Invented by Seok-Hwan Hwang, Young-Kook Kim, Chang-Ho Lee, Seok-Jong Lee, Seung-gak Yang, Hee-Yeon Kim, Samsung Display Co Ltd

The market for Phenylcarbazole-based compounds and organic electroluminescent devices employing the same is experiencing significant growth due to the increasing demand for energy-efficient lighting solutions and advancements in display technologies. Phenylcarbazole-based compounds are organic materials that possess excellent electroluminescent properties, making them ideal for use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. These compounds exhibit high thermal stability, good charge transport characteristics, and efficient light emission, making them suitable for various applications in the electronics industry. One of the key drivers for the market growth is the rising demand for energy-efficient lighting solutions. Phenylcarbazole-based compounds are used as emissive materials in OLEDs, which are known for their low power consumption and high energy efficiency. As governments and consumers worldwide are increasingly focused on reducing energy consumption and carbon emissions, the demand for OLED-based lighting solutions is expected to surge. This, in turn, will drive the market for Phenylcarbazole-based compounds. Furthermore, the advancements in display technologies, particularly in the smartphone and television industry, are also contributing to the market growth. OLED displays offer several advantages over traditional liquid crystal displays (LCDs), such as higher contrast ratios, wider viewing angles, and faster response times. Phenylcarbazole-based compounds are crucial in the manufacturing of OLED displays, as they enable efficient light emission and color reproduction. With the growing popularity of OLED displays in consumer electronics, the demand for Phenylcarbazole-based compounds is expected to witness substantial growth. In addition to lighting and display applications, Phenylcarbazole-based compounds are also used in other optoelectronic devices, such as photovoltaic cells and sensors. The ability of these compounds to efficiently transport charges and emit light makes them suitable for various applications in the renewable energy and sensing industries. As the demand for renewable energy sources and advanced sensing technologies continues to rise, the market for Phenylcarbazole-based compounds is expected to expand further. Geographically, Asia Pacific is anticipated to dominate the market for Phenylcarbazole-based compounds and organic electroluminescent devices employing the same. The region is home to several major electronics manufacturers and has witnessed significant investments in OLED production facilities. The increasing adoption of OLED displays in smartphones, televisions, and other consumer electronics in countries like China, South Korea, and Japan is driving the demand for Phenylcarbazole-based compounds in the region. Overall, the market for Phenylcarbazole-based compounds and organic electroluminescent devices employing the same is poised for substantial growth in the coming years. The rising demand for energy-efficient lighting solutions, advancements in display technologies, and the increasing adoption of OLED displays in consumer electronics are the key factors driving this growth. As the electronics industry continues to evolve, Phenylcarbazole-based compounds will play a crucial role in enabling innovative and sustainable optoelectronic devices.

The Samsung Display Co Ltd invention works as follows

A phenylcarbazole-based compound is represented by Formula 1, and has superior electric properties and charge transport abilities, and thus is useful as a hole injection material, a hole transport material, and/or an emitting material which is suitable for fluorescent and phosphorescent devices of all colors, including red, green, blue, and white colors. The phenylcarbazole-based compound is synthesized by reacting carbazole with diamine. The organic electroluminescent device manufactured using the phenylcarbazole-based compound has high efficiency, low voltage, high luminance, and a long lifespan.

Background for Phenylcarbazole-based compound and organic electroluminescent device employing the same

1. “1.

The present invention relates to a phenylcarbazole-based compound and an organic electroluminescent device employing the same, and more particularly, to a phenylcarbazole-based compound which has electric stability, superior charge transport ability and high glass transition temperature and can prevent crystallization, and an organic electroluminescent device using an organic layer including the same.

2. “2.

An Electroluminescent Device (EL) is a Self-Emission Type Display Device and has attracted significant attention due to its merits such as a wide viewing area, superior contrast and rapid response. ELs are classified into two types: inorganic ELs, where the emitting layer consists of an inorganic substance, and organic ELs, in which the emitting surface is made of an organic substance. Organic EL devices have superior luminance, response rate, driving voltage and response to inorganic EL devices. They can also display multiple colors.

The organic EL device has a layered anode/organic emission layer/cathode structure. If a hole transport or electron injection layer are further interposed between anode and emitting or cathode or between emitting and cathode then an anode/hole transportation layer/organic emission layer/cathode or an anode/hole injection layer/organic transmitting layer/electron transport layer/cathode is formed.

The hole transport layer is composed of polyphenylhydrcarbon or anthracene derivatives (see U.S. Pat. Nos. Nos.

Organic electronic devices, including holes transport layers made of conventional materials, are not satisfactory with regard to lifespan, efficiency, or power consumption. Therefore, a material that can significantly improve these characteristics is needed for the hole transport layer.

The present invention is an organic layer that has superior charge transport abilities, high glass transition temperatures, and can prevent crystallization. It is also suitable for fluorescent or phosphorescent devices of all colors including red, white, green, and blue.

The present invention also provides a organic EL device that uses an organic layer made of the material described above and has high efficiency, low-voltage, high luminance, and a long lifespan.

According to an aspect of the present invention, there is provided a phenylcarbazole-based compound represented by Formula (1):

where X represents a C1-C30 substituted alkylene, C2-C30 substituted alkenylene, C6-C30 substituted arylene, C2-C30 substituted heteroarylene, C2-C30 substituted heterocycle, and each of R1,R2,R3,R1?,R2? Each of R1, R2, and R3, is independently mono-substituted or multi-substituted, with a hydrogen atom. The R1?, the R2? Two or more adjacent groups among R1, R2, and R3, as well as between the R1?,R2? “Ar can be connected together to form a saturated carbocycle or an unsaturated one; each Ar is either a C6-C30 substituted aryl or heteroaryl or C2-C30 substituted aryl.

According to another aspect of the present invention, there is provided an organic EL device including a first electrode, a second electrode, and an organic layer interposed therebetween, in which the organic layer contains the phenylcarbazole-based compound.

The organic layer can be either a layer for hole injection, a layer for hole transport, or one layer that serves as both the layer for hole injection and the layer to transport holes.

In one embodiment, the organic layer can be a hole injection or hole transport layer. The organic EL device may have a structure consisting of a second electrode, a hole transport or emitting layer, a hole transport or emitting layer, a second electrode, or a combination of a hole transport or emitting layer and a second electrode.

The organic layer is a layer that emits light, and the layer emitting light is made of phosphorescent material or fluorescent materials.

In the emitting layer, the phenylcarbazole-based compound represented by Formula (1) is used as a fluorescent or phosphorescent host.

The present invention is described in greater detail below.

The present invention relates to a phenycarbazole based compound that has at least two phenylcarbazoles as side chains, a method for preparing it, and a device that uses the compound in an organic layer as a material, such as a layer of hole transport, a layer of hole injection, or a layer emitting light.

The phenylcarbazole-based compound may be preferably represented by Formula 1:

where X represents a C1-C30 substituted alkylene, C2-C30 substituted alkenylene, C6-C30 substituted arylene, C2-C30 substituted heteroarylene, C2-C30 substituted heterocycle, and each of R1,R2,R3,R1?,R2? Each of R1, R2, and R3, is independently mono-substituted or multi-substituted, with a hydrogen atom. The R1?, the R2? Two or more adjacent groups among R1, R2, and R3, as well as between the R1?,R2? “Ar can be connected together to form a saturated carbocycle or an unsaturated one; each Ar is either a C6-C30 substituted aryl or heteroaryl or C2-C30 substituted aryl.

Each Ar may be a phenyl group, an ethylphenyl group, an ethylbiphenyl group, an o-, m-, or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, or p-tolyl group, an o-, m-, and p-cumenyl group, a mesityl group, a phenoxyphenyl group, a (?,?-dimethylbenzene)phenyl group, a (N,N?-dimethyl)aminophenyl group, a (N,N?-diphenyl)aminophenyl group, a pentarenyl group, an indenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azurenyl group, a heptarenyl group, an acenaphthylrenyl group, a phenanthrenyl group, a fluorenyl group, an anthraquinolyl group, a triphenylene group, a pyrenyl group, a pherylenyl group, a chloropherylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a coroneryl group, a trinaphthylenyl group, a heptaphenyl group, or a carbazolyl group.

Click here to view the patent on Google Patents.