Organic electroluminescence device

The introduction of a novel material combination, featuring a specific first compound and host materials with high triplet state energy levels, addresses the limitations of current blue phosphorescent OLEDs, enhancing device performance in terms of voltage, efficiency, and lifespan.

JP7690220B2Active Publication Date: 2025-06-10BEIJING SUMMER SPROUT TECH CO LTD
View PDF 8 Cites 0 Cited by

Patent Information

Application Number
JP2023219842
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2023-11-10
Filing Date
2023-12-26
Publication Date
2025-06-10
Estimated Expiration
2043-12-26

AI Technical Summary

Technical Problem

Current blue phosphorescent organic electroluminescence (OLED) devices face limitations in voltage, efficiency, and lifespan, and the efficiency of phosphorescent OLEDs decreases at high brightness.

Method used

A novel material combination is introduced, comprising a first compound with a specific structure and a combination of a first host material and a second host material with high triplet state energy levels, used in the light-emitting layer of the OLED device.

Benefits of technology

This novel material combination achieves excellent comprehensive device performance, including low voltage, high efficiency, and long service life, significantly improving the performance of blue light OLED devices.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 0007690220000135
    Figure 0007690220000135
  • Figure 0007690220000136
    Figure 0007690220000136
  • Figure 0007690220000001
    Figure 0007690220000001
Patent Text Reader

Abstract

To provide an organic electroluminescent element.SOLUTION: The organic electroluminescent element includes a positive electrode 110, a negative electrode 190, and an organic layer between the positive electrode 110 and the negative electrode 190. The organic layer includes at least a light-emitting layer 150. The light-emitting layer 150 includes a first compound having a structure expressed by Formula 1 and a first host material and a second host material having a high triplet state energy level.SELECTED DRAWING: Figure 1
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] The present invention relates to organic electronic devices, such as organic electroluminescence devices. In particular, the present invention relates to an organic electroluminescence device including a first compound having a structure represented by Formula 1 in an organic light-emitting layer, and a novel material combination including a first host material and a second host material having a high triplet state energy level, an electronic device including the organic electroluminescence device, a first compound having a structure represented by Formula 1, and a compound composition of a first host material and a second host material having a high triplet state energy level.

Background Art

[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field effect quantum dots (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a two-layer organic electroluminescent device that includes an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12):913 - 915). Once a bias is applied to the device, green light is emitted from the device. This invention has laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may include multiple layers such as charge injection / transport layers, charge / exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-emitting solid-state devices, they offer great potential for display and lighting applications. Also, the inherent properties of organic materials, such as their flexibility, are well-suited for special applications such as manufacturing on flexible substrates.

[0004] OLEDs are classified into three different types according to their emission mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs, which use only singlet emission. This limitation hinders the commercialization of OLEDs because the triplets generated in the device are wasted through non-radiative decay pathways, and the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. In 1997, phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters were reported by Forrest and Thompson. Therefore, both singlets and triplets can be harvested to achieve 100% IQE. Due to their high efficiency, the discovery and development of phosphorescent OLEDs directly contribute to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiency by thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling excitons to transition from triplets to singlets. In TADF devices, the IQE is high due to the generation of singlet excitons by the penetration of triplet excitons between reverse systems (reverse intersystem crossing).

[0005] OLEDs can also be further divided into small molecule and polymer OLEDs according to the form of the materials used. Small molecules refer to either organic or organometallic materials that are not polymers, and even if the molecular weight of small molecules is large, they can have an exact structure. Dendrimers with a definite structure are recognized as small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with luminescent groups in the side chains. When post-polymerization occurs during the manufacturing process, small molecule OLEDs can become polymer OLEDs.

[0006] Various manufacturing methods of OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the material can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.

[0007] The emission color of an OLED can be realized by the structural design of the luminescent material. The OLED may include one or more emission layers so as to realize a desired spectrum. In green, yellow, and red OLEDs, phosphorescent materials have already been successfully commercialized. However, for blue phosphorescent devices, there are still problems such as unsaturated blue, short lifespan, and high operating voltage. Commercially available full-color OLED displays generally use a hybrid strategy, using blue fluorescence and yellow, red, or green phosphorescence. Currently, there is a problem that the efficiency of phosphorescent OLEDs rapidly decreases at high brightness. Also, it is desired to have a more saturated emission spectrum, higher efficiency, and longer device lifespan.

[0008] US20210284672A1 discloses a metal complex including the following general formula structure and its use in an organic electroluminescence device. [Chemical formula] or [Chemical formula] However, at least one of R A1 , R A2 , R A4 , R A5 , R A6 includes a structure represented by [Chemical formula] [Chemical formula] or [Chemical formula] and the compound is [Chemical formula] When selected from the structure, R A1 and R A2 One of them is [Chemical formula] and R M R N and R O At least one of them is selected from the group consisting of deuterium, alkyl group, cycloalkyl group, heteroalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, and combinations thereof. In the application, in a specific structure, some platinum metal compounds, such as [Chemical formula] and [Chemical formula] are disclosed. In an embodiment of the device, when the metal complex is used as a light-emitting material and the compound is [Chemical formula] applied to an organic electroluminescence device as a single host, it is disclosed that good effects can be obtained. However, in the application, the combination of the metal complex and the double host material is not disclosed or taught, and further, the use of the combination of the metal complex and the double host material in an organic electroluminescence device is not disclosed or taught.

[0009] US20220112231A1 discloses a light-emitting device. Its light-emitting layer contains a guest metal light-emitting material, and its general formula is [Chemical formula] However, CY 1 ~CY 6 are each independently C3 ~C 60 selected from the carbon rings of or C 1 ~C 60 heterocyclic rings of. As can be seen from this, the application discloses a metal complex having a specific condensed ring structure in benzimidazole. In the application, the following structures are disclosed in specific structures. [Chemical formula] [Chemical formula]

[0010] In an embodiment of the device, it is disclosed that by using the metal complex as a light-emitting material and CBP as a single host, the performance of the light-emitting device is examined. However, in the application, the combination of the metal complex and the double host material is not disclosed or taught, and further, the use of the combination of the metal complex and the double host material in an organic electroluminescence device is not disclosed or taught.

[0011] In the above-mentioned prior art, metal complexes having a plurality of substituted aromatic groups at the N position of some imidazole carbenes are disclosed and can be used in blue light devices in combination with different types of host materials. However, in the study of these blue phosphorescent devices, there are still certain limitations in their voltage, device efficiency, service life, etc., so it is necessary to conduct in-depth research and development on blue phosphorescent devices. The present inventor has discovered, through in-depth research, a novel material combination in which a metal complex having a specific plurality of substituted aromatic groups in the imidazole carbene ring is combined with a double host material having a high triplet state as a light-emitting material. By using this novel material combination in a blue phosphorescent light-emitting device, unexpectedly excellent device performance can be obtained. [Prior art documents] [Patent documents]

[0012] [Patent Document 1] U.S. Patent Application Publication No. 20210284672 [Patent Document 2] U.S. Patent Application Publication No. 20220112231 [Non-Patent Document]

[0013] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12): 913 - 915 [Summary of the Invention] [Problems to be Solved by the Invention]

[0014] The present invention provides an organic electroluminescence device having a novel material combination to solve at least some of the above-described problems. The organic electroluminescence device uses a first compound having a structure represented by Formula 1, and a novel material combination composed of a first host material and a second host material having a high triplet state energy level. This novel material combination can be used in the light-emitting layer of the organic electroluminescence device. This novel material combination exhibits excellent comprehensive device performance in the device, for example, low voltage, high efficiency, and / or long service life. These advantages contribute significantly to the improvement of the level of blue light devices. [Means for Solving the Problems]

[0015] According to an embodiment of the present invention, there is provided an organic electroluminescence device including an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer includes a light-emitting layer, and the light-emitting layer contains a first compound, a first host material, and a second host material, the triplet state energy levels of both the first host material and the second host material are higher than the triplet state energy level of the first compound, the first compound has a structure represented by Formula 1, [Chemical formula] In Formula 1, ring A, ring B, and ring E are each independently selected, every time they appear, from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; ring D is each independently selected, every time it appears, from an unsaturated heterocyclic ring having 3 to 30 carbon atoms. Metal M is selected from metals having a relative atomic mass greater than 40. L 1 , L 2 are each independently selected, every time they appear, from a single bond, O, S, Se, (SiR’’R’’) y , PR’’, NR’’, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof. y is 1, 2, 3, 4, or 5. K 1 ~K 4 are each independently selected, every time they appear, from a single bond, O, or S. Z 1 ~Z 3 are each independently selected, every time they appear, from C or N. R in Formula 1 has a structure represented by Formula 2. [Chemical formula] In Formula 2, ring F, ring G, and ring N are each independently selected, every time they appear, from an unsaturated carbocyclic ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof. Z 4 ~Z 7 are each independently selected, every time they appear, from C or N. R a , R b , R d , R e , R f , R g each independently represent, every time they appear, monosubstituted, polysubstituted, or unsubstituted. R n each independently represent, every time they appear, monosubstituted or polysubstituted. R'', R a , R b , R d , R e , R f , R g , R n are, each time they appear, the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, In ring N in Formula 2, at least one R nis selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, "*" represents the bonding position of Formula 2, adjacent substituents R'', R a 、R b 、R d 、R e 、R f 、R g 、R n An organic electroluminescence device is disclosed, wherein adjacent substituents R'', R, R, R, R, R, R, R may combine to form a ring.

[0016] According to another embodiment of the present invention, an electronic device including the above-described organic electroluminescence device is further disclosed.

[0017] According to another embodiment of the present invention, a compound composition including at least a first compound, a first host material, and a second host material is disclosed.

[0018] The present invention discloses a novel organic electroluminescence device. A novel material combination consisting of a first compound, a first host material, and a second host material is used in the organic electroluminescence device. This novel material combination can be used in the light-emitting layer of the electroluminescence device. This novel material combination exhibits excellent comprehensive device performance in the device, such as low voltage, high efficiency, long service life, etc.

Brief Description of the Drawings

[0019]

Figure 1

Figure 2

Embodiments for Carrying Out the Invention

[0020] OLEDs can be manufactured on various substrates such as glass, plastic, and metal. FIG. 1 shows the organic light-emitting device 100 without being limited exemplarily. The drawings are not necessarily made to scale, and in the figures, some layer structures may be omitted as necessary. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be manufactured by depositing the described layers in sequence. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of US Patent US7279704B2, and all of its contents are incorporated herein by reference.

[0021] There are more examples for each of these layers. Exemplarily, in U.S. Patent No. 5,844,363 incorporated herein by reference in its entirety, a flexible and transparent substrate-anode combination is disclosed. For example, in U.S. Patent Application Publication No. 2003 / 0230980 incorporated herein by reference in its entirety, an example of a p-type doped hole transport layer is m-MTDATA doped with F 4 -TCNQ at a molar ratio of 50:1. In U.S. Patent No. 6,303,238 by Thompson et al. incorporated herein by reference in its entirety, examples of host materials are disclosed. For example, in U.S. Patent Application Publication No. 2003 / 0230980 incorporated herein by reference in its entirety, an example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1. In U.S. Patents No. 5,703,436 and 5,707,745 incorporated herein by reference in their entirety, examples of cathodes are disclosed that include a composite cathode having a thin metal layer such as Mg:Ag and a sputter-deposited transparent conductive ITO layer coated thereon. In U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980 incorporated herein by reference in their entirety, more specifically, the principle and use of blocking layers are described. In U.S. Patent Application Publication No. 2004 / 0174116 incorporated herein by reference in its entirety, examples of injection layers are provided. In U.S. Patent Application Publication No. 2004 / 0174116 incorporated herein by reference in its entirety, protective layers are described.

[0022] The above-described layered structure is provided by non-limiting examples. By combining the various layers described above, the functions of the OLED can be realized, or some layers can be completely omitted. It may also include other layers not specifically described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any of the functional layers may include multiple sub-layers. For example, the light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0023] In one embodiment, the OLED may be described as having an "organic layer" provided between a cathode and an anode. The organic layer may include one or more layers.

[0024] An OLED also requires a encapsulation layer. As shown in FIG. 2, the organic light-emitting device 200 is shown by way of example without limitation. The difference from FIG. 1 is that an encapsulation layer 102 may be included on the cathode 190 so as to prevent harmful substances from the outside world such as moisture and oxygen. Any material capable of providing an encapsulation function such as glass or an organic-inorganic hybrid layer may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly outside the OLED element. Multilayer thin-film encapsulation is described in U.S. Patent US7968146B2, the entire content of which is incorporated herein by reference.

[0025] The device manufactured according to an embodiment of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. These consumer products include, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting lamps and / or signal lamps, head-up displays, all or partially transparent displays, flexible displays, smart phones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, in-vehicle displays and tail lights.

[0026] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0027] "Top" means furthest from the substrate, and "bottom" means closest to the substrate. When it is described that the first layer is provided "on" the second layer, the first layer is provided to be relatively far from the substrate. Unless the first layer is defined to "contact" the second layer, other layers may exist between the first layer and the second layer. Exemplarily, even if various organic layers exist between the cathode and the anode, it can still be described that the cathode is provided "on" the anode.

[0028] "The solution is processable" means that it can be dissolved, dispersed or transported in a liquid medium in the form of a solution or suspension, and / or can be deposited from the liquid medium.

[0029] It is believed that a ligand may be called "photosensitive" if it directly facilitates the photosensitive properties of the emissive material. A ligand may be called "auxiliary" if it does not facilitate the photosensitive properties of the emissive material. However, it is believed that an auxiliary ligand can modify the properties of a photosensitive ligand.

[0030] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED may exceed the 25% spin statistical limit due to the presence of delayed fluorescence. Delayed fluorescence may generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0031] On the one hand, E-type delayed fluorescence depends not on the collision of two triplets but on the conversion of the excited state between the triplet and the singlet state. Compounds capable of generating E-type delayed fluorescence need to have a very small singlet-triplet gap so as to perform the conversion of the energy state. Thermal energy can activate the transition from the triplet state to the singlet state. Such a type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component improves with the increase in temperature. When the rate of penetration (reverse intersystem crossing) between reverse intersystem crossing (RISC) is fast enough, non-radiative decay from the triplet state is minimized, and the proportion of the excited state of the backfilled singlet can reach 75%. The total proportion of the singlet may be 100%, far exceeding 25% of the spin statistics of the excitons by electrons.

[0032] The characteristics of E-type delayed fluorescence can be seen from the excited complex system or a single compound. Without being limited to theory, for E-type delayed fluorescence, the luminescent material needs to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials have the potential to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT) type emission. In these donor-acceptor type compounds, the spatial separation between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) generally results in a small ΔE S-T . These states may include CT states. Usually, donor-acceptor luminescent materials are constructed by bonding an electron donor part (for example, an amine group or a carbazole derivative) and an electron acceptor part (for example, an N-containing six-membered aromatic ring).

[0033] Regarding the definition of the terminology of substituents

[0034] As used herein, halogen or halide includes fluorine, chlorine, bromine, and iodine.

[0035] As used herein, the alkyl group includes linear and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among them, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. Further, the alkyl group may be substituted.

[0036] As used herein, the cycloalkyl group includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of the cycloalkyl group include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl group, 2-norbornyl group and the like. Among them, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. Further, the cycloalkyl group may be substituted.

[0037] As used herein, a heteroalkyl group is one in which one or more carbons in the alkyl chain are substituted with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom, and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of the heteroalkyl group include a methoxymethyl group, an ethoxymethyl group, an ethoxyethyl group, a methylthiomethyl group, an ethylthiomethyl group, an ethylthioethyl group, a methoxymethoxymethyl group, an ethoxymethoxymethyl group, an ethoxyethoxyethyl group, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a mercaptomethyl group, a mercaptoethyl group, a mercaptopropyl group, an aminomethyl group, an aminoethyl group, an aminopropyl group, a dimethylaminomethyl group, a trimethylgermanilylmethyl group, a trimethylgermanilylethyl group, a trimethylgermanilylisopropyl group, a dimethylethylgermanilylmethyl group, a dimethylisopropylgermanilylmethyl group, a tert-butyldimethylgermanilylmethyl group, a triethylgermanilylmethyl group, a triethylgermanilylethyl group, a triisopropylgermanilylmethyl group, a triisopropylgermanilylethyl group, a trimethylsilylmethyl group, a trimethylsilylethyl group, a trimethylsilylisopropyl group, a triisopropylsilylmethyl group, and a triisopropylsilylethyl group. Further, the heteroalkyl group may be substituted.

[0038] As used herein, the alkenyl group includes linear, branched, and cyclic olefin groups. The chain alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include vinyl group, propylene group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group, cyclopentenyl group, cyclopentadienyl group, cyclohexenyl group, cycloheptenyl group, cycloheptatrienyl group, cyclooctenyl group, cyclooctatetraenyl group, and norbornyl alkenyl group. Further, the alkenyl group may be substituted.

[0039] As used herein, the alkynyl group includes linear alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of the alkynyl group include ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3,3-dimethyl-1-butynyl group, 3-ethyl-3-methyl-1-pentynyl group, 3,3-diisopropyl 1-pentynyl group, phenylethynyl group, phenylpropynyl group, etc. Among them, ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, phenylethynyl group are preferred. Further, the alkynyl group may be substituted.

[0040] As used herein, the aryl group or aromatic group takes into account non-condensed and condensed systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, and preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-dimethylphenyl, mesitylene and m-tetraphenyl. Also, the aryl group may be substituted.

[0041] As used herein, the heterocyclic group refers to an acyclic group. The acyclic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated acyclic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. The acyclic heterocyclic group preferably has 3 to 7 ring atoms and contains at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of the acyclic heterocyclic group include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydro-silol. Further, the heterocyclic group may be substituted.

[0042] As used herein, the heteroaryl group may include non-condensed and condensed heteroaromatic groups having 1 to 5 heteroatoms, and at least one of the heteroatoms is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. The isoaryl group also refers to the heteroaryl group. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, and more preferably a heteroaryl group having 3 to 12 carbon atoms. Preferred heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furandipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably includes dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogs. Further, the heteroaryl group may be substituted.

[0043] As used herein, an alkoxy group is represented by -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group or -O-heterocyclic group. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Further, the alkoxy group may be substituted.

[0044] As used herein, an aryloxy group is represented by -O-aryl group or -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. Further, the aryloxy group may be substituted.

[0045] As used herein, an aralkyl group includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among them, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred. Further, the aralkyl group may be substituted.

[0046] As used herein, an alkylsilyl group includes a silyl group substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Also, the alkylsilyl group may be substituted.

[0047] As used herein, an arylsilyl group includes a silyl group substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl, phenyldibiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyl-tert-butylsilyl. Also, the arylsilyl group may be substituted.

[0048] As used herein, an alkylgermanium group includes a germanium group substituted with an alkyl group. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of the alkylgermanium group include trimethylgermanium group, triethylgermanium group, methyldiethylgermanium group, ethyldimethylgermanium group, tripropylgermanium group, tributylgermanium group, triisopropylgermanium group, methyldiisopropylgermanium group, dimethylisopropylgermanium group, tri-tert-butylgermanium group, triisobutylgermanium group, dimethyl-tert-butylgermanium group, and methyldi-tert-butylgermanium group. Further, the alkylgermanium group may be substituted.

[0049] As used herein, an arylgermanium group includes a germanium group substituted with at least one aryl group or heteroaryl group. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include triphenylgermanium group, phenyldibiphenylgermanium group, diphenylbiphenylgermanium group, phenyldiethylgermanium group, diphenylethylgermanium group, phenyldimethylgermanium group, diphenylmethylgermanium group, phenyldiisopropylgermanium group, diphenylisopropylgermanium group, diphenylbutylgermanium group, diphenylisobutylgermanium group, and diphenyl-tert-butylgermanium group. Further, the arylgermanium group may be substituted.

[0050] In azadibenzofuran, azadibenzothiophene, etc., "aza" refers to the substitution of one or more C-H groups in the corresponding aromatic fragment by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. A person skilled in the art can easily conceive of other nitrogen analogs of the above-described aza derivatives, and all of these analogs are determined to be included in the technical terms described herein.

[0051] In the present invention, unless otherwise specified, when any term from the group consisting of a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanyl group, a substituted arylgermanyl group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, a substituted sulfinyl group, a substituted sulfonyl group, and a substituted phosphino group is used, it means that an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, an aralkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, an alkylgermanyl group, an arylgermanyl group, an amino group, an acyl group, a carbonyl group, a carboxyl group, an ester group, a sulfinyl group, a sulfonyl group, and a phosphino group may be substituted by one or more selected from deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, an unsubstituted arylgermanyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0052] Regarding a molecular fragment, when it is described that it is attached to another moiety in the form of a substituent or otherwise, it should be understood that the name can be determined depending on whether it is a fragment (e.g., phenyl group, phenylene group, naphthyl group, dibenzofuranyl group) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, different forms of substituent designation or attachment of a fragment are considered to be equivalent.

[0053] In the compounds referred to herein, the hydrogen atoms may be partially or fully substituted with deuterium. Other atoms, such as carbon and nitrogen, may also be substituted with their other stable isotopes. Substitution with other stable isotopes in the compounds may be preferred in order to improve the efficiency and stability of the device.

[0054] In the compounds referred to herein, multiple substitution refers to the range up to the most possible substitutions including double substitution. When a certain substituent in the compounds referred to herein means multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on its bonding structure, and the substituents present at all of the multiple available substitution positions may have the same structure or different structures.

[0055] In the compounds referred to in this specification, unless otherwise particularly limited such that adjacent substituents may combine to form a ring, the adjacent substituents in said compounds cannot combine to form a ring. In the compounds referred to in this specification, the fact that adjacent substituents may combine to form a ring includes not only the case where adjacent substituents may combine to form a ring, but also the case where adjacent substituents do not combine to form a ring. When adjacent substituents may combine to form a ring, the ring formed may be a monocyclic or polycyclic ring, and may be an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a heteroaryl ring. In such a description, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0056] The description that adjacent substituents may combine to form a ring is also recognized to mean that two substituents bonded to the same carbon atom combine with each other by a chemical bond to form a ring, and can be exemplified by the following formula.

Chemical formula

[0057] The description that adjacent substituents may combine to form a ring is also recognized to mean that two substituents bonded to carbon atoms directly bonded to each other combine with each other by a chemical bond to form a ring, and can be exemplified by the following formula.

Chemical formula

[0058] The description that adjacent substituents may combine to form a ring is also recognized to mean that two substituents bonded to carbon atoms further apart combine with each other by a chemical bond to form a ring, and can be exemplified by the following formula. [Chemistry]

[0059] Also, the description that adjacent substituents may combine to form a ring is also recognized to mean that when one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position where a hydrogen atom is bonded to form a ring. This is exemplified by the following formula. [Chemistry]

[0060] According to one embodiment of the present invention, there is provided an organic electroluminescence device including an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer contains a first compound, a first host material, and a second host material, the triplet state energy levels of the first host material and the second host material are both higher than the triplet state energy level of the first compound, the first compound has a structure represented by Formula 1, [Chemistry] In Formula 1, ring A, ring B, and ring E are each independently selected, each time they appear, from an unsaturated carbon ring having 5 to 30 carbon atoms, an unsaturated heterocycle having 3 to 30 carbon atoms, or a combination thereof; ring D is each independently selected, each time it appears, from an unsaturated heterocycle having 3 to 30 carbon atoms, metal M is selected from metals having a relative atomic mass greater than 40, L 1 L 2 are each independently selected, each time they appear, from a single bond, O, S, Se, (SiR’’R’’) y , PR’’, NR’’, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof, y is 1, 2, 3, 4, or 5, K 1~K 4 is, each time it appears, the same or different, and is selected from a single bond, O or S, Z 1 ~Z 3 is, each time it appears, the same or different, and is selected from C or N, R in Formula 1 has a structure represented by Formula 2,

Chemical formula

[0061] In this example, two adjacent substituents R a may combine to form a ring. The ring is a ring that does not contain Te, O, S, or Se.

[0062] In this example, two adjacent substituents R aThe atoms may combine to form a carbocyclic ring or a heterocyclic ring containing one or more heteroatoms selected from B, N, Si, P, and Ge atoms. The carbocyclic ring includes an aromatic unsaturated carbocyclic ring and a non-aromatic unsaturated carbocyclic ring, and the heterocyclic ring includes an aromatic unsaturated heterocyclic ring and a non-aromatic unsaturated heterocyclic ring.

[0063] As used herein, the "unsaturated carbocyclic ring having 5 to 30 carbon atoms" includes an aromatic unsaturated carbocyclic ring and a non-aromatic unsaturated carbocyclic ring having 5 to 30 carbon atoms. The "unsaturated heterocyclic ring having 3 to 30 carbon atoms" includes an aromatic unsaturated heterocyclic ring and a non-aromatic unsaturated heterocyclic ring having 3 to 30 carbon atoms.

[0064] As used herein, when it is said that adjacent substituents R'', R a , R b , R d , R e , R f , R g , R n may combine to form a ring, it means that any one or more of adjacent substituent groups, for example, two substituents R'' with each other, two substituents R a with each other, two substituents R b with each other, two substituents R d with each other, two substituents R e with each other, two substituents R f with each other, two substituents R g with each other, two substituents R n with each other may combine to form a ring. Obviously, all of these adjacent substituent groups do not necessarily combine to form a ring.

[0065] According to an embodiment of the present invention, the first compound has a structure represented by the general formula M(L a )(L b ), where L a and L b are a first ligand and a second ligand that coordinate with the metal M, respectively, and the L a has a structure represented by Formula A.

Chemical formula

Chemical formula

Chemical formula

[0066] According to an embodiment of the present invention, the above-mentioned M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir or Pt

[0067] According to an embodiment of the present invention, the above-mentioned M is selected from Pt or Pd

[0068] According to an embodiment of the present invention, the above-mentioned M is selected from Pt

[0069] According to an embodiment of the present invention, the above-mentioned Ring A, Ring B, Ring E, Ring F, Ring G and Ring N are each independently selected from a 5-membered unsaturated carbon ring, an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 3 to 30 carbon atoms, or a combination thereof, each time they appear

[0070] According to an embodiment of the present invention, the above-mentioned Ring A, Ring B, Ring E, Ring F, Ring G and Ring N are each independently selected from a 5-membered unsaturated carbon ring, an aryl ring having 6 to 18 carbon atoms, a heteroaryl ring having 3 to 18 carbon atoms, or a combination thereof, each time they appear

[0071] According to an embodiment of the present invention, each occurrence of the ring A, ring B, ring E, ring F, ring G, and ring N is the same or different and is selected from a benzene ring, a pyridine ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, an indolocarbazole ring, a benzofuran ring, a dibenzofuran ring, a benzosilole ring, a dibenzosilole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof.

[0072] According to an embodiment of the present invention, each occurrence of the ring D is the same or different and is selected from unsaturated heterocycles having 3 to 18 carbon atoms.

[0073] According to an embodiment of the present invention, each occurrence of the ring D is the same or different and is selected from an imidazole carbene ring or a benzimidazole carbene ring.

[0074] According to an embodiment of the present invention, the L 1 is selected from a single bond, O, S, (SiR’’R’’) y , NR’’, or a combination thereof, and y is 1 or 2.

[0075] According to an embodiment of the present invention, the L 1 is selected from a single bond, O, or S.

[0076] According to an embodiment of the present invention, the L 1 is selected from a single bond.

[0077] According to an embodiment of the present invention, the K 1 ~K 4 is selected from a single bond.

[0078] According to an embodiment of the present invention, the Z 1 is selected from N, and Z 2 and Z 3 are selected from C.

[0079] According to an embodiment of the present invention, the Z 4~Z 7 is selected from C.

[0080] According to an embodiment of the present invention, the first compound has a structure represented by one of Formula 1-1 to Formula 1-20,

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0081] In this example, two adjacent substituents R x may combine to form a ring. The ring is a ring that does not contain Te, O, S, or Se.

[0082] In this example, two adjacent substituents R x may combine to form a carbocyclic ring or a heterocyclic ring containing one or more heteroatoms selected from B, N, Si, P, and Ge atoms. The carbocyclic ring includes an aromatic unsaturated carbocyclic ring and a non-aromatic unsaturated carbocyclic ring. The heterocyclic ring includes an aromatic unsaturated heterocyclic ring and a non-aromatic unsaturated heterocyclic ring.

[0083] In this specification, when adjacent substituents R’, R’’, R x , R f , R g , R n may combine to form a ring, it means that any one or more of adjacent substituent groups, for example, two substituents R’’ with each other, two substituents R x with each other, two substituents R f with each other, two substituents R g with each other, two substituents R n with each other may combine to form a ring. Obviously, it is not necessary for all of these adjacent substituent groups to combine to form a ring.

[0084] According to one embodiment of the present invention, the first compound has a structure represented by Formula 1-1 or Formula 1-2.

[0085] According to one embodiment of the present invention, the first compound

Chemical formula

[0086] According to one embodiment of the present invention, the R x , R’, R f , R g , R n all

Chemical formula

[0087] According to one embodiment of the present invention, the R x , R’, R f , R g , R nis, each occurrence being the same or different, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a heterocyclic group containing one or more heteroatoms selected from substituted or unsubstituted O, S, Se, Si, P and Ge atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a heteroaryl group containing one or more heteroatoms selected from substituted or unsubstituted O, S, Se, Si, P and Ge atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0088] According to one embodiment of the present invention, said N 2 is selected from CR n and said R n is, each occurrence being the same or different, deuterium, halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0089] According to one embodiment of the present invention, the N 2 is selected from CR n and the R n is, each time it appears, the same or different and is selected from the group consisting of deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0090] According to one embodiment of the present invention, the N 2 is selected from CR n and the R n is, each time it appears, the same or different and is selected from the group consisting of deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0091] According to one embodiment of the present invention, the N 2 is selected from CR n and the R nis selected from the group consisting of deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 4 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof, each occurrence being the same or different.

[0092] According to one embodiment of the present invention, the N 2 is selected from CR n and the R n is

Chemical formula

[0093] According to one embodiment of the present invention, the N 1 and N 3 are each independently selected from CH or CD.

[0094] According to one embodiment of the present invention, the N 2 is selected from CR n and the R nis selected from the group consisting of deuterium, fluorine, cyano group, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, and combinations thereof, each occurrence being the same or different.

[0095] According to one embodiment of the present invention, the N 2 is selected from CR n and the R n is selected from unsubstituted alkyl groups having 1 to 6 carbon atoms, partially or fully deuterated alkyl groups having 1 to 6 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, or partially or fully deuterated cycloalkyl groups having 3 to 6 ring carbon atoms, each occurrence being the same or different.

[0096] According to one embodiment of the present invention, the N 2 is selected from CR n and the R n is selected from methyl group, deuterated methyl group, ethyl group, partially or fully deuterated ethyl group, n-propyl group, partially or fully deuterated n-propyl group, isopropyl group, partially or fully deuterated isopropyl group, cyclopropyl group, partially or fully deuterated cyclopropyl group, n-butyl group, partially or fully deuterated n-butyl group, isobutyl group, partially or fully deuterated isobutyl group, tert-butyl, partially or fully deuterated tert-butyl, cyclopentyl group, partially or fully deuterated cyclopentyl group, cyclohexyl group, partially or fully deuterated cyclohexyl group, and combinations thereof, each occurrence being the same or different.

[0097] According to one embodiment of the present invention, the X 1 ~X 20 is selected from CR x each occurrence being the same or different.

[0098] According to one embodiment of the present invention, the above X 9 and X 10 are each independently selected from CR x and the above R x is, each time it appears, the same or different and is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a heterocyclic group containing one or more heteroatoms selected from substituted or unsubstituted O, S, Se, B, Si, P, and Ge atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a heteroaryl group containing one or more heteroatoms selected from substituted or unsubstituted O, S, Se, B, Si, P, and Ge atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a group consisting of combinations thereof.

[0099] According to one embodiment of the present invention, the above F 1 to F 5 are each independently selected from CR f

[0100] According to one embodiment of the present invention, the above G 1 to G 5 are each independently selected from CR g ​​

[0101] According to one embodiment of the present invention, the N 1 ~N 3 are each independently selected from CR n .

[0102] According to one embodiment of the present invention, the L 2 is selected from a single bond, O, S, (SiR’’R’’) y , NR’’, or a combination thereof.

[0103] According to one embodiment of the present invention, the R’’ is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0104] According to one embodiment of the present invention, the R’’ is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, tert-butyl, cyclopentyl group, cyclohexyl group, phenyl group, trimethylsilyl group, carbazole group, indole group, benzofuran group, dibenzofuran group, benzosilole group, dibenzosilole group, benzothiophene group, dibenzothiophene group, dibenzoselenophene group, and combinations thereof.

[0105] According to one embodiment of the present invention, the L 2 is selected from a single bond, O or S.

[0106] According to one embodiment of the present invention, the L 2 is selected from O.

[0107] According to one embodiment of the present invention, the R x , R’, R f , R g are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof, each occurrence being the same or different.

[0108] According to one embodiment of the present invention, the R x , R’, R f , R g are each independently selected from the group consisting of hydrogen, deuterium, fluorine, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, tert-butyl, cyclopentyl group, cyclohexyl group, phenyl group, trimethylsilyl group, carbazole group, indole group, benzofuran group, dibenzofuran group, benzosilole group, dibenzosilole group, benzothiophene group, dibenzothiophene group, dibenzoselenophene group, and combinations thereof, each occurrence being the same or different.

[0109] According to one embodiment of the present invention, at least one of the R f is selected from deuterium, halogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0110] According to one embodiment of the present invention, at least one of the R g is selected from deuterium, halogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0111] According to one embodiment of the present invention, the R f are all selected from deuterium.

[0112] According to an embodiment of the present invention, the R g are all selected from deuterium.

[0113] According to an embodiment of the present invention, each occurrence of the formula 2-1 is the same or different and is selected from the group consisting of An-1 to An-82 and An-92. The specific structures of An-1 to An-82 and An-92 are shown in claim 13.

[0114] According to an embodiment of the present invention, the hydrogen in the An-1 to An-82 and An-92 structures may be partially or fully deuterated.

[0115] According to an embodiment of the present invention, the first compound has a structure represented by Pt(L a )(L b ) or Pd(L a )(L b ). L a and L b are the first ligand and the second ligand that coordinate with the metal Pt or Pd, respectively. The L a is L a 1-1 to L a 1-76, L a 1-86 to L a 1-93, L a 2-1 to L a 2-42, L a 3-1 to L a 3-40, L a 4-1 to L a 4-17, and L a 4-19 to L a 4-53, and is selected from the group consisting of. The L b is L b 1-1 to L b 1-9, L b 1-12 to L b 1-22, L b 2-1 to L b 2-30, L b 3-1 to L b 3-26, L b 4-1 to L b 4-25, and L b 5-1 to L bSelected from the group consisting of 5 - 11. The said L a 1 - 1 to L a 1 - 76, L a 1 - 86 to L a 1 - 93, L a 2 - 1 to L a 2 - 42, L a 3 - 1 to L a 3 - 40, L a 4 - 1 to L a 4 - 17, L a 4 - 19 to L a 4 - 53, L b 1 - 1 to L b 1 - 9, L b 1 - 12 to L b 1 - 22, L b 2 - 1 to L b 2 - 30, L b 3 - 1 to L b 3 - 26, L b 4 - 1 to L b 4 - 25, and L b 5 - 1 to L b The specific structure of 5 - 11 is shown in claim 14.

[0116] According to an embodiment of the present invention, the first compound is selected from the group consisting of compound Pt1 to compound Pt76, compound Pt86 to compound Pt180, compound Pt182 to compound Pt260, compound Pt305 to compound Pt680 and compound Pd1 to compound Pd24, and the specific structures of compound Pt1 to compound Pt76, compound Pt86 to compound Pt180, compound Pt182 to compound Pt260, compound Pt305 to compound Pt680 and compound Pd1 to compound Pd24 are shown in claim 14.

[0117] According to an embodiment of the present invention, the first compound is selected from the group consisting of compounds Pt1 to Pt76, compounds Pt86 to Pt180, compounds Pt182 to Pt260, compounds Pt305 to Pt681, and compounds Pd1 to Pd24. The specific structures of the compounds Pt1 to Pt76, compounds Pt86 to Pt180, compounds Pt182 to Pt260, compounds Pt305 to Pt680, and compounds Pd1 to Pd24 are shown in claim 14. The specific structure of compound Pt681 is

Chemical formula

[0118] According to an embodiment of the present invention, the triplet state energy level of the first host material is higher than 2.69 eV.

[0119] According to an embodiment of the present invention, the first host material has a structure represented by any one of formulas 3 to 5,

Chemical formula

[0120] In this example, adjacent substituents R 4 may be bonded to form a ring means that any two substituents R 4 may be bonded to form a ring. Clearly, any two substituents R 4 do not have to be bonded to form a ring.

[0121] According to an embodiment of the present invention, the first host material is a deuterated compound.

[0122] As used herein, the "deuterated compound" refers to a compound in which at least one H in the compound is replaced by deuterium (D). For example, the compound may be at least 10% deuterated (where "% deuteration" refers to the ratio of deuterium to the sum of hydrogen and deuterium), or at least 20% deuterated, or at least 30% deuterated, or at least 40% deuterated, or at least 50% deuterated, or at least 60% deuterated, or at least 70% deuterated, or at least 80% deuterated, or at least 90% deuterated, or 100% deuterated.

[0123] According to one embodiment of the present invention, the first host material has a structure represented by Formula 4.

[0124] According to one embodiment of the present invention, the first host material has a structure represented by Formula 4-1,

Chemical formula

[0125] According to one embodiment of the present invention, in Formula 4-1, the Z 41 ~Z 48 at least one of which is selected from N, and at least two are selected from CR 4 ’.

[0126] According to one embodiment of the present invention, in Formula 4-1, only one of the Z 41 ~Z 48 is selected from N, and only two are selected from CR 4 ’.

[0127] According to one embodiment of the present invention, in Formula 4-1, the Z 42 is selected from N, and the Z 41 and Z 46 are selected from CR 4 ’.

[0128] According to one embodiment of the present invention, in Formula 3, the Z 1 ~Z 3 Among them, at least two are N.

[0129] According to one embodiment of the present invention, in Formula 3, Z 1 ~Z 3 is N.

[0130] According to one embodiment of the present invention, in Formula 3, L is, each occurrence being the same or different, a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, and a group consisting of combinations thereof.

[0131] According to one embodiment of the present invention, in Formula 3, L is, each occurrence being the same or different, a single bond, a phenylene group, a biphenylene group, a fluorenylene group, a triphenylenylene, a furylene group, a thienylene group, a dibenzofurylene group, a dibenzothienylene group, and a group consisting of combinations thereof.

[0132] According to one embodiment of the present invention, the R 1 ~R 4 are, each occurrence being the same or different, hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and a group consisting of combinations thereof.

[0133] According to one embodiment of the present invention, the R 1 ~R 4is independently selected, each occurrence, from the group consisting of hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

[0134] According to one embodiment of the present invention, the R 1 ~R 4 is independently selected, each occurrence, from the group consisting of hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, and combinations thereof.

[0135] According to one embodiment of the present invention, the R 1 ~R 4 is independently selected, each occurrence, from the group consisting of hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, terphenylene group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzosilole group, dibenzosilole group, benzothiophene group, dibenzothiophene group, dibenzoselenophene group, triazine group, and combinations thereof.

[0136] According to one embodiment of the present invention, the R 1 ~R 4 is independently selected, each occurrence, from the group consisting of hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, terphenylene group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzosilole group, dibenzosilole group, benzothiophene group, dibenzothiophene group, dibenzoselenophene group, triazine group, triphenylsilyl group, and combinations thereof.

[0137] According to one embodiment of the present invention, the first host material has a structure represented by Formula 3-1,

Chemical Formula

[0138] According to one embodiment of the present invention, said R 1 and R 2 are each independently selected from the group consisting of a carbazole group, an indole group, a benzofuran group, a dibenzofuran group, a benzosilole group, a dibenzosilole group, a benzothiophene group, a dibenzothiophene group, and combinations thereof.

[0139] According to one embodiment of the present invention, L is selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group, or a pyridylene group.

[0140] According to one embodiment of the present invention, the above-mentioned R L is selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, which may be the same or different each time it appears and may be substituted or unsubstituted, a cycloalkyl group having 3 to 20 carbon atoms in the ring, which may be substituted or unsubstituted, an aryl group having 6 to 30 carbon atoms, which may be substituted or unsubstituted, a heteroaryl group having 3 to 30 carbon atoms, which may be substituted or unsubstituted, and combinations thereof.

[0141] According to one embodiment of the present invention, the above-mentioned R L is selected from an aryl group having 6 to 30 carbon atoms, which may be the same or different each time it appears and may be substituted or unsubstituted.

[0142] According to one embodiment of the present invention, the above-mentioned R L is selected from the group consisting of a phenyl group, a biphenyl group, a terphenylene group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzosilole group, a dibenzosilole group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, and combinations thereof, which may be the same or different each time it appears.

[0143] According to one embodiment of the present invention, the first host material is selected from the group consisting of compounds N-1-1 to N-1-60 and compounds N-2-1 to N-2-35. The specific structures of the compounds N-1-1 to N-1-60 and compounds N-2-1 to N-2-35 are shown in claim 19.

[0144] According to one embodiment of the present invention, the first host material is selected from the group consisting of compounds N-1-1 to N-1-60 and compounds N-2-1 to N-2-45. The specific structures of the compounds N-1-1 to N-1-60 and compounds N-2-1 to N-2-35 are shown in claim 19. The specific structures of the compounds N-2-36 to N-2-45 are [Chemical formula] [Chemical formula]

[0145] According to one embodiment of the present invention, the hydrogen in the structures of the compounds N-1-1 to N-1-53, compound N-1-58, and compounds N-2-1 to N-2-32 may be partially or fully deuterated.

[0146] According to one embodiment of the present invention, the hydrogen in the structures of the compounds N-1-1 to N-1-53, compound N-1-58, compounds N-2-1 to N-2-32, and compounds N-2-36 to N-2-43 may be partially or fully deuterated.

[0147] According to one embodiment of the present invention, the triplet state energy level of the second host material is higher than 2.69 eV.

[0148] According to one embodiment of the present invention, the second host material has a structure represented by Formula 6, [Chemical formula] In Formula 6, L 11 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof, Ar 11 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a combination thereof, R 6 represents monosubstitution, polysubstitution, or no substitution, which may be the same or different each time it appears, R 6is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, adjacent substituents R 6 may combine to form a ring.

[0149] In the present specification, when adjacent substituents R 6 may combine to form a ring, it means that two substituents R 6 may combine with each other to form a ring. Obviously, two substituents R 6 do not have to combine with each other to form a ring.

[0150] According to an embodiment of the present invention, the second host material is a deuterated compound.

[0151] According to an embodiment of the present invention, the second host material has a structure represented by Formula 6-1 or Formula 6-2,

Chemical formula

[0152] According to one embodiment of the present invention, the second host material has a structure represented by Formula 6-3 or Formula 6-4, [Chemical formula] Ar 11 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a combination thereof. L 11 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof. R 6 represents monosubstitution, polysubstitution or no substitution, which may be the same or different each time it appears. R 6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof. Adjacent substituents R 6 may combine to form a ring.

[0153] According to one embodiment of the present invention, R 6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

[0154] According to one embodiment of the present invention, the above-mentioned R 6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, and combinations thereof.

[0155] According to one embodiment of the present invention, the above-mentioned R 6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, terphenylene group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzosilole group, dibenzosilole group, benzothiophene group, dibenzothiophene group, dibenzoselenophene group, and combinations thereof.

[0156] According to one embodiment of the present invention, in Formula 6-1 to Formula 6-4, there are a plurality of R 6 substituents, and among the plurality of R 6 substituents, at least one is a carbazole group, for example, one or two are carbazole groups.

[0157] According to one embodiment of the present invention, in Formula 6-1 to Formula 6-4, there are a plurality of R 6 substituents, and among the plurality of R 6 substituents and Ar 11 at least one is a carbazole group, for example, one or two are carbazole groups.

[0158] According to one embodiment of the present invention, the second host material is selected from the group consisting of Compounds P-1 to P-31, and the specific structures of Compounds P-1 to P-31 are shown in Claim 22.

[0159] According to one embodiment of the present invention, the hydrogen in the structures of Compounds P-1 to P-23, Compounds P-27 to P-31 may be partially or fully deuterated.

[0160] According to one embodiment of the present invention, the HOMO energy level of the second host material is greater than -5.69 eV and less than -5.39 eV.

[0161] According to one embodiment of the present invention, the light-emitting layer contains only the first compound, the first host material, and the second host material.

[0162] The HOMO energy level or LUMO energy level of the compounds described in this specification is the electrochemical property of the compound measured by cyclic voltammetry using anhydrous DMF as a solvent. For the measurement, an electrochemical station of model CorrTest CS120 manufactured by Wuhan KOST Instrument Co., Ltd. is used, and a three-electrode working system with a platinum disk electrode as the working electrode, an Ag / AgNO 3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode is used. Using anhydrous DMF as the solvent and 0.1 mol / L tetrabutylammonium hexafluorophosphate as the supporting electrolyte, the compound to be measured is prepared into a 10 -3 mol / L solution. Before the measurement, nitrogen gas is introduced into the solution for 10 min to remove oxygen. The parameter settings of the instrument are as follows. Scanning speed: 100 mV / s, potential interval: 0.5 mV, test window: -1 V to -2.9 V.

[0163] According to one embodiment of the present invention, the first compound is a phosphorescent material, the first host material is an n-type host material, and the second host material is a p-type host material.

[0164] In this specification, the p-type host material is an organic compound containing a carbazole group or a triarylamine organic compound, and its HOMO energy level is usually more than -5.8 eV. The n-type host material is an organic compound containing chemical groups such as pyridine, pyrimidine, triazine, azadibenzofuran, azadibenzothiophene, and azacarbazole, and its LUMO energy level is usually less than -2.3 eV.

[0165] According to one embodiment of the present invention, the organic electroluminescence device emits blue light.

[0166] According to another embodiment of the present invention, an electronic device including the organic electroluminescence device described in any one of the above-described embodiments is further disclosed.

[0167] According to another embodiment of the present invention, a compound composition including at least a first compound, a first host material, and a second host material is further disclosed, wherein the first compound, the first host material, and the second host material are as described in any one of the above-described embodiments.

[0168] Combinations with other materials

[0169] The materials of the specific layers used in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in paragraphs 0132 to 0161 of US Patent Application US2016 / 0359122A1, and the entire content thereof is incorporated herein by reference. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed in this specification, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0170] In this specification, it is described that the materials of specific layers used in the organic light-emitting device can be used in combination with various other materials present in the device. Exemplarily, the light-emitting dopants disclosed in this specification can be used in combination with various hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. The combinations of these materials are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, and the entire content thereof is incorporated herein by reference. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed in this specification, and for those skilled in the art, other materials that can be used in combination can be easily identified by referring to the literature.

[0171] In the examples of material synthesis, unless otherwise explained, all reactions are carried out under the protection of nitrogen. All reaction solvents are anhydrous and are used as commercially available products. For the synthesized products, one or more devices commonly used in this field (including, but not limited to, nuclear magnetic resonance devices manufactured by Bruker, liquid chromatography, liquid chromatography / mass spectrometers, gas chromatography / mass spectrometers, differential scanning calorimeters, fluorescence spectrometers manufactured by Shanghai ▲Liao▼guang Technology, electrochemical workstations manufactured by Wuhan Koster, sublimation devices manufactured by Anhui Beiyike, etc.) are used to perform structure confirmation and property testing in a method well-known to those skilled in the art. In the examples of the device, for the properties of the device, devices commonly used in this field (including, but not limited to, evaporation machines manufactured by Angstrom Engineering, optical test systems manufactured by Suzhou Fushi Da, service life test systems, ellipsometers manufactured by Beijing Liangtuo, etc.) are also used to perform tests in a method well-known to those skilled in the art. Since those skilled in the art know the related content such as the use of the above-mentioned devices and test methods, the specific data of the samples can be obtained reliably and without being affected, so the above-related content will not be repeatedly explained in this specification.

Example

[0172] Synthesis example of material:

[0173] The preparation method of the first compound selected in the present invention is not limited. Typically but not limitedly, taking the following compound as an example, its synthetic route and preparation method are as follows.

[0174] Synthesis Example 1: Synthesis of Compound Pt16

[0175] Step 1: Synthesis of Intermediate 1

Chemical formula

[0176] Step 2: Synthesis of Intermediate 2

Chemical formula

[0177] Step 3: Synthesis of Intermediate 3

Chemical formula

[0178] Step 4: Synthesis of Intermediate 4

Chemical formula

[0179] Step 5: Synthesis of Intermediate 5

Chemical formula

[0180] Step 6: Synthesis of Intermediate 6

Chemical formula

[0181] Step 7: Synthesis of Compound Pt16

Chemical formula

[0182] Synthesis Example 2: Synthesis of Compound Pt39

[0183] Step 1: Synthesis of Intermediate 7

Chemical formula

[0184] Step 2: Synthesis of Intermediate 8

Chemical formula

[0185] Step 3: Synthesis of Intermediate 9

Chemical formula

[0186] Step 4: Synthesis of Pt39

Chemical formula

[0187] Comparative Example 1 of Synthesis: Synthesis of Compound Pt-A

[0188] Step 1: Synthesis of Intermediate 10

Chemical formula

[0189] Step 2: Synthesis of Intermediate 11

Chemical formula

[0190] Step 3: Synthesis of Compound Pt-A

Chemical formula

[0191] Comparative Example 2 of Synthesis: Synthesis of Compound Pt-B

[0192] Step 1: Synthesis of Intermediate 12

Chemical Structure

[0193] Step 3: Synthesis of Intermediate 13

Chemical Structure

[0194] Step 4: Synthesis of Compound Pt-B

Chemical Structure

[0195] Those skilled in the art should know that the above preparation method is merely exemplary, and other compound structures of the present invention can be obtained by improving it.

[0196] Measurement of the triplet state energy level:

[0197] In this specification, the triplet state energy level (T 1 ) was measured under ultra-low temperature conditions by utilizing the characteristics of long-lived triplet excitons. Specifically, the compound to be measured was dissolved in a 2-methyltetrahydrofuran solvent to prepare a 10 -5 M solution, which was injected into a quartz tube, then placed in a Dewar flask, cooled to 77 K, irradiated with a 350 nm light source on the solution of the compound to be measured, and the phosphorescence spectrum was measured. A spectrophotometer with model number F98 manufactured by Shanghai ▲Ryo▼ Optics Technology Co., Ltd. was used for the spectrum measurement.

[0198] The phosphorescence spectrum has the phosphorescence intensity on the vertical axis and the wavelength on the horizontal axis. After taking the minimum value λ 1 (nm) for the peak on the short wavelength side of the phosphorescence spectrum, the wavelength value was introduced into the following conversion formula F 1 to calculate the triplet state energy of the compound to be measured.

[0199] Conversion formula F 1 : T 1 (eV) = 1240 / λ 1

[0200] By the above method, the triplet state energy level T of the following compounds 1 (eV) was measured. The specific results are shown in Table 1.

[0201]

Table 1

[0202] As can be seen from the above results in Table 1, since the triplet state energy levels of the first host material and the second host material in the present invention are both higher than the triplet state energy level of 2.69 eV of the first compound which is a luminescent material, the first host material, the second host material and the first compound can be well combined to achieve blue phosphorescent emission. Hereinafter, examples of the device will be provided for verification.

[0203] The manufacturing method of the electroluminescent device is not limited. The manufacturing methods in the following examples are merely illustrative and should not be construed as limiting. Those skilled in the art can reasonably improve the manufacturing methods in the following examples based on the prior art. Exemplarily, the ratios of various materials in the light-emitting layer are not particularly limited, and those skilled in the art can reasonably select within a certain range based on the prior art. For example, based on the total weight of the light-emitting layer materials, the host material may account for 80% - 99%, and the luminescent material may account for 1% - 20%, or the host material may account for 85% - 99%, and the luminescent material may account for 1% - 15%. Also, the host material may be two kinds of materials. Among them, the ratio of the two host materials to the host material may be 99:1 - 1:99, or 80:20 - 20:80. In the examples of the device, for the characteristics of the device as well, using ordinary equipment in this field (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical test systems manufactured by Suzhou FushiDa, service life test systems, ellipsometers manufactured by Beijing Liangtuo, etc.), tests were conducted by methods well-known to those skilled in the art.

[0204] Example 1 of the device

[0205] First, a glass substrate having an indium tin oxide (ITO) anode with a thickness of 80 nm was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. Then, the substrate was mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, when the degree of vacuum was about 10 -8 Torr, evaporation was sequentially performed on the ITO anode by hot vacuum evaporation at a rate of 0.2 - 2 angstroms / second. Compound HI and Compound HT were co-evaporated and used as a hole injection layer (HIL) with a thickness of 100 Å. Compound HT was used as a hole transport layer (HTL) with a thickness of 250 Å. Compound P-21 was used as an electron blocking layer (EBL) with a thickness of 50 Å. Then, Compound N-1-15 as the first host, Compound P-21 as the second host, and the first compound Pt16 as a dopant were co-evaporated and used as an emission layer (EML) with a thickness of 350 Å. Compound N-1-15 was used as a hole blocking layer (HBL) with a thickness of 50 Å. On the hole blocking layer, Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated and used as an electron transport layer (ETL) with a thickness of 310 Å. Finally, LiF with a thickness of 15 Å was evaporated and used as an electron injection layer, and aluminum with a thickness of 1200 Å was evaporated and used as a cathode. Finally, the device was transferred to a glove box and encapsulated using a glass cover and a moisture absorbent to complete the device.

[0206] Example 2 of the device

[0207] The preparation method of Example 2 of the device is the same as that of Example 1 of the device, except that in the emission layer (EML), Compound P-21 is replaced by Compound P-22 as the second host material, and the weight ratio of Compound P-22, Compound N-1-15, and Compound Pt16 is 52.8:35.2:12.

[0208] Example 3 of the device

[0209] The preparation method of Example 3 of the device is the same as that of Example 2 of the device, except that compound P-22 is replaced with compound P-25 as the second host material in the emission layer (EML).

[0210] Example 5 of the device

[0211] The preparation method of Example 5 of the device is the same as that of Example 1 of the device, except that compound HT is replaced with compound HT-1 in the hole injection layer (HIL), and the weight ratio of compound HT-1 to compound HI is 97:3, compound HT is replaced with compound HT-1 in the hole transport layer (HTL), compound P-21 is replaced with compound P-22 as the second host material in the emission layer (EML), compound Pt16 is replaced with compound Pt681 as the first compound, and the weight ratio of compound P-22, compound N-1-15 and compound Pt681 is 61.6:26.4:12.

[0212] Example 6 of the device

[0213] The preparation method of Example 6 of the device is the same as that of Example 1 of the device, except that compound HT is replaced with compound HT-1 in the hole injection layer (HIL), and the weight ratio of compound HT-1 to compound HI is 97:3, compound HT is replaced with compound HT-1 in the hole transport layer (HTL), compound N-1-15 is replaced with compound N-2-39 as the first host material in the emission layer (EML), and the weight ratio of compound P-21, compound N-2-39 and compound Pt16 is 35.2:52.8:12, and compound N-1-15 is replaced with compound N-2-39 in the hole blocking layer (HBL).

[0214] Example 7 of the device

[0215] The preparation method of Example 7 of the device is the same as that of Example 6 of the device, except that compound P-21 is replaced with compound P-22 as the second host material in the emission layer (EML), and the weight ratio of compound P-22, compound N-2-39 and compound Pt16 is 52.8:35.2:12.

[0216] Comparative Example 1 of the Element

[0217] The preparation method of Comparative Example 1 of the element is the same as that of Example 1 of the element, except that compound Pt16 is replaced with compound Pt-A in the light-emitting layer (EML).

[0218] Comparative Example 2 of the Element

[0219] The preparation method of Comparative Example 2 of the element is the same as that of Example 1 of the element, except that compound Pt16 is replaced with compound Pt-B in the light-emitting layer (EML).

[0220] Comparative Example 3 of the Element

[0221] The preparation method of Comparative Example 3 of the element is the same as that of Example 1 of the element, except that compound P-21 is used as the host material and compound Pt16 is used as the dopant in the light-emitting layer (EML), and the weight ratio of compound P-21 to compound Pt16 is 88:12.

[0222] Comparative Example 4 of the Element

[0223] The preparation method of Comparative Example 4 of the element is the same as that of Example 1 of the element, except that compound N-1-15 is used as the host material and compound Pt16 is used as the dopant in the light-emitting layer (EML), and the weight ratio of compound N-1-15 to compound Pt16 is 88:12.

[0224] Comparative Example 5 of the Element

[0225] The preparation method of Comparative Example 5 of the element is the same as that of Example 1 of the element, except that compound H-1 is used as the host material and compound Pt16 is used as the dopant in the light-emitting layer (EML), and the weight ratio of compound H-1 to compound Pt16 is 88:12.

[0226] The layer structure and thickness of the detailed element are shown in the following table. For layers with more than one kind of material used, they are obtained by doping different compounds in the above weight ratio.

[0227]

Table 2

[0228] The structure of the material used for the element is as follows.

Chem.

Chem.

Chem.

[0229] 1000 cd / m 2 Below, the CIE values, maximum emission wavelength (λ max ), current efficiency CE (cd / A), voltage (V), external quantum efficiency (EQE), and device lifetime (LT95) in Examples 1-3, Example 5, and Comparative Examples 1-5 were measured. The relevant data are shown in Table 3.

[0230]

Table 3

[0231] As can be seen from the data in Table 3, all the examples of the present invention had better comprehensive device performance. Example 1 using the first compound Pt16 of the structure of Formula 1 having a specific structural substitution of Formula 2 on the imidazole carbene ring according to the present invention and a specific combination of the first host material and the second host material according to the present invention, compared with Comparative Example 1 using compound Pt-A having no specific multiple substitution structures according to the present invention, the first host material and the second host material, had the same low voltage level as Comparative Example 1, with improved current efficiency CE and service life. More importantly, in addition to the very high efficiency level of Comparative Example 1, the EQE was further improved by 11.5%, and the efficiency in Example 1 could reach 16.82%, which was very rare for blue light devices. Similarly, Example 1 had a lower voltage, a significantly improved CE of 21.2%, a significantly improved EQE of 28.7%, and a significantly improved device service life of 29.5% compared with Comparative Example 2 using compound Pt-B having no other specific multiple substitution structures according to the present invention, the first host material and the second host material according to the present invention. Based on the comparison of these data, the advantages of the first compound of the structure of Formula 1 having a specific structural substitution of Formula 2 on the imidazole carbene ring according to the present invention, and a specific combination of the first host material and the second host material were shown.

[0232] Example 1, which used a specific combination with the first compound according to the present invention as the luminescent material, the first host material, and the second host material as the double host, showed that, compared with Comparative Example 3 which used the first compound according to the present invention as the luminescent material and separately the second host material according to the present invention as the single host, its voltage decreased by 0.71 V, the CE increased significantly by 135.2%, the EQE increased significantly by 127.6%, and the device lifetime increased significantly by 282.4%. Example 1, compared with Comparative Example 4 which used the first compound according to the present invention as the luminescent material and separately the first host material according to the present invention as the single host, had a voltage slightly higher than that of Comparative Example 4 but still at a low voltage level, the CE increased significantly by 25.5%, the EQE increased significantly by about 35.4%, and the device lifetime increased significantly by 167.2%. From the above data, the advantage of the specific combination of the first compound according to the present invention, the first host material according to the present invention, and the second host material over the case of using only one kind of host material was shown. Example 1, compared with Comparative Example 5 which used the first compound according to the present invention as the luminescent material and separately the host material H-1 with a high triplet state energy level in the prior art as the single host, had a voltage decrease significantly by 2.4 V, the CE increased significantly by 86.8%, the EQE increased significantly by 80.3%, and the device lifetime increased significantly by 241.4%. That is, the advantage of the specific combination of the first compound, the first host material, and the second host material according to the present invention over the single host materials used in the prior art has been proven.

[0233] Examples 2 to 3 respectively used Compound P-22 and Compound P-25, which are the second host materials selected for the present invention and have different structures, in combination with the first compound Pt16 selected for the present invention and the first host material N-1-15 selected for the present invention. Compared with Example 1, the voltage in Examples 2 to 3 was slightly improved but still at a relatively low voltage level. In addition to the very high levels of CE and EQE in Example 1, they were further improved, and the service life was also significantly improved. Incidentally, the EQE in Example 3 reached a maximum of 18.29%, while the service life was improved to 28.23 h, which greatly contributed to the improvement of the blue light element level. From these data, it is proved that specific combinations of the second host materials according to the present invention having different structures, the first compound according to the present invention, and the first host material can all achieve excellent comprehensive device performance. Furthermore, the superiority of specific combinations of the first compound, the first host material, and the second host material according to the present invention has been proved.

[0234] Example 5 used the first compound Pt681 with the structure of Formula 1 having a specific structural substitution of Formula 2 on the imidazole carbene ring according to the present invention, and a specific combination of the first host material and the second host material according to the present invention. Compared with Comparative Example 1 using a combination of Compound Pt-A, the first host material, and the second host material, which does not have a specific multiple substitution structure according to the present invention, its voltage was slightly higher than that of Comparative Example 1 but still at a low voltage level. Importantly, the CE was significantly improved by 65.2%, the EQE was significantly improved by 55.7%, and the service life of the device was significantly improved by 60.9%. From these data, the superiority of specific combinations of the first compound with the structure of Formula 1 having a specific structural substitution of Formula 2 on the imidazole carbene ring according to the present invention, the first host material, and the second host material has been proved.

[0235] 1000 cd / m 2 Below, the CIE values, maximum emission wavelengths (λ max) The current efficiency CE (cd / A), voltage (V), external quantum efficiency (EQE), and device lifetime (LT95) were measured. The relevant data are shown in Table 4.

[0236]

Table 4

[0237] Comparative Example 1 was combined using Compound N-1-15, which is the first host material according to the present invention, Compound P-21, which is the second host material according to the present invention, and a first compound Pt-A that does not belong to the present invention. As can be seen from Table 3 above, the device data are the most excellent among the comparative examples. Examples 6 and 7 were combined using Compound N-2-39, which is the first host material according to the present invention having different structures, the first compound Pt16 according to the present invention, and Compound P-21 or Compound P-22, which is the second host material according to the present invention. Compared with Comparative Example 1, the voltages in Example 6 and Comparative Example 1 are almost equivalent, and the voltage in Example 7 is slightly higher than that in Comparative Example 1 but still at a low voltage level. Importantly, the CE and EQE in Examples 6 and 7 are further significantly improved compared to Comparative Example 1, with the CE improving by 39.7% and 37.2% respectively, and the EQE improving by 33.4% and 43.1% respectively, while the device lifetime is doubled, improving by 3.72 times and 4.77 times respectively. Incidentally, the CE, EQE, and device lifetime in Examples 6 and 7 simultaneously reach a very high level, which is rare for blue phosphorescent devices and extremely greatly improves the device performance. From these data, it is proven that specific combinations of the first host material according to the present invention having different structures, the first compound according to the present invention, and the second host material can all achieve excellent comprehensive device performance, and furthermore, the superiority of specific combinations of the first compound, the first host material, and the second host material according to the present invention has been proven.

[0238] Example 4 of the device

[0239] The preparation method of Example 4 of the device is the same as that of Example 1 of the device, except that Compound Pt16 is replaced with Compound Pt39 in the light-emitting layer (EML).

[0240] The layer structure and thickness of the detailed device are shown in the following table. For layers with more than one kind of material used, they are obtained by doping different compounds in the above weight ratio.

[0241]

Table 5

[0242] The structure of the new material used in the device is as follows.

Chemical formula

[0243] 1000 cd / m 2 Under, the CIE values, maximum emission wavelength (λ max ), current efficiency CE (cd / A), voltage (V), and external quantum efficiency (EQE) of Example 4 were measured. The related data are shown in Table 6.

[0244]

Table 6

[0245] As can be seen from the data in Table 6, Example 4 using another first compound Pt39 having a specific structural substitution of Formula 2 on the imidazole carbene ring according to the present invention, a specific combination of the first host material and the second host material according to the present invention, also shows excellent device performance, with its voltage at a low voltage level, CE reaching 18.92, EQE reaching a maximum of 16.85%, and in particular CIEy being as low as 0.141, which was very advantageous for blue phosphorescent devices.

[0246] As can be seen from the above results, a first compound having a structure of Formula 1 with a plurality of specific substituted aromatic groups of Formula 2 on the imidazole carbene ring according to the present invention is introduced as a light-emitting material, and in combination with a first host material and a second host material having a high triplet state energy level and used in a blue phosphorescent electroluminescent device, a low voltage, high efficiency (EQE and CE), and long service life can be obtained, and it has excellent comprehensive device performance, and these advantages contribute extremely greatly to the improvement of the level of blue light devices.

[0247] It should be understood that the various examples described herein are merely illustrative and not intended to limit the scope of the present invention. Therefore, it is obvious to those skilled in the art that the present invention to be protected includes modifications of the specific examples and preferred examples described herein. Many of the materials and structures described herein can be replaced with other materials and structures on the premise of not departing from the concept of the present invention. It should be understood that the various theories about why the present invention functions are not limiting.

Claims

1. An organic electroluminescence device including an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer contains a first compound, a first host material, and a second host material, wherein the triplet state energy levels of the first host material and the second host material are both higher than the triplet state energy level of the first compound, wherein the first compound has a structure represented by Formula 1, 【Chemical 1】 In Formula 1, ring A, ring B, and ring E are each independently selected, each time they appear, from an unsaturated carbon ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; ring D is each independently selected, each time it appears, from an unsaturated heterocyclic ring having 3 to 30 carbon atoms, metal M is selected from metals having a relative atomic mass greater than 40, L 1 、L 2 is, each time it appears, the same or different and is selected from a single bond, O, S, Se, (SiR''R''), y PR'', NR'', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof, and y is 1, 2, 3, 4 or 5, K 1 ~K 4 is, for each occurrence, independently selected from a single bond, O or S, and may be the same or different for each occurrence, Z 1 to Z 3 is selected from C or N, either the same or different, each time of occurrence, R in Formula 1 has a structure represented by Formula 2, [Chemical Formula 2] In Formula 2, ring F, ring G, and ring N are each independently selected, each time they appear, from an unsaturated carbon ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof, Z 4 ~Z 7 is, each time it appears, selected independently from C or N, either the same or different, R a 、R b 、R d 、R e 、R f 、R g each represents a single substitution, multiple substitutions, or no substitution, which may be the same or different each time of occurrence, R n represents one substitution or a plurality of substitutions, which may be the same or different each time of occurrence, R'', R a , R b , R d , R e , R f , R g , R n are each, each time they appear, the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof. In the ring N in Formula 2, at least one R n is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, "*" represents the bonding position of Formula 2, Adjacent substituents R'', R a , R b , R d , R e , R f , R g , R n may combine to form a ring, An organic electroluminescence device.

2. wherein M is selected from Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, or Pt, The organic electroluminescence device according to Claim 1.

3. wherein M is selected from Pt or Pd, The organic electroluminescence device according to Claim 1.

4. wherein ring A, ring B, ring E, ring F, ring G, and ring N are each independently selected, each time they appear, from a 5-membered unsaturated carbon ring, an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 3 to 30 carbon atoms, or a combination thereof, The organic electroluminescence device according to Claim 1 or 2.

5. wherein ring A, ring B, ring E, ring F, ring G, and ring N are each independently selected, each time they appear, from a 5-membered unsaturated carbon ring, an aryl ring having 6 to 18 carbon atoms, a heteroaryl ring having 3 to 18 carbon atoms, or a combination thereof, The organic electroluminescence device according to Claim 4.

6. wherein ring D is each independently selected, each time it appears, from an unsaturated heterocyclic ring having 3 to 18 carbon atoms, The organic electroluminescence device according to Claim 1.

7. The ring D is selected from an imidazole carbene ring or a benzimidazole carbene ring, which may be the same or different each time it appears. The organic electroluminescence device according to claim 1.

8. Said L 1 is selected from a single bond, O, S, (SiR''R''), y NR'', or a combination thereof, and said y is 1 or 2. The organic electroluminescence device according to claim 1.

9. The L1 is selected from a single bond, O or S. The organic electroluminescence device according to claim 8.

10. Said K 1 to K 4 is selected from single bonds, The organic electroluminescence device according to claim 1.

11. Said Z 1 is selected from N, and Z 2 and Z 3 is selected from C, The organic electroluminescence device according to claim 1.

12. The first compound has a structure represented by one of Formula 1-1 to Formula 1-20. In Formula 1-1 to Formula 1-20, [Chemical Formula 3] 【Chemical 4】 [Chemical Formula 5] y is selected from 1, 2, 3, 4 or 5, which may be the same or different each time it appears. L 2 is, each time it appears, the same or different and is selected from a single bond, O, S, Se, (SiR''R''), y PR'', NR'', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof R has a structure represented by Formula 2-1. X 1 ~X 20 is, for each occurrence, the same as or different from CR x or N, and is selected from The organic electroluminescence device according to claim 1. 【Chemical Formula 6】 In Formula 2-1, F 1 to F 5 are each independently selected from CR f or N, G 1 to G 5 are each independently selected from CR g or N, N 1 to N 3 are each independently selected from CR n or N, and at least one of N 1 to N 3 is CR n and R', R'', R x , R f , R g , R n are, each time they appear, the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, At least one of said Rs n is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof. Adjacent substituents R', R'', R x , R f , R g , R n may combine to form a ring,

16. The first compound has a structure represented by Formula 1-1 or Formula 1-2. The organic electroluminescence device according to claim 12.

17. The organic electroluminescence device according to claim 12. Said N 1 or N 2 is selected from CR n and said R n is, each time it appears, the same or different and is selected from the group consisting of deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof

18.

19. The Rn is selected from the group consisting of deuterium, fluorine, a cyano group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 6 carbon atoms, and combinations thereof, which may be the same or different each time it appears. The organic electroluminescence device according to claim 14.

20. The Rn is selected from the group consisting of an unsubstituted alkyl group having 1 to 6 carbon atoms, a partially or fully deuterated alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, or a partially or fully deuterated cycloalkyl group having 3 to 6 ring carbon atoms, which may be the same or different each time it appears. The organic electroluminescence device according to claim 14.

21. Said X 1 ~X 20 are the same or different each time they appear and are selected from CR x and The organic electroluminescence device according to claim 12 or 14.

22. The foregoing L 2 is selected from a single bond, O, S, (SiR''R''), y NR'', or a combination thereof, and the foregoing R'' is the same or different each time it appears and is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof. The organic electroluminescence device according to claim 12 or 14.

23. The L2 is selected from a single bond, O or S. The organic electroluminescence device according to claim 18.

20. The L2 is selected from O, The organic electroluminescence device according to claim 18.

21. Said R x , R', R f , R g is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof. The organic electroluminescence device according to claim 12.

22. The R is selected from the group consisting of Structure An-1 to Structure An-82 and Structure An-92, which may be the same or different each time they appear, 【Chemical Formula 7】 【Chemical 8】 【Chemical Formula 9】 【Chemical 10】 【Chemical 11】 【Chemical 12】 The hydrogen in Structure An-1 to Structure An-82 and Structure An-92 may be partially or fully deuterated, The organic electroluminescence device according to claim 1.

23. The first compound is Pt(L a )(L b ) or Pd(L a )(L b ), and has a structure represented thereby. L a and L b are a first ligand and a second ligand that coordinate with the metal Pt or Pd, respectively. The L a is L a 1-1 to L a 1-76, L a 1-86 to L a 1-93, L a 2-1 to L a 2-42, L a 3-1 to L a 3-40, L a 4-1 to L a 4-17, and L a 4-19 to L a 4-53, and is selected from the group consisting of: 【Chemical 13】 【Chemical Formula 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical 18】 【Chemical 19】 【Chemical 20】 【Chemical Formula 21】 【Chemical 22】 【Chemical 23】 【Chemical 24】 【Chemical 25】 【Chemical 26】 【Chemical 27】 【Chemical Formula 28】 ​ 【Chemical Formula 30】 【Chemical Formula 31】 The above-mentioned L a "tBu" in the structure represents tert-butyl, The above-mentioned L a "#" in the structure represents the connection point between the structure and L b and Ligand L b is L b 1-1 to L b 1-9, L b 1-12 to L b 1-22, L b 2-1 to L b 2-30, L b 3-1 to L b 3-26, L b 4-1 to L b 4-25, and L b 5-1 to L b selected from the group consisting of 5-11 【Chemical 32】 【Chemical 33】 【Chemical 34】 【Chemical 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 The above-mentioned L b In the structure, "t-Bu" represents tert-butyl, "i-Pr" represents an isopropyl group, and "TMS" represents a trimethylsilyl group. The above-mentioned L b in the structure 【Chemical 39】 represents the connection point between the said structure and "L" a in The organic electroluminescence device according to claim 1.

24. The first compound is selected from the group consisting of Compound Pt1 to Compound Pt76, Compound Pt86 to Compound Pt180, Compound Pt182 to Compound Pt260, Compound Pt305 to Compound Pt680 and Compound Pd1 to Compound Pd24. The Compound Pt1 to Compound Pt76, Compound Pt86 to Compound Pt180, Compound Pt182 to Compound Pt260, Compound Pt305 to Compound Pt680 have a structure represented by Pt(La)(Lb), and the La and the Lb are respectively selected from the structures shown in the following table correspondingly, 【Table 1】 【Table 2】 【Table 3】 【Table 4】 【Table 5】 【Table 6】 【Table 7】 【Table 8】 【Table 9】 The Compound Pd1 to Compound Pd24 have a structure represented by Pd(La)(Lb), and the La and the Lb are respectively selected from the structures shown in the following table correspondingly, 【Table 10】 The organic electroluminescence device according to claim 23.

25. The triplet state energy level of the first host material is higher than 2.69 eV, The organic electroluminescence device according to claim 1.

26. The first host material has a structure represented by any one of Formula 3 to Formula 5, 【Chemical Formula 40】 In Formula 3, Z1 to Z3 are each independently selected from CR4 or N, which may be the same or different each time they appear, and at least one of Z1 to Z3 is N, L is each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof, which may be the same or different each time they appear, In Formula 4 or Formula 5, Z4 is each independently selected from CR4 or N, which may be the same or different each time they appear, and at least one Z4 is N, Z is the same or different each time it appears and is selected from O or S, R1 to R4 are the same or different each time they appear and are hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a group consisting of combinations thereof, Adjacent substituents R4 may be bonded to form a ring, The organic electroluminescence element according to claim 1.

27. In Formula 3, the aforementioned Z 1 to Z 3 at least two of which are N, The organic electroluminescence element according to claim 26.

28. In Formula 3, Z1 to Z3 are N, The organic electroluminescence element according to claim 26.

29. In Formula 3, the L is the same or different each time it appears and is selected from a group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, and combinations thereof, The organic electroluminescence element according to claim 26.

30. The L is the same or different each time it appears and is selected from a group consisting of a single bond, a phenylene group, a biphenylene group, a fluorenylene group, a triphenyleneylene, a furylene group, a thienylene group, a dibenzofurylene group, a dibenzothienylene group, and combinations thereof, The organic electroluminescence element according to claim 26.

31. Said R 1 to R 4 are, each time they appear, the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof. The organic electroluminescence element according to claim 26.

32. R1 to R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, and combinations thereof, and may be the same or different each time they appear. The organic electroluminescence element according to claim 31.

33. The first host material is selected from the group consisting of compound N-1-1 to compound N-1-60, and compound N-2-1 to compound N-2-45. 【Chemical Formula 41】 【Chemical 42】 【Chemical 43】 【Chemical 44】 【Chemical 45】 【Chemical 46】 【Chemical 47】 【Chemical 48】 【Chem.】 The organic electroluminescence element according to claim 26, wherein hydrogen in the structures of compound N-1-1 to compound N-1-53, compound N-1-58, compound N-2-1 to compound N-2-32, and compound N-2-36 to compound N-2-43 may be partially or fully deuterated.

34. The triplet state energy level of the second host material is higher than 2.69 eV. The organic electroluminescence element according to claim 1.

35. The second host material has a structure represented by Formula 6. 【Chemical 49】 In Formula 6, L11 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof. Ar11 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 carbon atoms, or a combination thereof. R6 represents monosubstituted, polysubstituted or unsubstituted, and may be the same or different each time it appears. R6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, adjacent substituents R6 may be bonded to form a ring, The organic electroluminescence device according to claim 1.

36. Said R 6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof. The organic electroluminescence device according to claim 35.

37. R6 is, each time it appears, the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, and combinations thereof, The organic electroluminescence device according to claim 35.

38. The second host material is selected from the group consisting of Compound P-1 to Compound P-31, 【Chemical Formula 50】 【Chemical 51】 【Chemical 52】 【Chemical 53】 【Chemical 54】 Hydrogen in the structures of Compound P-1 to Compound P-23 and Compound P-27 to Compound P-31 may be partially or fully deuterated, The organic electroluminescence device according to claim 34.

39. The first compound is a phosphorescent material, the first host material is an n-type host material, and the second host material is a p-type host material, The organic electroluminescence device according to claim 1.

40. The element emits blue light, The organic electroluminescence element according to claim 1.

41. An electronic device including the organic electroluminescence element according to claim 1, Electronic device.

42. A compound composition including a first compound, a first host material, and a second host material, The triplet state energy levels of the first host material and the second host material are both higher than the triplet state energy level of the first compound, The first compound has a structure represented by Formula 1, 【Chemical Formula 55】 In Formula 1, ring A, ring B, and ring E are each independently selected, every time they appear, from an unsaturated carbon ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof; ring D is each independently selected, every time it appears, from an unsaturated heterocyclic ring having 3 to 30 carbon atoms, Metal M is selected from metals having an atomic mass exceeding 40, L 1 and L 2 are each independently, upon each occurrence, a single bond, O, S, Se, (SiR''R''), y PR'', NR'', a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a combination thereof, y is 1, 2, 3, 4, or 5, K 1 ~K 4 is, for each occurrence, independently selected from a single bond, O or S and may be the same or different, Z 1 to Z 3 is selected from C or N, either the same or different each time of occurrence, R in Formula 1 has a structure represented by Formula 2, 【Chemical Formula 56】 In Formula 2, ring F, ring G, and ring N are each independently selected, every time they appear, from an unsaturated carbon ring having 5 to 30 carbon atoms, an unsaturated heterocyclic ring having 3 to 30 carbon atoms, or a combination thereof, Z 4 to Z 7 is selected from C or N, either the same or different, each time of occurrence R a 、R b 、R d 、R e 、R f 、R g each represents, upon each occurrence, the same or different single substitution, multiple substitutions, or no substitution, R n represents a single substitution or multiple substitutions, which may be the same or different each time they appear, R'', R a , R b , R d , R e , R f , R g , R n are, each time they appear, the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof. At least one R in ring N in formula 2 n is selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 ring atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof. “*” represents the bonding position of Formula 2, Adjacent substituents R'', R a , R b , R d , R e , R f , R g , R n may combine to form a ring, Compound composition.

Citation Information

Patent Citations

  • Organic light-emitting device and electronic device including the same

    JP2020136256A

  • Organometallic complex and light-emitting device

    JP2024052599A

  • Organic electroluminescent materials and devices

    US20210284672A1

  • Organic light-emitting device and electronic apparatus including the same

    US20210376252A1

  • Organometallic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device

    US20220112231A1