KR102636045B1 - Triphenylamin-based compounds and organic light-emitting diode comprising the same - Google Patents

Abstract

The present invention relates to a triphenylamine-based compound that can be crosslinked at low temperature and has excellent lifespan and luminous efficiency, and an organic light-emitting device containing the same.

Description

Triphenylamine-based compounds and organic light-emitting devices containing the same {TRIPHENYLAMIN-BASED COMPOUNDS AND ORGANIC LIGHT-EMITTING DIODE COMPRISING THE SAME}

The present invention relates to a triphenylamine-based compound and an organic light-emitting device containing the same.

Organic light emitting diode (OLED) has the advantage of superior image quality, viewing angle, and color purity compared to liquid crystal displays, and that it can be driven with low power consumption, so it is currently applied to small and large displays and lighting. It is attracting attention as the display method with the highest applicability to flexible displays.

A typical OLED has a structure in which an anode is formed on top of a glass or plastic substrate, and on top of this anode are organic layers such as a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer, and a cathode is formed sequentially on top of the anode. In general, the process for manufacturing OLED mainly uses a vacuum deposition method for all layers. However, in the case of vacuum deposition, the initial equipment investment cost is enormous, there are limits to increasing production, the material consumption rate is high, and there are significant limitations in manufacturing and producing large-area displays.

Accordingly, a new production process that can replace the vacuum deposition method is needed, and the most feasible ones at present are spin coating, doctor blade, bar coating, and slot die. Displays are manufactured through a solution process using slot die coating, micro gravure coating, inkjet printing, etc. However, in order to manufacture OLED devices using a solution process, several technical challenges must be solved. Among them, in the process of stacking the organic layer with a solution, when stacking the upper layer on the lower layer, it is necessary to prevent the lower layer from being washed out or mixing between layers. do. Due to the characteristics of OLED devices, each layer must be clearly separated to ensure advantageous characteristics in terms of efficiency and lifespan.

Accordingly, the methods used to ensure separation between layers in the solution process are broadly classified into two types. The first is a method of utilizing an orthogonal solvent system in which the properties of the materials that make up two adjacent layers are drastically different, so that the solvent used to dissolve these materials does not dissolve the different layers.

The second method is to modify the material into an insoluble form through a secondary reaction after applying the organic layer. The main method used in this way is a cross-linking reaction using heat or light, and when the molecular weight is rapidly increased through the cross-linking reaction, the dissolution or melting characteristics are reduced. Accordingly, when stacking the upper layer, the phenomenon of the lower layer being washed away or interlayer mixing is greatly reduced, making it possible to form a clean multilayer thin film.

Until recently, in the case of host materials formed through crosslinking methods using heat, materials with relatively high molecular weight were mainly used to increase crosslinking performance and degree of crosslinking. However, the relatively high crosslinking temperature of 150 to 180°C or more and the long crosslinking time of 30 to 60 minutes or more cause damage to the device, causing a sharp decrease in luminous efficiency and lifespan.

Therefore, in order to obtain high-performance characteristics when manufacturing OLED devices through a solution process, it is necessary to develop materials with lower cross-linking temperatures and shorter cross-linking times.

The present invention provides a triphenylamine-based compound that can be crosslinked at low temperature and has excellent lifespan and luminous efficiency, and an organic light-emitting device containing the same.

However, the problem to be solved by the present invention is not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the following description.

One embodiment of the present invention provides a triphenylamine-based compound represented by the following formula (1):

[Formula 1]

In the above formula,

R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; Or an alkoxy group having 1 to 3 carbon atoms,

n1 to n3 are each independently O or 1, and at least one of n1 to n3 is 1,

R ₂₁ to R ₂₃ are each independently an aryl group having 6 to 30 carbon atoms substituted with a vinyl group; -OR ₃₁ ; or (meth)acrylate group;

R ₃₁ is an alkyl group having 1 to 3 carbon atoms substituted with an aryl group having 6 to 30 carbon atoms substituted with a vinyl group; A fused ring group of an aliphatic ring having 4 to 10 carbon atoms and an aromatic ring having 6 to 30 carbon atoms; Vinyl group unsubstituted or substituted with at least one halogen atom; An alkyl group having 2 to 5 carbon atoms substituted with an oxetane group; or an alkyl group having 2 to 5 carbon atoms substituted with an epoxy group;

R ₂₄ is hydrogen; Or, it combines with adjacent R ₂₁ to form a heterocycle having 2 to 4 carbon atoms, and R ₂₅ is hydrogen; Or, it combines with adjacent R ₂₂ to form a heterocycle having 2 to 4 carbon atoms, and R ₂₆ is hydrogen; Or, it combines with adjacent R ₂₃ to form a heterocycle having 2 to 4 carbon atoms,

The heterocycle contains at least one of oxygen (O), nitrogen (N), and sulfur (S), and is substituted with an aryl group having 6 to 30 carbon atoms,

k1 to k3 are each independently O or 1, and at least two of k1 to k3 are 1.

Additionally, an exemplary embodiment of the present invention provides an organic light-emitting device containing the triphenylamine-based compound.

The triphenylamine-based compound according to an exemplary embodiment of the present invention can easily perform a crosslinking reaction at low temperature, and can effectively induce a curing reaction at a low process temperature.

In addition, the triphenylamine-based compound according to an exemplary embodiment of the present invention can effectively maintain high hole transport properties after crosslinking by pi-conjugation expansion.

In addition, the triphenylamine-based compound according to an exemplary embodiment of the present invention can effectively improve lifespan and luminous efficiency characteristics when applied to an organic light-emitting device.

Additionally, the organic light emitting device according to an exemplary embodiment of the present invention can implement excellent lifespan characteristics and luminous efficiency characteristics.

However, the effects of the present invention are not limited to the effects described above, and may be expanded in various ways without departing from the spirit and scope of the present invention.

1 is a diagram schematically showing an organic light-emitting device containing a triphenylamine-based compound according to an exemplary embodiment of the present invention.
Figure 2 is a diagram showing the UV absorption spectrum of the triphenylamine-based compounds prepared in Examples 1 to 3 of the present invention.
Figure 3 is a diagram showing the PL emission spectrum of the triphenylamine-based compounds prepared in Examples 1 to 3 of the present invention.
Figure 4 is a diagram showing the results of analysis of thermal stability (TGA) of the triphenylamine-based compounds prepared in Examples 1 to 3 of the present invention.
Figure 5a is a diagram showing the analysis results of the cross-linking temperature (DSC) of the triphenylamine-based compound prepared in Example 1, and Figure 5b is an analysis of the cross-linking temperature (DSC) of the triphenylamine-based compound prepared in Example 2 This is a diagram showing the results, and Figure 5c is a diagram showing the analysis results of the crosslinking temperature (DSC) of the triphenylamine-based compound prepared in Example 3.
Figure 6a is a diagram showing the results of analyzing the solvent resistance characteristics of the compound prepared in Example 1 after crosslinking, and Figure 6b is a diagram showing the results of analyzing the solvent resistance characteristics of the compound prepared in Example 2 after crosslinking. Figure 6c is a diagram showing the results of analyzing the solvent resistance characteristics of the compound prepared in Example 3 after crosslinking.
Figure 7a is a diagram showing the IV characteristics for measuring hole mobility by SCLC analysis by producing HOD using the triphenylamine-based compound prepared in Example 1 of the present invention, and Figure 7b is Example 2 of the present invention This is a diagram showing the IV characteristics for measuring hole mobility by SCLC analysis by producing HOD using the triphenylamine-based compound prepared in , and Figure 7c shows the triphenylamine-based compound prepared in Example 3 of the present invention. This is a diagram showing the IV characteristics for measuring hole mobility by producing HOD using SCLC analysis.
Figure 8 is a diagram showing the emission wavelength characteristics of a unit cell organic light-emitting device manufactured by using the triphenylamine-based compounds prepared in Examples 1, 2, and 3 of the present invention as hole transport materials in the hole transport layer. .
Figure 9 is a diagram showing the IVL characteristics of a unit cell organic light-emitting device manufactured by using the triphenylamine-based compounds prepared in Examples 1, 2, and 3 of the present invention as hole transport materials in the hole transport layer.
Figure 10 shows the results of measuring the external quantum efficiency of a unit cell organic light-emitting device manufactured by using the triphenylamine-based compound prepared in Examples 1, 2, and 3 of the present invention as a hole transport material in the hole transport layer. This is a drawing showing .

Throughout the specification of the present application, when a part is said to “include” a certain element, this means that it may further include other elements rather than excluding other elements, unless specifically stated to the contrary.

Throughout this specification, when a member is said to be located “on” another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

Throughout this specification, “(meth)acrylate” is used to collectively refer to acrylates and methacrylates.

Hereinafter, the present invention will be described in more detail.

One embodiment of the present invention provides a triphenylamine-based compound represented by the following formula (1):

[Formula 1]

In the above formula, R ₁ to R ₁₂ are each independently hydrogen; An alkyl group having 1 to 3 carbon atoms; or an alkoxy group having 1 to 3 carbon atoms; n1 to n3 are each independently O or 1, at least one of n1 to n3 is 1, and R ₂₁ to R ₂₃ are each independently 6 to 6 carbon atoms substituted with a vinyl group. Aryl group of 30; -OR ₃₁ ; or a (meth)acrylate group; and R ₃₁ is an alkyl group having 1 to 3 carbon atoms substituted with an aryl group having 6 to 30 carbon atoms substituted with a vinyl group; A fused ring group of an aliphatic ring having 4 to 10 carbon atoms and an aromatic ring having 6 to 30 carbon atoms; Vinyl group unsubstituted or substituted with at least one halogen atom; An alkyl group having 2 to 5 carbon atoms substituted with an oxetane group; or an alkyl group having 2 to 5 carbon atoms substituted with an epoxy group; and R ₂₄ is hydrogen; Or, it combines with adjacent R ₂₁ to form a heterocycle having 2 to 4 carbon atoms, and R ₂₅ is hydrogen; Or, it combines with adjacent R ₂₂ to form a heterocycle having 2 to 4 carbon atoms, and R ₂₆ is hydrogen; Or, it combines with adjacent R ₂₃ to form a heterocycle having 2 to 4 carbon atoms, and the heterocycle contains at least one of oxygen (O), nitrogen (N), and sulfur (S), and is an aryl ring having 6 to 30 carbon atoms. is substituted with a group, k1 to k3 are each independently O or 1, and at least two of k1 to k3 are 1.

The triphenylamine-based compound according to an exemplary embodiment of the present invention can easily perform a crosslinking reaction at low temperature, and can effectively induce a curing reaction at a low process temperature.

In addition, the triphenylamine-based compound according to an exemplary embodiment of the present invention can effectively maintain high hole transport properties after crosslinking by pi-conjugation expansion.

In addition, the triphenylamine-based compound according to an exemplary embodiment of the present invention can effectively improve lifespan and luminous efficiency characteristics when applied to an organic light-emitting device.

Additionally, the triphenylamine-based compound according to an exemplary embodiment of the present invention may have excellent chemical stability, electrical stability, and thermal stability.

According to one embodiment of the present invention, the triphenylamine-based compound represented by Formula 1 may contain at least one vinyl bond in the molecule and may contain at least two crosslinkable functional groups at the terminal. . The triphenylamine-based compound represented by Formula 1, which contains at least one vinyl bond in the molecule and has at least two crosslinkable functional groups bonded to the terminal, is a cross-linking reaction between the triphenylamine-based compounds represented by Formula 1 and themselves. This can happen easily. That is, the triphenylamine-based compound represented by Formula 1 can easily undergo a crosslinking reaction at a relatively low temperature (for example, 130° C. or lower). In addition, the triphenylamine-based compound represented by Formula 1 has excellent chemical and electrical stability and may have excellent thermal stability. In addition, the triphenylamine-based compound represented by Formula 1 has excellent hole and electron transfer properties due to extended pi-conjugation, and can control the energy levels of HOMO and LUMO. In addition, the triphenylamine-based compound represented by Formula 1 has reduced dissolution and melting characteristics through crosslinking, so that a solution process in manufacturing an organic light-emitting device can be easily performed, as will be described later, and through this, organic light emission. The luminous efficiency and lifespan of the device can be effectively improved.

According to an exemplary embodiment of the present invention, in Formula 1, R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; Or it may be an alkoxy group having 1 to 3 carbon atoms. Specifically, in Formula 1, R ₁ to R ₁₂ are each independently hydrogen; methyl group; Or it may be a methoxy group. More specifically, R ₁ to R ₁₂ are each independently hydrogen; Or it may be a methyl group. When the types of R ₁ to R ₁₂ are as described above, the triphenylamine-based compound can easily perform a crosslinking reaction, and the cured product of the composition containing the triphenylamine-based compound can be used in an organic light-emitting device. When applied, excellent lifespan characteristics and luminous efficiency characteristics can be realized. Additionally, the chemical stability, electrical stability, and thermal stability of the triphenylamine-based compound can be improved.

According to an exemplary embodiment of the present invention, in Formula 1, n1 to n3 are each independently O or 1, and at least one of n1 to n3 may be 1. That is, the triphenylamine-based compound represented by Formula 1 may contain 1 to 3 vinyl bonds in the molecule. As described above, the triphenylamine-based compound represented by Formula 1 containing 1 to 3 vinyl bonds in the molecule may have excellent chemical stability, electrical stability, and thermal stability, and can be used at relatively low temperatures (e.g., 130 °C). The crosslinking reaction can be easily performed at (°C or lower). Furthermore, the hole and electron transfer properties can be excellent due to the extended pi-conjugation.

According to an exemplary embodiment of the present invention, in Formula 1, R ₂₁ to R ₂₃ are each independently an aryl group having 6 to 30 carbon atoms substituted with a vinyl group; -OR ₃₁ ; Or it may be a (meth)acrylate group.

Specifically, in Formula 1, R ₂₁ to R ₂₃ are each independently an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an aryl group having 6 to 10 carbon atoms. It may be an aryl group or a phenyl group. That is, in Formula 1, R ₂₁ to R ₂₃ are each independently It can be. “*” indicates the binding position.

Additionally, in Formula 1, R ₂₁ to R ₂₃ may each independently be -OR ₃₁ , and in this case, R ₃₁ may be an alkyl group having 1 to 3 carbon atoms substituted with an aryl group having 6 to 30 carbon atoms substituted with a vinyl group. Specifically, R ₃₁ may be a propyl group, an ethyl group, or a methyl group, and may be an aryl group having 6 to 30 carbon atoms substituted with a vinyl group, an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an aryl group having 6 to 10 carbon atoms. It may be a substituted aryl group or a phenyl group. More specifically, R ₃₁ may be a methyl group to which a phenyl group substituted with a vinyl group is bonded. That is, in Formula 1, R ₂₁ to R ₂₃ are each independently It can be. “*” indicates the binding position.

In addition, in Formula 1, R ₂₁ to R ₂₃ may each independently be -OR ₃₁ , where R ₃₁ is an aliphatic ring (cycloalkyl) having 4 to 10 carbon atoms and an aromatic ring (aryl) having 6 to 30 carbon atoms. It may be a fused ring group. The “fused ring group” may mean that two rings share two or more atoms and are combined to form one ring. Specifically, R ₃₁ is an aliphatic ring with 4 to 10 carbon atoms, an aliphatic ring with 4 to 8 carbon atoms, or an aliphatic ring with 4 to 6 carbon atoms, an aromatic ring with 6 to 30 carbon atoms, an aromatic ring with 6 to 20 carbon atoms, and a carbon number. It may be an aromatic ring of 6 to 15 carbon atoms, or a fused ring group in which an aromatic ring of 6 to 10 carbon atoms is bonded. More specifically, R ₃₁ may be a fused ring group in which cyclobutyl and phenyl are bonded. That is, in Formula 1, R ₂₁ to R ₂₃ are each independently It can be. “*” indicates the binding position.

Additionally, in Formula 1, R ₂₁ to R ₂₃ may each independently be -OR ₃₁ , and in this case, R ₃₁ may be an unsubstituted vinyl group or substituted with at least one halogen atom. Specifically, R ₃₁ may be a vinyl group, a vinyl group substituted with F, a vinyl group substituted with Cl, a vinyl group substituted with Br, or a vinyl group substituted with I. That is, in Formula 1, R ₂₁ to R ₂₃ are each independently It can be. At this time, X ₁ to X ₃ are each independently hydrogen; F; Cl; Br; or I; “*” indicates the binding position.

Additionally, in Formula 1, R ₂₁ to R ₂₃ may each independently be -OR ₃₁ , and in this case, R ₃₁ may be an alkyl group having 2 to 5 carbon atoms substituted with an oxetane group. Specifically, R ₃₁ may be an alkyl group having 2 to 4 carbon atoms substituted with an oxetane group, or an alkyl group having 2 to 3 carbon atoms. That is, in Formula 1, R ₂₁ to R ₂₃ are each independently It can be. At this time, R ₄₁ is hydrogen; or an alkyl group having 1 to 3 carbon atoms. “*” indicates the binding position.

Additionally, in Formula 1, R ₂₁ to R ₂₃ may each independently be -OR ₃₁ , and in this case, R ₃₁ may be an alkyl group having 2 to 5 carbon atoms substituted with an epoxy group. Specifically, R ₃₁ may be an alkyl group having 2 to 4 carbon atoms in which an epoxy group is substituted, or an alkyl group having 2 to 3 carbon atoms. That is, in Formula 1, R ₂₁ to R ₂₃ are each independently It can be. At this time, R ₄₂ is hydrogen; or an alkyl group having 1 to 3 carbon atoms. “*” indicates the binding position.

Additionally, in Formula 1, R ₂₁ to R ₂₃ may each independently be a (meth)acrylate group. Specifically, R ₂₁ to R ₂₃ may each independently be an acrylate group.

When the types of R ₂₁ to R ₂₃ are as described above, the triphenylamine-based compound can easily perform a crosslinking reaction, and the cured product of the composition containing the triphenylamine-based compound can be used in an organic light-emitting device. When applied, excellent lifespan characteristics and luminous efficiency characteristics can be realized. Additionally, the chemical stability, electrical stability, and thermal stability of the triphenylamine-based compound can be improved. Additionally, the triphenylamine-based compound may have excellent hole and electron transfer properties due to extended pi-conjugation.

According to an exemplary embodiment of the present invention, R ₂₄ is hydrogen; or combined with adjacent R ₂₁ to form a heterocycle having 2 to 4 carbon atoms, and R ₂₅ is hydrogen; or combined with an adjacent R ₂₂ to form a heterocycle having 2 to 4 carbon atoms, and R ₂₆ is hydrogen; Alternatively, it may be combined with adjacent R ₂₃ to form a heterocycle having 2 to 4 carbon atoms. At this time, the heterocycle contains at least one of oxygen (O), nitrogen (N), and sulfur (S), and may be substituted with an aryl group having 6 to 30 carbon atoms. Specifically, the heterocycle may include at least two of oxygen (O), nitrogen (N), and sulfur (S), and more specifically, the heterocycle may include oxygen (O) and nitrogen (N). You can. That is, R ₂₄ combines with adjacent R ₂₁ Can be formed, and R ₂₅ combines with adjacent R ₂₂ Can be formed, and R ₂₆ combines with adjacent R ₂₃ can be formed. “*” indicates the binding position. At this time, the number of carbon atoms in the heterocyclic ring may refer to the number of carbon atoms forming the ring excluding heteroatoms. for example, In the case of a heterocycle, the heterocycle may include two heteroatoms and two carbon atoms.

When the types of R ₂₄ to R ₂₆ are as described above, the triphenylamine-based compound can easily perform a crosslinking reaction, and the cured product of the composition containing the triphenylamine-based compound can be used in an organic light-emitting device. When applied, excellent lifespan characteristics and luminous efficiency characteristics can be realized. Additionally, the chemical stability, electrical stability, and thermal stability of the triphenylamine-based compound can be improved. Additionally, the triphenylamine-based compound may have excellent hole and electron transfer properties due to extended pi-conjugation.

In Formula 1, k1 to k3 are each independently O or 1, and at least two of k1 to k3 may be 1. Specifically, in Formula 1, k1 to k3 may be 1. That is, the triphenylamine-based compound represented by Formula 1, in which two or more crosslinkable functional groups are bonded to the terminal, may have excellent chemical stability, electrical stability, and thermal stability, and can be used at relatively low temperatures (e.g., 130° C. or lower). The crosslinking reaction can be easily performed. Furthermore, the hole and electron transfer properties can be excellent due to the extended pi-conjugation.

According to one embodiment of the present invention, the triphenylamine-based compound may be a compound represented by the following formula (2).

[Formula 2]

In Formula 2, R ₁ to R ₁₂ , n1 to n3, R ₂₁ to R ₂₆ , and k1 to k3 are the same as defined in Formula 1. Compared to Formula 1, Formula 2 specifies the position where the phenyl group substituted with R ₂₁ to R ₂₆ is bonded to nitrogen. In the triphenylamine-based compound of Formula 2, where the position at which the phenyl group substituted by R ₂₁ to R ₂₆ is bonded to nitrogen is specified, a cross-linking reaction between compounds can be performed more easily. At this time, R ₁ to R ₁₂ may be the same as each other, R ₂₁ to R ₂₃ may be the same as each other, and R ₂₄ to R ₂₆ may be the same as each other. In this case, the triphenylamine-based compound can more easily perform a crosslinking reaction. Additionally, the triphenylamine-based compound may have excellent chemical stability, electrical stability, and thermal stability.

According to an exemplary embodiment of the present invention, in Formula 1 and Formula 2, R ₁ to R ₁₂ are each independently hydrogen; methyl group; or a methoxy group; and R ₂₁ to R ₂₃ are each independently, ; ; ; ; ; ; or an acrylate group; and X ₁ to X ₃ are each independently hydrogen; F; Cl; Br; or I; and R ₄₁ and R ₄₂ are each independently hydrogen; or an alkyl group having 1 to 3 carbon atoms; and R ₂₄ is hydrogen; or in combination with adjacent R ₂₁ ; and R ₂₅ is hydrogen; or in combination with adjacent R ₂₂ ; and R ₂₆ is hydrogen; or in combination with adjacent R ₂₃ ;, k1 to k3 are 1, and “*” may indicate the bonding position.

According to one embodiment of the present invention, the triphenylamine-based compound may be a compound represented by Formula 3-1 or a compound represented by Formula 3-2.

[Formula 3-1]

[Formula 3-2]

In Formulas 3-1 and 3-2, R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; or an alkoxy group having 1 to 3 carbon atoms; n1 to n3 are each independently O or 1, and at least one of n1 to n3 may be 1.

That is, in Formula 3-1, R ₂₁ to R ₂₃ in Formula 2 are and R ₂₄ to R ₂₆ are hydrogen. In addition, in Formula 3-2, R ₂₁ to R ₂₃ in Formula 2 are and R ₂₄ to R ₂₆ are hydrogen.

The triphenylamine-based compounds represented by Formula 3-1 and Formula 3-2 can more easily perform a crosslinking reaction as described above. Through this, the composition containing the triphenylamine-based compound represented by Formula 3-1 and Formula 3-2 can easily be thermally cured at a relatively low temperature through a solution process, and the cured product of the composition An organic light-emitting device containing can have improved lifespan characteristics and luminous efficiency characteristics. Additionally, the triphenylamine-based compound may have excellent chemical stability, electrical stability, and thermal stability. In particular, the triphenylamine-based compound represented by Chemical Formula 3-2 may have excellent physical properties described above.

According to an exemplary embodiment of the present invention, the triphenylamine-based compound may be any one of the following compounds.

.

That is, the triphenylamine-based compound represented by Formula 3-1 may be any one of Compounds 1 to 6, and the triphenylamine-based compound represented by Formula 3-2 may be any of Compounds 7 to 12. It could be any one. Compounds 1 to 12 can be easily thermally cured at relatively low temperatures, and can further improve the lifespan characteristics and luminous efficiency characteristics of organic light-emitting devices. Additionally, the triphenylamine-based compound may have excellent chemical stability, electrical stability, and thermal stability. In particular, the triphenylamine-based compounds of Compounds 7 to 12 may have very excellent physical properties as described above.

According to an exemplary embodiment of the present invention, the triphenylamine-based compound may be any one of a compound represented by Formula 3-3 to a compound represented by Formula 3-8.

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

In Formulas 3-3 to 3-8, R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; or an alkoxy group having 1 to 3 carbon atoms; n1 to n3 are each independently O or 1, at least one of n1 to n3 is 1, and X ₁ to X ₃ are each independently F; or Cl; and R ₄₁ and R ₄₂ are each independently an alkyl group having 1 to 3 carbon atoms.

That is, in Formula 3-3, R ₂₁ to R ₂₃ in Formula 2 are and R ₂₄ to R ₂₆ are hydrogen. In addition, in Formula 3-4, R ₂₁ to R ₂₃ in Formula 2 are and R ₂₄ to R ₂₆ are hydrogen. In addition, in Formula 3-5, R ₂₁ to R ₂₃ in Formula 2 are and R ₂₄ to R ₂₆ are hydrogen. In addition, in Formula 3-6, R ₂₁ to R ₂₃ in Formula 2 are and R ₂₄ to R ₂₆ are hydrogen. In addition, in Formula 3-7, R ₂₁ to R ₂₃ are an acrylate group and R ₂₄ to R ₂₆ are hydrogen.

In addition, Formula 3-8 is obtained by combining R ₂₄ with R ₂₁ in Formula 2. and R ₂₅ combines with R ₂₂ to form and R ₂₆ combines with R ₂₃ to form formed ;.

The triphenylamine-based compounds represented by Formulas 3-3 to 3-8 can more easily perform a crosslinking reaction as described above. Through this, the composition containing the triphenylamine-based compound represented by Formula 3-3 to Formula 3-8 can easily be thermally cured at a relatively low temperature through a solution process, and the cured product of the composition An organic light-emitting device containing can have improved lifespan characteristics and luminous efficiency characteristics. Additionally, the triphenylamine-based compound may have excellent chemical stability, electrical stability, and thermal stability.

According to an exemplary embodiment of the present invention, the triphenylamine-based compound may be any one of the following compounds.

.

That is, the triphenylamine-based compound represented by Formula 3-3 may be any one of Compounds 13 to 18, and the triphenylamine-based compound represented by Formula 3-4 may be any of Compounds 19 to 24. It may be any one, and the triphenylamine-based compound represented by Formula 3-5 may be any one of Compounds 25 to 30, and the triphenylamine-based compound represented by Formula 3-6 may be Compound 31. to compounds 36, and the triphenylamine-based compound represented by Formula 3-7 may be any one of compounds 37 to 42, and the triphenylamine-based compound represented by Formula 3-8 may be any one of compounds 43 to 48 above. Compounds 13 to 48 can be easily thermally cured at relatively low temperatures, and can further improve the lifespan characteristics and luminous efficiency characteristics of organic light-emitting devices. Additionally, the triphenylamine-based compound may have excellent chemical stability, electrical stability, and thermal stability.

According to one embodiment of the present invention, the triphenylamine-based compound can be used as a host material for an organic light-emitting device to be described later. Specifically, the cross-linked product of the triphenylamine-based compound can be used as a host material included in the light-emitting layer of an organic light-emitting device. Additionally, the triphenylamine-based compound can be used as a hole transport material in organic light-emitting devices. Specifically, the cross-linked product of the triphenylamine-based compound can be used as a hole transport material included in the hole transport layer of an organic light-emitting device. Additionally, the triphenylamine-based compound can be used as a material to form a hole injection layer of an organic light-emitting device. Specifically, a hole injection layer of an organic light-emitting device can be manufactured using a cross-linked product of the triphenylamine-based compound. Additionally, the triphenylamine-based compound can be used as a material to form the electron transport layer of an organic light-emitting device. Specifically, the electron transport layer of an organic light-emitting device can be manufactured using a cross-linked product of the triphenylamine-based compound.

The triphenylamine-based compound may be included in the organic material layer of an organic light-emitting display device, a perovskite display device, or a perovskite solar cell. Specifically, the cross-linked product of the triphenylamine-based compound may be included in a hole transport layer (or hole transport layer) of an organic light-emitting display device, a perovskite display device, or a perovskite solar cell. The organic light emitting display device or perovskite display device including an organic material layer containing the triphenylamine-based compound represented by Formula 1 may have improved lifespan characteristics and luminous efficiency characteristics. In addition, a perovskite solar cell containing an organic material layer containing the triphenylamine-based compound represented by Formula 1 may have improved luminescence life and improved durability of the photoelectric device.

One embodiment of the present invention provides a composition containing a triphenylamine-based compound.

A composition containing a triphenylamine-based compound according to an exemplary embodiment of the present invention can be cured at a relatively low temperature and can easily form an organic layer through a solution process. Additionally, a composition containing a triphenylamine-based compound can be heat-cured in a faster time.

According to an exemplary embodiment of the present invention, the composition may be a composition for manufacturing an organic light-emitting device, which will be described later. Specifically, the composition may be a composition for a solution process, and the composition may be heat-cured to form at least one layer included in the organic material layer of the organic light-emitting device. As described above, the composition containing the triphenylamine-based compound represented by Formula 1 can be thermally cured at a rapid rate at a relatively low temperature, and can stably and effectively form the organic material layer of the organic light-emitting device. there is. In addition, when forming the organic material layer of an organic light-emitting device through a solution process using the composition, when the upper layer is formed on the lower layer through a solution process, the lower layer is effectively prevented from being washed away or mixing between layers occurs, thereby producing Excellent characteristics of organic light-emitting devices can be secured. In addition, in the case of a solution process using the above composition, an organic light-emitting device with a multilayer structure with excellent stability can be easily manufactured.

In addition, as described above, the composition can be cured at a relatively low temperature, so it can be easily used in processes that apply plastic substrates in addition to glass substrates. In addition, since the composition is cured by heat, no additional additives are added, so there are no by-products or additives remaining after film formation, and the lifespan and luminous efficiency characteristics of the organic light-emitting device can be further improved.

According to one embodiment of the present invention, the composition may further include a solvent. The solvent may be a single organic solvent or a mixed organic solvent in which two or more organic solvents with different boiling points are mixed. For example, the solvent may include at least one of chlorobenzene, acetone, methanol, tetrahydrofuran, toluene, xylene, tetralin, 1,2-dichlorobenzene, and chloroform, but the type of the solvent is limited. It's not like that.

According to an exemplary embodiment of the present invention, a coating method used in the art can be used without limitation as a method for producing a layer included in the organic material layer using the composition. For example, the composition can be used in spin coating, doctor blade, bar coating, slot die coating, micro gravure coating, inkjet printing ( An organic material layer can be formed through a solution process such as inkjet printing.

According to an exemplary embodiment of the present invention, the composition can form a light-emitting layer of an organic light-emitting device, which will be described later. Specifically, the light-emitting layer of the organic light-emitting device may include a cured product of the composition. Additionally, the composition can form a hole transport layer of an organic light-emitting device, which will be described later. Specifically, the hole transport layer of the organic light emitting device may include a cured product of the composition. Additionally, the composition can form a hole injection layer of an organic light-emitting device, which will be described later. Specifically, the hole injection layer of the organic light emitting device may include a cured product of the composition. Additionally, the composition can form an electron transport layer of an organic light-emitting device, which will be described later. Specifically, the electron transport layer of the organic light emitting device may include a cured product of the composition.

One embodiment of the present invention provides an organic light-emitting device containing the triphenylamine-based compound. Specifically, the organic light emitting device includes a first electrode; second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the organic material layer includes a cured product of a composition containing the triphenylamine-based compound. That is, the organic material layer may include a crosslinking reaction product of the triphenylamine-based compound represented by Chemical Formula 1.

The organic light emitting device according to an exemplary embodiment of the present invention can implement excellent lifespan characteristics and luminous efficiency characteristics.

According to one embodiment of the present invention, the organic material layer may include at least one of a hole injection layer, a hole buffer layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer. However, the type of organic material layer included in the organic light emitting device is not limited.

According to one embodiment of the present invention, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a thermosetting product of the composition. That is, the light-emitting layer may include a triphenylamine-based compound represented by Formula 1 and/or a cross-linked product of the triphenylamine-based compound represented by Formula 1. Specifically, the light-emitting layer may include a cross-linked product containing a polymerized unit derived from the triphenylamine-based compound represented by Chemical Formula 1. For example, the cross-linked product may include a cross-linked product of the triphenylamine-based compound itself represented by Formula 1. An organic light-emitting device including the light-emitting layer containing a thermoset of the composition may have improved lifespan characteristics and luminous efficiency characteristics.

According to an exemplary embodiment of the present invention, the light emitting layer may further include a host compound. Specifically, the light emitting layer may further include two different host compounds, through which the lifespan and efficiency of the organic light emitting device can be further improved.

According to an exemplary embodiment of the present invention, a compound used in the art can be used as the host compound. For example, a condensed aromatic ring derivative compound or a heterocyclic ring-containing compound can be used as the host compound. For example, condensed aromatic ring derivative compounds include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Ladder-type furan compounds, pyrimidine derivatives, etc. are included, but are not limited thereto.

According to an exemplary embodiment of the present invention, materials used in the art can be used as materials for forming the light-emitting layer. Specifically, as a material for the light-emitting layer, a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, can be used, and a material with good quantum efficiency for fluorescence or phosphorescence can be used. . For example, 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to the above-mentioned ones.

According to an exemplary embodiment of the present invention, the light emitting layer may include a dopant compound. As the dopant compound, those used in the industry can be used. Specifically, the dopant compounds include aromatic amine derivative compounds, styrylamine compounds, aromatic hydrocarbon compounds substituted with carbazole groups, boron complexes, fluoranthene compounds, and metal complexes. The aromatic amine derivative compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group can be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine can be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. The metal complex may be an iridium complex, a platinum complex, etc., but is not limited thereto.

According to one embodiment of the present invention, the light emitting layer may further include an auxiliary dopant or a sensitizer.

At this time, the compound that acts as an assistant dopant or sensitizer receives holes and electrons from the host to form an exciton, and the generated exciton is fluorescent. It plays a role in delivering the dopant. As the auxiliary dopant and sensitizer, known appropriate compounds can be used in consideration of the energy relationship between the host compound and the triphenylamine-based compound represented by Formula 1.

According to one embodiment of the present invention, the organic light emitting device is a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, or a cathode and one layer on a substrate. It may be an inverted type organic light emitting device in which the above organic material layers and the anode are sequentially stacked.

According to an exemplary embodiment of the present invention, the organic light-emitting device is manufactured using materials and methods known in the art, except that the organic material layer includes a cured product of a composition containing the triphenylamine-based compound represented by Formula 1. can be manufactured. For example, the organic light emitting device can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.

At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

Additionally, when manufacturing the organic light emitting device, the organic material layer may be formed by a solution coating method as well as a vacuum deposition method. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. However, the manufacturing method is not limited to this.

According to an exemplary embodiment of the present invention, the first electrode may be an anode and the second electrode may be a cathode. Meanwhile, the first electrode may be a cathode and the second electrode may be an anode.

According to an exemplary embodiment of the present invention, a material with a large work function can be used as the anode material to ensure smooth hole injection into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO2:Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

According to one embodiment of the present invention, the hole injection layer is a layer that injects holes received from the electrode into the light-emitting layer or an adjacent layer provided toward the light-emitting layer. The hole injection material has the ability to transport holes and has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material. In addition, compounds with excellent thin film forming ability can be used. It may be preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrilehexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene. There are conductive polymers of the series such as organic materials, anthraquinone, polyaniline, and polythiophene, but are not limited to the above-mentioned types.

According to one embodiment of the present invention, the organic material layer includes a hole transport layer, and the hole transport layer may include a thermoset product of the composition. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer or an adjacent layer provided toward the light-emitting layer. The hole transport layer may include a general hole transport material in addition to the cured product of the composition. The hole transport material may be a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer, and may be a material with high mobility for holes. Specific examples of the hole transport material include NPD (N,Ndinaphthyl-N,N'-diphenylbenzidine), TPD (N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine) , s-TAD and MTDATA (4,4',4"-Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine), triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkanes. Derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazanes. Derivatives, polysilane-based, aniline-based copolymers, and conductive polymer oligomers (especially thiophene oligomers) may be included, but are not limited thereto.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer. As the hole buffer layer, hole injection or transport materials known in the art can be used.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron suppressing layer may be made of the spiro compound described above or a material known in the art.

According to one embodiment of the present invention, an electron blocking layer may be provided between the hole transport layer and the light emitting layer, and materials known in the art may be used. The electron blocking layer is a layer that prevents electrons from flowing into the anode from the light emitting layer and regulates the overall performance of the device by controlling the flow of holes flowing into the light emitting layer. The electron blocking material may preferably be a compound that prevents the inflow of electrons from the light-emitting layer to the anode and has the ability to control the flow of holes injected into the light-emitting layer or the light-emitting material. For example, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.

A hole blocking layer (blocking layer) may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used. The hole blocking layer is a layer that blocks holes from flowing into the cathode from the light-emitting layer and controls the overall performance of the device by controlling electrons flowing into the light-emitting layer. The hole blocking material is preferably a compound that prevents holes from entering the cathode from the light-emitting layer and has the ability to control electrons injected into the light-emitting layer or the light-emitting material. As a hole blocking material, an appropriate material can be used depending on the composition of the organic layer used in the device. The hole blocking layer is located between the light-emitting layer and the cathode, and is preferably provided in direct contact with the light-emitting layer.

The electron transport layer may play a role in facilitating the transport of electrons. Materials known in the art such as Alq3 (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, and SAlq can be used. The thickness of the electron transport layer may be 1 to 50 nm. Here, if the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is so thick that the driving voltage is increased to improve the movement of electrons. There is an advantage to preventing this.

According to one embodiment of the present invention, the electron injection layer may serve to facilitate the injection of electrons. It may be made of an organic substance, complex, or metal compound known in the art, such as Alq3 (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, or SAlq. Organic materials that can be used in the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzoimidazole, perylenetetracarboxylic acid, and preorenyl. Examples include, but are not limited to, denmethane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives. Metal halides may be used as the metal compound, for example, LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2 and RaF2. The thickness of the electron injection layer may be 1 to 50 nm. Here, if the thickness of the electron injection layer is 1 nm or more, there is an advantage in preventing the electron injection characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron injection layer is too thick and the driving voltage is required to improve the movement of electrons. There is an advantage in preventing it from rising. In one embodiment, the electron injection layer may be formed by mixing the organic material and the metal compound.

According to one embodiment of the present invention, the cathode material is preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO2/Al, but they are not limited to these. When the organic light emitting device has a front or double-sided emitting structure, the cathode can be formed to be thin enough to transmit light, and when the organic light emitting device has a bottom emitting structure, it can be formed thick enough to reflect light. You can.

Between the light emitting layer and the anode or cathode, and between the light emitting layer and the charge generation layer, one or more organic material layers such as the hole injection layer, hole buffer layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, and electron injection layer are further added. may be included.

According to one embodiment of the present invention, the organic light emitting device may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.

1 is a diagram schematically showing an organic light-emitting device containing a triphenylamine-based compound according to an exemplary embodiment of the present invention. Referring to FIG. 1, the organic light emitting device 10 includes a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, a blocking layer 5, an electron transport layer 6, and a cathode 7. may have a sequentially stacked structure. However, the stacked structure of the organic light emitting device is not limited to the structure shown in FIG. 1.

For example, the organic light emitting device may have a stacked structure as shown below.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(15) Anode/hole transport layer/light-emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode

According to one embodiment of the present invention, the organic light emitting device may be used for an organic light emitting display device, a perovskite display device, or a perovskite solar cell.

One embodiment of the present invention provides an organic light emitting display device including the organic light emitting element.

The organic light-emitting display device according to an embodiment of the present invention includes an organic light-emitting device containing a cross-linked product of the triphenylamine-based compound represented by Chemical Formula 1, thereby realizing excellent lifespan characteristics and luminous efficiency characteristics, Through this, excellent quality images can be realized.

One embodiment of the present invention provides a perovskite solar cell including the organic light-emitting device.

The perovskite solar cell according to an exemplary embodiment of the present invention includes an organic light-emitting device containing a cross-linked product of the triphenylamine-based compound represented by Chemical Formula 1, thereby improving luminescence life, stability, and durability. .

One embodiment of the present invention provides a perovskite display device including the organic light-emitting device.

The perovskite display device according to an exemplary embodiment of the present invention includes an organic light-emitting device containing a cross-linked product of the triphenylamine-based compound represented by Formula 1, thereby achieving excellent lifespan characteristics and luminous efficiency characteristics. , Through this, excellent quality images can be realized.

Hereinafter, the present invention will be described in detail with reference to examples. However, the embodiments according to the present invention may be modified into various other forms, and the scope of the present invention should not be construed as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present invention to those skilled in the art.

Example: Synthesis of triphenylamine-based compounds

Example 1: (E)-N ^One -Phenyl-N ⁴ -(4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)phenyl)-N ⁴ -(4-(4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)styryl)phenyl)-N ^One -(4-((4-vinylbenzyl)oxy)phenyl)benzene-1,4-diamine / Synthesis of compound 7

Example 1-1: Preparation of 1-iodo-4-((4-vinylbenzyl)oxy)benzene / Preparation of Compound A-1

4-Iodophenol (10.0 g, 45.4 mmol) was added to a 250 mL round bottom flask equipped with a condenser, and anhydrous tetrahydrofuran (THF, 100 mL) was injected under vacuum. Sodium hydride (NaH, 4.36 g, 181.7 mmol) was slowly added, stirred at room temperature for 2 hours, and then 1-(chloromethyl)-4-vinylbenzene (6.93 g, 45.4 mmol) was added to tetrahydrofuran. It was dissolved and added. After stirring at 60°C for 12 hours, upon completion of the reaction, fractional distillation was performed using ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and the solvent was purified through column chromatography to obtain pure Compound A-. 1 was obtained (15.0 g, 98.2%).

^1H NMR (300MHz, CDCl ₃ , ppm): δ 7.58 (d, 2H), 7.44 (d, 2H), 7.38 (d, 2H), 6.76 (d, 2H), 6.73 (m, 1H), 5.76 ( d, 1H), 5.28 (d, 1H), 5.04 (s, 2H).

Example 1-2: Preparation of N-phenyl-4-((4-vinylbenzyl)oxy)aniline / Preparation of Compound A-2

Compound A-1 (15.0 g, 44.6 mmol) and aniline (4.15 g, 44.6 mmol) were added to a 250 mL round bottom flask equipped with a condenser, and were dissolved by adding anhydrous toluene (150 mL). Pd ₂ (dba) ₃ catalyst (0.3 g, 0.33 mmol), tri-tert-butylphosphine (0.66 mL of 1M solution, 0.66 mmol), and sodium tert-butoxide (6.30 g, 65.4 mmol) were dissolved in toluene and added. After stirring at 100°C for 24 hours, when the reaction was completed, fractional distillation was performed through ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and the solvent was purified through column chromatography to obtain pure Compound A-. 2 was obtained (13.3 g, 98.6%).

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 7.45 (d, 2H), 7.40 (d, 2H), 7.27 (m, 2H), 7.11 (d, 2H), 6.98 (m, 4H), 6.86 ( t, 1H), 6.72 (m, 1H), 5.75 (d, 1H), 5.27 (d, 1H), 5.51 (br s, 1H), 5.06 (s, 2H).

Example 1-3: Preparation of 4-(diphenylamino)benzaldehyde / Preparation of compound B-1

Anhydrous dimethylformamide (200 mL) was added under vacuum to a 500s mL round bottom flask equipped with a condenser. Phosphonyl chloride (125.0 g, 815.2 mmol) was slowly added at 0 °C, stirred at 0 °C for 1 hour, and then triphenylamine (25.0 g, 101.9 mmol) was dissolved in dimethylformamide and slowly added. After 24 hours at 100°C, it was cooled to room temperature, ice cubes were slowly added at 0°C, and sodium chloride was neutralized with the solution. When the reaction was completed, it was fractionally distilled through ethyl acetate, the remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound B-1 (17.3 g, 62.1%). .

^1H NMR (300MHz, CDCl ₃ , ppm): δ 9.85 (s, 1H), 7.70 (d, 2H), 7.37 (m, 4H), 7.19 (m, 6H), 7.05 (d, 2H).

Example 1-4: Preparation of 4-(bis(4-bromophenyl)amino)benzaldehyde/Preparation of Compound B-2

Compound B-1 (17.0 g, 62.2 mmol) was added to a 250 mL round bottom flask, and dimethylformamide (DMF, 150 mL) was added under vacuum. N -Bromosuccinimide (22.3 g, 125.1 mmol) was slowly added at 0°C, the temperature was raised to room temperature, and the mixture was stirred at the same temperature for 12 hours. When the reaction was completed, it was washed with water. After fractional distillation through ethyl acetate, the remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound B-2 (25.6 g, 95.4%).

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 9.85 (s, 1H), 7.76 (d, 2H), 7.45 (m, 4H), 7.05 (m, 6H).

Example 1-5: Preparation of (E)-4-bromo-N-(4-bromophenyl)-N-(4-(4-bromostyryl)phenyl)aniline / Preparation of compound B-3

Diethyl 4-bromobenzylphosphonate (10.0 g, 32.5 mmol) and tetra n-butylammonium bromide (TBAB, 1.0 g, 3.25 mmol) were added to a 250 mL round bottom flask equipped with a condenser and anhydrous Toluene (150 mL) was added to dissolve. 50 wt% NaOH was added and stirred at 45°C for 30 minutes, then compound B-2 (14.0 g, 32.5 mmol) was dissolved in toluene and added. After stirring at 45°C for 24 hours, the reaction is terminated by adding HCl aqueous solution. After fractional distillation through ethyl acetate, the remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound B-3 (14.3 g, 75.4%).

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 7.45 (d, 2H), 7.39 (m, 8H), 7.05 (m, 8H).

Example 1-6: (E)-N ^One -Phenyl-N ⁴ -(4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)phenyl)-N ⁴ -(4-(4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)styryl)phenyl)-N ^One -Preparation of (4-((4-vinylbenzyl)oxy)phenyl)benzene-1,4-diamine / Preparation of compound 7

Compound B-3 (2.0 g, 3.42 mmol) and compound A-2 (3.8 g, 12.7 mmol) were added to a 250 mL round bottom flask equipped with a condenser, and anhydrous toluene (150 mL) was added to dissolve them. Pd ₂ (dba) ₃ catalyst (0.3 g, 0.33 mmol), tri-tert-butylphosphine (0.66 mL of 1M solution, 0.66 mmol), and sodium tert-butoxide (6.30 g, 65.4 mmol) were dissolved in toluene and added. After stirring at 100°C for 24 hours, when the reaction was completed, fractional distillation was performed using ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and the solvent was purified through column chromatography to obtain pure Compound 7. Obtained (1.7 g, 39.7%).

¹ H NMR (300MHz, CDCl ₃ , ppm): ¹ H NMR (300MHz, CDCl ₃ , ppm): 1H NMR (300MHz, CDCl3, ppm): δ 7.69-6.72 (m, 57H), 5.86 (d, 3H) , 5.25 (d, 3H), 5.04 (s, 6H).

Example 2: N ^One -Phenyl-N ⁴ ,N ⁴ -bis(4-((E)-4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)styryl)phenyl)-N ^One -(4-((4-vinylbenzyl)oxy)phenyl)benzene-1,4-diamine / Synthesis of compound 8

Example 2-1: Preparation of 4,4'-(phenylazandiyl)dibenzaldehyde / Preparation of Compound C-1

Anhydrous dimethylformamide (200 mL) was added under vacuum to a 500 mL round bottom flask equipped with a condenser. Phosphonyl chloride (125.0 g, 815.2 mmol) was slowly added at 0 °C and stirred at 0 °C for 1 hour. Triphenylamine (25.0 g, 101.9 mmol) was dissolved in dimethylformamide and then slowly added. After 24 hours at 100°C, it was cooled to room temperature, ice cubes were slowly added at 0°C, and sodium chloride was neutralized with a solution. When the reaction was completed, fractional distillation was performed using ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purification was performed through column chromatography to obtain pure compound C-1 (6.7 g, 21.9%). .

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 9.84 (s, 2H), 7.79 (d, 4H), 7.38 (m, 2H), 7.13 (m, 7H).

Example 2-1: Preparation of 4,4'-((4-bromophenyl)azanediyl)dibenzaldehyde / Preparation of Compound C-2

Compound C-1 (6.5 g, 21.6 mmol) was added to a 250 mL round bottom flask, and dimethylformamide (DMF, 150 mL) was added under vacuum. N-bromosuccinimide (5.6 g, 31.2 mmol) was slowly added at 0°C, the temperature was raised to room temperature, and the mixture was stirred at the same temperature for 12 hours. When the reaction was completed, it was washed with water. After fractional distillation through ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound C-2 (7.4 g, 89.7%).

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 9.90 (s, 2H), 7.76 (d, 4H), 7.48 (d, 2H), 7.15 (d, 4H), 7.06 (d, 2H).

Example 2-3: Preparation of 4-bromo-N,N-bis(4-((E)-4-bromostyryl)phenyl)aniline / Preparation of compound C-3

Diethyl 4-bromobenzylphosphonate (11.3 g, 36.8 mmol) and tetra n-butylammonium bromide (TBAB, 1.19 g, 3.68 mmol) were added to a 250 mL round bottom flask equipped with a condenser and anhydrous Toluene (150 mL) was added to dissolve. 50 wt% NaOH was added and stirred at 45°C for 30 minutes, then compound C-2 (7.0 g, 18.4 mmol) was dissolved in toluene and added. After stirring at 45°C for 24 hours, the reaction is terminated by adding HCl aqueous solution. After fractional distillation through ethyl acetate, the remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound C-3 (14.3 g, 75.4%).

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 7.45 (d, 4H), 7.33 (m, 10H), 6.98 (m, 10H).

Example 2-4: N ^One -Phenyl-N ⁴ ,N ⁴ -bis(4-((E)-4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)styryl)phenyl)-N ^One -Preparation of (4-((4-vinylbenzyl)oxy)phenyl)benzene-1,4-diamine / Preparation of compound 8

Compound C-3 (2.0 g, 2.91 mmol) and Compound A-2 (7.0 g, 10.2 mmol) were added to a 250 mL round bottom flask equipped with a condenser, and anhydrous toluene (150 mL) was added to dissolve them. Pd ₂ (dba) ₃ catalyst (0.3 g, 0.33 mmol), tri-tert-butylphosphine (0.66 mL of 1M solution, 0.66 mmol), and sodium tert-butoxide (6.30 g, 65.4 mmol) were dissolved in toluene and added. After stirring at 100°C for 24 hours, when the reaction was completed, fractional distillation was performed through ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and the solvent was purified through column chromatography to obtain pure Compound 8. Obtained (1.7 g, 42.5%).

^1H NMR (300MHz, CDCl ₃ , ppm): 1H NMR (300MHz, CDCl3, ppm): δ 7.78-6.65 (m, 63H), 5.88 (d, 3H), 5.25 (d, 3H), 5.05 (s, 6H).

Example 3: 4-((E)-4-(bis(4-((E)-4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)styryl)phenyl)amino) Synthesis of styryl)-N-phenyl-N-(4-((4-vinylbenzyl)oxy)phenyl)aniline / Preparation of compound 9

Example 3-1: Preparation of 4,4',4''-nitrile tribebenzaldehyde / Preparation of compound D-1

Anhydrous dimethylformamide (200 mL) was added under vacuum to a 500s mL round bottom flask equipped with a condenser. After slowly adding phosphonyl chloride (125.0 g, 815.2 mmol) at 0°C and stirring for 1 hour at 0°C, triphenylamine (25.0 g, 101.9 mmol) was dissolved in dimethylformamide and slowly added. After being kept at 100°C for 24 hours, it was cooled to room temperature, ice cubes were slowly added at 0°C, and sodium chloride was neutralized with a solution. When the reaction was completed, it was fractionated through ethyl acetate, the remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound D-1 (5.2 g, 15.6%). .

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 9.84 (s, 3H), 7.78 (d, 6H), 7.23 (d, 6H).

Example 3-2: Preparation of tris(4-((E)-4-bromostyryl)phenyl)amine / Preparation of compound D-2

Diethyl 4-bromobenzylphosphonate (14.0 g, 45.6 mmol) and tetra n-butylammonium bromide (TBAB, 1.47 g, 4.56 mmol) were added to a 250 mL round bottom flask equipped with a condenser and anhydrous Toluene (150 mL) was added to dissolve. 50 wt% NaOH was added and stirred at 45°C for 30 minutes, then compound D-1 (5.0 g, 15.2 mmol) was dissolved in toluene and added. After stirring at 45°C for 24 hours, the reaction was terminated by adding HCl aqueous solution. After fractional distillation through ethyl acetate, the remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and purified through column chromatography to obtain pure compound D-2 (6.7 g, 55.6%).

¹ H NMR (300 MHz, CDCl ₃ , ppm): δ 7.47 (d, 6H), 7.36 (m, 12H), 6.93 (m, 12H).

Example 3-3: 4-((E)-4-(bis(4-((E)-4-(phenyl(4-((4-vinylbenzyl)oxy)phenyl)amino)styryl)phenyl) Preparation of amino) styryl) -N-phenyl-N-(4-((4-vinylbenzyl)oxy)phenyl)aniline / Preparation of compound 9

Compound D-2 (2.0 g, 2.54 mmol) and Compound A-2 (2.5 g, 8.29 mmol) were added to a 250 mL round bottom flask equipped with a condenser, and anhydrous toluene (100 mL) was added to dissolve them. Pd ₂ (dba) ₃ catalyst (0.3 g, 0.33 mmol), tri-tert-butylphosphine (0.66 mL of 1M solution, 0.66 mmol), and sodium tert-butoxide (3.15 g, 32.7 mmol) were dissolved in toluene and added. After stirring at 100°C for 24 hours, when the reaction was completed, fractional distillation was performed through ethyl acetate, remaining moisture was removed with anhydrous magnesium sulfate, the solvent was evaporated, and the solvent was purified through column chromatography to obtain pure Compound 9. obtained (1.6 g, 43.4%).

^1H NMR (300MHz, CDCl ₃ , ppm): 1H NMR (300MHz, CDCl3, ppm): δ 7.56-6.78 (m, 66H), 6.64 (m, 3H), 5.86 (d, 3H), 5.23 (d, 3H), 5.05 (s, 6H).

Experiment example

1. UV-vis absorption and luminescence properties

The UV-vis absorption and emission characteristics of compound 7 synthesized in Example 1, compound 8 synthesized in Example 2, and compound 9 synthesized in Example 3 were measured. Specifically, each of compounds 7 to 9 was dissolved in dichloromethane, and the UV-vis absorption spectrum was measured using a V-570 UV-vis spectrometer (Jasco), and an F-7000 fluorometer (Hitachi). The emission spectrum was measured using.

Figure 2 is a diagram showing the UV absorption spectrum of the triphenylamine-based compounds prepared in Examples 1 to 3 of the present invention.

Figure 3 is a diagram showing the PL emission spectrum of the triphenylamine-based compounds prepared in Examples 1 to 3 of the present invention.

Referring to Figures 2 and 3, it was confirmed that Compound 7, Compound 8, and Compound 9 prepared in Examples 1, 2, and 3 showed strong absorption around 400 nm. In particular, referring to Figure 3, Compound 7, Compound 8, and Compound 9 showed maximum emission wavelengths at 460 nm, 479 nm, and 511 nm, respectively, and the change in emission wavelength to a longer wavelength was due to an increase in the number of vinyl bonds in the molecule. This result is consistent with the change in absorption from compound 7 to compound 9 at longer wavelengths. Through these optical properties, it can be seen that Compound 7, Compound 8, and Compound 9 prepared in Examples 1, 2, and 3 can be applied as a positive transport material.

2. Thermal behavior and solvent resistance analysis

Thermal stability, crosslinking temperature, and solvent resistance properties of triphenylamine compound 7 synthesized in Example 1, triphenylamine compound 8 synthesized in Example 2, and triphenylamine compound 9 synthesized in Example 3 was analyzed.

Specifically, the thermal stability is analyzed by checking the Td value of the compound through TGA thermal analysis, the crosslinking temperature of the compound is analyzed by checking the exothermic peak of DSC, and the composition containing the synthesized compound is applied and crosslinked. After manufacturing it into a film form, solvent resistance was analyzed by observing the change in UV-vis absorption spectrum before and after rinsing with solvent (toluene).

Figure 4 is a diagram showing the results of analysis of thermal stability (TGA) of the triphenylamine-based compounds prepared in Examples 1 to 3 of the present invention.

Figure 5a is a diagram showing the analysis results of the cross-linking temperature (DSC) of the triphenylamine-based compound prepared in Example 1, and Figure 5b is an analysis of the cross-linking temperature (DSC) of the triphenylamine-based compound prepared in Example 2 This is a diagram showing the results, and Figure 5c is a diagram showing the analysis results of the crosslinking temperature (DSC) of the triphenylamine-based compound prepared in Example 3.

Figure 6a is a diagram showing the results of analyzing the solvent resistance characteristics of the compound prepared in Example 1 after crosslinking, and Figure 6b is a diagram showing the results of analyzing the solvent resistance characteristics of the compound prepared in Example 2 after crosslinking. Figure 6c is a diagram showing the results of analyzing the solvent resistance characteristics of the compound prepared in Example 3 after crosslinking.

Referring to Figure 4, it was confirmed that the Td values of Compound 7 prepared in Example 1, Compound 8 prepared in Example 2, and Compound 9 prepared in Example 3 were all 350°C or higher. This shows sufficient thermal stability to be applied as a hole transport material in organic light-emitting devices. Also, referring to FIGS. 5A to 5C, it was confirmed that the triphenylamine-based compounds prepared in Examples 1, 2, and 3 exhibited crosslinking temperatures in the range of 120 to 150 °C.

Referring to FIGS. 6A to 6C, in the case of the triphenylamine-based compounds prepared in Examples 1, 2, and 3, 90% was obtained by calculating the change in UV-vis absorption spectrum before and after rinsing with a solvent. It was confirmed that it had a solvent resistance of more than %.

3. Hole mobility analysis

A HOD (hole only device) device was manufactured using triphenylamine-based compound 7 synthesized in Example 1 as a hole transport material, and hole mobility was analyzed through SCLC analysis.

Specifically, poly(3,4-ethylenedioxthiophene):poly(styrenesulfonic acid) (PEDOT:PSS, AI4083) was spin-coated as a hole injection layer on a glass substrate coated with indium tin oxide (ITO) treated with air-plasma. (40 seconds, 2000 rpm) and heat treated (180°C, 30 minutes). Compound 7 synthesized as a hole transport layer was layered at 100 nm by spin coating (30 seconds, 1000 rpm) and heat treated (140° C., 30 minutes) to cross-link the films. Finally, 10 nm manganese trioxide (MnO ₃ ) and 100 nm thick aluminum (Al) cathodes were vacuum deposited at a pressure of 1x10 ^-6 Torr at a rate of 0.1 Å/s and 5.0 Å/s, respectively. A shadow mask was used for metal deposition, and the manufacturing process was carried out in a glove box to avoid exposing the devices to atmospheric conditions.

In the same manner as above, an HOD device was manufactured in which triphenylamine-based compound 8 and triphenylamine-based compound 9 synthesized in Examples 2 and 3 were used as hole transport materials.

Afterwards, the I-V characteristics of the HOD device fabricated above were measured using Keithley 2400, and the hole mobility was analyzed through SCLC section analysis.

Figure 7a is a diagram showing the I-V characteristics for measuring hole mobility by SCLC analysis by producing HOD using the triphenylamine-based compound prepared in Example 1 of the present invention, and Figure 7b is Example 2 of the present invention This is a diagram showing the I-V characteristics for measuring hole mobility by SCLC analysis by producing HOD using the triphenylamine-based compound prepared in , and Figure 7c shows the triphenylamine-based compound prepared in Example 3 of the present invention. This is a diagram showing the I-V characteristics for measuring hole mobility by producing HOD using SCLC analysis.

Referring to Figures 7a to 7c, Compound 7 prepared in Example 1 was 7.40×10 ^-5 cm ² v ^-1 s ^-1 , and Compound 8 prepared in Example 2 was 1.05×10 ^-4 cm ² v ^{- 1} s ^-1 , Compound 9 prepared in Example 3 showed a hole mobility of 1.13×10 ^-4 cm ² v ^-1 s ^-1 .

The above experimental data results show the applicability of the triphenylamine-based compounds prepared in Examples 1, 2, and 3 as cross-linked hole transport materials for solution processing.

4. Analysis of unit cell organic light emitting device properties

A unit cell organic light-emitting device was manufactured in which triphenylamine-based compound 7 synthesized in Example 1 was used as a hole transport material.

Specifically, poly(3,4-ethylenedioxthiophene):poly(styrenesulfonic acid) (PEDOT:PSS, AI4083) was spin-coated as a hole injection layer on a glass substrate coated with indium tin oxide (ITO) treated with air-plasma. (40 seconds, 2000 rpm) and heat treated (180°C, 30 minutes). Compound 7 synthesized as a hole transport layer was laminated by spin coating (40 seconds, 2000 rpm) and heat treated (140° C., 30 minutes) to cross-link the films. Next, on top of the cross-linked hole transport layer, Poly(9-vinylcarbazole) (PVK) as a host material and 4,4′-Bis(N-carbazolyl)-1,1′-biphenyl (CBP) as a dopant were added to Ir(mppy). The solution containing ₃ was laminated by spin coating (40 seconds, 900 rpm) and heat treated (80°C, 15 minutes). 2,2′,2-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi) was used as an electron transport layer on top of the emitting layer at 0.5 Å/s at a pressure of 1x10 ^-6 Torr. 30 nm was vacuum deposited at a rate of . Finally, as an electron injection layer, 1.0 nm lithium fluoride (LiF) and 100 nm thick aluminum (Al) cathode were vacuum deposited at a pressure of 1x10 ^-6 Torr and at a rate of 0.1 Å/s and 5.0 Å/s, respectively. A shadow mask was used for metal deposition, and the manufacturing process was carried out in a glove box to avoid exposing the devices to atmospheric conditions.

In the same manner as above, a unit cell organic light-emitting device was manufactured in which triphenylamine-based compound 8 and triphenylamine-based compound 9 synthesized in Examples 2 and 3 were used as hole transport materials.

Afterwards, the emission wavelength characteristics, color coordinate characteristics, I-V-L characteristics, and external quantum efficiency of the unit cell organic light emitting device manufactured above were measured using a photometer (CS-2000).

Figure 8 is a diagram showing the emission wavelength characteristics of a unit cell organic light-emitting device manufactured by using the triphenylamine-based compounds prepared in Examples 1, 2, and 3 of the present invention as hole transport materials in the hole transport layer. . Referring to FIG. 8, the unit cell organic light emitting device manufactured by using the same dopant had a maximum emission wavelength of 520 nm and had the same green emission characteristics.

Figure 9 is a diagram showing the I-V-L characteristics of a unit cell organic light-emitting device manufactured by using the triphenylamine-based compounds prepared in Examples 1, 2, and 3 of the present invention as hole transport materials in the hole transport layer.

Figure 10 shows the results of measuring the external quantum efficiency of a unit cell organic light-emitting device manufactured by using the triphenylamine-based compound prepared in Examples 1, 2, and 3 of the present invention as a hole transport material in the hole transport layer. This is a drawing showing .

Referring to Figures 9 and 10, the maximum luminance of the organic light-emitting device using Compound 7 prepared in Example 1 as a hole transport material is 4291 cd/m ² and the EQE is 8.87%, and Compound 8 prepared in Example 2 The maximum luminance of the organic light emitting device using as a hole transport material was observed to be 6831 cd/m ² and the EQE was 12.0%. In particular, the maximum luminance of the organic light-emitting device using Compound 9 prepared in Example 3 as a hole transport material was observed to be 7160 cd/m ² and the EQE was 11.6%.

The above experimental data results show that the compounds prepared in Examples 1, 2, and 3 can be used as cross-linked hole transport materials for solution processing.

The foregoing detailed description illustrates and explains the invention. In addition, the foregoing merely shows and describes preferred embodiments of the present invention, and as described above, the present invention can be used in various other combinations, modifications, and environments, and the scope of the inventive concept disclosed herein, the foregoing Changes or modifications may be made within the scope of equivalent disclosure and/or skill or knowledge in the art. Accordingly, the above detailed description of the invention is not intended to limit the invention to the disclosed embodiments. Additionally, the appended claims should be construed to include other embodiments as well.

10: Organic light emitting device
1: substrate
2: Anode
3: Hole transport layer
4: Light-emitting layer
5: Blocking layer
6: Electron transport layer
7: cathode

Claims (9)

Triphenylamine-based compound represented by the following formula (1):
[Formula 1]

In the above formula,
R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; Or an alkoxy group having 1 to 3 carbon atoms,
n1 to n3 are each independently O or 1, and at least one of n1 to n3 is 1,
R ₂₁ to R ₂₃ are each independently -OR ₃₁ ,
R ₃₁ is an alkyl group having 1 to 3 carbon atoms substituted with an aryl group having 6 to 30 carbon atoms substituted with a vinyl group,
R ₂₄ is hydrogen, R ₂₅ is hydrogen, R ₂₆ is hydrogen,
k1 to k3 are each independently O or 1, and at least two of k1 to k3 are 1.
According to paragraph 1,
The triphenylamine-based compound is a triphenylamine-based compound represented by the following formula (2):
[Formula 2]

In the above formula,
R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; Or an alkoxy group having 1 to 3 carbon atoms,
n1 to n3 are each independently O or 1, and at least one of n1 to n3 is 1,
R ₂₁ to R ₂₃ are each independently -OR ₃₁ ,
R ₃₁ is an alkyl group having 1 to 3 carbon atoms substituted with an aryl group having 6 to 30 carbon atoms substituted with a vinyl group,
R ₂₄ is hydrogen, R ₂₅ is hydrogen, R ₂₆ is hydrogen,
k1 to k3 are each independently O or 1, and at least two of k1 to k3 are 1.
delete According to paragraph 1,
The triphenylamine-based compound is a compound represented by the following formula 3-2:
[Formula 3-2]

In the above formula,
R ₁ to R ₁₂ are each independently hydrogen; an alkyl group having 1 to 3 carbon atoms; Or an alkoxy group having 1 to 3 carbon atoms,
n1 to n3 are each independently O or 1, and at least one of n1 to n3 is 1.
According to paragraph 1,
The triphenylamine-based compound is any one of the following compounds:
.
According to paragraph 1,
The triphenylamine-based compound is any one of the following compounds:

.
delete An organic light-emitting device comprising the triphenylamine-based compound according to claim 1.
According to clause 8,
The organic light emitting device is for an organic light emitting display device, a perovskite display device, or a perovskite solar cell.