ORGANIC LIGHT EMISSIONING ELEMENT

Abstract

Organic light-emitting element (100, 200, 300, 400), comprising: a first electrode (110); a second electrode (120); and an organic material layer (130) arranged between the first electrode (110) and the second electrode (120), wherein the organic material layer (130) contains a compound represented by the chemical formula 1 below: in chemical formula 1 is: either X or Y equals N, and the other is S or O, where a is an integer from 0 to 5, R1 each independently selected from the group consisting of a C1-C 20 -Alkyl group; a C3-C 30 -Cycloalkyl group; an aryloxy group; an arylthioxy group; a fluorenyl group; and a C6-C 60 -Aryl group, R2 selected from the group consisting of a C3-C 30-Cycloalkyl group, an aryloxy group, an arylthioxy group, a fluorenyl group and a C6-C 60 -Aryl group, R3 and R4 each independently selected from the group consisting of i) a C1-C 20 -Alkyl group and a C6-C 60 -aryl groups, or are bonded together to form a ring, b is an integer from 0 to 3, R5 each independently a C6-C 60 -Aryl group, and The alkyl group, cycloalkyl group, aryloxy group, arylthioxy group, fluorenyl group and aryl group are each further substituted with one or more substituents selected from the group consisting of a halogen group; a C1-C 20 -Alkyl group; a C2-C 20 -Alkenyl group; a C2-C 20 -Alkynyl group; a fluorenyl group; a C6-C 20 -aryl group; and a heterocyclic C2-C2o group.

Description

BACKGROUND Technical area

[0001] Embodiments of the disclosure relate to an organic light-emitting element. Discussion of the related technology

[0002] In general, organic light emission refers to a phenomenon in which electrical energy is converted into light energy by an organic material. An organic light-emitting element is a light-emitting device that utilizes this phenomenon. Such an element has a structure consisting of an anode, a cathode, and a layer of organic material sandwiched between them.

[0003] The organic material layer can have a multi-layer structure, composed of different materials to increase the efficiency and stability of the organic light-emitting element, and may contain a light-emitting layer (also known as an emissive material layer (EML)).

[0004] Lifespan and efficiency are the most important factors for organic light-emitting devices. Efficiency, lifespan, and operating voltage are interrelated. Increasing efficiency requires a relatively lower operating voltage, thus reducing crystallization of the organic material due to Joule heating during operation, which in turn increases the lifespan.

[0005] The function of the light-emitting layer (EML) is important for improving the light-emitting properties of the organic light-emitting element and extending its lifetime. To achieve high efficiency, the host material of the light-emitting layer must have a high triplet level, and material stability is essential.

[0006] The following publications are cited as representing the state of the art: CN 1 12 341 449 A, CN 1 11 892 586 A. SUMMARY

[0007] Accordingly, embodiments of the present disclosure are directed towards an organic light-emitting element which substantially eliminates one or more of the problems arising from limitations and disadvantages of the related technology.

[0008] For the organic light-emitting element to fully realize its excellent properties, the materials from which the organic layer is constructed should be stable and exhibit excellent efficiency. Since the phosphorescent organic light-emitting element in the light-emitting layer has a higher hole mobility than electron mobility and a long triplet state lifetime, the excitons generated in the light-emitting layer are distributed over a large area, thus reducing light emission. Accordingly, the inventors of the disclosure have invented an organic light-emitting element that can exhibit excellent efficiency or a long lifetime.

[0009] One aspect of the present disclosure is the provision of an organic light-emitting element with high efficiency or long lifetime.

[0010] Additional features and aspects are set out in the following description and are partly evident from the description or can be learned by applying the inventive concepts contained herein. Other features and aspects of the concepts according to the invention can be realized and achieved via the structure particularly highlighted in or derivable from the written description and via the claims and the accompanying drawings.

[0011] To realize these and other aspects of the concepts according to the invention, as embodied and generally described herein, an organic light-emitting element according to claim 1 is provided. Further embodiments are described in the dependent claims. According to one aspect of the present invention, an organic light-emitting element comprises: a first electrode, a second electrode, and an organic material layer arranged between the first electrode and the second electrode.

[0012] The organic material layer contains a compound represented by the following chemical formula 1:

[0013] According to embodiments of the disclosure, an organic light-emitting element with high efficiency or long lifetime can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] The accompanying drawings, which are attached to further understand the disclosure and form part of this application, illustrate embodiments of the disclosure and, together with the description, serve to explain various principles. The drawings include: Fig. 1 and Fig. Figure 2 are views that schematically show an organic light-emitting element according to embodiments of the disclosure; Fig. Figure 3 is a view schematically showing an organic light-emitting element according to embodiments of the disclosure; and Fig. Figure 4 is a view that schematically shows an organic light-emitting element according to embodiments of the disclosure. DETAILED DESCRIPTION

[0015] In the following description of examples or embodiments of the disclosure, reference is made to the accompanying drawings, which show specific examples or embodiments that can be implemented for illustration purposes, and in which the same reference numerals and symbols can be used to denote the same or similar components, even if they are shown in different of the accompanying drawings.Furthermore, in the following description of examples or embodiments of the disclosure, detailed descriptions of known functions and components contained herein are omitted where it is determined that such a description might render the subject matter rather unclear in some embodiments of the disclosure. The terms used herein, such as "including," "with," "containing," "constituting," "built from," "formed from," and "molded from," are generally intended to permit the addition of other components, unless the terms are used with the expression "only." As used herein, singular forms are to be understood as including plural forms, unless the context clearly indicates otherwise.

[0016] Terms such as “first”, “second”, “A”, “B”, “(A)”, or “(B)” may be used herein to describe elements of revelation. Each of these terms is not used to define the nature, order, sequence, or number of the elements, etc., but merely to distinguish the respective element from other elements.

[0017] When it is mentioned that a first element is "connected or coupled" to a second element, "touches or overlaps" it, etc., this is not to be understood as meaning that only the first element can "be directly connected or coupled to" or "directly touch or overlap" the second element, but rather that a third element can also be arranged between the first and second elements, or that the first and second elements are "connected or coupled" to each other via a fourth element, "touch or overlap" it, etc. Here, the second element can be contained within at least one of two or more elements that are "connected or coupled" to each other, "touch or overlap" each other, etc.

[0018] When time-related terms such as "after", "following", "next", "before" and the like are used to describe processes or operations of elements or configurations, or of sequences or steps in operational, processing and manufacturing procedures, these terms may be used to describe non-consecutive or non-sequential processes or operations unless the term is used together with "immediately" or "as soon as".

[0019] Furthermore, when mentioning dimensions, relative sizes, etc., it should be considered that numerical values ​​for elements or characteristics, or corresponding information (e.g., level, range, etc.), include a tolerance or error range that can be caused by various factors (e.g., process factors, internal or external influences, noise, etc.), even if no specific description is provided. Moreover, the term "may" encompasses all meanings of the term "can."

[0020] Various embodiments of the disclosure are described in detail below with reference to the accompanying drawings.

[0021] As used herein, the term “halo” or “halogen” encompasses fluorine (F), chlorine (Cl), bromine (Br) and iodine (I) and the like, unless otherwise specified.

[0022] As used herein, the term 'alkyl' or 'alkyl group' may mean a radical of a saturated aliphatic functional group having 1 to 60 carbon atoms, bound by a single bond, including a straight-chain alkyl group, a branched-chain alkyl group, a (alicyclic) cycloalkyl group, an alkyl-substituted cycloalkyl group or a cycloalkyl-substituted alkyl group, unless otherwise specified.

[0023] As used herein, the term ‘haloalkyl group’ or ‘halogenalkyl group’, unless otherwise specified, can mean a halogen-substituted alkyl group.

[0024] As used herein, the term “alkenyl” or “alkynyl” can encompass a double bond or a triple bond, and can encompass a straight-chain or branched-chain group, and can contain 2 to 60 carbon atoms, unless otherwise specified.

[0025] As used herein, the term ‘cycloalkyl’ can refer to an alkyl forming a ring with 3 to 60 carbon atoms, unless otherwise stated.

[0026] As used herein, the term 'alkoxy group' or 'alkyloxy group' can refer to an alkyl group to which an oxygen radical is bonded, and can have 1 to 60 carbon atoms unless otherwise specified.

[0027] As used herein, the term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group” or “alkenyloxy group” refers to an alkenyl group to which an oxygen radical is bonded and may contain 2 to 60 carbon atoms, unless otherwise specified.

[0028] As used herein, the terms “aryl group” and “arylene group” may, unless otherwise specified, encompass 6 to 60 carbon atoms, but are not limited to such numbers. In the disclosure, the aryl group or the arylene group may comprise a monocyclic type, a ring compound, a condensed polycyclic system, a spiro compound, and the like. The aryl group includes, for example, phenyl, biphenyl, naphthyl, anthryl, indenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, or fluoranthenyl. The naphthyl may comprise 1-naphthyl and 2-naphthyl, and the anthryl may comprise 1-anthryl, 2-anthryl, and 9-anthryl.

[0029] In the disclosure, the term "fluorenyl group" or "fluorenylene group" can refer to a monovalent or divalent functional group of fluorene, unless otherwise specified. The "fluorenyl group" or "fluorenylene group" can mean a substituted fluorenyl group or a substituted fluorenylene group. "Substituted fluorenyl group" or "substituted fluorenylene group" can refer to a monovalent or divalent functional group of substituted fluorene. "Substituted fluorene" can mean that at least one of the following substituents R, R', R'', and R''' is a functional group other than hydrogen. This can include the case where R and R' are linked together to form a spiro compound with the carbon to which they are bonded.

[0030] As used herein, the term "spiro compound" has a "spiro union," and the spiro union refers to a union that is formed when two rings share only one atom. In this case, the atom shared by the two rings can be called the "spiro atom."

[0031] As used herein, the term "heterocyclic group" can include not only an aromatic ring, such as a "heteroaryl group" or "heteroarylene group," but also a non-aromatic ring, and unless otherwise specified, means a ring with 2 to 50 carbon atoms and one or more heteroatoms, but is not limited to this. As used herein, the term "heteroatom," unless otherwise specified, refers to N, O, S, P, or Si, and the heterocyclic group can mean a monocyclic group containing a heteroatom, a ring system, a condensed polycyclic system, or a spiro compound.

[0032] The "heterocyclic group" can comprise a ring that contains SO2 instead of carbon, which forms the ring. Examples of compounds that can comprise the "heterocyclic group" include the following.

[0033] As used herein, the term ‘ring’ can include monocycles and polycycles, hydrocarbon rings as well as heterocycles containing at least one heteroatom, or aromatic and non-aromatic rings.

[0034] As used herein, the term “polycycle” can include ring arrangements, condensed polycyclic systems and spiro compounds, can include both aromatic and non-aromatic compounds, or can include heterocycles which have at least one heteroatom as well as hydrocarbon rings.

[0035] As used herein, the term "aliphatic ring group" refers to a cyclic hydrocarbon that is not an aromatic hydrocarbon, may include a monocyclic type, a ring complex, a condensed polycyclic system, and a spiro compound, and, unless otherwise specified, may mean a ring with 3 to 60 carbon atoms. For example, a fusion of benzene, an aromatic ring, and cyclohexane, a non-aromatic ring, also corresponds to an aliphatic ring.

[0036] As used herein, the term 'alkylsilyl group' can refer to a monovalent substituent in which three alkyl groups are bonded to one Si atom.

[0037] As used herein, the term 'arylsilyl group' can refer to a monovalent substituent in which three aryl groups are bonded to one Si atom.

[0038] As used herein, the term 'alkylarylsilyl group' can refer to a monovalent substituent in which one alkyl group and two aryl groups are bonded to one Si atom, or two alkyl groups and one aryl group are bonded to the Si atom.

[0039] As used herein, the term "ring complex" means that two or more ring systems (single or fused ring systems) are directly linked to one another by single or double bonds. For example, in the case of an aryl group, a biphenyl group or a terphenyl group can be a ring complex, but this is not limited to them.

[0040] As used herein, the term "condensed polycyclic system" refers to a type of condensed ring that shares at least two atoms. For example, in the case of an aryl group, a naphthalenyl group, a phenanthrenyl group, or a fluorenyl group may be, but are not limited to, a condensed polycyclic system.

[0041] When prefixes are listed consecutively, this can mean that the substituents are listed in the order given first. For example, an arylalkoxy group can mean an alkoxy group substituted with an aryl group, an alkoxycarbonyl group can mean a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group can mean an alkenyl group substituted with an arylcarbonyl group. The arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0042] With regard to “substituted” or “unsubstituted” as used herein and unless expressly stated otherwise, the term “substituted” may mean: substituted with one or more substituents selected from the group consisting of halogen, an amino group, a nitrile group, a nitro group, a C1-C 20 -Alkyl group, a C1-C 20 -Alkoxy group, a C1-C 20 -Alkylamine group, a C1-C 20 -Alkylthiophene group, a C6-C 20 -Arylthiophene group, a C2-C 20 -Alkenyl group, a C2-C 20 -Alkynyl group, a C3-C 20 -Cycloalkyl group, a C6-C 20 -Aryl group, a C8-C 20 -Arylalkenyl group, a silane group, a boron group, a germanium group and a heterocyclic C2-C 20 -group which contains at least one heteroatom selected from the group consisting of O, N, S, Si and P, but is not restricted to these substituents.

[0043] In the disclosure, the “names of the functional groups” corresponding to the aryl group, the arylene group, and the heterocyclic group, which are given as examples of the short names and their substituents, can be described as “the names of the functional groups reflecting the valence” or as “the names of the parent compounds.” For example, in the case of “phenanthrene,” a type of aryl group, the name can be given with the identified group, such as “phenanthryl(group)” for the monovalent group and “phenanthrylen(group)” for the divalent group, but it can also be given as “phenanthrene,” which is the name of the parent compound, regardless of the valence. Similarly, pyrimidine can be given as “pyrimidine,” regardless of the valence, or as pyrimidinyl(group) for the monovalent state and pyrimidylene(group) for the divalent state.If the type of substituent is specified in the disclosure along with the name of the parent compound, it may therefore be an n-valent “group” formed by the removal of the hydrogen atom bonded to a carbon atom and / or a heteroatom of the parent compound.

[0044] Furthermore, unless expressly stated otherwise, the formulas used in the disclosure can be applied in the same way as the definition of the substituent by the following formulas.

[0045] If a equals 0, this means that the substituent R1 is not present, which means that hydrogen is bonded to each of the carbon atoms forming the benzene ring. In this case, the chemical formula or compound can be given without specifying the hydrogen bonded to the carbon. If a equals 1, a substituent R1 is bonded to any of the carbon atoms forming the benzene ring, and if a equals 2 or 3, it can be bonded as follows. If a is an integer from 4 to 6, it is bonded to the carbon atom of the benzene ring in a similar way, and if a is an integer of 2 or more, R1 can be the same or different.

[0046] If, in the disclosure, substituents are bonded together to form a ring, this may mean that adjacent groups are bonded together to form a monocycle or condensed polycycle, and the monocycle or condensed polycycle may include heterocycles containing at least one heteroatom, as well as hydrocarbon rings, and may include aromatic and non-aromatic rings.

[0047] In the revelation, the organic light-emitting element can mean (a) component(s) between the anode and the cathode, or an organic light-emitting diode with an anode, a cathode and (a) component(s) arranged between them.

[0048] In some cases, the organic light-emitting element in the disclosure may mean: an organic light-emitting diode and a panel incorporating it, or an electronic device containing the panel and a circuit. The electronic device may, for example, include a display device, a lighting device, a solar cell, a portable or mobile device (e.g., a smartphone, a tablet, a PDA, an electronic dictionary, or a PMP), a navigation terminal, a gaming device, various television sets, and various computer monitors, but is not limited to these. It may refer to any type of device containing the component(s).

[0049] Fig. Figure 1 is a schematic view of an organic light-emitting element according to embodiments of the disclosure.

[0050] The organic light-emitting element 100 according to embodiments of the disclosure comprises a first electrode 110, a second electrode 120 and an organic material layer 130 arranged between the first electrode 110 and the second electrode 120.

[0051] For example, the first electrode 110 can be the anode electrode and the second electrode 120 can be the cathode electrode.

[0052] For example, the first electrode 110 can be a transparent electrode and the second electrode 130 can be a reflective electrode. In another example, the first electrode 110 can be a reflective electrode and the second electrode 130 can be a transparent electrode.

[0053] The organic material layer 130 is a layer that is arranged between the first electrode 110 and the second electrode 120 and contains an organic material and can be composed of a plurality of layers.

[0054] The organic material layer 130 contains a compound represented by chemical formula 1. This compound, represented by chemical formula 1, is described in detail below.

[0055] The organic material layer 130 can contain a light-emitting layer. The organic layer 130 can also contain at least one hole injection layer, a hole transport layer, an electron transport layer, or an electron injection layer.

[0056] The organic material layer 130 can, for example, include a hole injection layer arranged on the first electrode 110, a hole transport layer arranged on the hole injection layer, a light-emitting layer arranged on the hole transport layer, an electron transport layer arranged on the light-emitting layer, and an electron injection layer arranged on the electron transport layer. In such an example, the first electrode 110 can be the anode electrode, and the second electrode 120 can be the cathode electrode.

[0057] The light-emitting layer is a layer in which the holes and electrons transferred from the first electrode 110 and the second electrode 130 meet to emit light, and may contain, for example, a host material and a dopant.

[0058] The light-emitting layer can contain the compound represented by chemical formula 1 described above. The compound represented by chemical formula 1 can be the host compound of the light-emitting layer. For example, the compound represented by chemical formula 1 can be a phosphorescent host compound of the light-emitting layer.

[0059] The light-emitting layer may further contain a host compound that differs from the compound represented by chemical formula 1 described above. The type of host compound that may be additionally contained is not particularly restricted; any known host compound may be used.

[0060] Fig. Figure 2 is a schematic view of an organic light-emitting element according to embodiments of the disclosure.

[0061] The organic light-emitting element 200 according to embodiments of the disclosure comprises a first electrode 110, a second electrode 120 and an organic material layer 130 arranged between the first electrode 110 and the second electrode 120.

[0062] For example, the first electrode 110 can be the anode electrode and the second electrode 120 can be the cathode electrode.

[0063] 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.

[0064] The organic material layer 130 is a layer that is arranged between the first electrode 110 and the second electrode 120 and contains an organic material and can be composed of a plurality of layers.

[0065] The organic material layer 130 contains a compound represented by chemical formula 1. This compound, represented by chemical formula 1, is described in detail below.

[0066] The organic material layer 130 can contain: a hole injection layer 231 arranged on the first electrode 110, a hole transport layer 232 arranged on the hole injection layer 231, a light-emitting layer 233 arranged on the hole transport layer 232, an electron transport layer 234 arranged on the light-emitting layer 233, and an electron injection layer 235 arranged on the electron transport layer 234. In such an example, the first electrode 110 can be the anode electrode and the second electrode 120 can be the cathode electrode. The organic material layer 130 can contain some of the components described in Fig. The two layers shown may not be included, or may contain an additional functional layer, such as a light-emitting auxiliary layer.

[0067] The light-emitting layer 233 can contain the compound represented by the chemical formula 1 described above.

[0068] The light-emitting layer 233 can contain a host compound 2331 and a dopant 2332. The host compound 2331 can be a compound represented by chemical formula 1 as described above. The host compound 2331 can also contain another compound that differs from the one represented by chemical formula 1 as described above. For example, the host compound 2331 can contain the compound represented by chemical formula 1 and a biscarbazole-based compound.

[0069] The type of dopant 2332 is not particularly restricted. For example, dopant 2332 can be a green phosphorescent dopant. Dopant 2332 can also be a metal complex, such as one made of iridium.

[0070] Fig. Figure 3 is a schematic view of an organic light-emitting element according to embodiments of the disclosure.

[0071] Referring to Fig. 3 the organic material layer 130 contains a first stack 331, a second stack 332 and a charge-generating layer 333 which is arranged between the first stack 331 and the second stack 332.

[0072] The organic light-emitting element 300 can be a tandem-type organic light-emitting element containing multiple stacks, each with a light-emitting layer. The multiple light-emitting layers can be made of the same material or of different materials. The first stack 331 can contain a first light-emitting layer 3313. The second stack 332 can contain a second light-emitting layer 3323. The first light-emitting layer 3313 and the second light-emitting layer 3323 can be made of the same material or of different materials.

[0073] The first stack 331 can contain a first light-emitting layer 3313. The first light-emitting layer 3313 can, for example, contain a first host compound 33131 and a first dopant 33132.

[0074] The first stack 231 can furthermore contain at least one of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer.

[0075] For example, the first stack 331 can contain: a first hole injection layer 3311 arranged on the first electrode 110, a first hole transport layer 3312 arranged on the first hole injection layer 3311, a first light-emitting layer 3313 arranged on the first hole transport layer 3312, a first electron transport layer 3314 arranged on the first light-emitting layer 3313, and a first electron injection layer 3315 arranged on the first electron transport layer 3314. In such an example, the first electrode 110 can be the anode electrode, and the second electrode 120 can be the cathode electrode. The first stack 331 can contain some of the Fig. The 3 layers shown may not be included or may contain an additional functional layer, for example a light-emitting auxiliary layer.

[0076] The first light-emitting layer 3313 can contain the compound described above, represented by chemical formula 1.

[0077] The first light-emitting layer 3313 can contain a first host compound 33131 and a first dopant 33132. The first host compound 33131 can be a compound represented by chemical formula 1 as described above. The first host compound 33131 can also contain a different compound than the one represented by chemical formula 1 as described above. For example, the first host compound 33131 can contain a compound represented by chemical formula 1 and a biscarbazole-based compound.

[0078] The type of the first dopant 33132 is not particularly restricted. 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 one made of iridium.

[0079] The second stack 332 can contain a second light-emitting layer 3323. The second light-emitting layer 3323 can, for example, contain a second host compound and a second dopant.

[0080] The second stack 332 can furthermore contain at least one of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer.

[0081] The second stack 332 can, for example, comprise: a second hole injection layer 3321 arranged on the second electrode 110, a second hole transport layer 3322 arranged on the second hole injection layer 3321, a second light-emitting layer 3323 arranged on the second hole transport layer 3322, a second electron transport layer 3324 arranged on the second light-emitting layer 3323, and a second electron injection layer 3325 arranged on the second electron transport layer 3324. In such an example, the first electrode 110 can be the anode electrode and the second electrode 120 can be the cathode electrode. The second stack 332 can comprise some of the Fig. do not contain the 3 layers shown or have an additional functional layer, for example a light-emitting auxiliary layer.

[0082] The second light-emitting layer 3323 can emit light of the same color or a different color than the light emitted by the first light-emitting layer 3313. In the disclosure, the fact that the light-emitting layers emit light of the same color means that the light-emitting layers emit not only light of colors with the same color coordinates, but also light of colors that are similar to each other and are suitable, in the technical field of the disclosure, to be classified as pixels of the same color.

[0083] The second light-emitting layer 3323 can contain a second host compound and a second dopant.

[0084] The type of the second host connection is not particularly restricted. The second host connection can be the same as the first host connection 33131 or different from it.

[0085] The type of the second dopant is not particularly restricted. The second dopant can be the same as the first dopant 33132 or different from it.

[0086] In embodiments of the disclosure, the second light-emitting layer 3323 can emit light of the same color as the light emitted by the first light-emitting layer 3313. In the embodiments described above, the first light-emitting layer 3323 can contain the compound represented by chemical formula 2 described above.

[0087] In embodiments in which the first light-emitting layer 3313 and the second light-emitting layer 3323 emit light of the same color, the second host compound can be a compound represented by chemical formula 1 described above. The second host compound can further comprise a different compound from the one represented by chemical formula 1 described above. For example, the second host compound can comprise a compound represented by chemical formula 1 and a biscarbazole-based compound.

[0088] In embodiments in which 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 restricted and can be the same as the first dopant 33132. The second dopant can, for example, be a green phosphorescent dopant. The second dopant can, for example, be a metal complex, such as one of iridium.

[0089] The charge-generating layer 333 can be formed between the multiple light-emitting layers to distribute charges evenly and thereby increase the current efficiency of the light-emitting layer. Accordingly, the charge-generating layer 333 is arranged between the first stack 331 with the first light-emitting layer 3313 and the second stack 332 with the second light-emitting layer 3323.

[0090] The charge-generating layer 333 can contain a p-type charge-generating layer and an n-type charge-generating layer to distribute charges evenly. If the first electrode 110 is the anode electrode and the second electrode 120 is the cathode electrode, the p-type charge-generating layer can be located on the cathode electrode side and the n-type charge-generating layer on the anode electrode side.

[0091] Although Fig. Figure 3 shows a tandem-type organic light-emitting element with two stacks. However, embodiments of the disclosure are not limited to this, but may include tandem-type organic light-emitting elements with two or more stacks. If the organic light-emitting element 300 contains an additional stack, an additional charge-generating layer may be arranged between the additional stack and the adjacent first stack 331 or second stack 332.

[0092] Fig. Figure 4 is a view that schematically shows an organic light-emitting element according to embodiments of the disclosure.

[0093] Referring to Fig. In Figure 4, the organic material layer 130 contains a first stack 431, a second stack 432, a third stack 433, a first charge-generating layer 434 arranged between the first stack 431 and the second stack 432, and a second charge-generating layer 435 arranged between the first stack 431 and the third stack 433. In the Fig. In the embodiments shown in Figure 4, the first stack 431 is arranged between the second stack 432 and the third stack 433, but embodiments of the disclosure with 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 can be interchanged.

[0094] The organic light-emitting element 400 can be a tandem-type organic light-emitting element, comprising multiple stacks, each with a light-emitting layer. The multiple light-emitting layers can be made of the same material or of different materials.

[0095] The first stack 431 can contain a first light-emitting layer 4313. The first light-emitting layer 4313 can, for example, contain a first host compound 43131 and a first dopant 43132.

[0096] The first stack 431 can furthermore contain at least one of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer.

[0097] For example, the first stack 431 can have: a first hole injection layer 4311 arranged on the first electrode 110, a first hole transport layer 4312 arranged on the first hole injection layer 4311, a first light-emitting layer 4313 arranged on the first hole transport layer 4312, a first electron transport layer 4314 arranged on the first light-emitting layer 4313, and a first electron injection layer 4315 arranged on the first electron transport layer 4314. In such an example, the first electrode 110 can be the anode electrode, and the second electrode 120 can be the cathode electrode. The first stack 431 can have some of the Fig. not contain the 4 layers shown or have an additional functional layer, for example a light-emitting auxiliary layer.

[0098] The first light-emitting layer 4313 can contain the compound represented by the chemical formula 1 described above.

[0099] The first light-emitting layer 4313 can contain a first host compound 43131 and a first dopant 43132. The first host compound 43131 can be a compound represented by chemical formula 1 as described above. The first host compound 43131 can also contain a different compound than the one represented by chemical formula 1 as described above. For example, the first host compound 43131 can contain a compound represented by chemical formula 1 and a biscarbazole-based compound.

[0100] The type of the first dopant 43132 is not particularly restricted. For example, the first dopant can be a green phosphorescent dopant. For example, the first dopant 43132 can be a metal complex, such as one made of iridium.

[0101] The second stack 432 can contain a second light-emitting layer 4323. The second light-emitting layer 4323 can, for example, contain a second host compound 43231 and a second dopant 43232.

[0102] The second stack 432 can further contain at least one of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer.

[0103] The second stack 432 can, for example, comprise: a second hole injection layer 4321 arranged on the second electrode 110, a second hole transport layer 4322 arranged on the second hole injection layer 4321, a second light-emitting layer 4323 arranged on the second hole transport layer 4322, a second electron transport layer 4324 arranged on the second light-emitting layer 4323, and a second electron injection layer 4325 arranged on the second electron transport layer 4324. In such an example, the first electrode 110 can be the anode electrode and the second electrode 120 can be the cathode electrode. The second stack 432 can comprise some of the Fig. The 4 layers shown may not be included or may contain an additional functional layer, for example a light-emitting auxiliary layer.

[0104] The second light-emitting layer 4323 can emit light of the same color or a different color than the light emitted by the first light-emitting layer 4313.

[0105] The second light-emitting layer 4323 can contain a second host compound and a second dopant.

[0106] The type of the second host connection is not particularly restricted. The second host connection can be the same as the first host connection 43131 or different from it.

[0107] The type of the second dopant is not particularly restricted. The second dopant can be the same as the first dopant 43132 or different from it.

[0108] In embodiments of the disclosure, the second light-emitting layer 4323 can emit light of the same color as the light emitted by the first light-emitting layer 4313. In the embodiments described above, the first light-emitting layer 4323 can contain the compound represented by chemical formula 2 described above.

[0109] In embodiments in which the first light-emitting layer 4313 and the second light-emitting layer 4323 emit light of the same color, the second host compound can be a compound represented by chemical formula 1 described above. The second host compound can further comprise a different compound from the one represented by chemical formula 1 described above. For example, the second host compound can comprise a compound represented by chemical formula 1 and a biscarbazole-based compound.

[0110] In embodiments in which 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 restricted 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 one of iridium.

[0111] The third stack 433 can contain a third light-emitting layer 4333. The third light-emitting layer 4333 can, for example, contain a third host compound and a third dopant.

[0112] The third stack 432 can also contain at least one of a hole injection layer, a hole transport layer, an electron transport layer or an electron injection layer.

[0113] For example, the third stack 432 can comprise: a third hole injection layer 4331 arranged on the third electrode 110, a third hole transport layer 4332 arranged on the third hole injection layer 4331, a third light-emitting layer 4333 arranged on the third hole transport layer 4332, a third electron transport layer 4334 arranged on the third light-emitting layer 4333, and a third electron injection layer 4335 arranged on the third electron transport layer 4334. In such an example, the first electrode 110 can be the anode electrode and the second electrode 120 can be the cathode electrode. The third stack 433 can comprise some of the Fig. do not contain the 4 layers shown or have an additional functional layer, for example a light-emitting auxiliary layer.

[0114] The third light-emitting layer 4333 can emit light of the same or a different color than the light emitted by the first light-emitting layer 4313.

[0115] The third light-emitting layer 4333 can contain a third host compound and a third dopant.

[0116] The type of the third host connection is not particularly restricted. The third host connection can be the same as the first host connection 43131 or different from it.

[0117] The type of the third dopant is not particularly restricted. The third dopant can be the same as the first dopant 43132 or different from it.

[0118] In embodiments of the disclosure, the third light-emitting layer 4333 can emit light of the same color as the light emitted by the first light-emitting layer 4313. In the embodiments described above, the first light-emitting layer 4333 can contain the compound represented by chemical formula 3 described above.

[0119] In embodiments in which the first light-emitting layer 4313 and the third light-emitting layer emit light 4333 of the same color, the third host compound can be a compound represented by chemical formula 1 as described above. The third host compound can further comprise a different compound from the one represented by chemical formula 1 as described above. For example, the third host compound can comprise a compound represented by chemical formula 1 and a biscarbazole-based compound.

[0120] In embodiments in which the first light-emitting layer 4313 and the third light-emitting layer 4333 emit light of the same color, the type of the second dopant is not particularly restricted 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 one of iridium.

[0121] The first host connection 43131, the second host connection, and the third host connection can be the same or different from each other. One or more of the first host connection 43131, the second host connection, and the third host connection can contain a compound represented by chemical formula 1 as described above. Accordingly, one of the first host connection 43131, the second host connection, and the third host connection can contain a compound represented by chemical formula 1 as described above. Two of the first host connection 43131, the second host connection, and the third host connection can contain a compound represented by chemical formula 1 as described above. All of the first host connection 43131, the second host connection, and the third host connection can contain a compound represented by chemical formula 1 as described above.If there are two or more light-emitting layers containing a host compound that has the compound represented by chemical formula 1 described above, the two or more of the light-emitting layers can emit light of the same color.

[0122] The first dopant 33132, the second dopant and the third dopant can be the same or different from each other.

[0123] Since the first stack 431, the second stack 432 and the third stack 433 are designed as described above, the 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 and emit light.

[0124] The first charge-generating layer 434 and the second charge-generating layer 435 can be formed between the plurality of light-emitting layers to distribute charges evenly and thereby increase the current efficiency of the light-emitting layer. Accordingly, the first charge-generating layer 434 can be arranged between the first stack 431, which contains the first light-emitting layer 4313, and the second stack 432, which contains the second light-emitting layer 4323, and the second charge-generating layer 435 can be arranged between the second stack 432, which contains the second light-emitting layer 433, and the third stack 433, which contains the third light-emitting layer 4333.

[0125] The first charge-generating layer 434 and the second charge-generating layer 435 can contain a p-type charge-generating layer and an n-type charge-generating layer, respectively, to distribute charges evenly. If the first electrode 110 is the anode electrode and the second electrode 120 is the cathode electrode, the p-type charge-generating layer can be located on the cathode electrode side and the n-type charge-generating layer can be located on the anode electrode side.

[0126] The first charge-generating layer 434 and the second charge-generating layer 435 can be the same or different from each other. The first charge-generating layer 434 and the second charge-generating layer 435 can be made of the same material or of different materials.

[0127] The compound represented by the chemical formula 1 described above is described below.

[0128] The compound represented by the chemical formula 1 described above can be represented by the chemical formula 1 as follows.

[0129] In chemical formula 1, either X or Y equals N, and the other is S or O.

[0130] a is an integer from 0 to 5.

[0131] R1 is selected independently from the group consisting of C1-C 20 -Alkyl group; a C3-C 30 -Cycloalkyl group; an aryloxy group; an arylthioxy group; a fluorenyl group; and a C6-C 60 -Aryl group.

[0132] If R1 is an aryl group, the aryl group can independently form a C6-C 30 -Aryl group, a C6-C 20 -Aryl group or a C6-C 12 -aryl group.

[0133] R2 is selected from the group consisting of a C3-C 30-Cycloalkyl group; an aryloxy group; an arylthioxy group; a fluorenyl group; and a C6-C 60 -Aryl group.

[0134] If R2 is an aryl group, the aryl group can each independently form a C6-C 30 -Aryl group, a C6-C 20 -Aryl group or a C6-C 12 -aryl group.

[0135] R3 and R4 can each be selected independently from the group consisting of i) a C1-C 20 -Alkyl group and a C6-C 60 -aryl group, or they can be bonded together to form a ring.

[0136] If one or more of R3 and R4 are aryl groups, the aryl groups can each independently form a C6-C 30 -Aryl group, a C6-C 20 -Aryl group or a C6-C 12 -aryl group.

[0137] b is an integer from 0 to 3.

[0138] R5 is each independently a C6-C 60-Aryl group.

[0139] If R5 is an aryl group, the aryl group can independently form a C6-C 30 -Aryl group, a C6-C 20 -Aryl group or a C6-C 12 -aryl group.

[0140] The alkyl group, cycloalkyl group, aryloxy group, arylthioxy group, fluorenyl group and aryl group are each further substituted with one or more substituents, selected from the group consisting of a halogen group, a C1-C 20 -Alkyl group, a C2-C 20 -Alkenyl group, a C2-C 20 -Alkynyl group, a fluorenyl group, a C6-C 20 -aryl group and a heterocyclic C2-C 20 -Group.

[0141] One or more of the hydrogen atoms contained in the compound represented by chemical formula 1 can be replaced by deuterium or tritium.

[0142] By incorporating the compound represented by the chemical formula 1 described above, the organic light-emitting elements 100 and 200 can have high efficiency or a long lifetime.

[0143] The compound represented by chemical formula 1 can be represented by any of the following chemical formulas 1a and 1b.

[0144] In chemical formula 1a and chemical formula 1b, X and Y are S or O, respectively.

[0145] R1, R2, R3, R4, R5, a and b are the same as defined above in chemical formula 1.

[0146] One or more of the hydrogen atoms contained in the compound represented by chemical formula 1a and chemical formula 1b may be replaced by deuterium or tritium.

[0147] The compound represented by the chemical formula 1 described above can be one or more of the following compounds:

[0148] One or more of the hydrogen atoms contained in AZ1 to AK160 can be replaced by deuterium or tritium.

[0149] An example of the manufacture of an organic light-emitting element according to embodiments of the disclosure is described in detail below with reference to embodiments thereof, but the embodiments of the disclosure are not limited to the following embodiments. Example of compound synthesis method for AZ3 Synthesis of intermediate A

[0150] Benzoic acid (10 g, 0.082 mol), 2-amino-4-bromophenol (33.9 g, 0.180 mol), diisopropylethylamine (37.1 mL, 0.213 mol), aqueous 4 M K₂CO₃ solution (80 mL), and methylene chloride (300 mL) are placed in a round-bottom flask and stirred while the temperature is reduced to 0°C. Deoxo-Fluor reagent, 50% in THF (66.4 mL, 0.180 mol), diluted with 45 mL of MC, is added slowly dropwise to the solution. After the dropwise addition is complete, the solution is stirred for 2 hours at 0°C. After the reaction is stopped by adding 150 mL of saturated aqueous sodium bicarbonate solution to the reaction solution, the solution is warmed to room temperature. After the reaction solution was separated into layers to obtain the organic layer, the organic layer was dried with MgSO4 and concentrated under reduced pressure. The concentrated crude product was subjected to column separation to obtain 19.1 g of intermediate A. Synthesis of AZ3

[0151] An intermediate A (5 g, 0.018 mol), 2-(4-biphenylyl)amino-9,9-dimethylfluorene (7.9 g, 0.022 mol), palladium acetate (II) (0.08 g, 0.365 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.23 g, 0.365 mmol), sodium tert-butoxide (2.63 g, 0.027 mol), and 100 mL of toluene are placed in a round-bottom flask and heated to 100°C for 8 hours with stirring. The reaction solution was hot-filtered through silica gel to remove impurities, and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified with MC / acetone to yield 6.9 g of AZ3. Synthesis method for AZ5

[0152] The synthesis was carried out in the same manner as in the synthesis procedure for AZ3, with the difference that 2-(2-biphenylyl)amino-9,9-dimethylfluorene (7.9 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 6.6 g of AZ5 were obtained. Synthesis method for AZ10

[0153] The synthesis was carried out in the same manner as in the synthesis procedure for AZ3, with the difference that 2-(3-Dibenzofuranyl)amino-9,9-dimethylfluorene (8.2 g, 0.022 mol) was used instead of 2-(4-Biphenylyl)amino-9,9-dimethylfluorene. 7.1 g of AZ10 were obtained. Synthesis method for AZ11

[0154] The synthesis was carried out in the same manner as in the synthesis procedure for AZ3, with the difference that 2-(3-dibenzothiophenyl)amino-9,9-dimethylfluorene (8.6 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 7.3 g of AZ11 were obtained. Synthesis method for AZ18

[0155] The synthesis was carried out using the same reagents, dosage and procedure as in the synthesis procedure for AZ3, using bis(9,9-dimethyl-9H-fluoren-2-yl)amine (8.8 g, 0.022 mol) instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene and yielded 7.6 g of AZ18. Synthesis method for AZ20

[0156] The synthesis was carried out in the same manner as in the synthesis procedure for AZ3, with the difference that (9,9-dimethylfluoren-2-yl)-9,9-spirobifluoren-2-amine (11.5 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. As a result, 9.0 g of AZ20 were obtained. Synthesis method for AZ23

[0157] The synthesis was carried out in the same manner as in the synthesis procedure for AZ3, with the difference that 2-(4-biphenylyl)amino-9,9-diphenylfluorene (10.6 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. As a result, 8.8 g of AZ23 were obtained. Synthesis method for AZ43 Synthesis of intermediate B

[0158] 4-Bromobenzoic acid (20 g, 0.099 mol), phenylboric acid (14.6 g, 0.119 mol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.99 mmol), 400 mL toluene, and 100 mL 4M K₂CO₃ (potassium carbonate) were placed in a round-bottom flask and stirred under reflux for 12 hours. After completion of the reaction, the solution was separated into several layers. The organic layer was collected and concentrated under reduced pressure to obtain a crude product. The filtered crude product was subjected to column separation to obtain 17.7 g of intermediate B. Synthesis of intermediate C

[0159] An intermediate B (15 g, 0.076 mol), 2-amino-4-bromophenol (31.3 g, 0.166 mol), diisopropylethylamine (34.3 mL, 0.197 mol), aqueous 4M K₂CO₃ solution (75 mL), and methylene chloride (350 mL) are placed in a round-bottom flask and stirred while the temperature is reduced to 0°C. Deoxo-Fluor reagent, 50% in THF (61.4 mL, 0.166 mol), diluted with 45 mL of MC, is added slowly dropwise to the solution. After completion of the dropwise addition, the solution was stirred for 2 hours at 0°C. The subsequent procedure was the same as that for intermediate A, and 22.5 g of intermediate C were obtained. Synthesis of AZ43

[0160] An intermediate C (5 g, 0.014 mol), 2-(4-biphenylyl)amino-9,9-dimethylfluorene (6.2 g, 0.017 mol), instead of intermediate A in the synthesis procedure for AZ3, palladium acetate(II) (0.06 g, 0.365 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.18 g, 0.365 mmol), sodium tert-butoxide (2.06 g, 0.021 mol), and 100 mL of toluene are added and heated at 100°C for 8 hours with stirring. The reaction solution was hot-filtered through silica gel to remove impurities, and the filtrate was concentrated under reduced pressure to obtain the crude product. After purification of the crude product obtained with MC / acetone, 6.9 g of AZ43 were obtained. Synthesis method for AZ83 Synthesis of intermediate D

[0161] The same procedure as for the synthesis of intermediate A was carried out, except that 2-amino-4-bromobenzene (36.8 g, 0.180 mol) was used instead of 2-amino-4-bromophenol. As a result, 18.5 g of intermediate D were obtained. Synthesis of AZ83

[0162] An intermediate D (5 g, 0.017 mol), 2-(4-biphenylyl)amino-9,9-dimethylfluorene (7.5 g, 0.021 mol), instead of intermediate A in the synthesis procedure for AZ3, palladium acetate(II) (0.08 g, 0.345 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.21 g, 0.345 mmol), sodium tert-butoxide (2.48 g, 0.026 mol), and toluene (100 mL) are added and heated to 100°C for 8 hours with stirring. The reaction solution was hot-filtered through silica gel to remove impurities, and the filtrate was concentrated under reduced pressure to obtain the crude product. After purification of the crude product obtained with MC / acetone, 6.7 g of AZ83 were obtained. Synthesis of AZ92

[0163] The synthesis was carried out in the same manner as in the synthesis procedure for AZ3, with the difference that 2-(4-dibenzofuranyl)amino-9,9-dimethylfluorene (7.8 g, 0.021 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. As a result, 6.9 g of AZ92 were obtained. Synthesis of AZ98

[0164] The synthesis was carried out using the same reagents, dosage, and procedure as in the synthesis procedure for AZ83, except that bis(9,9-dimethyl-9H-fluoren-2-yl)amine (8.8 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 7.8 g of AZ98 were obtained. Synthesis of AZ103

[0165] The synthesis was carried out in the same manner as in the synthesis procedure for AZ83, with the difference that 2-(4-biphenylyl)amino-9,9-diphenylfluorene (10.6 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. As a result, 9.0 g of AZ103 were obtained. Synthesis method for AK3 Synthesis of intermediate A

[0166] Benzoic acid (10 g, 0.082 mol), 2-amino-5-bromophenol (33.9 g, 0.180 mol), diisopropylethylamine (37.1 mL, 0.213 mol), aqueous 4 M K₂CO₃ solution (80 mL), and methylene chloride (300 mL) are placed in a round-bottom flask and stirred while the temperature is reduced to 0°C. Deoxo-Fluor reagent, 50% in THF (66.4 mL, 0.180 mol), diluted with 45 mL of MC, is added slowly dropwise to the solution. After the dropwise addition is complete, the solution is stirred for 2 hours at 0°C. After the reaction is stopped by adding 150 mL of saturated aqueous sodium bicarbonate solution to the reaction solution, the solution is heated to room temperature. After the reaction solution was separated into layers to obtain the organic layer, the organic layer was dried with MgSO4 and concentrated under reduced pressure. The concentrated crude product was subjected to column separation to obtain 18.4 g of intermediate A. Synthesis of AK3

[0167] An intermediate A (5 g, 0.018 mol), 2-(4-biphenylyl)amino-9,9-dimethylfluorene (7.9 g, 0.022 mol), palladium acetate(II) (0.08 g, 0.365 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.23 g, 0.365 mmol), sodium tert-butoxide (2.63 g, 0.027 mol), and 100 mL of toluene were placed in a round-bottom flask and heated at 100°C for 8 hours with stirring. The reaction solution was hot-filtered through silica gel to remove impurities, and the filtrate was concentrated under reduced pressure to obtain a crude product. After purification of the crude product with MC / acetone, 6.7 g of AK3 were obtained. Synthesis of AK5

[0168] The synthesis was carried out in the same manner as for AK3, except that 2-(2-biphenylyl)amino-9,9-dimethylfluorene (7.9 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 6.6 g of AK5 were obtained. Synthesis of AK10

[0169] The synthesis was carried out in the same manner as in the synthesis procedure for AK3, with the difference that 2-(3-Dibenzofuranyl)amino-9,9-dimethylfluorene (8.2 g, 0.022 mol) was used instead of 2-(4-Biphenylyl)amino-9,9-dimethylfluorene. 6.9 g of AK10 were obtained. Synthesis of AK11

[0170] The synthesis was carried out in the same manner as for AK3, except that 2-(3-dibenzothiophenyl)amino-9,9-dimethylfluorene (8.6 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 7.3 g of AK11 were obtained. Synthesis of AK18

[0171] The synthesis was carried out using the same reagents, dosage, and procedure as in the synthesis procedure for AK3, except that bis(9,9-dimethyl-9H-fluoren-2-yl)amine (8.8 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 7.5 g of AK18 were obtained. Synthesis of AK20

[0172] The synthesis was carried out in the same manner as for AK3, except that (9,9-dimethylfluoren-2-yl)-9,9-spirobifluoren-2-amine (11.5 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. As a result, 9.1 g of AK20 were obtained. Synthesis of AK23

[0173] The synthesis was carried out in the same manner as for AK3, except that 2-(4-biphenylyl)amino-9,9-diphenylfluorene (10.6 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 8.7 g of AK23 were obtained. Synthesis method for AK43 Synthesis of intermediate B

[0174] 4-Bromobenzoic acid (20 g, 0.099 mol), phenylboric acid (14.6 g, 0.119 mol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.99 mmol), 400 mL toluene, and 100 mL 4M K₂CO₃ (potassium carbonate) are placed in a round-bottom flask and stirred under reflux for 12 hours. After completion of the reaction, the solution is separated into layers, the organic layer is collected, and concentrated under reduced pressure to obtain a crude product. The filtered crude product was subjected to column separation to obtain 17.7 g of intermediate B. Synthesis of intermediate C

[0175] An intermediate B (15 g, 0.076 mol), 2-amino-5-bromophenol (31.3 g, 0.166 mol), diisopropylethylamine (34.3 mL, 0.197 mol), aqueous 4 M K₂CO₃ solution (75 mL), and methylene chloride (350 mL) are placed in a round-bottom flask and stirred while the temperature is reduced to 0°C. Deoxo-Fluor reagent, 50% in THF (61.4 mL, 0.166 mol), diluted with 45 mL of MC, is added slowly dropwise to the solution. After completion of the dropwise addition, the solution was stirred for 2 hours at 0°C. The subsequent procedure was the same as that for intermediate A, and 22.2 g of intermediate C were obtained. Synthesis of AK43

[0176] An intermediate C (5 g, 0.014 mol), 2-(4-biphenylyl)amino-9,9-dimethylfluorene (6.2 g, 0.017 mol), instead of intermediate A in the synthesis procedure for AK3, palladium acetate(II) (0.06 g, 0.365 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.18 g, 0.365 mmol), sodium tert-butoxide (2.06 g, 0.021 mol), and toluene (100 mL) are added and heated to 100°C for 8 hours with stirring. The reaction solution was hot-filtered through silica gel to remove impurities, and the filtrate was concentrated under reduced pressure to obtain the crude product. After purification of the crude product obtained with MC / acetone, 6.7 g of AK43 were obtained. Synthesis method for AK83 Synthesis of intermediate D

[0177] The same procedure as for the synthesis of intermediate A was carried out, except that 2-amino-4-bromobenzethiol (36.8 g, 0.180 mol) was used instead of 2-amino-4-bromophenol. As a result, 18.5 g of intermediate D were obtained. Synthesis of AK83

[0178] An intermediate D (5 g, 0.017 mol), 2-(4-Biphenylyl)amino-9,9-dimethylfluorene (7.5 g, 0.021 mol), instead of intermediate A in the synthesis procedure for AK3, palladium acetate(II) (0.08 g, 0.345 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.21 g, 0.345 mmol), sodium t-butoxide (2.48 g, 0.026 mol) and toluene 100 mL are added and heated to 100°C for 8 hours with stirring.

[0179] The reaction solution was hot-filtered through silica gel to remove impurities, and the filtrate was concentrated under reduced pressure to obtain a crude product. Purification of the crude product with MC / acetone yielded 6.7 g of AK83. Synthesis of AK92

[0180] The synthesis was carried out in the same manner as in the synthesis procedure for AK83, with the difference that 2-(4-dibenzofuranyl)amino-9,9-dimethylfluorene (7.8 g, 0.021 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 7.0 g of AK92 were obtained. Synthesis of AK98

[0181] The synthesis was carried out using the same reagents, dosage, and procedure as in the synthesis procedure for AK83, except that bis(9,9-dimethyl-9H-fluoren-2-yl)amine (8.8 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 7.8 g of AK98 were obtained. Synthesis of AK103

[0182] The synthesis was carried out in the same manner as in the synthesis procedure for AK83, except that 2-(4-biphenylyl)amino-9,9-diphenylfluorene (10.6 g, 0.022 mol) was used instead of 2-(4-biphenylyl)amino-9,9-dimethylfluorene. 9.0 g of AK103 were obtained. Production and evaluation of an organic light-emitting element: Comparative example 1

[0183] 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 were formed on a substrate to fabricate an organic light-emitting element with a monostructure, as shown in Table 1 below. All properties of the organic light-emitting element fabricated according to the disclosure were evaluated at room temperature using a constant current source and a photometer. Table 1 Components materials anode ITO (Indium Tin Oxide) Hole injection layer HI1 Hole transport layer HT1 light-emitting layer EM1, EM2, EM3 electron transport layer ET1 Electron injection layer LiF cathode Al

[0184] The compounds used in the comparison examples are as follows. Comparative example 2 and embodiments 1 to 16

[0185] The organic light-emitting element was produced in the same way as in Comparative Example 1, except that the materials listed in Table 2 below were used instead of EM2 for the light-emitting layer. [Table 2] Light-emitting material Voltage difference Efficiency (Example of Implementation / Comparison Example 1, %) Service life (exemplar design example 1, %) Comparative example 1 EM2 - - - Comparative example 2 CF1 0.18 98% 98% Implementation example 1 AZ3 -0.14 112% 105% Implementation example 2 AZ5 -0.12 112% 108% Implementation example 3 AZ10 -0.23 116% 110% Implementation example 4 AZ11 -0.20 118% 108% Implementation example 5 AZ18 -0.32 104% 102% Implementation example 6 AZ20 -0.20 104% 105% Implementation example 7 AZ23 -0.18 113% 110% Implementation example 8 AZ43 -0.12 111 % 108% Implementation example 9 AZ83 -0.10 112% 105% Implementation example 10 AZ92 -0.14 115% 106% Implementation example 11 AZ98 -0.28 104% 101% Implementation example 12 AZ103 -0.16 113% 107%

[0186] Referring to Table 2, it can be seen that the organic light-emitting element according to embodiments of the disclosure has a better efficiency or lifetime than the organic light-emitting elements of the comparison examples.

[0187] In Comparative Example 1, EM2 was used as the host compound for the light-emitting layer. It is evident that the embodiments using compounds containing a core represented by chemical formula 1 exhibit higher efficiency and lifetime than Comparative Example 1.

[0188] In Comparative Example 2, CF1 was used as the host compound for the light-emitting layer. CF1 differs from the compound represented by chemical formula 1 in that the benzoxazole is bonded to the nitrogen of the amine via a phenylene group. It is evident that embodiments using compounds represented by chemical formula 1, in which the benzoxazole is directly bonded to the nitrogen of the amine, exhibit better efficiency and lifetime than Comparative Example 2.

Claims

[1] Organic light-emitting element (100, 200, 300, 400), comprising: a first electrode (110); a second electrode (120); and an organic material layer (130) arranged between the first electrode (110) and the second electrode (120), wherein the organic material layer (130) contains a compound represented by the chemical formula 1 below: in chemical formula 1 is: either X or Y equals N, and the other is S or O, where a is an integer from 0 to 5, R1 each independently selected from the group consisting of a C1-C 20 -Alkyl group; a C3-C 30 -Cycloalkyl group; an aryloxy group; an arylthioxy group; a fluorenyl group; and a C6-C 60 -Aryl group, R2 selected from the group consisting of a C3-C 30-Cycloalkyl group, an aryloxy group, an arylthioxy group, a fluorenyl group and a C6-C 60 -Aryl group, R3 and R4 each independently selected from the group consisting of i) a C1-C 20 -Alkyl group and a C6-C 60 -aryl groups, or are bonded together to form a ring, b is an integer from 0 to 3, R5 each independently a C6-C 60 -Aryl group, and The alkyl group, cycloalkyl group, aryloxy group, arylthioxy group, fluorenyl group and aryl group are each further substituted with one or more substituents selected from the group consisting of a halogen group; a C1-C 20 -Alkyl group; a C2-C 20 -Alkenyl group; a C2-C 20 -Alkynyl group; a fluorenyl group; a C6-C 20 -aryl group; and a heterocyclic C2-C2o group. [2] Organic light-emitting element (100, 200, 300, 400) according to claim 1, wherein the compound represented by chemical formula 1 is represented either by chemical formula 1a or chemical formula 1b below: where in chemical formula 1a and chemical formula 1b X and Y are S or O respectively, and R1, R2, R3, R4, R5, a and b are the same as defined above in chemical formula 1. [3] Organic light-emitting element (100, 200, 300, 400) according to claim 1, wherein the compound represented by chemical formula 1 is one or more of the following compounds: [4] Organic light-emitting element (100, 200, 300, 400) according to claim 1, wherein the organic material layer (130) contains a light-emitting layer (233, 3313, 3323, 4313, 4323, 4333), and wherein the light-emitting layer (233, 3313, 3323, 4313, 4323, 4333) contains the compound. [5] Organic light-emitting element (100, 200, 300, 400) according to claim 4, wherein the organic material layer (130) further comprises at least one of a hole injection layer (231, 3311, 3321, 4311, 4321, 4331), a hole transport layer (232, 3312, 3322, 4312, 4322, 4332), an electron transport layer (234, 3314, 3324, 4314, 4324, 4334) and an electron injection layer (235, 3315, 3325, 4315, 4325, 4335). [6] Organic light-emitting element (100, 200, 300, 400) according to claim 4 or 5, wherein the compound is a host compound (2331, 33131, 43131) of the light-emitting layer (233, 3313, 3323, 4313, 4323, 4333). [7] Organic light-emitting element (100, 200, 300, 400) according to claim 6, wherein the light-emitting layer (233, 3313, 3323, 4313, 4323, 4333) further comprises a host compound different from the compound. [8] Organic light-emitting element (300, 400) according to any one of claims 1 to 7, wherein the organic material layer (130) comprises a first stack (331, 431) with a first light-emitting layer (3313, 4313) and a second stack (332, 432) with a second light-emitting layer (3323, 4323). [9] Organic light-emitting element (300, 400) according to claim 8, wherein the first light-emitting layer (3313, 4313) contains the compound. [10] Organic light-emitting element (300, 400) according to claim 9, wherein the compound is a host compound (33131, 43131) of the first light-emitting layer (3313, 4313). [11] Organic light-emitting element (300, 400) according to claim 10, wherein the first light-emitting layer (3313, 4313) further comprises a host compound different from the compound.

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