KR20230041950A - Organic electroluminescent device - Google Patents

Abstract

The present invention provides an organic electroluminescent device. The corresponding organic electroluminescent device comprises an anode, a cathode, and an organic layer arranged between the anode and the cathode. The organic layer includes at least an organic light emitting layer. The organic light emitting layer includes a first host material and a second host material having a high triplet state with a first compound having the structure of formula 1. The organic electroluminescent device of the present invention has an excellent comprehensive device performance and exhibits, for example, a narrower half-width, longer life, and higher efficiency. Also disclosed is electronic equipment including the corresponding organic electroluminescent device. Also disclosed is a composition of a first host material and a second host material having a high triplet state with a first compound having the structure of formula 1.

Description

Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT DEVICE}

The present invention relates to organic electronic devices, such as organic electroluminescent devices. In particular, an organic electroluminescent device including a novel material combination consisting of a first compound having Formula 1 structure, a first host material and a second host material having a high triplet state in an organic light emitting layer, and an organic electroluminescent device comprising the organic light emitting device Electronic equipment and a composition of a first compound having a structure of Formula 1 and a first host material and a second host material having a high triplet state.

Organic electronic devices include organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photoelectric devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasma light emitting devices, but are not limited thereto.

Tang and Van Slyke of Eastman Kodak in 1987, a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline aluminum layer as an electron transport layer and a light emitting layer reported (Applied Physics Letters, 1987,51(12): 913-915). When a bias is applied to the device, green light is emitted from the device. This invention 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 and transport layers, charge and exciton blocking layers, and one or multiple light emitting layers between the cathode and anode. Because OLEDs are self-luminous solid-state devices, they offer tremendous potential for display and lighting applications. In addition, the inherent properties of organic materials (eg their flexibility) make them suitable for special applications (eg manufacturing on flexible substrates).

OLEDs can be classified into three different types according to their light emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state light emission. The triplet state created in the device is wasted through the non-radiative decay channel. Therefore, the internal quantum efficiency (IQE) of the fluorescent OLED is only 25%. These limitations hinder the commercialization of OLEDs. In 1997, Forrest and Thompson reported a phosphorescent OLED using triplet state emission from a heavy metal containing complex as a light emitting body. Therefore, the singlet state and the triplet state can be obtained, and an IQE of 100% can be achieved. Because of their high efficiency, the discovery and development of phosphorescent OLEDs has directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. Such a light emitting body has a small singlet-triplet state gap so that exciton can return from a triplet state to a singlet state. In the TADF device, triplet excitons can generate singlet excitons through reverse intersystem crossing, so that a high IQE can be achieved.

OLEDs can also be divided into low-molecular and high-molecular OLEDs depending on the type of material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of a small molecule can be very large if it has the correct structure. Dendritic polymers with well-defined structures are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers with pendant emitting groups. When post-polymerization occurs during the manufacturing process, low-molecular OLEDs can be transformed into high-molecular OLEDs.

There are already various OLED manufacturing methods. Small molecule OLEDs are typically manufactured through vacuum thermal evaporation. Polymer OLEDs are prepared by solution processes such as spin coating, inkjet printing and nozzle printing. If the material can be dissolved or dispersed in a solvent, even low-molecular OLEDs can be prepared by a solution process.

The emission color of OLED can be realized by structural design of light emitting materials. An OLED may include one light emitting layer or a plurality of light emitting layers to realize a desired spectrum. In green, yellow and red OLEDs, phosphorescent materials have already successfully realized commercialization. Blue phosphorescent devices still have problems such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically use a hybrid strategy using blue fluorescence and phosphorescent yellow or red and green. Currently, there still exists a problem that the efficiency of phosphorescent OLEDs is rapidly reduced in the case of high luminance. Besides, it is desired to have a more saturated emission spectrum, higher efficiency and longer device life.

을 개시하였고, 여기서 Y₁, Y₂, Y₃은 각각 B, N에서 선택된다. 해당 출원에서는 해당 유형의 붕소-질소 화합물이 발광 게스트 재료로 사용되는 것을 개시하였고, 구체적으로 이의 소자 실시예에서 CBP를 TADF 소자에서의 호스트 재료로서 사용하여, 비교적 우수한 녹색광 TADF 소자 성능을 얻었다. 그러나, 해당 출원은 발광층에 제2 호스트 재료를 도입함으로써 소자 성능에 일으키는 변화를 연구하지 않았고, 또한 해당 유형의 붕소-질소 화합물을 청색광 방출 소자에 사용할 때의 소자 성능에 대해 연구하지 않았다.In CN112745342A, a compound of the general formula

disclosed, where Y ₁ , Y ₂ , Y ₃ are selected from B and N, respectively. This application discloses that this type of boron-nitrogen compound is used as a light emitting guest material, and specifically, in the device examples thereof, CBP is used as a host material in the TADF device to obtain relatively good green light TADF device performance. However, the application did not study the change in device performance caused by introducing the second host material into the light emitting layer, nor did the device performance when a boron-nitrogen compound of that type was used in a blue light emitting device.

을 개시하였고, 이는 더 나아가 일반식이

인 화합물을 개시하였으며, 여기서 고리 A에 대해 수많은 헤테로고리 구조, 예를 들어,

,

등을 개시하였다. 해당 출원에서는 해당 유형의 붕소-질소 화합물이 발광 재료로 사용되는 것을 개시하였고, 구체적으로, 소자 실시예에서 ADN을 호스트 재료로서 소자에 응용하여, 비교적 우수한 청색 형광 소자 성능을 얻었다. 그러나, 해당 출원에서는 해당 유형의 화합물이 TADF 소자에 응용되는 것을 개시하지 않았고, 해당 유형의 붕소-질소 화합물과 높은 삼중항 상태를 갖는 이중 호스트 재료의 특정 조합을 개시하지 않았다.In CN113045595A, a compound of the general formula

disclosed, which further general formula

Phosphorus compounds are disclosed wherein, for ring A, a number of heterocyclic structures are disclosed, for example,

,

etc. have been initiated. This application discloses that a boron-nitrogen compound of this type is used as a light emitting material, and specifically, ADN was applied to the device as a host material in device examples to obtain relatively excellent performance of a blue fluorescent device. However, the application does not disclose the application of this type of compound to a TADF device, nor does it disclose a specific combination of a boron-nitrogen compound of that type and a dual host material having a high triplet state.

인 화합물을 개시하였으며, 여기서, 불포화 고리 Z₂와 고리 Z₅에는 포화 결합이 존재하고, 더 나아가, 해당 출원에서는 일반식이

인 화합물을 개시하였으며, 도 5의 핵자기 결과에 따르면, 이는 화합물

의 합성을 완료하였음을 알 수 있다. 해당 출원에서는 불포화 고리 Z₂와 고리 Z₅에 포화 결합이 존재하기 때문에, 방향족 고리로 쉽게 산화되어, 결국 소자 수명을 단축시킬 수 있다. 또한, 해당 출원은 해당 유형의 화합물이 발광 재료로서 단일 호스트 재료와 배합하여 사용하는 응용만을 개시하였고, 이중 호스트 재료와의 특정 조합으로서의 응용 및 해당 특정 조합이 소자에 미치는 영향을 개시하지 않았다.In CN107501311A, the general formula is

Disclosed is a phosphorus compound, wherein a saturated bond is present in an unsaturated ring Z ₂ and a ring Z ₅ , and furthermore, in the application, the general formula

A phosphorus compound was disclosed, and according to the nuclear magnetic results of FIG. 5, it is a compound

It can be seen that the synthesis of In this application, since a saturated bond is present in the unsaturated ring Z ₂ and the ring Z ₅ , it is easily oxidized to an aromatic ring, which can eventually shorten the life of the device. In addition, the application only discloses an application in which the compound of this type is used in combination with a single host material as a light emitting material, and does not disclose an application as a specific combination with a dual host material and an effect of the specific combination on the device.

을 개시하였으며, 여기서 G는 치환 또는 비치환된 헤테로방향족기이고, 상기 G에서 헤테로방향족기의 고리원자는 적어도 하나의 붕소 원자 및 두 개의 질소 원자를 포함하며; 이에 개시된 구체적인 화합물은

,

,

등을 포함한다. 해당 출원의 화합물에서는 4 개의 질소 원자와 2 개의 붕소 원자의 큰 평면 시스템을 사용하여 우수한 소자 성능을 달성하였지만, 이는 4 개의 질소 원자와 2 개의 붕소 원자가 발광 재료의 LUMO를 너무 깊게 만들어, 발광 재료와 호스트 재료 사이의 HOMO가 가까워져, 발광 재료의 정공 포획(hole trap) 능력이 저하되고, 결국 소자 효율을 저하시키는 것에 대해 고려하지 않았다. 또한, 해당 유형의 화합물은 분자량이 비교적 커서 실제 응용에서 지나치게 높은 증착 온도를 초래한다. TADF 소자의 연구에서, 해당 출원은 단일 호스트 및 발광 재료로서 해당 유형의 화합물만 사용하여 소자 성능을 연구하였고, 이와 이중 호스트 재료가 TADF 소자에 응용되어 소자에 미치는 영향을 연구하지 않았다.In CN112341482A, a compound of the general formula:

Disclosed, wherein G is a substituted or unsubstituted heteroaromatic group, wherein the ring atoms of the heteroaromatic group in G include at least one boron atom and two nitrogen atoms; Specific compounds disclosed herein are

,

,

Include etc. In the compound of the application, excellent device performance was achieved by using a large planar system of 4 nitrogen atoms and 2 boron atoms, but this made the LUMO of the light emitting material too deep because the 4 nitrogen atoms and 2 boron atoms made the light emitting material and The fact that the HOMO between the host materials becomes closer, the hole trapping ability of the light emitting material is lowered, and consequently the device efficiency is lowered is not considered. In addition, this type of compound has a relatively large molecular weight, resulting in excessively high deposition temperatures in practical applications. In the study of the TADF device, the application studied the device performance using only a compound of that type as a single host and light emitting material, and did not study the effect of this dual host material applied to the TADF device.

In the prior art, many polycyclic condensation structures having boron, nitrogen, etc. as central atoms have been disclosed, and among them, boron-nitrogen heterocyclic compounds having a specific closed-loop structure have also been reported, which can be used in combination with various single host materials. there is. However, the prior art did not disclose a specific combination of a boron-nitrogen heterocyclic compound having a specific closed-loop structure and a dual host material having a high triplet state. After in-depth research, the present inventors use a boron-containing heterocyclic compound having a specific closed-loop structure as a light emitting material, and mix a high triplet state hole transporting host material and an electron transporting host material to use as a host material. A new material combination was discovered, and application of this new material combination to a TADF light emitting device can provide better device performance.

The present invention aims to provide an organic electroluminescent device having a novel material combination, in order to solve at least some of the above problems. The organic electroluminescent device uses a novel material combination consisting of a first compound having a structure of formula 1, a first host material and a second host material having a high triplet state; This novel material combination can be used for a light emitting layer of an organic electroluminescent device. This new material combination exhibits good overall device performance in the device, for example narrower full width at half maximum, longer lifetime and higher efficiency.

According to one embodiment of the present invention, an organic electroluminescent device is disclosed, which includes:

anode,

cathode, and

an organic layer disposed between an anode and a cathode, wherein the organic layer includes at least an organic light emitting layer;

Here, the organic light emitting layer includes at least a first compound, a first host material and a second host material;

Here, the energy levels of the triplet state of the first host material and the second host material are both higher than 2.69 eV;

Here, the first compound has a structure represented by Formula 1,

In Formula 1, ring A, ring B, ring C, ring D, and ring E are each independently selected from an unsaturated carbon ring having 5 to 30 carbon atoms or an unsaturated hetero ring having 3 to 30 carbon atoms;

Y ₁ is selected from B, P=O, P=S, As, As=O, As=S, SiR' or GeR';

Each occurrence of R _a , R _b , R _c , R _d , R _e identically or differently represents mono-substitution, poly-substitution or non-substitution;

R', R _a , R _b , R _c , R _d , R _e are identical or different each time they appear, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 rings A substituted or unsubstituted cycloalkyl group having 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, and a 7 to 30 carbon atoms A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 2 to 20 carbon atoms cyclic alkenyl group, 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 having 3 to 20 carbon atoms group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgerma group having 6 to 20 carbon atoms Nyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino selected from the group consisting of groups, and combinations thereof;

L ₁ and L ₂ are each independently a single bond, O, S, Se, SiRR, PR, a substituted or unsubstituted vinylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. It is selected from the group consisting of a substituted or unsubstituted heteroarylene group having a group, and a combination thereof; When a plurality of R's are present at the same time, the plurality of R's are the same or different;

Each occurrence of R, identically or differently, is 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, and 1 to 20 carbon atoms. substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

Adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring.

According to another embodiment of the present invention, an electronic device is further disclosed, which includes the organic electroluminescent device described above.

According to another embodiment of the present invention, a composition is further disclosed, which includes at least a first compound, a first host material and a second host material.

The present invention discloses a novel electroluminescent device, wherein the electroluminescent device uses a novel material combination consisting of a first compound, a first host material, and a second host material, and this novel material combination is used in a light emitting layer of an organic electroluminescent device. can be used This novel material combination allows the novel electroluminescent device to obtain a narrower half-width, longer lifetime and higher efficiency, providing better device performance.

1 is a schematic diagram of an organic light emitting device including the compounds and compositions disclosed herein.
2 is a schematic diagram of another organic light emitting device incorporating the compounds and compositions disclosed herein.

OLEDs can be fabricated on several types of substrates (eg glass, plastic and metal). 1 schematically and non-limitingly shows an organic light emitting device 100 . The drawings are not necessarily drawn to scale, and some layer structures in the drawings may be omitted if necessary. The device 100 includes 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. Device 100 may be fabricated by sequentially depositing the described layers. The nature and function of each layer and exemplary materials are described in more detail in US Pat. No. 7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.

Each layer in this layer has more examples. An example is the flexible and transparent substrate-anode combination disclosed in U.S. Patent No. 5,844,363 bonded in an inclusive manner. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a molar ratio of 50:1 as disclosed in US Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. US Pat. No. 6,303,238 (to Thompson et al.), incorporated by reference in its entirety, discloses an example of a host material. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1 as disclosed in US Patent Application Publication No. 2003/0230980 combined in an inclusive manner. U.S. Patent Nos. 5703436 and 5707745, incorporated by reference in their entirety, disclose examples of cathodes, which are transparent, conductive, and sputter-deposited over a thin metal layer such as Mg:Ag. It includes a composite anode having an ITO layer deposited thereon. U.S. Patent No. 6097147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entirety, describe the principle and use of the barrier layer in more detail. US Patent Application Publication No. 2004/0174116, incorporated by reference in its entirety, provides an example of an injection layer. A description of the protective layer can be found in US Patent Application Publication No. 2004/0174116, incorporated herein by reference in its entirety.

The hierarchical structure is provided through a non-limiting embodiment. The function of the OLED can be realized by combining several types of layers described above, or some layers can be completely omitted. It may further include other layers not explicitly described. Optimum performance can be achieved by using a single material or a mixture of different materials within each layer. Any functional layer may include several sub-layers. For example, the light emitting layer may include two layers of different light emitting materials to realize a desired light emitting spectrum.

In one embodiment, an OLED can be described as having an “organic layer” disposed between a cathode and an anode. The organic layer may include one or a plurality of layers.

OLED also requires an encapsulation layer, and FIG. 2 schematically and non-limitingly illustrates the organic light emitting device 200 . The difference between this and FIG. 1 is that an encapsulation layer 102 is further included on the cathode 190 to prevent harmful substances (eg, moisture and oxygen) from the environment. Any material capable of providing an encapsulation function can be used as the encapsulation layer (eg glass or organic-inorganic mixed layer). The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer encapsulation is described in US patent US7968146B2, the entire contents of which are incorporated herein by reference.

A device fabricated according to an embodiment of the present invention may be integrated into various types of consumer goods having one or a plurality of electronic member modules (or units) of the device. Some examples of such consumer products are flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signal launchers, head-up displays, fully transparent or partially transparent displays, flexible displays, Includes smartphones, tablets, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays and taillights do.

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

As used herein, "top" means the farthest from the substrate, and "bottom" means the closest to the substrate. When a first layer is described as being “disposed” “on” a second layer, the first layer is disposed relatively far from the substrate. Other layers may be present between the first layer and the second layer, unless it is specified that the first layer "and" the second layer "contact." For example, it can be described that the negative electrode is still “placed” “on” the positive electrode, even though there are several kinds of organic layers between the negative electrode and the positive electrode.

As used herein, “solution processable” means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and/or capable of being precipitated from a liquid medium.

When it is considered that the ligand directly affects the photosensitivity of the light emitting material, the ligand may be referred to as a "photosensitive ligand". When it is considered that the ligand does not affect the photosensitive performance of the light emitting material, the ligand can be referred to as an "auxiliary ligand", and the auxiliary ligand can change the properties of the photosensitive ligand.

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the spin statistics limit of 25% through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet quenching (TTA).

On the other hand, E-type delayed fluorescence does not depend on collisions between two triplet states, but rather on a transition between a triplet state and a singlet-excited state. A compound capable of generating E-type delayed fluorescence must have a very small singlet-triplet gap so that transition between energy states can proceed. Thermal energy can activate a transition from the triplet state to the singlet state. This type of delayed fluorescence is also referred to as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delay factor increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative attenuation by triplet states, the proportion of back-filled singlet excited states can reach 75%. . The total fraction of singlet states can be 100%, which far exceeds 25% of the field-generated excitons' spin statistics.

Characteristics of type E delayed fluorescence can be found in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small singlet-triplet energy gap (ΔES-T). Organic shell-acceptor luminescent materials containing non-metals have the potential to realize these characteristics. The release of these materials is generally characterized as anti-receptor charge transfer (CT) type release. Spatial separation of HOMO and LUMO in these antireceptor-receptor compounds usually results in small ΔES-T. Such conditions may include CT conditions. In general, a craft-acceptor luminescent material is constituted by connecting an electron crafting body moiety (eg, an amino group or a carbazole derivative) and an electron acceptor moiety (eg, a 6-membered aromatic ring containing N).

Regarding the definition of substituent terms,

Halogen or halide-as used herein includes fluorine, chlorine, bromine and iodine.

Alkyl groups as used herein include straight chain alkyl groups 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 are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, secondary butyl group (Sec-butyl), isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n -Heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group Decyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3 -Contains a methylpentyl group. In the above, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, secondary butyl group, isobutyl group, t-butyl group, n-pentyl group, neopentyl group and n-hexyl group are preferred. Also, the alkyl group may be optionally substituted.

Cycloalkyl groups as used herein include cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and a cycloalkyl group having 4 to 10 carbon atoms is preferable. Examples of the cycloalkyl group are cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4,4-dimethylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group (1-norbornyl), 2-norbornyl groups, and the like. In the above, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 4,4-dimethylcyclohexyl group are preferable. Also, the cycloalkyl group may be optionally substituted.

The heteroalkyl group is as used herein, and the heteroalkyl group is 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 in which one or a plurality of carbons in the alkyl group chain It includes those formed by being substituted by a hetero 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 methoxymethyl group, ethoxymethyl group, ethoxyethyl group, methylthiomethyl group, ethylthiomethyl group, ethylthioethyl group, methoxymethoxymethyl group, ethoxymethoxymethyl group, ethoxyethoxyethyl group, Hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, sulfanylmethyl group, sulfanylethyl group, sulfanylpropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylgermanylmethyl group, trimethylgermanylethyl group, Trimethylgermanylisopropyl group, dimethylethylgermanylmethyl group, dimethylisopropylgermanylmethyl group, tert-butyldimethylgermanylmethyl group, triethylgermanylmethyl group, triethylgermanylethyl group, triisopropylgermanylmethyl group, triisopropyl germanylethyl group, trimethylsilylmethyl group, trimethylsilylethyl group, trimethylsilylisopropyl group, triisopropylsilylmethyl group, and triisopropylsilylethyl group. Also, the heteroalkyl group may be optionally substituted.

Alkenyl groups as used herein include straight chain olefin groups, branched olefin groups and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylvinyl group, a 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 norbornenyl group. Also, the alkenyl group may be optionally substituted.

Alkynyl groups as used herein include straight-chain alkynyl groups. The alkynyl group may be an alkynyl group containing 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 and the like. In the above, ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group and phenylethynyl group are preferred. Also, an alkynyl group may be optionally substituted.

Aryl groups or aromatic groups, as used herein, consider condensed and unfused 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 the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a tetraphenylene group, a naphthyl group, an anthracene group, a phenalene group, a phenanthrene group, a fluorene group, a pyrene group ( pyrene), a chrysene group, a perylene group, and an azulene group, preferably a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a fluorene group, and a naphthalene group. do. Examples of non-fused aryl groups are phenyl group, biphenyl-2-yl group (biphenyl-2-yl), biphenyl-3-yl group, biphenyl-4-yl group, p-terphenyl-4-yl group, p-terphenyl -3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group , p-tolyl group, p-(2-phenylpropyl)phenyl group, 4'-methylbiphenylyl group, 4"-tertbutyl group-p-terphenyl-4-yl group, o-cumenyl group (o-cumenyl), m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, mesityl group and m-quaterphenyl group (m-quaterphenyl) In addition, the aryl group may be optionally substituted.

Heterocyclic group or heterocyclyl, as used herein, refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is a nitrogen atom or an oxygen atom. , It is selected from the group consisting of a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and a preferred non-aromatic heterocyclic group containing 3 to 7 ring atoms, such as nitrogen, oxygen, silicon or sulfur. contains at least one heteroatom. Examples of the non-aromatic heterocyclic group include an oxiranyl group, an oxetanyl group, a tetrahydrofuran group, a tetrahydropyran group, and a dioxolane group. group), dioxane group, aziridinyl group, dihydropyrrole group, tetrahydropyrrole group, piperidine group, oxazolidinyl group group), morpholino group, piperazinyl group, oxepine group, thiepine group, azepine group and tetrahydrosilole group include Also, the heterocyclic group may be optionally substituted.

Heteroaryl groups, as used herein, include unfused and fused heteroaromatic groups which may contain from 1 to 5 heteroatoms, wherein at least one heteroatom is a nitrogen atom, an oxygen atom, a sulfur atom, or a selenium atom. It is selected from the group consisting of an atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. An isoaryl group also means a 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. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene. (benzoselenophene), carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole (oxazole), thiazole group, oxadiazole group, oxatriazole group, dioxazole group, thiadiazole group, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine , oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole , benzothiazole group, quinoline group, isoquinoline group, cinnoline group, quinazoline group, quinoxaline group, naphthyridine group, phthalazine group, pteridine group, xan Ten group (xanthene), acridine group, phenazine group, phenothiazine group, benzofuranopyridine group, furanodipyridine group, benzothienopyridine group, thienodipyridine group ), benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarba sol group, imidazole group, pyridine group, triazine group, benzimidazole group, 1,2-azaborane group ), 1,3-azaborane group, 1,4-azaborane group, borazine group and their aza analogues. Also, a heteroaryl group may be optionally substituted.

Alkoxy groups, as used herein, are represented by -O-alkyl groups, -O-cycloalkyl groups, -O-heteroalkyl groups, or -O-heterocyclic groups. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are as 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 a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and tetrahydrofuranyloxy. It includes a tetrahydrofuranyloxy group, a tetrahydropyranyloxy group, a methoxypropyloxy group, an ethoxyethyloxy group, a methoxymethyloxy group and an ethoxymethyloxy group. Also, the alkoxy group may be optionally substituted.

An aryloxy group, as used herein, is denoted by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and the heteroaryl group are as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and is preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy groups and biphenyloxy groups. Also, the aryloxy group may be optionally substituted.

Aralkyl group as used herein 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 the aralkyl group are benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl t-butyl group, α-naphthylmethyl group, 1-α-naphthyl group -Ethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthyl-ethyl group, 2-β- Naphthyl-ethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group (p -chlorobenzyl), m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group (p-bromobenzyl), m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group (p- iodobenzyl), m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group (p-hydroxybenzyl), m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-amino Benzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1- It includes a hydroxy-2-phenylisopropyl group and a 1-chloro-2-phenylisopropyl group. In the above, the benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group and 2-phenylisopropyl group desirable. Also, an aralkyl group may be optionally substituted.

An alkylsilyl group as used herein includes a silyl group substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group are trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethyl and an isopropylsilyl group, a tri-t-butylsilyl group, a triisobutylsilyl group, a dimethyl-t-butylsilyl group, and a methyl-di-t-butylsilyl group. Also, the alkylsilyl group may be optionally substituted.

An arylsilyl group as used herein 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, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include a triphenylsilyl group, a phenyldibiphenylsilyl group, a diphenylbiphenylsilyl group, a phenyldiethylsilyl group, a diphenylethylsilyl group, a phenyldimethylsilyl group, and a diphenylmethylsilyl group. , A phenyldiisopropylsilyl group, a diphenylisopropylsilyl group, a diphenylbutylsilyl group, a diphenylisobutylsilyl group, and a diphenyl-t-butylsilyl group. Also, the arylsilyl group may be optionally substituted.

An alkylgermanyl group as used herein includes a germanyl group substituted with an alkyl group. The alkylgermanyl group may be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of the alkyl germanyl group include a trimethylgermanyl group, a triethylgermanyl group, a methyldiethylgermanyl group, an ethyldimethylgermanyl group, a tripropylgermanyl group, a tributylgermanyl group, a triisopropylgermanyl group, A methyldiisopropylgermanyl group, a dimethylisopropylgermanyl group, a trit-butylgermanyl group, a triisobutylgermanyl group, a dimethyl t-butylgermanyl group, and a methyldi-t-butylgermanyl group are included. Also, the alkylgermanyl group may be optionally substituted.

An arylgermanyl group, as used herein, includes a germanyl group substituted with at least one aryl group or heteroaryl group. The arylgermanyl group may be an arylgermanyl group having 6 to 30 carbon atoms, preferably an arylgermanyl group having 8 to 20 carbon atoms. Examples of the arylgermanyl group include a triphenylgermanyl group, a phenyldibiphenylgermanyl group, a diphenylbiphenylgermanyl group, a phenyldiethylgermanyl group, a diphenylethylgermanyl group, a phenyldimethylgermanyl group, and a diphenyl group. methyl germanyl group, phenyl diisopropyl germanyl group, diphenyl isopropyl germanyl group, diphenyl butyl germanyl group, diphenyl isobutyl germanyl group, and diphenyl t-butyl germanyl group. Also, the arylgermanyl group may be optionally substituted.

The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic fragment are replaced with 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. Other nitrogenous analogs of the aza derivatives described above can readily be envisioned by those skilled in the art, and all such analogs are intended to be included within the term set forth herein.

In the present invention, unless otherwise defined, 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 alkoxy group, Nyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted alkylgermanyl group, substituted arylgermanyl group, substituted amino group, substituted When a term of any one of the group consisting of an acyl group, a substituted carbonyl group, a substituted carboxylic acid group, a substituted ester group, and a substituted sulfinyl group is used, it is an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, Aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, alkylgermanyl group, arylgermanyl group, amino group, acyl group, carbonyl group, carboxyl group Any one group of an acid group, an ester group, a sulfinyl group, a sulfonyl group, and a phosphino group is deuterium, a halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. An unsubstituted cycloalkyl group having, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, and an unsubstituted group having 7 to 30 carbon atoms aralkyl group having 1 to 20 carbon atoms, unsubstituted alkoxy group having 6 to 30 carbon atoms, unsubstituted aryloxy group having 2 to 20 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, An unsubstituted alkynyl group having 6 to 30 carbon atoms, an unsubstituted aryl group having 3 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 20 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, unsubstituted with 0 to 20 carbon atoms One or more selected from an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof means that it can be substituted by a dog.

It should be understood that if a molecule fragment is described by a substituent or linked to other moieties in other ways, it is a fragment (e.g. phenyl group, phenylene group, naphthyl group, dibenzofuran group) or it is the entire molecule (e.g. , benzene, naphthyl group, dibenzofuran group). As used herein, these different ways of designating substituents or fragment linkages are considered equivalent.

In the compounds mentioned in this application, hydrogen atoms may be partially or entirely replaced by deuterium. Other elements such as carbon and nitrogen may also be replaced by other stable isotopes of these. As this improves the efficiency and stability of the device, it may be desirable to substitute other stable isotopes in the compound.

In the compounds mentioned in this application, polysubstitution refers to a range up to the maximum usable substitution, including disubstitutions. In the compounds mentioned in this application, when any substituent represents polysubstitution (including di-, tri-, tetra-substitution, etc.), it indicates that the substituent may be present at a plurality of available substitution positions in the linkage structure, Substituents present at a plurality of available substitution positions may be of the same structure or may be of different structures.

In the compounds mentioned in the present invention, for example, adjacent substituents in the compound cannot be optionally linked to form a ring, unless it is specifically defined that the adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present invention, adjacent substituents may be optionally linked to form a ring, including cases where adjacent substituents may be linked to form a ring, and also when adjacent substituents are not linked to form a ring. Including case When adjacent substituents can be arbitrarily connected to link rings, the formed rings are monocyclic rings, polycyclic rings (including spiro rings, bridging rings, and condensed rings) alicyclic rings, heteroalicyclic rings, It may be an aromatic ring or a heteroaromatic ring. In this expression, 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 bonded directly to each other.

The intention of the expression that adjacent substituents may be optionally linked to form a ring is also to consider that two substituents bonded to the same carbon atom are linked to each other by chemical bonds to form a ring, which is exemplified through the following formula :

.

.

The intention of the expression that adjacent substituents may be optionally linked to form a ring is also to consider that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by chemical bonds to form a ring, which represents the following formula exemplified via:

.

.

The expression that adjacent substituents may be arbitrarily linked to form a ring is also intended to consider that two substituents bonded to carbon atoms farther apart are linked to each other by chemical bonds to form a ring, which is expressed through the following formula exemplified by:

.

.

In addition, the intention of the expression that adjacent substituents can be arbitrarily linked to form a ring is also that when one of the two adjacent substituents represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded to form a ring. to be considered. This is illustrated through the formula:

According to one embodiment of the present invention, an organic electroluminescent device is disclosed, which:

anode,

cathode, and

an organic layer disposed between an anode and a cathode, wherein the organic layer includes at least an organic light emitting layer;

Here, the organic light emitting layer includes at least a first compound, a first host material and a second host material;

Here, the energy levels of the triplet state of the first host material and the second host material are both higher than 2.69 eV;

Here, the first compound has a structure represented by Formula 1,

In Formula 1, ring A, ring B, ring C, ring D, and ring E are each independently selected from an unsaturated carbon ring having 5 to 30 carbon atoms or an unsaturated hetero ring having 3 to 30 carbon atoms;

Y ₁ is selected from B, P=O, P=S, As, As=O, As=S, SiR' or GeR';

Each occurrence of R _a , R _b , R _c , R _d , R _e identically or differently represents mono-substitution, poly-substitution or non-substitution;

R', R _a , R _b , R _c , R _d , R _e are identical or different each time they appear, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 rings A substituted or unsubstituted cycloalkyl group having 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, and a 7 to 30 carbon atoms A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 2 to 20 carbon atoms cyclic alkenyl group, 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 having 3 to 20 carbon atoms group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgerma group having 6 to 20 carbon atoms Nyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino selected from the group consisting of groups, and combinations thereof;

L ₁ and L ₂ are each independently a single bond, O, S, Se, SiRR, PR, a substituted or unsubstituted vinylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. It is selected from the group consisting of a substituted or unsubstituted heteroarylene group having a group, and a combination thereof; When a plurality of R's are present at the same time, the plurality of R's are the same or different;

Each occurrence of R, identically or differently, is 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, and 1 to 20 carbon atoms. substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

Adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring.

In the present text, adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring, which means that in adjacent substituent groups among them, for example, two substituents R Between _a , between two substituents R _b , between two substituents R _c , between two substituents R _d , between two substituents R _e , between two substituents R, between substituents R and R _a , between substituents R and R _d , between the substituents R and R _c , between the substituents R and R _e , any one or a plurality of these substituent groups may be connected to form a ring. Obviously, all of these substituent groups may not be linked to form a ring.

According to one embodiment of the present invention, all compounds included in the organic light emitting layer do not contain metal.

According to one embodiment of the present invention, wherein, in Formula 1, ring A, ring B, ring C, ring D and ring E are each independently a 5-membered unsaturated carbon ring, an aromatic ring having 6-30 carbon atoms, or 3 It is selected from heteroaromatic rings having ~30 carbon atoms.

According to one embodiment of the present invention, where, in Formula 1, Ring A, Ring B, Ring C, Ring D and Ring E are the same or different each time they appear, a 5-membered unsaturated carbon ring having 6 to 18 carbon atoms. It is selected from an aromatic ring or a heteroaromatic ring having 3-18 carbon atoms.

According to one embodiment of the present invention, where, in Formula 1, Ring A, Ring B, Ring C, Ring D and Ring E are identically or differently each time they appear, a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, Anthracene ring, indene ring, fluorene ring, indole ring, carbazole ring, benzofuran ring, dibenzofuran ring, benzosilol ring, dibenzosilol ring, benzothiophene ring, dibenzothiophene ring, dibenzoselenophene rings, cyclopentadiene rings, furan rings, thiophene rings, silol rings, or combinations thereof.

According to one embodiment of the present invention, where, in Equation 1, Y ₁ is selected from B, P=0 or P=S.

According to one embodiment of the present invention, where, in Formula 1, Y ₁ is B.

According to one embodiment of the present invention, wherein the first compound has a structure represented by Formula 2,

Each occurrence of R _a , R _b , R _c , R _d , R _e identically or differently represents mono-substitution, poly-substitution or non-substitution;

Each occurrence of R _a , R _b , R _c , R _d , R _e is identically or differently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a ring having 3 to 20 ring carbon atoms. A substituted or unsubstituted cycloalkyl group, 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 heterocyclic group having 7 to 30 carbon atoms Unsubstituted aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 2 to 20 carbon atoms Nyl group, 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, 6 A substituted or unsubstituted arylsilyl group having to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, 0 A substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and It is selected from the group consisting of combinations thereof;

Each time L ₁ , L ₂ appears identically or differently, a single bond, O, S, Se, SiRR, PR, a substituted or unsubstituted vinylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, 3 It is selected from the group consisting of a substituted or unsubstituted heteroarylene group having about 30 carbon atoms, and combinations thereof; When a plurality of R's are present at the same time, the plurality of R's are the same or different;

Each occurrence of R, identically or differently, is 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, and 1 to 20 carbon atoms. substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

Adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring.

According to one embodiment of the present invention, L ₁ and L ₂ are single bonds.

According to one embodiment of the present invention, L ₁ or L ₂ is a single bond.

According to one embodiment of the present invention, R _a , R _b , R _c , R _d , R _e are identically or differently each time they appear, hydrogen, deuterium, halogen, cyano group, hydroxyl group, sulfanyl group, 1 to 6 A substituted or unsubstituted alkyl group having two carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroalkyl group having 6 to 24 carbon atoms Or an unsubstituted aryl group, 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 group having 6 to 12 carbon atoms arylsilyl group, substituted or unsubstituted alkylgermanyl group having 3 to 6 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 12 carbon atoms, substituted or unsubstituted having 0 to 12 carbon atoms It is selected from the group consisting of amino groups, and combinations thereof;

According to one embodiment of the present invention, each occurrence of R _a , R _b , R _c , R _d , R _e is identically or differently hydrogen, deuterium, fluorine, cyano group, hydroxyl group, sulfanyl group, methyl group, ethyl group , n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, neopentyl group, cyclohexyl group, trimethylsilyl group, trimethylgermanyl group, phenyl group , Biphenyl group, terphenyl group, quaterphenyl group, triphenylene group, tetraphenylene group, naphthyl group, phenanthrene group, anthracene group, indenyl group, fluorene group, indolyl group, carbazole group, benzofuran group, dibenzofuran group, It is selected from the group consisting of a benzosilol group, a dibenzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, a diphenylamino group, a dibenzofuranylphenylamino group, and combinations thereof.

According to one embodiment of the present invention, where at least one of R _a , R _b , R _c , R _d , and R _e is identically or differently deuterium, halogen, substituted or unsubstituted having 1 to 20 carbon atoms each time it appears. substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms group, 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, and a 2 to 30 carbon atom group. A substituted or unsubstituted alkenyl group having 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, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. A substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, A substituted or unsubstituted arylgermanyl group, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, It is selected from the group consisting of a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

According to one embodiment of the present invention, whenever at least one of R _a , R _b , R _c , R _d , and R _e appears, identically or differently, deuterium, halogen, cyano group, hydroxy group, sulfanyl group, 1 to 1 A substituted or unsubstituted alkyl group having 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted heteroalkyl group having 6 to 24 carbon atoms A substituted or unsubstituted aryl group, 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 alkylsilyl group having 6 to 12 carbon atoms A cyclic arylsilyl group, a substituted or unsubstituted alkylgermanyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 12 carbon atoms, a substituted or unsubstituted group having 0 to 12 carbon atoms It is selected from the group consisting of cyclic amino groups, and combinations thereof;

According to an embodiment of the present invention, whenever at least one of R _a , R _b , R _c , R _d , and R _e appears, identically or differently, deuterium, fluorine, cyano group, hydroxyl group, sulfanyl group, methyl group, Ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, neopentyl group, cyclohexyl group, trimethylsilyl group, trimethylgermanyl group, Phenyl group, biphenyl group, terphenyl group, quaterphenyl group, triphenylene group, tetraphenylene group, naphthyl group, phenanthrene group, anthracene group, indenyl group, fluorene group, indolyl group, carbazole group, benzofuran group, dibenzofuran group , A benzosilol group, a dibenzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, a diphenylamino group, a dibenzofuranylphenylamino group, and combinations thereof.

According to one embodiment of the present invention, wherein, in Formula 2, at least one R _a is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. It is selected from the group consisting of, and combinations thereof.

According to one embodiment of the present invention, wherein, in Formula 2, at least one R _a is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms. It is selected from the group consisting of, and combinations thereof.

According to one embodiment of the present invention, wherein, in Formula 2, at least one R _a is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted tetra A phenylene group, a naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzofuran group, a substituted Or an unsubstituted dibenzofuran group, a substituted or unsubstituted benzosilol group, a substituted or unsubstituted dibenzosilol group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzothiophene group, and It is selected from the group consisting of combinations thereof.

According to one embodiment of the present invention, here, at least one R _a in Formula 2 is selected from a substituted or unsubstituted carbazole group or a substituted or unsubstituted azacarbazole group.

According to one embodiment of the present invention, the HOMO energy level of the first compound is less than -5.2eV.

According to one embodiment of the present invention, the HOMO energy level of the first compound is less than or equal to -5.3eV.

According to one embodiment of the present invention, the HOMO energy level of the first compound is less than or equal to -5.4eV.

In this paper, the HOMO energy level and LUMO energy level of a compound are the electrochemical properties of the compound measured using anhydrous DMF as a solvent through cyclic voltammetry. A specific measurement method will be described in detail below.

According to one embodiment of the present invention, the first compound is compound BD-1-1 to compound BD-1-31, compound BD-2-1 to compound BD-2-28, compound BD-3-1 to compound The group consisting of BD-3-22, compound BD-4-1 to compound BD-4-36, compound BD-5-1 to compound BD-5-36, compound BD-6-1 to compound BD-6-42 is selected from; Compound BD-1-1 to Compound BD-1-31, Compound BD-2-1 to Compound BD-2-28, Compound BD-3-1 to Compound BD-3-22, Compound BD-4-1 to For specific structures of Compound BD-4-36, Compound BD-5-1 to Compound BD-5-36, Compound BD-6-1 to Compound BD-6-42, see Claim 9.

According to one embodiment of the present invention, the first compound is compound BD-1-1 to compound BD-1-31, compound BD-2-1 to compound BD-2-28, compound BD-3-1 to compound The group consisting of BD-3-24, compound BD-4-1 to compound BD-4-36, compound BD-5-1 to compound BD-5-36, compound BD-6-1 to compound BD-6-42 is selected from; Compound BD-1-1 to Compound BD-1-31, Compound BD-2-1 to Compound BD-2-28, Compound BD-3-1 to Compound BD-3-24, Compound BD-4-1 to For specific structures of Compound BD-4-36, Compound BD-5-1 to Compound BD-5-36, Compound BD-6-1 to Compound BD-6-42, see Claim 9.

According to one embodiment of the present invention, the compound BD-1-1 to compound BD-1-31, the compound BD-2-1 to compound BD-2-28, the compound BD-3-1 to compound BD-3- 22, compound BD-4-1 to compound BD-4-36, compound BD-5-1 to compound BD-5-36, compound BD-6-1 to compound BD-6-42, hydrogen in the structure is may be partially or wholly substituted by

According to one embodiment of the present invention, the compound BD-1-1 to compound BD-1-31, the compound BD-2-1 to compound BD-2-28, the compound BD-3-1 to compound BD-3- 24, compound BD-4-1 to compound BD-4-36, compound BD-5-1 to compound BD-5-36, compound BD-6-1 to compound BD-6-42, hydrogen in the structure is may be partially or wholly substituted by

According to one embodiment of the present invention, the first host material has a structure represented by any one of Formulas 3 to 5,

,

,

,

,

,

,

In Formula 3, each occurrence of X ₁ to X ₃ is identically or differently selected from CR ₄ or N, and at least one of X ₁ to X ₃ is selected from N;

Whenever L appears, identically or differently, a 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 is selected from;

In Formula 4 or Formula 5, each occurrence of X ₄ is identically or differently selected from CR ₄ or N, and at least one X ₄ of Formula 4 or 5 is selected from N;

Z is the same or different O each time it appears or S;

Each time R ₁ -R ₄ appears identically or differently, 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, 1 Substituted or unsubstituted heteroalkyl group having to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1 to 20 A substituted or unsubstituted alkoxy group having two 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, and a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms. A substituted or unsubstituted alkynyl group, 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 group having 3 to 20 carbon atoms substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms Arylgermanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group It is selected from the group consisting of , phosphino groups, and combinations thereof;

Adjacent substituents R ₄ may be optionally linked to form a ring.

In this Example, the fact that adjacent substituents R ₄ may be optionally linked to form a ring means that two substituents R ₄ may be linked to form a ring. Obviously, between the two substituents R ₄ may not form a ring by not connecting at all.

According to an embodiment of the present invention, in Formula 3, at least two of X ₁ to X ₃ are N.

According to one embodiment of the present invention, where, in Formula 3, X ₁ to X ₃ are N.

According to one embodiment of the present invention, where, in Formula 3, L is identically or differently each time it appears, a single bond, a substituted or unsubstituted arylene group having 6-18 carbon atoms, a substituted arylene group having 3-18 carbon atoms or an unsubstituted heteroarylene group, and is selected from the group consisting of combinations thereof;

According to one embodiment of the present invention, where, in Formula 3, L is identically or differently each time it appears, a single bond, a phenylene group, a biphenylene group, a fluorenylene group, a triphenylenylene group, a furanylene group, thienyl It is selected from the group consisting of a rene group, a dibenzofuranylene group, a dibenzothiophenylene group, and combinations thereof.

According to one embodiment of the present invention, whenever R ₁ to R ₄ appear identically or differently, hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 rings In the group consisting of a substituted or unsubstituted cycloalkyl group having 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 is chosen

According to one embodiment of the present invention, whenever R ₁ to R ₄ appear identically or differently, hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and 3 to 18 carbon atoms are selected. It is selected from the group consisting of a substituted or unsubstituted heteroaryl group having two carbon atoms, and combinations thereof.

According to one embodiment of the present invention, whenever R ₁ to R ₄ appear, they are identically or differently hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, triphenylene group, tetraphenylene group, indenyl group, fluorene group, indolyl group, carbazole group, benzofuran group, dibenzofuran group, benzosilol group, dibenzosilol group, benzothiophene group, dibenzothiophene group, dibenzoselenophene group, triazine group, and combinations thereof selected from the group consisting of

According to one embodiment of the present invention, the first host material is selected from the group consisting of compound N-1-1 to compound N-1-53 and compound N-2-1 to compound N-2-32; For the specific structure of the compound N-1-1 to compound N-1-53 and the compound N-2-1 to compound N-2-32, see claim 14.

According to one embodiment of the present invention, hydrogen in the structures of the compounds N-1-1 to N-1-53 and compounds N-2-1 to N-2-32 may be partially or entirely substituted by deuterium. can

According to one embodiment of the present invention, the second host material has a structure represented by Equation 6,

In Equation 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 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 any of these is selected from a combination of;

Each occurrence of R ₆ identically or differently represents mono-substitution, poly-substitution or non-substitution;

Whenever R ₆ appears, identically or differently, 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, or 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 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, and a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 6 to 30 carbon atoms. cyclic aryl group, 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 aryl group having 6 to 20 carbon atoms Silyl group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms , It is selected from the group consisting of an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R ₆ may be optionally linked to form a ring.

In the present specification, the fact that adjacent substituents R ₆ may be optionally linked to form a ring means that two substituents R ₆ may be linked to form a ring. Obviously, the two substituents R ₆ may not form a ring by not connecting at all.

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

,

,

,

,

L ₁₁ and L ₁₂ are 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 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 any of these is selected from a combination of;

Each occurrence of R ₆ identically or differently represents mono-substitution, poly-substitution or non-substitution;

Whenever R ₆ appears, identically or differently, 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, or 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 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, and a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 6 to 30 carbon atoms. cyclic aryl group, 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 aryl group having 6 to 20 carbon atoms Silyl group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms , It is selected from the group consisting of an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R ₆ may be optionally linked to form a ring.

According to one embodiment of the present invention, the second host material has a structure represented by Formula 6-3 or Formula 6-4,

,

,

,

,

Ar ₁₁ is 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 any of these is selected from a combination of;

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;

Each occurrence of R ₆ identically or differently represents mono-substitution, poly-substitution or non-substitution;

Whenever R ₆ appears, identically or differently, 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, or 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 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, and a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 6 to 30 carbon atoms. cyclic aryl group, 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 aryl group having 6 to 20 carbon atoms Silyl group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms , It is selected from the group consisting of an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R ₆ may be optionally linked to form a ring.

According to one embodiment of the present invention, whenever R ₆ appears, identically or differently, hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms are selected. A substituted or unsubstituted cycloalkyl group, 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 group having 3 to 20 carbon atoms It is selected from the group consisting of an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof.

According to one embodiment of the present invention, whenever R ₆ appears, identically or differently, hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or 3 to 18 carbon atoms It is selected from the group consisting of a substituted or unsubstituted heteroaryl group having, and a combination thereof.

According to one embodiment of the present invention, whenever R ₆ appears, the same or different is hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, triphenylene group, tetraphenylene group, indenyl group, fluorene group, indole group. It is selected from the group consisting of a reel group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzosilol group, a dibenzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, and combinations thereof .

According to one embodiment of the present invention, the second host material is selected from the group consisting of compound P-1 to compound P-24, and the specific structure of the compound P-1 to compound P-24 refers to claim 19 .

According to an embodiment of the present invention, the first compound is a delayed fluorescence light emitting material, the first host material is an n-type host material, and the second host material is a p-type host material.

In this context, the p-type host material is an organic compound containing a carbazole group or a triarylamine organic compound, and its HOMO value is generally greater than -5.8 eV; The n-type host material is an organic compound containing a chemical group such as a pyridine group, a pyrimidine group, a triazine group, an azadibenzofuran group, an azadibenzothiophene group, and an azacarbazole group, and its LUMO value is generally -2.3eV smaller than

According to one embodiment of the present invention, the organic electroluminescent device emits blue light.

According to another embodiment of the present invention, an electronic equipment is further disclosed, which includes the organic electroluminescent device described in any one of the embodiments described above.

According to another embodiment of the present invention, a composition is further disclosed, comprising at least a first compound, a first host material and a second host material, wherein the first compound, the first host material and the second host material are As described in any one of the embodiments described above.

Combination with other materials

Materials used for a specific layer in the organic light emitting device described in the present invention may be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132 to 0161 of US patent application US2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily refer to the literature to identify combinations and other materials that can be used.

In this text, it is explained that materials usable for a specific layer in an organic light emitting device can be used in combination with various types of other materials present in the device. For example, the compounds disclosed herein may be used in combination with various types of hosts, dopants, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of patent application US2015/0349273A1, the entire contents of which are incorporated herein by reference. The materials described or referenced herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily refer to the literature to identify combinations and other materials that can be used.

In the material synthesis example, all reactions are conducted under nitrogen gas protection unless otherwise noted. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized product is synthesized using one or several types of equipment routine in this field (BRUKER's nuclear magnetic resonance spectrometer, SHIMADZU's liquid chromatography, liquid chromatograph-mass spectrometry, gas chromatograph mass spectrometer ( gas chromatograph-mass spectrometry), differential scanning calorimeter, fluorescence spectrophotometer of Shanghai LENGGUANG TECH., electrochemical workstation of Wuhan CORRTEST, and sublimation apparatus of Anhui BEQ, etc. ), the structure is confirmed and the properties are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device also include regular equipment in this field (evaporator produced by ANGSTROM ENGINEERING, optical test system and life test system produced by Suzhou FATAR, ellipsometer produced by Beijing ELLITOP, etc. (but not limited thereto) is tested by methods well known to those skilled in the art. A person skilled in the art is well aware of the use of the equipment, the test method, and the like, so that the unique data of the sample can be obtained reliably and unaffected, so the above related details are not further described herein.

Material Synthesis Example:

The preparation method of the compound of the present invention is not limited, and typically includes the following compounds as examples, but is not limited thereto, and the synthesis route and preparation method thereof are as follows.

Synthesis Example 1: Synthesis of Compound BD-1-1

Step 1: Synthesis of Intermediate 1

Under the protection of nitrogen gas at room temperature, sequentially 2-bromo-9-phenyl-9H-carbazole (15.0 g, 46.5 mmol), carbazole (7.8 g, 46.5 mmol), palladium acetate (1.0 g, 4.6 mmol) , tri-tert-butylphosphine tetrafluoroborate (2.7 g, 9.3 mmol) and sodium-tert-butoxide (11.0 g, 114.7 mmol) were added to xylene (150.0 mL), then the temperature was raised to 140 °C. and react until the reaction is complete. After the reaction was completed, the reaction solution was filtered through celite while hot, concentrated, and recrystallized from toluene to obtain Intermediate 1 (13.6 g, 33.3 mmol, 72%) as a white solid.

Step 2: Synthesis of Compound BD-1-1

Under the protection of nitrogen gas at room temperature, Intermediate 1 (13.6 g, 33.3 mmol) was dissolved in o-dichlorobenzene (150.0 mL), then boron tribromide (BBr ₃ , 20.0 mL) was added, and the system was autoclaved. heated to 180 ° C and reacted for 36 h. After the reaction was cooled to room temperature, the solid was filtered and the solid was recrystallized to obtain BD-1-1 (0.75 g, 1.8 mmol, 5.4%) as a yellow solid, which was identified as the target product with a molecular weight of 416.2 It became.

Synthesis Example 2: Synthesis of Compound BD-1-2

Step 1: Synthesis of Intermediate 2

5-Bromo-4-fluoro-2-methylaniline (60 g, 294 mmol) was put in a 2 L three-necked flask, hydrochloric acid (12 M, 226 mL) was added, and when a white solid precipitated, stirred at 0 ° C. for 30 min, An aqueous solution of sodium nitrite (40 g, 580 mmol) was slowly dropped. After stirring for 30 min, potassium iodide (160 g, 962 mmol) is added. After stirring for 2 h while maintaining at 0° C., sodium thiosulfate solid solution is added and stirred for 30 min. After extracting the aqueous phase with ethyl acetate, the organic phases were combined and purified by column chromatography to obtain intermediate 2 (66.2 g, 210 mmol).

Step 2: Synthesis of Intermediate 3

Under the condition of nitrogen gas, Intermediate 2 (58.9g, 187mmol) was mixed with cesium carbonate (122g, 374mmol) and carbazole (31.2g, 187mmol), NMP (370mL) was added, and heated to 130°C for 2h. react while After the reactants were cooled to room temperature, a large amount of water was added, extracted with ethyl acetate, and the organic phases were combined and purified by column chromatography to obtain an intermediate 3 (86.4 g, 187 mmol).

Step 3: Synthesis of Intermediate 4

Intermediate 3 (86.4 g, 187 mmol) and isopropoxy pinacola toborate (45.7 mL, 224 mmol) were mixed, tetrahydrofuran (200 mL) was added, stirred at 0 ° C, and isopropyl magnesium chloride (200 mmol) was added. , 100 mL) is slowly dropped. The reaction temperature was slowly raised to room temperature and stirred overnight. After the reaction is complete, a large amount of water is added, and the aqueous phase is extracted with ethyl acetate. The organic phases were combined and purified by column chromatography to finally obtain Intermediate 4 (31.1 g, 93 mmol).

Step 4: Synthesis of Intermediate 5

Under the condition of nitrogen gas, intermediate 4 (31.1 g, 93 mmol), o-nitrobromobenzene (18.8 g, 93 mmol), tetrakis (triphenylphosphine) palladium (2.68 g, 2.3 mmol), potassium carbonate (25 g) , 186 mmol) was added to the flask, and toluene/ethanol/water=3/1/1 (total 180 mL) was added, heated to 90° C. and reacted for 2 h. After the reactants were cooled to room temperature, the aqueous phase was extracted with dichloromethane, the organic phases were combined, and purified by column chromatography to finally obtain intermediate 5 (31.9 g, 70 mmol).

Step 5: Synthesis of Intermediate 6

Intermediate 5 (31.9g, 70mmol), triphenylphosphine (55g, 210mmol), and dichlorobenzene (100mL) were mixed under the condition of nitrogen gas, and reacted overnight by heating to 180°C. After the reactant was cooled to room temperature, most of the dichlorobenzene was spin-dried and purified by column chromatography to finally obtain an intermediate 6 (20.7 g, 48.6 mmol).

Step 6: Synthesis of Intermediate 7

Under the condition of nitrogen gas, intermediate 6 (20.7 g, 48.6 mmol), copper powder (1.5 g, 24 mmol), sodium sulfate (20 g, 145.5 mmol), and potassium carbonate (19.7 g, 145.5 mmol) were added to the flask and reacted. Nitrobenzene (300 mL) as a solvent was added, and the temperature was raised to 200° C. to react overnight. After the reactant was cooled to room temperature, filtered through celite, distilled under reduced pressure to remove most of the nitrobenzene, and purified by column chromatography to obtain an intermediate 7 (19.3 g, 38.6 mmol).

Step 7: Synthesis of Compound BD-1-2

Under the condition of nitrogen gas, intermediate 7 (20.1 g, 38.6 mmol) was added to t-butylbenzene (100 mL), then the temperature was lowered to -30 ° C, and n-butyllithium (2.4 M, 24 mL) was dropped. , After the addition was completed, the ice bath was removed, the temperature was returned to room temperature, then the temperature was raised to 60 ° C and reacted for 1 h, the temperature was lowered to -30 ° C, boron tribromide (7 mL, 77 mmol) was dropped, Return to room temperature and stir for 30 min, then cool to 0 °C, dropwise N,N-diisopropylethylamine (DIPEA, 13 mL, 77 mmol), remove the ice bath, and when the system no longer exotherms and reacted overnight by raising the temperature to 120°C. Quenched by adding ammonium chloride solution in an ice bath, extracted with ethyl acetate, concentrated the organic phase, dissolved the filtered solid with toluene, and recrystallized to obtain compound BD-1-2 (2.4 g, 5.5 mmol). The product was identified as the target product with a molecular weight of 430.2.

Synthesis Example 3: Synthesis of BD-3-23

Step 1: Synthesis of Intermediate 8

2-bromo-5-fluoro-nitrobenzene (220 g, 1 mol), phenylboronic acid (146 g, 1.2 mol), tetrakis (triphenylphosphine) palladium (2 g, 1.7 mmol) were sequentially added to a 2 L reaction flask. , Potassium carbonate (272 g, 2 mol), toluene 720 mL, ethanol 240 mL and water 240 mL were added, nitrogen gas was continuously passed through the reaction solution for 5 min, heated to 90 ° C. under the protection of nitrogen gas, and reacted for 2 h. After the reaction was cooled to room temperature, it was extracted with dichloromethane, and the organic phases were combined and purified by column chromatography to obtain intermediate 8 (160 g, 736 mmol).

Step 2: Synthesis of Intermediate 9

Intermediate 8 (88 g, 405 mmol), carbon tetrabromide (181 g, 546 mmol), lithium t-butoxide (43.6 g, 546 mmol) and 100 mL DMF were sequentially added to a 250 mL reaction flask. After the reaction was completed by stirring at room temperature, extraction was performed with dichloromethane, the organic phases were combined, and purified by column chromatography to obtain intermediate 9 (20 g, 67.5 mmol).

Step 3: Synthesis of Intermediate 11

Intermediate 10 (11.4g, 38.8mmol) was put in DMF (190mL), stirred in an ice-water bath, and then sodium hydride (60%, 2.3g, 58mmol) was added in batches, followed by room temperature Return to and react for half an hour, put the reactant back into ice water, add intermediate 9, and react for 2 hours at low temperature. After the reaction was completed, 200 mL of water was added, extracted with ethyl acetate, the organic phases were combined, the solvent was removed by rotation under reduced pressure, and purified by column chromatography to obtain intermediate 11 (24.6 g, 37 mmol) as a pale yellow solid. get

Step 4: Synthesis of Intermediate 12

Intermediate 11 (24.6g, 37mmol), PPh ₃ (26g, 100mmol), o-dichlorobenzene (1,2-Dichlorobenzene) 70mL were mixed, nitrogen gas was continuously passed through the reaction solution for 5 minutes, and nitrogen gas React for 12 h by heating to 180° C. under protection. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 12 (11.5 g, 18 mmol) as a white solid.

Step 5: Synthesis of Intermediate 13

Mix intermediate 12 (11.5 g, 18 mmol), iodobenzene (10 g, 54 mmol), copper powder (1 g, 15 mmol), potassium carbonate (6.2 g, 45 mmol), sodium sulfate (6.4 g, 45 mmol), and 30 mL of nitrobenzene. and heated to 200° C. to react for 12 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 13 (9g, 12.7mmol) as a white solid.

Step 6: Synthesis of BD-3-23

Intermediate 13 (9 g, 12.7 mmol) was dissolved in t-butylbenzene (60 mL), evacuated with nitrogen gas, and cooled in dry ice-ethanol. Add n-butyllithium (2.5M, 6mL) then return to room temperature. After raising the temperature to 60° C. and reacting for half an hour, the temperature was lowered to 0° C., and boron tribromide (1.5 mL, 15.2 mmol) was added. After reacting for half an hour, the system was cooled down to 0°C again, diisopropylethylamine (DIPEA, 4.5mL, 25mmol) was added, heated to 130°C, and reacted for 12h. After the reaction was completed, purification was performed by column chromatography to obtain BD-3-23 (1 g, 1.57 mmol) as a yellow solid. The product was identified as the target product with a molecular weight of 637.3.

Synthesis Example 4: Synthesis of BD-3-24

Step 1: Synthesis of Intermediate 15

Intermediate 14 (14g, 36.1mmol) was put in DMF (180mL), stirred in an ice-water bath, and then sodium hydride (60%, 2.1g, 54mmol) was added in a batchwise manner and then brought to room temperature. After returning and reacting for half an hour, the reactants were again placed in ice water, intermediate 9 was added, and reacted at low temperature for 2 hours. After the reaction was completed, 200 mL of water was added, extracted with ethyl acetate, the organic phases were combined, the solvent was removed by rotation under reduced pressure, and the product was purified by column chromatography to obtain an intermediate 15 (23 g, 35.8 mmol) as a pale yellow solid. get

Step 2: Synthesis of Intermediate 16

Intermediate 15 (23g, 35.8mmol), PPh ₃ (27.6g, 93.5mmol), and 70mL of o-dichlorobenzene were mixed, evacuated with nitrogen gas, and heated to 180°C to react for 12h. Purification by column chromatography gave intermediate 16 (9.5 g, 15 mmol) as a white solid.

Step 3: Synthesis of Intermediate 17

Mix intermediate 16 (9.5g, 15mmol), iodobenzene (9.18g, 45mmol), copper powder (960mg, 15mmol), potassium carbonate (6.2g, 45mmol), sodium sulfate (6.4g, 45mmol), and 30mL of nitrobenzene. and heated to 200° C. to react for 12 h. Nitrobenzene was removed by filtration and distillation under reduced pressure, followed by purification by column chromatography to obtain intermediate 17 (9.5 g, 13.4 mmol) as a white solid.

Step 4: Synthesis of BD-3-24

Intermediate 17 (12 g, 17 mmol) was dissolved in t-butylbenzene (85 mL), evacuated with nitrogen gas, and cooled in dry ice-ethanol. Add n-butyllithium (2.5M, 8mL) then return to room temperature. After raising the temperature to 60° C. and reacting for half an hour, the temperature was lowered to 0° C., and boron tribromide (2 mL, 20.4 mmol) was added. After reacting for half an hour, the system was again cooled to 0°C, diisopropylethylamine (6mL, 20.4mmol) was added, heated to 130°C, and reacted for 12h. After the reaction is complete, the mixture is extracted with ethyl acetate, filtered with magnesium sulfate-alkaline alumina, and then rotated under reduced pressure to remove the solvent. Purified by column chromatography to obtain BD-3-24 (4 g, 3.2 mmol) as a yellow solid. The product was identified as the target product with a molecular weight of 637.3.

Synthesis Example 5: Synthesis of BD-3-8

Step 1: Synthesis of Intermediate 18

1,5-Dibromo-2,4-dichlorobenzene (23 g, 84.5 mmol) was placed in a 250 mL bottle, placed in ice water, concentrated sulfuric acid (110 mL) was added, and HNO ₃ (7 mL, 110 mmol) was slowly added dropwise. , stirred for 12 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 18 (10 g, 31 mmol) as a white solid.

Step 2: Synthesis of Intermediate 19

Intermediate 18 (35 g, 110 mmol), phenylboronic acid (14 g, 114 mmol), tetrakis(triphenylphosphine)palladium (3.2 g, 2.7 mmol), potassium carbonate (30 g, 220 mmol), 110 mL toluene, 35 mL ethanol and water 35 mL was added, nitrogen gas was continuously passed through the reaction solution for 5 min, and the mixture was heated to 90° C. and reacted for 2 hours. After the reaction was completed, purification was performed by column chromatography to obtain Intermediate 19 (26 g, 82.8 mmol) as a white solid.

Step 3: Synthesis of Intermediate 20

Carbazole (13.8 g, 82.8 mmol) was added to DMF (200 mL), stirred in ice water, and sodium hydride (60%, 3.3 g, 82.8 mmol) was added several times in small portions, then returned to room temperature for half an hour. After reacting for 2 hours, the reactant was placed in ice water again, intermediate 19 (26 g, 82.8 mmol) was added, and reacted at low temperature for 2 hours. After the reaction was completed, purification was performed by column chromatography to obtain an intermediate 20 (18 g, 29.6 mmol) as a pale yellow solid.

Step 4: Synthesis of Intermediate 21

Intermediate 20 (18 g, 29.6 mmol), PPh ₃ (23 g, 88.8 mmol), and 50 mL of o-dichlorobenzene were mixed, nitrogen gas was continuously passed through the reaction solution for 5 min, and the reaction was heated to 180 ° C and reacted for 12 h. . After the reaction was completed, purification was performed by column chromatography to obtain an intermediate 21 (8g, 13.9mmol) as a white solid.

Step 5: Synthesis of Intermediate 22

Intermediate 21 (8g, 13.9mmol), iodobenzene (8.5g, 41.7mmol), copper powder (448mg, 7mmol), potassium carbonate (5.7g, 41.7mmol), sodium sulfate (6g, 41.7mmol), nitrobenzene 70mL are mixed, heated to 200 ° C, and reacted for 12 h. After the reaction was completed, the product was purified by column chromatography to obtain an intermediate 22 (5.6 g, 8.6 mmol) as a white solid.

Step 6: Synthesis of BD-3-8

Intermediate 22 (5.6 g, 8.6 mmol) was dissolved in t-butylbenzene (40 mL), evacuated with nitrogen gas, and cooled in dry ice-ethanol. Add n-butyllithium (2.5M, 5mL) then return to room temperature. After raising the temperature to 60° C. and reacting for half an hour, the temperature was lowered to 0° C. and boron tribromide (1.6 mL, 17.2 mmol) was added. After reacting for half an hour, the system was cooled again to 0°C, diisopropylethylamine (2.8mL, 17.2mmol) was added, heated to 130°C, and reacted for 12h. After the reaction was completed, purification was performed by column chromatography to obtain BD-3-8 (0.8 g, 1.37 mmol) as a yellow solid. The product was identified as the target product with a molecular weight of 581.2.

Synthesis Comparative Example 1: Synthesis of Comparative Compound A

Step 1: Synthesis of 2-chloro-N ¹ ,N ¹ ,N ³ ,N ³ -tetraphenyl-1,3-diamine

Under the protection of nitrogen gas, Pd ₂ (dba) ₃ (850.0mg, 0.93mmol) was added to xylene (500.0mL), and Sphos (1.52g, 3.72mmol) was added and stirred for 20min, followed by 1 -Bromo-2,3-dichlorobenzene (20g, 88.5mmol), diphenylamine (33g, 195.2mmol), and sodium-tert-butoxide (34g, 354.2mmol) were mixed, and the temperature was raised to 140℃ to cause reaction. React until complete. After the reaction was completed, the reaction solution was filtered through celite, concentrated, dissolved in toluene, filtered through a short silica gel column, concentrated, and finally recrystallized twice with toluene to obtain 2- This gives chloro-N ¹ ,N ¹ ,N ³ ,N ³ -tetraphenyl-1,3-diamine (32.6 g, 73 mmol, 82.5%).

Step 2: Synthesis of Comparative Compound A

Under the protection of nitrogen gas, after adding 2-chloro-N ¹ ,N ¹ ,N ³ ,N ³ -tetraphenyl-1,3-diamine (20.0 g, 44.7 mmol) to t-butylbenzene (200.0 mL) , the temperature was lowered to -30 ° C, t-butyllithium (46.0 mL, 59.8 mmol) was dropped, the addition was completed, the ice bath was removed, the temperature was returned to room temperature, and then the temperature was raised to 60 ° C for 1 h. After the reaction, the temperature was lowered to -30 ° C, boron tribromide (5.5 mL, 58.5 mmol) was dropped, returned to room temperature, stirred for 30 min, cooled to 0 ° C, and N, N-diisopropylethyl Amine (14.8mL, 89.4mmol) is dropped, the ice bath is removed, and the system is allowed to react until it no longer exotherms, then heated to 120° C. and allowed to react overnight. Quenched by the addition of potassium acetate solution in an ice bath, extracted with ethyl acetate, concentrated the organic phase and dissolved with toluene, filtered sequentially with magnesium sulfate and a short silica gel column, and concentrated the filtrate with a toluene-normal-heptane system. recrystallized to obtain Comparative Compound A (2.1g, 5.0mmol, 11%) as a yellow solid.

Synthesis Comparative Example 2: Synthesis of Comparative Compound B

Step 1: Synthesis of 9,9',9"-(2-bromobenzene-1,3,5-triyl)tris(9H-carbazole)

Under the protection of nitrogen gas, 2,4,6-trifluorobromobenzene (4.2 g, 20 mmol) was added to DMF (50 ml), and carbazole (13.2 g, 80 mmol), NaH (60%, 3.3 g) was added at room temperature. , 82 mmol) was added and the reaction was allowed to complete at room temperature. After diluting the organic phase with water, a solid was precipitated, and the solid was collected by filtration and purified by column chromatography to obtain a white solid of 9,9',9"-(2-bromobenzene-1,3,5-tri 1) Tris (9H-carbazole) (6.5 g, 10 mmol) is obtained.

Step 2: Synthesis of Comparative Compound B

Under the protection of nitrogen gas, 9,9',9"-(2-bromobenzene-1,3,5-triyl)tris(9H-carbazole) (6.5 g, 10 mmol) was dissolved in t-butylbenzene (150 mL). ), the temperature was lowered to -30 ° C, n-butyllithium (5 mL, 12.5 mmol) was dropped, and after the addition was complete, the ice bath was removed, the temperature was returned to room temperature, and then the temperature was returned to 60 ° C. The temperature was raised to and reacted for 1 h, the temperature was lowered to -30 ° C, boron tribromide (1.2 mL, 12 mmol) was dropped, returned to room temperature, stirred for 30 min, cooled to 0 ° C, N, N -Diisopropylethylamine (3.5 mL, 20 mmol) was dropped, the ice bath was removed, and the reaction was continued until the system no longer exothermed, then the temperature was raised to 120° C. and reacted for 12 h. Quenched by adding potassium solution, extracted with ethyl acetate, rotated under reduced pressure to remove the solvent, dissolved with toluene, sequentially filtered with magnesium sulfate and silica gel, concentrated the filtrate and recrystallized with toluene to obtain Compound B as a yellow solid (0.6 g, 1 mmol) The product was identified as the target product with a molecular weight of 581.2.

As can be appreciated by those skilled in the art, the above preparation method is only one illustrative example, and a person skilled in the art can obtain the structure of other compounds of the present invention by elucidating them.

In order to confirm the effect of a specific molecular structure on the energy and electron distribution of the compound, the electrochemical properties of the compound were measured through cyclic voltammetry. The test uses an electrochemical workstation model CorrTest CS120 produced by Wuhan Corrtest Instrument Corp., Ltd, and uses a three-electrode working system. A platinum disk electrode is used as the working electrode, an Ag/AgNO ₃ electrode is used as the reference electrode, and a platinum wire electrode is used as the auxiliary electrode. Using anhydrous DMF as a solvent and 0.1 mol/L of tetrabutylammonium hexafluorophosphate as a supporting electrolyte, the compound to be measured was made into a 10 ^-3 mol/L solution, and nitrogen gas was blown into the solution for 10 min before testing. pass through to remove oxygen. Instrument parameter settings: scan rate is 100mV/s, potential interval is 0.5mV, and test window is -1V to -2.9V.

The HOMO and LUMO energy levels of the following compounds were measured by cyclic voltammetry (CV), and the specific results are shown in Table 1.

Table 1 Electrochemical properties of compounds

As can be seen from the results of Table 1, the unique boron-nitrogen bond closed loop structure of the first compound of the present invention can effectively reduce the LUMO energy level and the HOMO energy level of the compound. Comparing the boron-nitrogen comparative compound A without a bonded closed loop structure, the LUMO energy level of the first compound described herein is more than 0.67 eV deeper, and the HOMO energy level is more than 0.13 eV deeper. These data demonstrated that the boron-nitrogen bond closed-loop structure of the first compound of the present invention can effectively reduce the LUMO energy level and the HOMO energy level of the compound. Compound B was too soluble to obtain corresponding electrical data.

Measurement of triplet state energy levels:

The triplet state energy level (T ₁ ) was measured in an ultra-low temperature state using the characteristics of a triplet state exciton having a long lifetime. Specifically, the compound was dissolved in 2-methyltetrahydrofuran solvent to prepare a solution of 10 ^-5 M concentration, the solution was placed in a quartz sample tube, put in a Dewar bottle, cooled to 77K, and a 350nm light source was applied to the sample for phosphorescence measurement. to measure the phosphorescence spectrum. Spectra were measured using a spectrophotometer, Model F98, produced by Shanghai Lengguang Technology Co., Ltd.

The vertical axis of the phosphorescence spectrum is the phosphorescence intensity, and the horizontal axis is the wavelength. After taking the minimum value λ ₁ (nm) for the wavelength corresponding to the peak on the shorter wavelength side of the phosphorescence spectrum, the triplet state energy is calculated by substituting the corresponding wavelength value into the conversion formula F ₁ below.

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

The triplet state energy level T ₁ (eV) of the following compounds was measured by the above method, and the specific results are shown in Table 2.

Table 2 Triplet States of Compounds

As can be seen from the results of Table 2 above, the triplet states of the first host material and the second host material used in the present invention are both higher than 2.69 eV. Obviously, as a host material applied to a deep blue light TADF electroluminescent device, its triplet state must be higher than all light emitting materials used in the deep blue light TADF electroluminescent device. As in the present invention, the first host material and the second host material Both of the triplet states of the two host materials are higher than those of the first compound, which is the light emitting material.

It should be understood that the manufacturing method of the electroluminescent device is not limited, and the manufacturing method of the following examples is only an example and is not intended to be limiting. A person skilled in the art can rationally improve the manufacturing methods of the following examples according to the prior art. Illustratively, the ratio of various materials in the light emitting layer is not particularly limited, and a person skilled in the art may reasonably select within a certain range according to the prior art. For example, based on the total weight of the light emitting layer materials, the host material accounts for 80 to 99% and the light emitting material accounts for 1 to 20%; The host material accounts for 90 to 99%, and the light emitting material accounts for 1 to 10%; The host material may occupy 95%-99%, and the light emitting material may occupy 1%-5%. In addition, the host material may be one or two materials, wherein the ratio of the two host materials to the host material is 100:0 to 1:99, 80:20 to 20:80, or 60:40 to 60:40. It could be 40:60. In the embodiment of the device, the characteristics of the device include, but are not limited to, conventional equipment in the field (evaporator produced by Angstrom Engineering, optical test system and life test system produced by Suzhou Fstar, ellipsometer produced by Beijing ELLITOP, etc.). not limited), and tested by a method known to those skilled in the art.

Device Example 1

First, a glass substrate having an 80 nm thick indium tin oxide (ITO) anode is cleaned and then treated using oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. Next, the substrate is mounted on the substrate holder and placed in a vacuum chamber. The organic layers specified below are sequentially deposited on the ITO anode through thermal vacuum evaporation at a vacuum degree of about 10 ⁻⁸ Torr and at a rate of 0.2-2 angstroms/sec. Compound HI was used as the hole injection layer (HIL), but the thickness was 100 Å. Compound HT was used as the hole transport layer (HTL), but the thickness was 300 Å. Compound P-3 was used as the electron blocking layer (EBL), but the thickness was 50 Å. Then, the compound N-2-24 as the first host, the compound P-3 as the second host, and the first compound BD-1-1 as the dopant are co-deposited and used as the light emitting layer (EML), The thickness is 300 Å. Compound N-2-24 was used as the hole blocking layer (HBL), but the thickness was 50 Å. A compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the hole blocking layer to be used as an electron transport layer (ETL), the thickness of which was 300 Å. Finally, 10 Å thick 8-hydroxyquinoline-lithium (Liq) is deposited and used as an electron injection layer, and 1200 Å aluminum is deposited and used as a cathode. Next, the corresponding element is moved back to the glove box, and the corresponding element is completed by encapsulating it using a glass lid and a moisture absorbent.

Device Example 2

Except for using the compound N-1-15 instead of the compound N-2-24 in the light emitting layer (EML), the implementation of Device Example 2 is the same as Device Example 1.

Device Example 3

Except for using the compound BD-1-2 instead of the compound BD-1-1 in the light emitting layer (EML), the implementation of Device Example 3 is the same as Device Example 1.

Device Example 4

Except for using the compound N-1-15 instead of the compound N-2-24 in the light emitting layer (EML), the implementation of Device Example 4 is the same as Device Example 3.

Device Example 5

Except for using the compound N-2-10 instead of the compound N-2-24 in the light emitting layer (EML), the implementation of Device Example 5 is the same as Device Example 3.

Device Example 6

Except for using the compound BD-3-23 instead of the compound BD-1-1 in the light emitting layer (EML), the implementation of Device Example 6 is the same as Device Example 1.

Device Example 7

Except for using the compound N-1-15 instead of the compound N-2-24 in the light emitting layer (EML), the implementation of Device Example 7 is the same as Device Example 6.

Device Example 8

Except for using the compound BD-3-24 instead of the compound BD-1-1 in the light emitting layer (EML), the implementation of Device Example 8 is the same as Device Example 1.

Device Example 9

The embodiment of Device Example 9 is the same as Device Example 8, except for using the compound N-1-15 instead of the compound N-2-24 in the light emitting layer (EML).

Device Comparative Example 1

Except for using Compound A instead of Compound BD-1-1 in the light emitting layer (EML), the embodiment of Device Comparative Example 1 is the same as Device Example 1.

Device Comparative Example 2

Except for using Compound A instead of Compound BD-1-1 in the light emitting layer (EML), the embodiment of Device Comparative Example 2 is the same as Device Example 2.

Device Comparative Example 3

Device Comparative Example 3 was implemented in the same manner as Device Example 3, except that Compound P-3 was used as a host instead of Compound N-2-24 and Compound P-3 in the light emitting layer (EML).

Device Comparative Example 4

Except for using the compound N-2-24 as a host instead of the compound N-2-24 and the compound P-3 in the light emitting layer (EML), the embodiment of Device Comparative Example 4 is the same as Device Example 3.

Device Comparative Example 5

Except for using the compound N-1-15 as a host instead of the compound N-1-15 and the compound P-3 in the light emitting layer (EML), the embodiment of Device Comparative Example 5 is the same as Device Example 4.

The detailed device layer partial structure and thickness are shown in Table 3 below. A layer of two or more kinds of materials used herein is obtained by doping different compounds in the weight ratios mentioned therein.

Table 3 Device Structures of Device Examples and Comparative Examples

The material structure used for the device is as follows:

Table 4 shows the CIE value, maximum emission wavelength (λ _max ), full width at half maximum (FWHM), device lifetime (LT95), and external quantum efficiency (EQE) measured under the condition of 300 cd/m ² .

Table 4 Device Data

As can be seen from Table 4 above, Examples 1 and 3 using a specific combination of the first compound having a specific closed-loop structure of the present invention and the first host material and the second host material of the present invention, Compared to Comparative Example 1 using a combination of the compound A not having a closed loop structure and the first host material and the second host material of the present invention, the Example has excellent overall device performance, for example, a narrower half-full width and a longer life span, etc. Comparative Example 1 has a relatively high EQE, but since the HOMO energy level (-5.20 eV) of Compound A is relatively shallow, this is an n-type host material with a relatively deep LUMO energy level (-2.82 eV), that is, the first host material of the present invention By generating an exciplex with the phosphorus compound N-2-24, the emission wavelength is significantly red-shifted in the end, so that blue light emission cannot be obtained, and deep blue light emission as in the embodiment of the present invention cannot be obtained. , In addition, its full width at half maximum is widened, the saturation of light is lowered, and the lifetime is greatly reduced. This indicates that using the first compound having a deep HOMO energy level of the present invention as a blue light TADF light emitting material can obtain superior overall device performance compared to applying Compound A having a relatively shallow HOMO energy level.

Examples 2 and 4 using a specific combination of the first compound having a specific closed-loop structure of the present invention and the first host material and the second host material of the present invention were compared with Compound A not having a specific closed-loop structure. and Comparative Example 2 using a combination of the first host material and the second host material of the present invention, the EQEs of Examples 2 and 4 are slightly lower than those of Comparative Example 2, but more importantly, Example 2 and Example 4 were significantly improved, each improved by 10 times or more, and excellent overall device performance was obtained.

Examples 3-5 using a specific combination of the first compound as the light emitting material of the present invention and the first host material and the second host material as the dual host use the first compound of the present invention as the light emitting material and alone Compared to Comparative Example 3 using the second host material of the invention as a single host material, respectively, its EQE was improved by 181% at most, and the life of the device was improved by 169% at most. In particular, in Example 5, compared to Comparative Example 3, its maximum emission wavelength was blue-shifted by 3 nm and its full width at half maximum was narrowed by 11.2 nm, which is a great improvement in the performance study of blue light TADF devices, and excellent overall device performance was obtained.

Example 3 using a specific combination of the first compound, which is the light emitting material of the present invention, and the first host material and the second host material, which are double hosts, uses the first compound of the present invention as the light emitting material and alone Compared to Comparative Example 4 in which the first host material was used as a single host material, the EQE thereof was improved by 83.4%, and the lifespan of the device was improved by more than 4 times. Similarly, Example 4 using a specific combination of the first compound as the light emitting material of the present invention and the first host material and the second host material as a dual host, using the first compound of the present invention as the light emitting material and alone Compared to Comparative Example 5 using the first host material of the invention, its EQE was improved by 17.8%, and the life of the device was greatly extended and improved by about 50 times. These data indicate that certain combinations of the present application can achieve good overall device performance.

In addition, based on the first compound BD-1-1 of the present invention, new light emitting materials BD-3-23 and BD-3-24 were designed by inducing it. On the basis of the excellent device performance of BD-1-1 used in the device, BD-3-23 and BD-3-24 further improved the device performance in the device. In Examples 6 and 8, BD-3-23 and BD-3-24 were used instead of BD-1-1 in Example 1, and the EQE was improved by 33% and 39%, respectively, and the lifespan was greatly improved. was improved by 88% and 43%, respectively; In Examples 7 and 9, BD-3-23 and BD-3-24 were used instead of BD-1-1 in Example 2, and the EQE was improved by 59% and 66%, respectively, and the lifespan was greatly improved. and improved by 70% and 53%, respectively. These data indicate that certain combinations of the present application can yield better overall device performance.

Device Example 10

Execution of Device Example 10, except that compound BD-3-8 was used instead of compound BD-1-1 in the light emitting layer (EML) and compound N-1-15 was used instead of compound N-2-24 in HBL. The manner is the same as that of Device Example 1.

Device Example 11

Except for using the compound N-1-15 instead of the compound N-2-24 in the light emitting layer (EML), the implementation of Device Example 11 is the same as Device Example 10.

Device Comparative Example 6

Except for using compound B instead of compound BD-3-8 in the light emitting layer (EML), the embodiment of Device Comparative Example 6 is the same as Device Example 10.

Device Comparative Example 7

Except for using the compound N-1-15 instead of the compound N-2-24 in the light emitting layer (EML), the embodiment of Device Comparative Example 7 is the same as Device Comparative Example 6.

Table 5 Device Structures of Device Examples 10-11 and Comparative Examples 6-7

The new material structure used in the device is as follows:

.

.

Table 6 shows the CIE value, maximum emission wavelength (λ _max ), full width at half maximum (FWHM), device lifetime (LT95), and external quantum efficiency (EQE) measured under the condition of 300 cd/m ² .

Table 6 Device data of Examples 10-11 and Comparative Examples 6-7 at 300 cd/m ²

As can be seen from Table 6, comparing Example 10 with Comparative Example 6 and comparing Example 11 with Comparative Example 7, the only difference is the condensed ring manner of ring D in compound BD-3-8 and compound B. It's just different. Compared to Comparative Example 6 in Example 10 and Comparative Example 7 in Example 11, their EQEs were improved by 52.3% and 37.6%, respectively, and lifespans were greatly improved by 9.15 times and 3.76 times, respectively.

All of the above indicates that a combination of specific compounds of the present application can obtain better overall device performance.

Table 7 shows _{the CIE values, maximum emission wavelength (λ max} ⁾ , full width at half maximum (FWHM), device lifetime (LT95) and external quantum efficiency ( EQE).

Table 7 Device data of Device Examples 10-11 and Comparative Examples 6-7 at 1000 cd/m ²

As can be seen from Table 7, when Example 10 and Comparative Example 6 are compared, and Example 11 and Comparative Example 7 are compared, the only difference is the condensation method of Ring D in Compound BD-3-8 and Compound B. only Compared to Comparative Example 6 in Example 10 and Comparative Example 7 in Example 11, their EQEs were improved by 78.5% and 87.3%, respectively, and lifespans were greatly improved by 9.14 times and 3.76 times, respectively.

In the study of delayed fluorescence, 25% of the excitons originally occupied in the S1 state are inactivated by rapid emission to generate nanosecondary prompt fluorescence (PF), and 75% of the excitons in the T1 state are released into the S1 state through the RISC process. After up-conversion to the state, they are inactivated by radiation to produce microsecond or even millisecond lifetime delayed fluorescence (DF). Since the lifetime of DF is generally relatively long, this means that the quenching of triplet state excitons at high luminance is usually more severe, and consequently, the efficiency of the delayed light emitting device at high luminance rolls off. Therefore, research on how to reduce the roll-off of the delayed fluorescence device's efficiency under high luminance conditions is one of the main focuses of delayed fluorescence research. As can be seen from Tables 6 and 7 above, when Example 10 and Comparative Example 6 and Example 11 and Comparative Example 7 are compared, the only difference is the connection method of Ring D in Compound BD-3-8 and Compound B. Only at different luminance conditions, both EQE and LT95 improved significantly. In addition, when the test condition of Example 10 was changed from 300 cd/m ² to 1000 cd/m ² , the external quantum efficiency was reduced from 19.76% to 18.00%, and the roll-off ratio was 8.9%, whereas the test condition of Comparative Example 6 was reduced. When is changed from 300 cd/m ² to 1000 cd/m ² , the external quantum efficiency is reduced from 12.97% to 10.08%, and the roll-off ratio is 22.3%; Similarly, comparing Example 11 and Comparative Example 7, when the test conditions of Example 11 were changed from 300 cd/m ² to 1000 cd/m ² , the external quantum efficiency decreased from 16.88% to 15.29%, and the roll-off ratio was 9.4 %, whereas when the test conditions of Comparative Example 7 were changed from 300 cd/m ² to 1000 cd/m ² , the external quantum efficiency was reduced from 12.26% to 8.16%, and the roll-off ratio was 33.4%. In the selection of the boron-nitrogen type compound, the compound having the connection mode of the present invention (ring A is connected to ring D, ring C is connected to ring E), the connection mode (ring B is connected to ring D and , ring C is connected to ring E), the efficiency roll-off is significantly improved, which is a great improvement in the study of delayed fluorescence and a relatively great improvement in the performance of the device.

In summary, in the present invention, a first host material and a second host material having a high triplet state are combined with a first compound having a specified relatively deep LUMO energy level to be used as a light emitting material, and used in a blue light TADF electroluminescent device The overall performance of the bottom device can be greatly improved, which is due to the use of a first host material having a high triplet state of the present invention, a second host material and a first compound having a specified relatively deep LUMO energy level in a specific combination. Its excellent performance was fully demonstrated.

It should be understood that the various embodiments described herein are merely illustrative and are not intended to limit the scope of the present invention. Accordingly, it is apparent to those skilled in the art that the claimed invention may include modifications of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted for other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why this invention works are not limiting.

Claims (23)

In the organic electroluminescent device,
anode,
cathode, and
an organic layer disposed between an anode and a cathode, wherein the organic layer includes at least an organic light emitting layer;
Here, the organic light emitting layer includes at least a first compound, a first host material and a second host material;
Here, the energy levels of the triplet state of the first host material and the second host material are both higher than 2.69 eV;
Here, the first compound has a structure represented by Formula 1,

In Formula 1, ring A, ring B, ring C, ring D, and ring E are each independently selected from an unsaturated carbon ring having 5 to 30 carbon atoms or an unsaturated hetero ring having 3 to 30 carbon atoms;
Y ₁ is selected from B, P=O, P=S, As, As=O, As=S, SiR' or GeR';
Each occurrence of R _a , R _b , R _c , R _d , R _e identically or differently represents mono-substitution, poly-substitution or non-substitution;
R', R _a , R _b , R _c , R _d , R _e are identical or different each time they appear, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 rings A substituted or unsubstituted cycloalkyl group having 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, and a 7 to 30 carbon atoms A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 2 to 20 carbon atoms cyclic alkenyl group, 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 having 3 to 20 carbon atoms group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgerma group having 6 to 20 carbon atoms Nyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino selected from the group consisting of groups, and combinations thereof;
L ₁ and L ₂ are each independently a single bond, O, S, Se, SiRR, PR, a substituted or unsubstituted vinylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. It is selected from the group consisting of a substituted or unsubstituted heteroarylene group having a group, and a combination thereof; When a plurality of R's are present at the same time, the plurality of R's are the same or different;
Each occurrence of R, identically or differently, is 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, and 1 to 20 carbon atoms. substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring. The method according to claim 1, wherein in Formula 1, ring A, ring B, ring C, ring D and ring E each independently represent a 5-membered unsaturated carbon ring, an aromatic ring having 6 to 30 carbon atoms, or a ring having 3 to 30 carbon atoms. It is selected from heteroaromatic rings having;
Preferably Ring A, Ring B, Ring C, Ring D and Ring E, identically or differently each time they appear, are a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms or a heteroaromatic ring having 3-18 carbon atoms. selected from rings;
More preferably, ring A, ring B, ring C, ring D and ring E are identically or differently each time they appear, benzene ring, pyridine ring, naphthalene ring, phenanthrene ring, anthracene ring, indene ring, fluorene ring, indole ring, carbazole ring, benzofuran ring, dibenzofuran ring, benzosilol ring, dibenzosilol ring, benzothiophene ring, dibenzothiophene ring, dibenzoselenophene ring, cyclopentadiene ring, furan ring, thio An organic electroluminescent device selected from an open ring, a silole ring, or a combination thereof. According to claim 1 or 2,
In Formula 1, Y ₁ is selected from B, P=0 or P=S; Preferably, Y ₁ is B, an organic electroluminescent device. According to claim 1,
The first compound has a structure represented by Formula 2,

,
Each occurrence of R _a , R _b , R _c , R _d , R _e identically or differently represents mono-substitution, poly-substitution or non-substitution;
Each occurrence of R _a , R _b , R _c , R _d , R _e is identically or differently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a ring having 3 to 20 ring carbon atoms. A substituted or unsubstituted cycloalkyl group, 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 heterocyclic group having 7 to 30 carbon atoms Unsubstituted aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 2 to 20 carbon atoms Nyl group, 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, 6 A substituted or unsubstituted arylsilyl group having to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, 0 A substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and It is selected from the group consisting of combinations thereof;
Each time L ₁ , L ₂ appears identically or differently, a single bond, O, S, Se, SiRR, PR, a substituted or unsubstituted vinylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, 3 It is selected from the group consisting of a substituted or unsubstituted heteroarylene group having about 30 carbon atoms, and combinations thereof; When a plurality of R's are present at the same time, the plurality of R's are the same or different;
Each occurrence of R, identically or differently, is 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, and 1 to 20 carbon atoms. substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring. According to any one of claims 1 to 4,
An organic electroluminescent device in which L ₁ and/or L ₂ is a single bond. According to any one of claims 1 to 5,
Each occurrence of R _a , R _b , R _c , R _d , R _e is identically or differently hydrogen, deuterium, halogen, cyano group, hydroxy group, sulfanyl group, substituted or unsubstituted group having 1 to 6 carbon atoms. Alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 6 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 carbon atoms, 3 to 6 carbon atoms A substituted or unsubstituted heteroaryl group having 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 12 carbon atoms, and a 3 to 6 carbon atom group. A substituted or unsubstituted alkylgermanyl group having carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 12 carbon atoms, a substituted or unsubstituted amino group having 0 to 12 carbon atoms, and combinations thereof selected from the group;
Preferably, each occurrence of R _a , R _b , R _c , R _d , R _e is identically or differently hydrogen, deuterium, fluorine, cyano group, hydroxyl group, sulfanyl group, methyl group, ethyl group, n-propyl group , isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, neopentyl group, cyclohexyl group, trimethylsilyl group, trimethylgermanyl group, phenyl group, biphenyl group, ter Phenyl group, quaterphenyl group, triphenylene group, tetraphenylene group, naphthyl group, phenanthrene group, anthracene group, indenyl group, fluorene group, indolyl group, carbazole group, benzofuran group, dibenzofuran group, benzosilol group, di An organic electroluminescent device selected from the group consisting of a benzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, a diphenylamino group, a dibenzofuranylphenylamino group, and combinations thereof. According to any one of claims 1 to 5,
Whenever at least one of R _a , R _b , R _c , R _d , R _e appears identically or differently, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or 3 to 20 ring carbon atoms substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms Or an unsubstituted aralkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 2 to 20 carbon atoms. An alkenyl group, 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 alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl 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 carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, And it is selected from the group consisting of combinations thereof;
Preferably, at least one of R _a , R _b , R _c , R _d , R _e is identically or differently each time it appears, deuterium, halogen, cyano group, hydroxyl group, sulfanyl group, having 1 to 6 carbon atoms. A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted group having 6 to 24 carbon atoms Aryl group, 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 arylsilyl group having 6 to 12 carbon atoms , A substituted or unsubstituted alkylgermanyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 12 carbon atoms, a substituted or unsubstituted amino group having 0 to 12 carbon atoms, and It is selected from the group consisting of combinations thereof;
More preferably, at least one of R _a , R _b , R _c , R _d , R _e is, identically or differently, deuterium, fluorine, cyano group, hydroxyl group, sulfanyl group, methyl group, ethyl group, n- Propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, neopentyl group, cyclohexyl group, trimethylsilyl group, trimethylgermanyl group, phenyl group, biphenyl group , terphenyl group, quaterphenyl group, triphenylene group, tetraphenylene group, naphthyl group, phenanthrene group, anthracene group, indenyl group, fluorene group, indolyl group, carbazole group, benzofuran group, dibenzofuran group, benzosilol group , A dibenzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, a diphenylamino group, a dibenzofuranylphenylamino group, and an organic electroluminescent device selected from the group consisting of combinations thereof. According to claim 1,
The HOMO energy level of the first compound is less than -5.2eV;
Preferably, the HOMO energy level of the first compound is less than or equal to -5.3 eV;
More preferably, the HOMO energy level of the first compound is less than or equal to -5.4eV organic electroluminescent device. The method of claim 1, wherein the first compound is selected from the group consisting of the following structure,

Optionally, hydrogen in the structure may be partially or entirely substituted by deuterium. According to claim 1,
The first host material has a structure represented by any one of Formulas 3 to 5,

,

,

,
In Formula 3, each occurrence of X ₁ to X ₃ is identically or differently selected from CR ₄ or N, and at least one of X ₁ to X ₃ is selected from N;
Whenever L appears, identically or differently, a 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 is selected from;
In Formula 4 or Formula 5, each occurrence of X ₄ is identically or differently selected from CR ₄ or N, and at least one X ₄ is selected from N;
Z is the same or different O each time it appears or S;
Each time R ₁ -R ₄ appears identically or differently, 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, 1 Substituted or unsubstituted heteroalkyl group having to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1 to 20 A substituted or unsubstituted alkoxy group having two 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, and a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms. A substituted or unsubstituted alkynyl group, 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 group having 3 to 20 carbon atoms substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms Arylgermanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group It is selected from the group consisting of , phosphino groups, and combinations thereof;
An organic electroluminescent device wherein adjacent substituents R ₄ may be optionally connected to form a ring. According to claim 10,
In Formula 3, at least two of X ₁ to X ₃ are N; Preferably, X ₁ to X ₃ are N organic electroluminescent devices. According to claim 10 or 11,
In Formula 3, whenever L appears, identically or differently, 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 It is selected from the group consisting of combinations;
Preferably, each time L appears, identically or differently, a single bond, a phenylene group, a biphenylene group, a fluorenylene group, a triphenylenylene group, a furanylene group, a thienylene group, a dibenzofuranylene group, a dibenzothiophenyl group An organic electroluminescent device selected from the group consisting of rene groups and combinations thereof. According to claim 10,
Each time R ₁ -R ₄ appears, identically or differently, hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and substituted or unsubstituted ring carbon atoms having 3 to 20 carbon atoms are selected. It is selected from the group consisting of a cycloalkyl group, 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;
Preferably, whenever R ₁ -R ₄ appear, identically or differently, hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted group having 3 to 18 carbon atoms Or an unsubstituted heteroaryl group, and is selected from the group consisting of combinations thereof;
More preferably, each occurrence of R ₁ -R ₄ is identically or differently hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, triphenylene group, tetraphenylene group, indenyl group, fluorene group, indolyl group , selected from the group consisting of a carbazole group, a benzofuran group, a dibenzofuran group, a benzosilol group, a dibenzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenophene group, a triazine group, and combinations thereof organic electroluminescent device. The method of claim 1, wherein the first host material is selected from the group consisting of the following structure,

;
Optionally, hydrogen in the structure may be partially or entirely substituted by deuterium. According to claim 1,
The second host material has a structure represented by Formula 6,

In Equation 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 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 any of these is selected from a combination of;
Each occurrence of R ₆ identically or differently represents mono-substitution, poly-substitution or non-substitution;
Whenever R ₆ appears, identically or differently, 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, or 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 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, and a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 6 to 30 carbon atoms. cyclic aryl group, 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 aryl group having 6 to 20 carbon atoms Silyl group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms , It is selected from the group consisting of an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
An organic electroluminescent device wherein adjacent substituents R ₆ may be optionally connected to form a ring. According to claim 15,
The second host material has a structure represented by Formula 6-1 or Formula 6-2,

,

,
L ₁₁ and L ₁₂ are 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 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 any of these is selected from a combination of;
Each occurrence of R ₆ identically or differently represents mono-substitution, poly-substitution or non-substitution;
Whenever R ₆ appears, identically or differently, 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, or 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 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, and a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 6 to 30 carbon atoms. cyclic aryl group, 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 aryl group having 6 to 20 carbon atoms Silyl group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms , It is selected from the group consisting of an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
An organic electroluminescent device wherein adjacent substituents R ₆ may be optionally connected to form a ring. 17. The method of claim 16,
The second host material has a structure represented by Formula 6-3 or Formula 6-4,

,

,
Ar ₁₁ is 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 any of these is selected from a combination of;
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;
Each occurrence of R ₆ identically or differently represents mono-substitution, poly-substitution or non-substitution;
Whenever R ₆ appears, identically or differently, 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, or 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 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, and a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted group having 6 to 30 carbon atoms. cyclic aryl group, 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 aryl group having 6 to 20 carbon atoms Silyl group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms , It is selected from the group consisting of an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
An organic electroluminescent device wherein adjacent substituents R ₆ may be optionally connected to form a ring. According to any one of claims 15 to 17,
Each time R ₆ appears, identically or differently, 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, 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, 6 to 20 It is selected from the group consisting of a substituted or unsubstituted arylsilyl group having two carbon atoms, and combinations thereof;
Preferably, whenever R ₆ appears, identically or differently, hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted group having 3 to 18 carbon atoms, It is selected from the group consisting of a heteroaryl group, and combinations thereof,
More preferably, whenever R ₆ appears, identically or differently, hydrogen, deuterium, fluorine, cyano group, phenyl group, biphenyl group, triphenylene group, tetraphenylene group, indenyl group, fluorene group, indolyl group, carbazole group , An organic electroluminescent device selected from the group consisting of a benzofuran group, a dibenzofuran group, a benzosilol group, a dibenzosilol group, a benzothiophene group, a dibenzothiophene group, a dibenzoselenopene group, and combinations thereof . The method of claim 1, wherein the second host material is selected from the group consisting of the following structure,

Optionally, hydrogen in the structure may be partially or entirely substituted by deuterium. According to claim 1,
The first compound is a delayed fluorescence light emitting material, the first host material is an n-type host material, and the second host material is a p-type host material. 21. The method of any one of claims 1 to 20,
The organic electroluminescent device is an organic electroluminescent device that emits blue light. An electronic device comprising the organic electroluminescent device according to any one of claims 1 to 21. comprising at least a first compound, a first host material and a second host material;
Here, the energy levels of the triplet state of the first host material and the second host material are both higher than 2.69 eV;
Here, the first compound has a structure represented by Formula 1,

In Formula 1, ring A, ring B, ring C, ring D, and ring E are each independently selected from an unsaturated carbon ring having 5 to 30 carbon atoms or an unsaturated hetero ring having 3 to 30 carbon atoms;
Y ₁ is selected from B, P=O, P=S, As, As=O, As=S, SiR' or GeR';
Each occurrence of R _a , R _b , R _c , R _d , R _e identically or differently represents mono-substitution, poly-substitution or non-substitution;
R', R _a , R _b , R _c , R _d , R _e are identical or different each time they appear, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 rings A substituted or unsubstituted cycloalkyl group having 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, and a 7 to 30 carbon atoms A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 2 to 20 carbon atoms cyclic alkenyl group, 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 having 3 to 20 carbon atoms group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgerma group having 6 to 20 carbon atoms Nyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino selected from the group consisting of groups, and combinations thereof;
L ₁ and L ₂ are each independently a single bond, O, S, Se, SiRR, PR, a substituted or unsubstituted vinylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. It is selected from the group consisting of a substituted or unsubstituted heteroarylene group having a group, and a combination thereof; When a plurality of R's are present at the same time, the plurality of R's are the same or different;
Each occurrence of R, identically or differently, is 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, and 1 to 20 carbon atoms. substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, It is selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
wherein adjacent substituents R _a , R _b , R _c , R _d , R _e , R may be optionally linked to form a ring.

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