented by Chemical Formula 1 described above. The second host compound may also include another compound different from the compound represented by Chemical Formula 1. For example, the second host compound may include the compound represented by Chemical Formula 1 and a biscarbazole-based compound.
[0141] In embodiments where the first light-emitting layer 4313 and the second light-emitting layer 4323 emit light of the same color, the type of the second dopant is not particularly limited and can be the same as the first dopant 43132. For example, the second dopant can be a green phosphorescent dopant. For example, the second dopant can be a metal complex, such as a metal complex of iridium.
[0142] The third stack 433 may include a third light-emitting layer 4333. The third light-emitting layer 4333 may contain, for example, a third host compound and a third dopant.
[0143] The third stack 433 may also include at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
[0144] For example, the third stack 433 may include a third hole injection layer 4331 positioned on the first electrode 110, a third hole transport layer 4332 positioned on the third hole injection layer 4331, a third light-emitting layer 4333 positioned on the third hole transport layer 4332, a third electron transport layer 4334 positioned on the third light-emitting layer 4333, and a third electron injection layer 4335 positioned on the third electron transport layer 4334. In such an example, the first electrode 110 may be an anode electrode, and the second electrode 120 may be a cathode electrode. The third stack 433 may not include... Figure 4 Some of the layers shown may include additional functional layers, such as light-emitting auxiliary layers.
[0145] The third light-emitting layer 4333 can emit light of the same color or a different color as the light emitted by the first light-emitting layer 4313.
[0146] The third luminescent layer 4333 may contain a third host compound and a third dopant.
[0147] There are no particular restrictions on the type of the third subject compound. The third subject compound may be the same as or different from the first subject compound 43131.
[0148] There are no particular restrictions on the type of the third dopant. The third dopant can be the same as or different from the first dopant 43132.
[0149] In embodiments of this disclosure, the third light-emitting layer 4333 may emit light of the same color as that emitted by the first light-emitting layer 4313. In the above embodiments, the third light-emitting layer 4333 may comprise the compound represented by Chemical Formula 1.
[0150] In embodiments where the first light-emitting layer 4313 and the third light-emitting layer 4333 emit light of the same color, the third host compound may be the compound represented by Chemical Formula 1 described above. The third host compound may also include another compound different from the compound represented by Chemical Formula 1 described above. For example, the third host compound may include the compound represented by Chemical Formula 1 and a biscarbazole-based compound.
[0151] In embodiments where the first emitting layer 4313 and the third emitting layer 4333 emit light of the same color, the type of the third dopant is not particularly limited and can be the same as the first dopant 43132. For example, the third dopant can be a green phosphorescent dopant. For example, the third dopant can be a metal complex, such as a metal complex of iridium.
[0152] The first main compound 43131, the second main compound, and the third main compound may be the same as or different from each other. One or more of the first main compound 43131, the second main compound, and the third main compound may be the compound represented by Chemical Formula 1 described above. Therefore, one of the first main compound 43131, the second main compound, and the third main compound may include the compound represented by Chemical Formula 1 described above. Two of the first main compound 43131, the second main compound, and the third main compound may include the compound represented by Chemical Formula 1 described above. All of the first main compound 43131, the second main compound, and the third main compound may include the compound represented by Chemical Formula 1 described above. When two or more light-emitting layers containing a main compound representing a compound of Chemical Formula 1 are present, the two or more light-emitting layers may emit light of the same color.
[0153] The first dopant 33132, the second dopant, and the third dopant can be the same as or different from each other.
[0154] Since the first stack 431, the second stack 432, and the third stack 433 are configured as described above, holes and electrons transferred from the first electrode 110 and the second electrode 120 meet at the first light-emitting layer 4313, the second light-emitting layer 4323, and the third light-emitting layer 4333, thereby emitting light.
[0155] The first charge generation layer 434 and the second charge generation layer 435 can be formed between a plurality of light-emitting layers to smoothly distribute charge, thereby improving the current efficiency of the light-emitting layers. Therefore, the first charge generation layer 434 can be positioned between a first stack 431 including a first light-emitting layer 4313 and a second stack 432 including a second light-emitting layer 4323, and the second charge generation layer 435 can be positioned between the first stack 431 including the first light-emitting layer 4313 and a third stack 433 including a third light-emitting layer 4333.
[0156] The first charge generation layer 434 and the second charge generation layer 435 may include a p-type charge generation layer and an n-type charge generation layer to smoothly distribute the charge. When the first electrode 110 is an anode electrode and the second electrode 120 is a cathode electrode, the p-type charge generation layer may be positioned on one side of the cathode electrode, and the n-type charge generation layer may be positioned on one side of the anode electrode.
[0157] The first charge generating layer 434 and the second charge generating layer 435 may be the same as or different from each other. The first charge generating layer 434 and the second charge generating layer 435 may be formed of the same material or different materials.
[0158] The following describes the compound represented by chemical formula 1.
[0159] The following describes the compound represented by chemical formula 1.
[0160] The compounds represented by the above chemical formula 1 can be represented by the following chemical formula 1.
[0161] [Chemical Formula 1]
[0162]
[0163] In chemical formula 1, A is chemical formula a, B is chemical formula b, and L is a direct bond, chemical formula L-1, chemical formula L-2, and chemical formula L-3.
[0164] [Chemical formula a]
[0165]
[0166] In chemical formula a, X1, X2, X3, and X4 are selected from N, S, O, and R. 16 i) If X1 is N, then X2 is selected from O and S and together with X1 forms a pentagonal ring, and X3 and X4 are R. 16 ii) If X2 is N, then X1 or X3 is selected from O and S and forms a pentagonal ring together with X2; X1, X3, and X4 that do not form a pentagonal ring are R. 16iii) If X3 is N, then X2 or X4 is selected from O and S and forms a pentagonal ring together with X3. X1, X2, and X4, which do not form a pentagonal ring, are R. 16 , and iv) if X4 is N, then X3 is selected from O and S and together with X4 forms a pentagonal ring, and X1 and X2 are R. 16 .
[0167] R1, R2, and R3 are each independently selected from hydrogen; C1 to C 20 Alkyl; C3 to C 30 Cycloalkyl; alkoxy; aryloxy; alkylthio; arylthio; alkylsulfonyl; arylsulfonyl; C6 to C 60 aryl; fluorenyl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group.
[0168] When one or more of R1, R2, and R3 are aryl groups, each of the aryl groups can be independently C6 to C6. 30 Aryl, C6 to C 20 Aryl, or C6 to C 12 Aryl.
[0169] When one or more of R1, R2, and R3 are heterocyclic groups, each of the heterocyclic groups can be independently C2 to C3. 30 Heterocyclic groups, C2 to C 20 Heterocyclic groups, or C2 to C 12 Heterocyclic group.
[0170] R4, R5, R6, R7 and R 16 Each is independently hydrogen or C6 to C 60 Aryl group, and one of R4, R5, R6 and R7 is a direct bond connected to L.
[0171] [Chemical formula L-1]
[0172]
[0173] [Chemical formula L-2]
[0174]
[0175] [Chemical formula L-3]
[0176]
[0177] R8 to R in chemical formula L-1 16 R8 to R in chemical formula L-2 15 and R8 to R in chemical formula L-3 15One of them is a direct bond connected to A of Formula 1, another is a direct bond connected to B of Formula 1, and the remainder, which are not direct bonds connected to A or B, are each independently selected from hydrogen; cyano; halogen; C1 to C2. 20 Alkyl; C3 to C 30 Cycloalkyl; alkoxy; aryloxy; alkylthio; arylthio; alkylsulfonyl; arylsulfonyl; silyl; arylphosphinyl; phosphine oxide group; C6 to C 60 aryl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group.
[0178] [Chemical formula b]
[0179]
[0180] In chemical formula b, Z is a direct bond connected to L in chemical formula 1.
[0181] R 17 and R 18 Each was independently selected from C6 to C 60 aryl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group.
[0182] The alkyl, cycloalkyl, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, fluorenyl, aryl, heterocyclic, silyl, and arylphosphinyl groups are each optionally further substituted by one or more substituents selected from the following: halogen groups; C1 to C2. 20 Alkyl; C2 to C 20 Alkenyl; C2 to C 20 Alkyne group; fluorene group; C6 to C 20 Aryl groups; and C2 to C 20 Heterocyclic group.
[0183] Chemical formula a can be represented by one of chemical formulas a1, a2, and a3.
[0184] [Chemical formula a1]
[0185]
[0186] [Chemical formula a2]
[0187]
[0188] [Chemical formula a3]
[0189]
[0190] In chemical formula a1, X1 and X2 are N, S or O, and if one is N, the other is S or O, and R1, R4, R5, R6 and R7 are the same as those defined in chemical formula 1.
[0191] In chemical formula a2, X2 and X3 are N, S or O, and if one is N, the other is S or O, and R2, R4, R5, R6 and R7 are the same as those defined in chemical formula 1.
[0192] In chemical formula a3, X3 and X4 are N, S or O, and if one is N, the other is S or O, and R3, R4, R5, R6 and R7 are the same as those defined in chemical formula 1.
[0193] One or more of the hydrogen atoms contained in the compound represented by chemical formula 1 may be substituted with deuterium or tritium.
[0194] The compound represented by chemical formula 1 can be one or more of the following compounds.
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225]
[0226]
[0227]
[0228]
[0229]
[0230]
[0231] One or more of the hydrogen atoms contained in H1 to PH120 may be substituted with deuterium or tritium.
[0232] The above embodiments are merely examples, and those skilled in the art will understand that various changes can be made without departing from the scope of this disclosure. Therefore, the embodiments described herein are provided for illustrative purposes but do not limit the scope of this disclosure, and it should be understood that the scope of this disclosure is not limited by the described embodiments. The scope of this disclosure should be interpreted by the appended claims, and all technical spirit within its equivalents should be interpreted as falling within the scope of this disclosure.
[0233] Examples of manufacturing an organic light-emitting element according to an embodiment of the present disclosure are described in detail below with reference to the embodiments of the present disclosure, but the embodiments of the present disclosure are not limited to the following embodiments.
[0234] Examples of compound preparation
[0235] The compound represented by chemical formula 1 can be prepared by synthesizing the final compound according to the synthetic method described below.
[0236]
[0237] In the synthesis method, R1, R 16 and R 17 The same as those defined in the descriptions associated with chemical formula 1. L1 is one of the following: direct bond, chemical formula L-1, chemical formula L-2, and chemical formula L-3.
[0238] Synthesis of intermediate D
[0239] Intermediate C (0.1 equivalents), intermediate A (or intermediate B, 2 equivalents), diisopropylethylamine (2.5 equivalents), 4MK2CO3 aqueous solution, and dichloromethane were placed in a round-bottom flask and stirred while the temperature was lowered to 0°C. 50% deoxyfluoride reagent (2 equivalents) in THF diluted with a small amount of MC was slowly added dropwise to the solution. After the addition was complete, the solution was stirred at 0°C for 2 hours. After the reaction was completed by adding 100 mL of saturated sodium bicarbonate aqueous solution, the solution was heated to room temperature. After separating the reaction solution into layers to recover the organic layer, the organic layer was dried with MgSO4 and concentrated under reduced pressure. The concentrated crude material was subjected to column chromatography to obtain the compound in 68% yield.
[0240] Synthesis of intermediate E
[0241] Intermediate D (1 equivalent), bis(pinacolyl)diboron (1.5 equivalent), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.02 equivalent), KOAc (potassium acetate) (2 equivalent), and 1,4-diphenylacetic acid as solvent were used. The alkane was placed in a round-bottom flask, heated, and stirred under reflux for 12 hours. After the reaction was complete, the reaction solution was cooled to room temperature and then filtered using diatomaceous earth. The filtrate was concentrated under reduced pressure and then recrystallized using dichloromethane to obtain the compound in 80% yield.
[0242] Synthesis of intermediate F
[0243] Methyl 5-bromo-iodobenzoate (1 equivalent), intermediate E (1.1 equivalent), tetrakis(triphenylphosphine)palladium (0) (0.02 equivalent), and 4M K₂CO₃ (potassium carbonate) were placed in a round-bottom flask, and toluene and EtOH were added as solvents. The mixture was stirred under reflux for 12 hours. After the reaction was complete, the reaction solution was filtered to obtain the crude product. The filtered crude material was subjected to column chromatography with dichloromethane / hexane to obtain the compound in 71% yield.
[0244] Synthesis of intermediate G
[0245] Intermediate F (1 equivalent) and 150 mL of anhydrous THF were placed in a round-bottom flask and stirred under a nitrogen atmosphere. Methylmagnesium bromide (2.4 equivalents) diluted with a small amount of anhydrous THF was slowly added dropwise to the solution, followed by stirring for 6 hours. After the reaction was complete, 10% NH4Cl aqueous solution was added to the reaction solution and stirred for 1 hour. The solution was then separated into layers by EA to recover the organic layer, which was then concentrated under reduced pressure to obtain the compound in 70% yield.
[0246] Synthesis of intermediate H
[0247] Intermediate G (1 equivalent) and hydrochloric acid (1.5 equivalent) were placed in a round-bottom flask, acetic acid was added as a solvent, and the mixture was heated and stirred under reflux for 2 hours. After the reaction was complete, the reaction solution was poured into distilled water, which precipitated crystals. The precipitate was filtered. The filtrate was dissolved in MC and dried over MgSO4, and then reprecipitated with MC and ethanol to obtain the compound in 83% yield.
[0248] Synthesis of the final compound
[0249] Intermediate H (1 equivalent), intermediate J (1.2 equivalent), tetrakis(triphenylphosphine)palladium (0) (0.02 equivalent), and 4MK₂CO₃ (potassium carbonate, 2 equivalent) were placed in a round-bottom flask, and toluene and EtOH (ethanol) were added. The mixture was then stirred under reflux for 12 hours. After the reaction was complete, the reaction solution was filtered to obtain the crude product. The filtered crude material was subjected to column chromatography to obtain the compound in 69% yield.
[0250] Manufacturing evaluation of organic light-emitting elements
[0251] Comparative Example 1
[0252] An organic light-emitting element having a single structure as shown in Table 1 below is fabricated by forming an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode on a substrate. All characteristics of the organic light-emitting element fabricated in this disclosure are evaluated at room temperature using a constant current source and a photometer.
[0253] [Table 1]
[0254] anode ITO (Indium Tin Oxide) Hole injection layer HI1 Hole transport layer HT1 Emissive layer EM1, EM2, EM3 Electron transport layer ET1 Electron injection layer LiF cathode Al
[0255] The compounds used in the comparative examples are as follows.
[0256]
[0257]
[0258] <Implementation Plan 1 to 54>
[0259] The organic light-emitting element was manufactured in the same manner as in Comparative Example 1, except that the material shown in Table 2 below was used instead of the light-emitting layer EM2.
[0260] [Table 2]
[0261]
[0262]
[0263]
[0264] Referring to Table 2, it can be seen that the organic light-emitting element according to the embodiments of this disclosure has better efficiency or lifetime than the organic light-emitting element of the comparative example.
[0265] In Comparative Example 1, EM2 was used as the host compound for the luminescent layer. It can be seen that the embodiment using a compound containing a core represented by Chemical Formula 1 has better efficiency and lifetime than Comparative Example 1.
[0266] It will be apparent to those skilled in the art that various modifications and variations can be made to the organic light-emitting elements of this disclosure without departing from the technical spirit or scope thereof. Therefore, this disclosure is intended to cover any modifications and variations thereof that fall within the scope of the appended claims and their equivalents.
Claims
1. An organic light-emitting element, comprising: First electrode; Second electrode; as well as An organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer comprises a compound represented by the following chemical formula 1: [Chemical Formula 1] In chemical formula 1, A is one of the chemical formulas a1, a2, and a3, and B is chemical formula b. When A is chemical formula a1, L is one of chemical formulas L-1, L-2, and L-3, and When A is chemical formula a2 or chemical formula a3, L is one of the following: a direct bond, chemical formula L-1, chemical formula L-2, and chemical formula L-3. [Chemical formula a1] [Chemical formula a2] [Chemical formula a3] In the chemical formula a1, X1 and X2 are N, S, or O. If either one is N, then the other is S or O. In the chemical formula a2, X2 and X3 are N, S, or O; if one is N, then the other is S or O. In the chemical formula a3, X3 and X4 are N, S, or O. If one is N, then the other is S or O. Among chemical formulas a1, a2, and a3, R1, R2, and R3 are each independently selected from hydrogen; C1 to C 20 Alkyl; C3 to C 30 cycloalkyl; C1 to C 20 Alkyl group; C6 to C 60 Aryloxy group; C1 to C 20 Alkyl thio; C6 to C 60 Arylthio; C1 to C 20 alkylsulfonyl; C6 to C 60 Arylsulfonyl; C6 to C 60 aryl; fluorenyl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group, R4, R5, R6, and R7 are each independently hydrogen or C6 to C7. 60 Aryl group, and one of R4, R5, R6, and R7 is a direct bond connected to L. [Chemical formula L-1] [Chemical formula L-2] [Chemical formula L-3] In chemical formulas L-1 to L-3, R8 to R in chemical formula L-1 16 R8 to R in chemical formula L-2 15 and R8 to R in chemical formula L-3 15 One of them is a direct bond connected to A of Formula 1, another is a direct bond connected to B of Formula 1, and the remainder, which are not direct bonds connected to A or B, are each independently selected from hydrogen; cyano; halogen; C1 to C2. 20 Alkyl; C3 to C 30 cycloalkyl; C1 to C 20 Alkyl group; C6 to C 60 Aryloxy group; C1 to C 20 Alkyl thio; C6 to C 60 Arylthio; C1 to C 20 alkylsulfonyl; C6 to C 60 arylsulfonyl; silyl; C6 to C 60 arylphosphine group; phosphine oxide group; C6 to C 60 aryl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic group, [Chemical formula b] In chemical formula b, Z is a direct bond or a C6 to C6 bond connected to L in chemical formula 1. 20 Aryl, R 17 and R 18 Each was independently selected from C6 to C 60 aryl; and C2 to C3 groups containing at least one heteroatom selected from O, N, S, Si, and P. 60 Heterocyclic groups, and The alkyl group, the cycloalkyl group, the alkoxy group, the aryloxy group, the alkylthio group, the arylthio group, the alkylsulfonyl group, the arylsulfonyl group, the fluorenyl group, the aryl group, the heterocyclic group, the silyl group, and the arylphosphinyl group are each optionally further substituted by one or more substituents selected from the following: halogen groups; C1 to C2. 20 Alkyl; C2 to C 20 Alkenyl; C2 to C 20 Alkyne group; fluorene group; C6 to C 20 Aryl groups; and C2 to C 20 Heterocyclic group.
2. The organic light-emitting element according to claim 1, wherein the compound represented by chemical formula 1 is one or more of the following compounds: 。 3. The organic light-emitting element according to claim 1, wherein the organic material layer comprises a light-emitting layer, and wherein the light-emitting layer contains the compound.
4. The organic light-emitting element according to claim 3, wherein the organic material layer further comprises at least one of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
5. The organic light-emitting element according to claim 3, wherein the compound is the host compound of the light-emitting layer.
6. The organic light-emitting element according to claim 5, wherein the light-emitting layer further comprises a host compound different from the compound.
7. The organic light-emitting element according to claim 1, wherein the organic material layer comprises a first stack and a second stack, the first stack comprising a first light-emitting layer, and the second stack comprising a second light-emitting layer.
8. The organic light-emitting element according to claim 7, wherein the first light-emitting layer comprises the compound.
9. The organic light-emitting element according to claim 8, wherein the compound is the host compound of the first light-emitting layer.
10. The organic light-emitting element according to claim 9, wherein the first light-emitting layer further comprises a host compound different from the compound.
Citation Information
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