KR20210115968A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device comprising the organic electric element. According to the present invention, it is possible to provide the organic electric element having high luminous efficiency, low driving voltage, and high heat resistance, and it is possible to improve color purity and lifespan of the organic electric element.

Description

Compound for organic electric device, organic electric device using same, and electronic device thereof

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these problems of efficiency and lifespan must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.

However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time.

In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.

However, most materials used for the hole transport layer have a low T1 value because they have to have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. ) resulting in light emission at the hole transport layer interface. When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened.

In order to solve the problem of light emission in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emitting auxiliary layers are formed according to each light emitting layer (R, G, B). is being developed

In order to fully exhibit the excellent characteristics of an organic electric device, materials constituting the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc., are used as stable and efficient materials. It should be supported by the above, and in particular, it is necessary to develop materials for the hole transport layer and the light emitting auxiliary layer.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifespan of the device, an organic electric device using the same, and an electronic device including the organic electric device.

In one aspect, the present invention provides a compound represented by the following formula.

<Formula 1>

In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.

By using the compound according to the present invention, high luminous efficiency and low driving voltage of the device can be achieved, and color purity and lifespan of the device can be improved.

1 to 3 schematically show an organic electric device according to embodiments of the present invention.
4 shows a chemical formula according to an aspect of the present invention.

Hereinafter, preferred embodiments of the present invention will be described with reference to the accompanying drawings.

In order to explain the present embodiments, it should be noted that in adding reference numerals to components of each drawing, the same components are given the same reference numerals as much as possible even though they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted. In the drawings referenced below, no scale ratio applies.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the components from other components, and the essence, order, or order of the components are not limited by the terms.

When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may be “connected,” “coupled,” or “connected.”

Also, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” the other component, but also when there is another component in between. It should be understood that cases may be included. Conversely, it should be understood that when an element is said to be "on top of" another part, it means that there is no other part in the middle.

The terms used in this specification and the appended claims are as follows, unless otherwise stated, without departing from the spirit of the present invention.

As used herein, the term "halo" or "halogen" includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has 1 to 60 carbons linked by a single bond, and is a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted means a radical of saturated aliphatic functional groups including cycloalkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group substituted with halogen unless otherwise specified.

The term "alkenyl" or "alkynyl" as used in this application has a double bond or a triple bond, respectively, unless otherwise specified, includes a straight or branched chain group, and has 2 to 60 carbon atoms, but is limited thereto it's not going to be

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

As used herein, the term “alkoxy group” or “alkyloxy group” refers to an alkyl group to which an oxygen radical is bonded, and has 1 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" refer to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 has a carbon number of, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present application have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present application, the aryl group or the arylene group includes a single ring type, a ring aggregate, a fused multiple ring-based compound, and the like. For example, the aryl group may include a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, and a substituted fluorenyl group, and the arylene group may include a fluorenylene group, a substituted fluorenylene group. group may be included.

As used herein, the term "ring assemblies" means that two or more ring systems (monocyclic or fused ring systems) are directly connected to each other through a single bond or a double bond, and between such rings It means that the number of direct links is one less than the total number of ring systems in the compound. In a ring aggregate, the same or different ring systems may be directly connected to each other through single or double bonds.

In the present application, since the aryl group includes a ring aggregate, the aryl group includes biphenyl and terphenyl in which a benzene ring, which is a single aromatic ring, is connected by a single bond. In addition, the aryl group also includes compounds in which an aromatic single ring and a fused aromatic ring system are connected by a single bond, for example, a compound in which a benzene ring, which is an aromatic single ring, and a fluorene, a fused aromatic ring system, are connected by a single bond. do.

As used herein, the term “fused multiple ring system” refers to a fused ring type sharing at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. and a form in which at least one heterocyclic system is fused. These fused multiple ring systems may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings. For example, in the case of an aryl group, it may be a naphthalenyl group, a phenanthrenyl group, a fluorenyl group, etc., but is not limited thereto.

As used herein, the term "spiro compound" has a 'spiro union', and the spiro linkage means a linkage formed by sharing only one atom in two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

As used herein, the terms "fluorenyl group", "fluorenylene group", and "fluorentriyl group" mean that R, R', R" and R'" are all hydrogen in the following structures, respectively, unless otherwise specified. It refers to a monovalent, divalent or trivalent functional group, and the "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorentriyl group" is a substituent R, R', R", R' "means that at least one of " is a substituent other than hydrogen, and includes cases in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In the present specification, the fluorenyl group, the fluorenylene group, and the fluorentriyl group may all be referred to as fluorene groups regardless of valences such as monovalent, divalent, trivalent, and the like.

In addition, the R, R', R" and R'" are each independently an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 to It may be a heterocyclic group having 30 carbon atoms, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, imidazole, triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline. For example, the substituted fluorenyl group and the fluorenylene group are monovalent to 9,9-dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spirobi[9H-fluorene], respectively. It may be a functional group or a divalent functional group.

The term "heterocyclic group" used in the present application includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, each carbon number including at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.

For example, "heterocyclic group" may include a compound including a heteroatom group such as _{SO 2} , P=O, etc., such as the following compounds instead of carbon forming a ring.

As used herein, the term "ring" includes monocyclic and polycyclic rings, and includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems and spiro compounds, and includes aromatic as well as non-aromatic, hydrocarbon Rings include, of course, heterocycles containing at least one heteroatom.

The term "aliphatic ring group" used in the present application refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group, where The arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in this application, "substitution" means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, C ₁ -C ₂₀ Alkylamine group, C ₁ -C ₂₀ Alkylthiophene group, C ₆ -C ₂₀ Arylthiophene group, C ₂ -C ₂₀ Alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group of, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron group, germanium group, and O, N, S, Si and P containing at least one heteroatom selected _{from the group consisting of C 2} -C ₂₀ heterocyclic group means substituted with one or more substituents selected from the group consisting of and is not limited to these substituents.

In the present application, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the functional group reflecting the valence', but is described as 'the name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl (group)', and the divalent group is 'phenanthrylene (group)', etc. It can be described, but it can also be described as 'phenanthrene', which is the name of the parent compound, regardless of the valence.

Similarly, in the case of pyrimidine, regardless of the valence, it is described as 'pyrimidine', or if it is monovalent, it is pyrimidinyl (group), and if it is divalent, the 'group of the valence, such as pyrimidinylene (group), etc. It can also be written in the name of '. Therefore, in the present application, when the type of the substituent is described as the name of the parent compound, it may mean an n-valent 'group' formed by the detachment of a hydrogen atom bonding to a carbon atom and/or a hetero atom of the parent compound.

In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in the present application is the same as the definition of the substituent by the exponential definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same as or different from each other.

Unless otherwise specified in the present application, forming a ring means that adjacent groups combine with each other to form a single ring or fused multiple rings, and the single ring and the formed fused multiple rings are at least one hydrocarbon ring as well as a hydrocarbon ring. It includes heterocycles containing heteroatoms, and may include aromatic and non-aromatic rings.

In addition, unless otherwise specified in the present specification, when representing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.

Meanwhile, the term "bridged bicyclic compound" as used in the present application refers to a compound in which two rings share three or more atoms to form a ring, unless otherwise specified. In this case, the shared atom may include carbon or a hetero atom.

Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown); An organic material layer including the compound according to the present invention is included between the second electrodes 170 .

The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 . Specifically, the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .

Preferably, the capping layer 180 may be formed on one surface of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer. The light efficiency of the device may be improved.

For example, a capping layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the capping layer 180 is formed in the second electrode 170 . It is possible to reduce optical energy loss due to surface plasmon polaritons (SPPs) of SPPs, and in the case of a bottom emission organic light emitting device, the capping layer 180 may serve as a buffer for the second electrode 170 . .

Meanwhile, a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .

Referring to FIG. 2 , the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120 , a hole transport layer 130 , a buffer layer 210 sequentially formed on the first electrode 110 , It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a capping layer 180 is formed on the second electrode. can

Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .

Referring to FIG. 3 , an organic electric device 300 according to another embodiment of the present invention includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, the organic electric device according to an embodiment of the present invention includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode. 170 and a capping layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer ( 350) may be included.

The second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 .

As such, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.

A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 . The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 . The charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and to smoothly distribute charges.

The first light emitting layer 340 may include a light emitting material including a blue fluorescent dopant in a blue host, and the second light emitting layer 440 includes a green host in which a greenish yellow dopant and a red dopant are doped together. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.

In this case, the second hole transport layer 430 includes the second stack ST2 in which the energy level is set higher than the triplet excited state energy level of the second light emitting layer 440 .

Since the energy level of the second hole transport layer 430 is higher than that of the second light emitting layer 440 , triplet excitons of the second light emitting layer 440 pass to the second hole transport layer 430 and the luminous efficiency is lowered. it can be prevented That is, the second hole transport layer 430 functions as an exciton blocking layer that functions to transport holes from the inherent second light emitting layer 440 and prevents triplet excitons from crossing over. .

In addition, for the function of the exciton blocking layer, the first hole transport layer 330 may also be set to a higher energy level than the triplet excitation energy level of the first light emitting layer 340 . In addition, the first electron transport layer 350 is also set to an energy level higher than the energy level of the triplet excited state of the first light emitting layer 340 , and the second electron transport layer 450 is also triplet excited by the second light emitting layer 440 . It is preferable to set the energy level higher than the energy level of the state.

In FIG. 3 , n may be an integer of 1 to 5. When n is 2, the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .

When a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3 , an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.

The compound represented by Chemical Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer 210, a light emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material of the capping layer 180, preferably the hole transport layer 130, 330, 430, the light emitting auxiliary layer 220 ), the light emitting layers 140 , 340 , 440 , and/or the capping layer 180 may be used as a material.

The organic electric device according to FIGS. 1 to 3 may further include a protective layer (not shown) and an encapsulation layer (not shown). The protective layer may be disposed on the capping layer, and the encapsulation layer is disposed on the capping layer, and a side portion of at least one of the first electrode, the second electrode, and the organic material layer to protect the first electrode, the second electrode, and the organic material layer. may be formed to cover the

The protective layer may provide a planarized surface so that the encapsulation layer is uniformly formed, and may serve to protect the first electrode, the second electrode, and the organic material layer during the manufacturing process of the encapsulation layer.

The encapsulation layer may serve to prevent the penetration of external oxygen and moisture into the organic electric device.

On the other hand, even with the same and similar core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of sub-substituents coupled thereto In particular, when the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

Therefore, in the present invention, by using the compound represented by Chemical Formula 1 as a material for the light-emitting auxiliary layer 220, the light-emitting layer 140, 340, 440, and/or the capping layer 180, the energy level and T1 value between each organic material layer, By optimizing the intrinsic properties (mobility, interfacial properties, etc.) of the material, the lifetime and efficiency of the organic electric device could be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120, 320, 420), the hole transport layers 130, 330, 430, the light emitting layers 140, 340, 440, the electron transport layers 150, 350, 450, and the electron injection layer 160 after forming an organic material layer including the It may be manufactured by depositing a material that can be used as the cathode 170 thereon. In addition, a light-emitting auxiliary layer 220 between the hole transport layers 130 , 330 , 430 and the light emitting layers 140 , 340 , 440 , and an electron transport auxiliary layer between the light emitting layer 140 and the electron transport layer 150 (not shown) may be further formed or may be formed in a stack structure as described above.

In addition, the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

The organic electric device according to an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

The organic electric device according to an embodiment of the present invention may include an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, a device for a quantum dot display, and the like.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.

Hereinafter, the compound according to one aspect of the present invention will be described.

The compound according to one aspect of the present invention is represented by the following formula (1).

<Formula 1>

In Formula 1,

1) A is a thiophene ring or a furanyl ring,

2) Ar ¹ to Ar ⁸ are each independently a C ₆ to C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or C ₃ ~ C ₆₀ An aliphatic ring and a C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; -L'-N(R _a )(R _b ); or a combination thereof,

3) R _a ~ R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or C ₃ ~ C ₆₀ An aliphatic ring and a C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; or a combination thereof,

4) L' and L ¹ to L ⁴ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} or a combination thereof,

5) Ar _a ~ Ar _b are each independently a C ₆ ~ C ₆₀ arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} or a combination thereof,

6) e1 and e2 are each independently 0 or an integer of 1; e3 is an integer from 0 to 4; e4 is an integer from 0 to 2; provided that e1+e2+e3+e4 ≥ 1,

7) R ¹ to R ² are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,

8) a is an integer from 0 to 4; b is an integer from 0 to 2,

9) R ^{1 to 2} , Ar ¹ to Ar ⁸ , R _a to R _b , L′, L ¹ to L ⁴ , Ar _a to Ar _b and the rings formed by bonding adjacent groups to each other are deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; boron group; germanium group; cyano group; amino group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; _{a C 6} -C ₂₀ aryl group substituted with deuterium; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof, and adjacent substituents may form a ring.

When R ¹ to R ² , R _a to R _b and Ar ¹ to Ar ⁸ are aryl groups, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl. , biphenyl, naphthyl, terphenyl, and the like.

Wherein R ^{1 to 2} , Ar ¹ to Ar ⁸ , R _a to R _b , L′, L ¹ to L ⁴ and Ar _a to Ar _b are heterocyclic groups, Preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, such as dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, etc. .

When R ¹ to R ² , R _a to R _b and Ar ¹ to Ar ⁸ are fluorenyl groups, preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-flu orenyl group, 9,9'-spirobifluorene, and the like.

When L', L ¹ to L ⁴ and Ar _a to Ar _b are an arylene group, preferably a C ₆ to C ₃₀ arylene group, more preferably a C ₆ to C ₁₈ arylene group, such as phenyl, bi phenyl, naphthyl, terphenyl, and the like.

When R ¹ to R ² and Ar ¹ to Ar ⁸ are alkyl groups, they may be preferably C ₁ to C ₁₀ alkyl groups, for example, methyl, t-butyl, or the like.

When R ¹ to R ² and Ar ¹ to Ar ⁸ are alkoxyl groups, preferably a C ₁ to C ₂₀ alkoxyl group, more preferably a C ₁ to C ₁₀ alkoxyl group, such as methoxy, t-part Toxic, etc. may be used.

The ring formed by bonding adjacent groups of ^{R 1 to 2} , Ar ¹ to Ar ⁸ , R _a to R _b , L′, L ¹ to L ⁴ and Ar _a to Ar _{b is C 6} to C ₆₀ aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or it may be a C ₃ ~ C ₆₀ aliphatic ring group, for example, when adjacent groups are bonded to each other to form an aromatic ring, preferably a C ₆ ~ C ₂₀ aromatic ring, more preferably C ₆ ~ C ₁₄ of aromatic rings, such as benzene, naphthalene, phenanthrene, and the like.

Preferably, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 5, but is not limited thereto.

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

In Formulas 2 to 5, R ^{1 to 2} , L ¹ to L ⁴ , Ar ¹ to Ar ⁸ , Ar _a to Ar _b , a to b and e1 to e4 are the same as defined in Formula 1 above.

Also preferably, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 6 to 13, but is not limited thereto.

<Formula 6> <Formula 7> <Formula 8>

<Formula 9> <Formula 10> <Formula 11>

<Formula 12> <Formula 13>

In Formulas 6 to 13,

1) X is S or O;

2) L ¹ to L ⁴ , Ar ¹ to Ar ⁸ , Ar _a to Ar _b and e1 to e4 are the same as defined in Formula 1 above.

Also preferably, the Ar ¹ to Ar ⁸ may be each independently represented by Formula A-1 or A-2 below, but is not limited thereto.

<Formula A-1> <Formula A-2>

In Formulas A-1 and A-2,

1) Z is O, S, CR'R" or N-L'-Ar',

2) R _a ~R _d , R′ and R” are the same as the definition ^{of R 1 in Formula 1 above,}

3) n is an integer from 0 to 3; m, o and p are each independently an integer from 0 to 4,

4) L' is the same as the definition ^{of L 1 in Formula 1,}

4) Ar' is the same as the definition ^{of Ar 1 in Formula 1 above.}

Meanwhile, The compound represented by Formula 1 may be one of the following P-1 to P-69, but is not limited thereto.

In another embodiment of the present invention, the present invention provides a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Formula 1 alone or in combination.

As another embodiment of the present invention, the present invention provides a first electrode; a second electrode; an organic material layer formed between the first electrode and the second electrode; and a capping layer, wherein the capping layer is formed on one side of both surfaces of the first electrode and the second electrode that is not in contact with the organic material layer, and the organic material layer or the capping layer is represented by Formula 1 compounds used alone or in combination.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. That is, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer included in the organic material layer may include a compound represented by Formula (1). .

Preferably, the organic material layer includes at least one of the hole transport layer, the light emitting auxiliary layer and the light emitting layer. That is, the compound may be included in at least one of the hole transport layer, the light emitting auxiliary layer, and the light emitting layer.

The organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode.

Preferably, the organic material layer further includes a charge generating layer formed between the two or more stacks.

As another embodiment of the present invention, the present invention provides an electronic device including a display device including an organic electric device including the compound represented by Formula 1, and a controller for driving the display device.

In an embodiment of the present invention, the compound of Formula 1 may be included alone, the compound may be included in a combination of two or more different types, or the compound may be included in a combination of two or more other compounds.

Hereinafter, examples of the synthesis of the compound represented by Formula 1 and the preparation of the organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

< Synthesis example >

The final product represented by Formula 1 according to the present invention may be synthesized as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

In Scheme 1 above

1) Hal ₁ to Hal ₄ are each independently I, Br or Cl,

2) h1 to h4 correspond to e1 to e4 independently of each other; At least one of h1 to h4 is 1,

3) Ar _n and Ar _m are the same as the definition ^{of Ar 1} in Formula 1 above,

4) Other substituents are as defined in Formula 1 above.

I. Synthesis of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2>

In Scheme 2, Hal ₁ to Hal ₄ are each independently I, Br, or Cl.

1. Sub 1-3 Synthesis example

(1) Sub 1-3a synthesis

2-bromo-6-phenyl-6H-furo[2,3-b]pyrrole (50 g, 190.7 mmol) and 5-chloro-2-iodoaniline (50.7 g, 200.3 mmol), Pd ₂ (dba) ₃ (5.2 g, 5.7 mmol), 50% P(t-Bu) ₃ (2.3 ml, 11.4 mmol) and NaOt-Bu (55 g, 572.2 mmol) were added to toluene (1955 ml) and stirred at 90°C. Upon completion of the reaction, _{after extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was subjected to silica gel column and recrystallization to obtain 69.6 g (84%) of the product Sub 1-3a.

(2) Sub 1-3b synthesis

Sub 1-3a (69. g, 160.3 mmol) and Pd(OAc) ₂ (3.7 g, 16.8 mmol), P(t-Bu) ₃ (2.6 g, 12.8 mmol) and K ₂ CO ₃ (69.7 g, 504.7) mmol) in DMA (1642 ml) and refluxed at 170° C. for 12 hours. When the reaction was completed, 40.3 g (82%) of the product Sub 1-3b was obtained by using the separation method described in the synthesis of Sub 1-3a.

(3) Sub 1-3 synthesis

Sub 1-3b (40.3 g, 131.4 mmol) with bromobenzene (21.6 g, 137.9 mmol), Pd ₂ (dba) ₃ (3.6 g, 3.9 mmol), 50% P(t-Bu) ₃ (1.6 ml, 7.8 mmol) ), NaOt-Bu (37.8 g, 394.2 mmol) was added to toluene (1347ml) and stirred at 90°C. Upon completion of the reaction, 42.7 g (85%) of Sub 1-3 was obtained by using the separation method described in the synthesis of Sub 1-3a.

2. Sub 1-8 Synthesis

(1) Sub 1-8a synthesis

3-bromo-5-(3-chlorophenyl)-4-phenyl-4H-furo[3,2-b]pyrrole (40 g, 107.3 mmol) and 2-iodoaniline (24.6 g, 112.7 mmol), Pd ₂ (dba ) ₃ (2.9 g, 3.2 mmol), 50% P(t-Bu) ₃ (1.3 ml, 6.4 mmol) and NaOt-Bu (30.9 g, 322 mmol) were added to toluene (1100 ml) and stirred at 90° C. . When the reaction was completed, 44.4 g (81%) of the product Sub 1-8a was obtained by using the separation method described in the synthesis of Sub 1-3a.

(2) Sub 1-8b synthesis

Sub 1-8a (44.4 g, 86.9 mmol) in Pd(OAc) ₂ (2 g, 9.1 mmol), P(t-Bu) ₃ (1.4 g, 6.9 mmol), K ₂ CO ₃ (37.8 g, 273.8 mmol) ) and DMA (891 ml) were added and refluxed at 170° C. for 12 hours. Upon completion of the reaction, 24.6 g (74%) of Sub 1-8b was obtained by using the separation method described in the synthesis of Sub 1-3b.

(3) Sub 1-8 synthesis

Sub 1-8b (24.6 g, 64.3 mmol) with 1-bromonaphthalene (13.9 g, 67.5 mmol), Pd ₂ (dba) ₃ (1.7 g, 1.9 mmol), 50% P(t-Bu) ₃ (0.7 ml, 3.8 mmol), NaOt-Bu (18.5 g, 193 mmol) was added to toluene (659 ml) and stirred at 90°C. Upon completion of the reaction, 25.7 g (78.5%) of Sub 1-8 was obtained by using the separation method described in the synthesis of Sub 1-3a.

3. Sub 1-12 Synthesis

(1) Sub 1-12a synthesis

2-bromo-6-(4-chlorodibenzo[b,d]thiophen-2-yl)-6H-furo[2,3-b]pyrrole (31 g, 76.9 mmol) and 2-iodoaniline (17.7 g, 80.8 mmol) ), Pd ₂ (dba) ₃ (2.1 g, 2.3 mmol), 50% P(t-Bu) ₃ (0.9 ml, 4.6 mmol) and NaOt-Bu (22.2 g, 230.9 mmol) were added to toluene (789 ml) and stirred at 90 °C. Upon completion of the reaction, 31.6 g (75.9%) of Sub 1-12a was obtained by using the separation method described in the synthesis of Sub 1-3a.

(2) Sub 1-12b synthesis

Sub 1-12a (31.6 g, 58.4 mmol) in Pd(OAc) ₂ (1.3 g, 6.1 mmol), P(t-Bu) ₃ (0.9 g, 4.6 mmol), K ₂ CO ₃ (25.4 g, 184 mmol) ) and DMA (599 ml) were added and refluxed at 170° C. for 12 hours. Upon completion of the reaction, 17.7 g (73.4%) of Sub 1-12b was obtained by using the separation method described in the synthesis of Sub 1-3b.

(3) Sub 1-12 synthesis

Sub 1-12b (17.7 g, 42.8 mmol) with bromobenzene (7 g, 45 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), 50% P(t-Bu) ₃ (0.5 ml, 2.5 mmol) ) and NaOt-Bu (12.3 g, 128.6 mmol) were added to toluene (440 ml) and stirred at 90°C. When the reaction was completed, 15 g (71.6%) of the product Sub 1-12 was obtained by using the separation method described in the synthesis of Sub 1-3a.

4. Sub 1-31 Synthesis

(1) Sub 1-31a synthesis

3-bromo-4-(9,10-dihydro-9,10-[1,2]benzenoanthrcen-1-yl)-4H-furo[3,2-b]pyrrole (35 g, 79.8 mmol) and 4- (4-chloro-9H-fluoren-1-yl)-2-iodoaniline (35 g, 83.8 mmol), Pd ₂ (dba) ₃ (2.1 g, 2.4 mmol), 50% P(t-Bu) ₃ (0.9 ml, 4.7 mmol) and NaOt-Bu (23 g, 239.5 mmol) were added to toluene (775 ml) and stirred at 90°C. When the reaction was completed, 40.4 g (65.4%) of the product Sub 1-31a was obtained by using the separation method described in the synthesis of Sub 1-1a.

(2) Synthesis of Sub 1-31b

Sub 1-31a (40.4 g, 52.2 mmol) in Pd(OAc) ₂ (1.2 g, 5.4 mmol), P(t-Bu) ₃ (0.8 g, 4.1 mmol), K ₂ CO ₃ (22.7 g, 164.5 mmol) ) and DMA (535 ml) were added and refluxed at 170° C. for 12 hours. When the reaction was completed, 21.6 g (64.1%) of the product Sub 1-31b was obtained by using the separation method described in the synthesis of Sub 1-1b.

(3) Sub 1-31 synthesis

Sub 1-31b (21.6 g, 33.4 mmol) with bromobenzene (5.5 g, 35.1 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), 50% P(t-Bu) ₃ (0.4 ml, 2.0 mmol) ) and NaOt-Bu (9.6 g, 100.4 mmol) were added to toluene (343 ml) and stirred at 90°C. Upon completion of the reaction, 14.7 g (61%) of Sub 1-31 was obtained by using the separation method described in the synthesis of Sub 1-1a.

5. Sub 1-38 Synthesis

(1) Sub 1-38a synthesis

3-bromo-6-chloro-4-phenyl-4H-thieno[3,2-b]pyrrole (41 g, 131.1 mmol) and 2-iodoaniline (30.1 g, 137.7 mmol), Pd ₂ (dba) ₃ (3.6 g, 3.9 mmol), 50% P(t-Bu) ₃ (1.5 ml, 7.8 mmol) and NaOt-Bu (37.8 g, 393.4 mmol) were added to toluene (1344 ml) and stirred at 90°C. When the reaction was completed, 52 g (88.1%) of the product Sub 1-38a was obtained by using the separation method described in the synthesis of Sub 1-3a.

(2) Sub 1-38b synthesis

Sub 1-38a (52 g, 115.5 mmol) in Pd(OAc) ₂ (2.7 g, 12.1 mmol), P(t-Bu) ₃ (1.8 g, 9.2 mmol), K ₂ CO ₃ (50.3 g, 363.9 mmol) ) and DMA (1184 ml) were added and refluxed at 170° C. for 12 hours. When the reaction was completed, 32.2 g (86.4%) of the product Sub 1-38b was obtained by using the separation method described in the synthesis of Sub 1-3b.

(3) Sub 1-38 synthesis

Sub 1-38b (32.2 g, 99.8 mmol) with bromobenzene (16.4 g, 104.8 mmol), Pd ₂ (dba) ₃ (2.7 g, 3 mmol), 50% P(t-Bu) ₃ (1.2 ml, 5.9 mmol) ) and NaOt-Bu (28.7 g, 299.5 mmol) were added to toluene (1023 ml) and stirred at 90°C. When the reaction was completed, 34.8 g (87.6%) of Sub 1-38 was obtained by using the separation method described in the synthesis of Sub 1-3a.

6. Sub 1-44 Synthesis

(1) Sub 1-44a synthesis

3-bromo-4-phenyl-4H-thieno[3,2-b]pyrrole (22 g, 79.0 mmol) and 3'-chloro-2-iodo-[1,1':2',1''-terphenyl ]-3-amine (33.6 g, 83 mmol), Pd ₂ (dba) ₃ (2.1 g, 2.3 mmol), 50% P(t-Bu) ₃ (0.9 ml, 4.7 mmol) and NaOt-Bu (22.8 g) , 237.2 mmol) was added to toluene (811 ml) and stirred at 90°C. When the reaction was completed, 33.9 g (71.1%) of the product Sub 1-44a was obtained by using the separation method described in the synthesis of Sub 1-3a.

(2) Sub 1-44b synthesis

Sub 1-44a (33.9 g, 56.2 mmol) in Pd(OAc) ₂ (1.3 g, 5.9 mmol), P(t-Bu) ₃ (0.9 g, 4.5 mmol), K ₂ CO ₃ (24.4 g, 177.1 mmol) ) and DMA (576 ml) and refluxed at 170° C. for 12 hours. Upon completion of the reaction, 18.1 g (67.8%) of the product Sub 1-44b was obtained by using the separation method described in the synthesis of Sub 1-3b.

(3) Sub 1-44 synthesis

Sub 1-44b (18.1 g, 38.1 mmol) and 1-bromobenzene-2,3,4,5,6-d5 (6.4 g, 40 mmol), Pd ₂ (dba) ₃ (1 g, 1.14 mmol), 50 % P(t-Bu) ₃ (0.4 ml, 2.2 mmol) and NaOt-Bu (10.9 g, 114.3 mmol) were added to toluene (391 ml) and stirred at 90°C. Upon completion of the reaction, 14.9 g (70.4%) of Sub 1-44 was obtained by using the separation method described in the synthesis of Sub 1-3a.

7. Sub 1-59 Synthesis

(1) Sub 1-59a synthesis

3-(2-bromo-6H-thieno[2,3-b]pyrrol-6-yl)-4-chloro-N,N-diphenylaniline (18 g, 37.5 mmol) and 2-iodoaniline (8.6 g, 39.3 mmol) ), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), 50% P(t-Bu) ₃ (0.4 ml, 2.2 mmol) and NaOt-Bu (10.8 g, 112.5 mmol) were added to toluene (385 ml). and stirred at 90 °C. Upon completion of the reaction, 17.2 g (74.5%) of Sub 1-59a was obtained by using the separation method described in the synthesis of Sub 1-3a.

(2) Sub 1-59b synthesis

Sub 1-59a (17.2 g, 27.9 mmol) in Pd(OAc) ₂ (0.6 g, 2.9 mmol), P(t-Bu) ₃ (0.4 g, 2.2 mmol), K ₂ CO ₃ (12.1 g, 88 mmol) ) and DMA (286 ml) were added and refluxed at 170° C. for 12 hours. Upon completion of the reaction, 9.9 g (72.8%) of Sub 1-59b was obtained by using the separation method described in the synthesis of Sub 1-3b.

(3) Sub 1-59 synthesis

Sub 1-3b (9.9 g, 20.3 mmol) and 3-(4-bromophenyl)-9,9-dimethyl-9H-fluorene (7.4 g, 21.3 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol) , 50% P(t-Bu) ₃ (0.2 ml, 1.2 mmol) and NaOt-Bu (5.8 g, 61 mmol) were added to toluene (209 ml) and stirred at 90°C. Upon completion of the reaction, 10.9 g (70.7%) of Sub 1-59 was obtained by using the separation method described in the synthesis of Sub 1-3a.

8. Sub 1-62 Synthesis

(1) Sub 1-62a synthesis

3-bromo-4-(dibenzo[b,d]furan-1-yl)-4H-thieno[3,2-b]pyrrole (27 g, 73.3 mmol) and 5-(5-chloroanthracen-1-yl) -2-iodoaniline (33 g, 76.9 mmol), Pd ₂ (dba) ₃ (2 g, 2.2 mmol), 50% P(t-Bu) ₃ (0.8 ml, 4.4 mmol) and NaOt-Bu (21.1 g, 219.9 mmol) was added to toluene (752 ml) and stirred at 90°C. Upon completion of the reaction, 35.9 g (68.4%) of the product Sub 1-62a was obtained by using the separation method described in the synthesis of Sub 1-3a.

(2) Sub 1-62b synthesis

Sub 1-62a (35.9 g, 50.1 mmol) in Pd(OAc) ₂ (1.1 g, 5.2 mmol), P(t-Bu) ₃ (0.8 g, 4 mmol), K ₂ CO ₃ (21.8 g, 157.9 mmol) ) and DMA (514 ml) were added and refluxed at 170° C. for 12 hours. When the reaction was completed, 20 g (67.8%) of the product Sub 1-62b was obtained by using the separation method described in the synthesis of Sub 1-3b.

(3) Sub 1-62 synthesis

Sub 1-62b (20 g, 34 mmol) with 3-bromo-N,N-diphenylaniline (11.5 g, 35.7 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), 50% P(t-Bu) ) ₃ (0.4 ml, 2 mmol) and NaOt-Bu (9.8 g, 102 mol) were added to toluene (349 ml) and stirred at 90°C. Upon completion of the reaction, 19.2 g (67.9%) of Sub 1-62 was obtained by using the separation method described in the synthesis of Sub 1-3a.

On the other hand, the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.

Table 1 below shows FD-MS values of compounds belonging to Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z=482.12 (C ₃₂ H ₁₉ ClN ₂ O=482.97) Sub 1-2 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-3 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-4 m/z=506.12 (C ₃₄ H ₁₉ ClN ₂ O=506.99) Sub 1-5 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-6 m/z=532.13 (C ₃₆ H ₂₁ ClN ₂ O=533.03) Sub 1-7 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-8 m/z=508.13 (C ₃₄ H ₂₁ ClN ₂ O=509.01) Sub 1-9 m/z=472.13 (C ₃₁ H ₂₁ ClN ₂ O=472.97) Sub 1-10 m/z=498.15 (C ₃₃ H ₂₃ ClN ₂ O=499.01) Sub 1-11 m/z=622.18 (C ₄₃ H ₂₇ ClN ₂ O=623.15) Sub 1-12 m/z=488.08 (C ₃₀ H ₁₇ ClN ₂ OS=488.99) Sub 1-13 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-14 m/z=407.08 (C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub 1-15 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-16 m/z=549.16 (C ₃₆ H ₂₄ ClN ₃ O=550.06) Sub 1-17 m/z=550.18 (C ₃₇ H ₂₇ ClN ₂ O=551.09) Sub 1-18 m/z=674.19 (C ₄₅ H ₂₇ ClN ₄ O=675.19) Sub 1-19 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-20 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-21 m/z=706.15 (C ₄₆ H ₂₇ ClN ₂ O ₂ S=707.24) Sub 1-22 m/z=510.12 (C ₃₂ H ₁₉ ClN ₄ O=510.98) Sub 1-23 m/z=628.26 (C ₃₉ H ₃₇ ClN ₄ O ₂ =629.2) Sub 1-24 m/z=501.11 (C ₂₈ H ₂₁ ClFN ₃ OS=502) Sub 1-25 m/z=554.19 (C ₃₆ H ₁₉ D ₅ ClN ₃ O=555.09) Sub 1-26 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-27 m/z=681.25 (C ₄₆ H ₃₆ ClN ₃ O=682.26) Sub 1-28 m/z=714.21 (C ₄₆ H ₃₅ ClN ₂ O ₂ S=715.31) Sub 1-29 m/z=715.2 (C ₄₈ H ₃₀ ClN ₃ O ₂ =716.24) Sub 1-30 m/z=625.19 (C ₄₂ H ₂₈ ClN ₃ O=626.16) Sub 1-31 m/z=722.21 (C ₅₁ H ₃₁ ClN ₂ O=723.27) Sub 1-32 m/z=819.21 (C ₅₅ H ₃₄ ClN ₃ OS=820.41) Sub 1-33 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-34 m/z=450.09 (C ₂₈ H ₁₆ ClFN ₂ O=450.9) Sub 1-35 m/z=726.24 (C ₅₁ H ₃₅ ClN ₂ O=727.3) Sub 1-36 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-37 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-38 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-39 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-40 m/z=654.15 (C ₄₃ H ₂₇ ClN ₂ OS=655.21) Sub 1-41 m/z=474.1 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub 1-42 m/z=772.18 (C ₅₁ H ₃₃ ClN ₂ S ₂ =773.41) Sub 1-43 m/z=474.1 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub 1-44 m/z=555.16 (C ₃₆ H ₁₈ D ₅ ClN ₂ S=556.13) Sub 1-45 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-46 m/z=731.18 (C ₄₈ H ₃₀ ClN ₃ OS=732.3) Sub 1-47 m/z=474.1 (C ₃₀ H ₁₉ ClN ₂ S=475.01) Sub 1-48 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-49 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-50 m/z=588.11 (C ₃₈ H ₂₁ ClN ₂ OS=589.11) Sub 1-51 m/z=564.11 (C ₃₆ H ₂₁ ClN ₂ OS=565.09) Sub 1-52 m/z=590.16 (C ₃₉ H ₂₇ ClN ₂ S=591.17) Sub 1-53 m/z=399.06 (C ₂₃ H ₁₄ ClN ₃ S=399.9) Sub 1-54 m/z=524.11 (C ₃₄ H ₂₁ ClN ₂ S=525.07) Sub 1-55 m/z=899.28 (C ₆₀ H ₄₂ ClN ₅ S=900.54) Sub 1-56 m/z=753.23 (C ₅₀ H ₃₂ ClN ₅ O=754.29) Sub 1-57 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-58 m/z=382.09 (C ₂₄ H ₁₅ ClN ₂ O=382.85) Sub 1-59 m/z=757.23 (C ₅₁ H ₃₆ ClN ₃ S=758.38) Sub 1-60 m/z=398.06 (C ₂₄ H ₁₅ ClN ₂ S=398.91) Sub 1-61 m/z=458.12 (C ₃₀ H ₁₉ ClN ₂ O=458.95) Sub 1-62 m/z=831.21 (C ₅₆ H ₃₄ ClN ₃ OS=832.42) Sub 1-63 m/z=942.29 (C ₆₄ H ₃₉ ClN ₆ O=943.51)

II. Synthesis of Sub 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.

<Scheme 3>

The compound belonging to Sub 2 may be a compound as follows, but is not limited thereto.

Table 2 below shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 2 .

compound FD-MS compound FD-MS Sub 2-1 m/z=169.09 (C ₁₂ H ₁₁ N=169.23) Sub 2-2 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-3 m/z=219.1 (C ₁₆ H ₁₃ N=219.29) Sub 2-4 m/z=219.1 (C ₁₆ H ₁₃ N=219.29) Sub 2-5 m/z=224.14 (C ₁₆ H ₈ D ₅ N=224.32) Sub 2-6 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 2-7 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-8 m/z _{=347.17 (C 26} H ₂₁ N=347.46) Sub 2-9 m/z=407.17 (C ₃₁ H ₂₁ N=407.52) Sub 2-10 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub 2-11 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-12 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub 2-13 m/z=275.09 (C ₁₈ H ₁₃ NO ₂ =275.31) Sub 2-14 m/z=301.15 (C ₂₁ H ₁₉ NO=301.39) Sub 2-15 m/z=197.12 (C ₁₄ H ₁₅ N=197.28) Sub 2-16 m/z=175.14 (C ₁₂ H ₁₇ N=175.28) Sub 2-17 m/z=121.09 (C ₈ H ₁₁ N=121.18) Sub 2-18 m/z=209.08 (C ₁₄ H ₁₁ NO=209.25) Sub 2-19 m/z=125.06 (C ₇ H ₈ FN=125.15) Sub 2-20 m/z=285.13 (C ₁₉ H ₁₅ N ₃ =285.35) Sub 2-21 m/z=174.12 (C ₁₂ H ₆ D ₅ N=174.26) Sub 2-22 m/z=473.21 (C ₃₆ H ₂₇ N=473.62) Sub 2-23 m/z=271.14 (C ₂₀ H ₁₇ N=271.36) Sub 2-24 m/z=423.16 (C ₃₁ H ₂₁ NO=423.52) Sub 2-25 m/z=427.14 (C ₃₀ H ₂₁ NS=427.57) Sub 2-26 m/z=325.09 (C ₂₂ H ₁₅ NS=325.43) Sub 2-27 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-28 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub 2-29 m/z=309.12 (C ₂₂ H ₁₅ NO=309.37) Sub 2-30 m/z=371.17 (C ₂₈ H ₂₁ N=371.48) Sub 2-31 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub 2-32 m/z=335.17 (C ₂₅ H ₂₁ N=335.45) Sub 2-33 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub 2-34 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub 2-35 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 2-36 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub 2-37 m/z=227.17 (C ₁₆ H ₂₁ N=227.35) Sub 2-38 m/z _{=347.17 (C 26} H ₂₁ N=347.46) Sub 2-39 m/z=325.09 (C ₂₂ H ₁₅ NS=325.43) Sub 2-40 m/z=194.08 (C ₁₃ H ₁₀ N ₂ =194.24) Sub 2-41 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub 2-42 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub 2-43 m/z=467.17 (C ₃₃ H ₂₅ NS=467.63)

III. Example of final compound synthesis

1. P-3 Synthesis example

After dissolving Sub 1-3 (24 g, 62.6 mmol) in toluene (643 ml) in a round-bottom flask, Sub 2-2 (16.1 g, 65.8 mmol), Pd ₂ (dba) ₃ (1.7 g, 1.8 mmol), P(t-Bu) ₃ (0.7 g, 3.7 mmol) and NaOt-Bu (18 g, 188 mmol) were added and stirred at 100°C. Upon completion of the reaction, _{after extraction with CH 2} Cl ₂ and water, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting compound was recrystallized by silica gel column to obtain 31.53 g of product P-3 (yield: 85%).

2. P-15 Synthesis example

Sub 1-7 (20 g, 43.5 mmol) to Sub 2-10 (11.8 g, 45.7 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.3 mmol), P(t-Bu) ₃ (0.5 g, 2.6 mmol), NaOt-Bu (12.5 g, 130.7 mmol) and toluene (447 ml) were added, and 24.6 g (yield: 83%) of product P-15 was obtained by using the above P-3 synthesis method.

3. P-25 Synthesis example

Sub 1-25 (19 g, 34.2 mmol) to Sub 2-22 (17 g, 32.9 mmol), Pd ₂ (dba) ₃ (0.9 g, 1.0 mmol), P(t-Bu) ₃ (0.4 g, 2.0 mmol), NaOt-Bu (9.8 g, 102.6 mmol) and toluene (351 ml) were added, and 22 g (yield: 65%) of product P-25 was obtained by using the above P-3 synthesis method.

4. P-29 Synthesis example

Sub 1-29 (16 g, 22.3 mmol) to Sub 2-24 (9.9 g, 23.4 mmol), Pd ₂ (dba) ₃ (0.6 g, 0.6 mmol) P(t-Bu)3 (0.2 g, 1.3 mmol) ), NaOt-Bu (6.4 g, 67 mmol) and toluene (229 ml) were added, and 15.5 g (yield: 63%) of product P-29 was obtained by using the above P-3 synthesis method.

5. P-37 Synthesis example

Sub 1-37 (30 g, 75.2 mmol) to Sub 2-28 (20.4 g, 78.9 mmol), Pd ₂ (dba) ₃ (2.1 g, 2.3 mmol), P(t-Bu) ₃ (0.9 g, 4.5 mmol), NaOt-Bu (21.7 g, 225.6 mmol) and toluene (771 ml) were added, and 41.2 g (yield: 88%) of the product P-37 was obtained by using the above P-3 synthesis method.

6. P-39 Synthesis example

Sub 1-39 (22 g, 55.1 mmol) to Sub 2-29 (17.9 g, 57.9 mmol), Pd ₂ (dba) ₃ (1.5 g, 1.6 mmol), P(t-Bu) ₃ (0.7 g, 3.3 mmol), NaOt-Bu (15.9 g, 165.4 mmol) and toluene (565 ml) were added, and 30 g (yield: 81%) of the product P-39 was obtained by using the above P-3 synthesis method.

7. P-45 Synthesis example

Sub 1-45 (25 g, 62.7 mmol) to Sub 2-33 (18.1 g, 65.8 mmol), Pd ₂ (dba) ₃ (1.7 g, 1.9 mmol), P(t-Bu) ₃ (0.7 g, 3.7 mmol), NaOt-Bu (18.1 g, 188 mmol) and toluene (642ml) were added, and 33.6 g (yield: 84%) of the product P-45 was obtained by using the above P-3 synthesis method.

8. P-52 Synthesis example

Sub 1-51 (10 g, 17.7 mmol) to Sub 2-4 (4 g, 18.5 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P(t-Bu) ₃ (0.2 g, 1.0 mmol), NaOt-Bu (5.1 g, 53 mmol) and toluene (181 ml) were added, and 9.6 g (yield: 73%) of product P-52 was obtained by using the above P-3 synthesis method.

9. P-54 Synthesis example

Sub 1-55 (11 g, 12.2 mmol) to Sub 2-1 (2.1 g, 12.8 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), P(t-Bu) ₃ (0.2 g, 0.7 mmol), NaOt-Bu (3.5 g, 36.6 mmol) and toluene (125 ml) were added, and 8.2 g (yield: 65%) of product P-54 was obtained by using the above P-3 synthesis method.

On the other hand, FD-MS values of the compounds P-1 to P-69 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=615.23 (C ₄₄ H ₂₉ N ₃ O=615.74) P-2 m/z=515.2 (C ₃₆ H ₂₅ N ₃ O=515.62) P-3 m/z=591.23 (C ₄₂ H ₂₉ N ₃ O=591.71) P-4 m/z=689.25 (C ₅₀ H ₃₁ N ₃ O=689.82) P-5 m/z=641.25 (C ₄₆ H ₃₁ N ₃ O=641.77) P-6 m/z=665.25 (C ₄₈ H ₃₁ N ₃ O=665.8) P-7 m/z=591.23 (C ₄₂ H ₂₉ N ₃ O=591.71) P-8 m/z=696.29 (C ₅₀ H ₂₈ D ₅ N ₃ O=696.86) P-9 m/z=605.25 (C ₄₃ H ₃₁ N ₃ O=605.74) P-10 m/z=681.28 (C ₄₉ H ₃₅ N ₃ O=681.84) P-11 m/z=921.34 (C ₆₇ H ₄₃ N ₃ O ₂ =922.1) P-12 m/z=697.22 (C ₄₈ H ₃₁ N ₃ OS=697.86) P-13 m/z=693.28 (C ₅₀ H ₃₅ N ₃ O=693.85) P-14 m/z=778.27 (C ₅₆ H ₃₄ N ₄ O=778.92) P-15 m/z=681.24 (C ₄₈ H ₃₁ N ₃ O ₂ =681.8) P-16 m/z=822.3 (C ₅₈ H ₃₈ N ₄ O ₂ =822.97) P-17 m/z=835.36 (C ₆₁ H ₄₅ N ₃ O=836.05) P-18 m/z=807.3 (C ₅₇ H ₃₇ N ₅ O=807.96) P-19 m/z=621.21 (C ₄₂ H ₂₇ N ₃ O ₃ =621.7) P-20 m/z=839.26 (C ₅₈ H ₃₇ N ₃ O ₂ S=840.01) P-21 m/z=723.29 (C ₅₁ H ₃₇ N ₃ O ₂ =723.88) P-22 m/z=671.27 (C ₄₆ H ₃₃ N ₅ O=671.8) P-23 m/z=801.37 (C ₅₃ H ₄₇ N ₅ O ₃ =801.99) P-24 m/z=750.26 (C ₄₇ H ₃₅ FN ₆ OS=750.9) P-25 m/z=991.43 (C ₇₂ H ₄₅ D ₅ N ₄ O=992.25) P-26 m/z=693.28 (C ₅₀ H ₃₅ N ₃ O=693.85) P-27 m/z=814.37 (C ₅₈ H ₄₆ N ₄ O=815.03) P-28 m/z=897.34 (C ₆₂ H ₄₇ N ₃ O ₂ S=898.14) P-29 m/z=1102.39 (C ₇₉ H ₅₀ N ₄ O ₃ =1103.29) P-30 m/z=758.3 (C ₅₄ H ₃₈ N ₄ O=758.93) P-31 m/z=952.32 (C ₆₇ H ₄₄ N ₄ OS=953.18) P-32 m/z=773.25 (C ₅₄ H ₃₅ N ₃ OS=773.95) P-33 m/z=773.25 (C ₅₄ H ₃₅ N ₃ OS=773.95) P-34 m/z=739.21 (C ₅₀ H ₃₀ FN ₃ OS=739.87) P-35 m/z=859.36 (C ₆₃ H ₄₅ N ₃ O=860.07) P-36 m/z=655.23 (C ₄₆ H ₂₉ N ₃ O ₂ =655.76) P-37 m/z=621.19 (C ₄₂ H ₂₇ N ₃ OS=621.76) P-38 m/z=621.19 (C ₄₂ H ₂₇ N ₃ OS=621.76) P-39 m/z=671.2 (C ₄₆ H ₂₉ N ₃ OS=671.82) P-40 m/z=787.27 (C ₅₅ H ₃₇ N ₃ OS=787.98) P-41 m/z=905.29 (C ₆₃ H ₄₃ N ₃ S ₂ =906.18) P-42 m/z=809.29 (C ₅₈ H ₃₉ N ₃ S=810.03) P-43 m/z=697.22 (C ₄₈ H ₃₁ N ₃ OS=697.86) P-44 m/z=854.35 (C ₆₁ H ₃₈ D ₅ N ₃ S=855.13) P-45 m/z=637.16 (C ₄₂ H ₂₇ N ₃ S ₂ =637.82) P-46 m/z=980.35 (C ₆₉ H ₄₈ N ₄ OS=981.23) P-47 m/z=683.24 (C ₄₈ H ₃₃ N ₃ S=683.87) P-48 m/z=727.18 (C ₄₈ H ₂₉ N ₃ OS ₂ =727.9) P-49 m/z=589.26 (C ₄₀ H ₃₅ N ₃ S=589.8) P-50 m/z=709.26 (C ₅₀ H ₃₅ N ₃ S=709.91) P-51 m/z=721.22 (C ₅₀ H ₃₁ N ₃ OS=721.88) P-52 m/z=747.23 (C ₅₂ H ₃₃ N ₃ OS=747.92) P-53 m/z=723.27 (C ₅₁ H ₃₇ N ₃ S=723.94) P-54 m/z=1032.4 (C ₇₂ H ₅₂ N ₆ S=1033.31) P-55 m/z=747.23 (C ₅₂ H ₃₃ N ₃ OS=747.92) P-56 m/z=688.18 (C ₄₅ H ₂₈ N ₄ S ₂ =688.87) P-57 m/z=911.34 (C ₆₃ H ₄₁ N ₇ O=912.07) P-58 m/z=697.22 (C ₄₈ H ₃₁ N ₃ OS=697.86) P-59 m/z=831.32 (C ₆₁ H ₄₁ N ₃ O=832.02) P-60 m/z=1014.38 (C ₇₃ H ₅₀ N ₄ S=1015.29) P-61 m/z=655.23 (C ₄₆ H ₂₉ N ₃ O ₂ =655.76) P-62 m/z=697.22 (C ₄₈ H ₃₁ N ₃ OS=697.86) P-63 m/z=733.26 (C ₅₂ H ₃₅ N ₃ S=733.93) P-64 m/z=964.32 (C ₆₈ H ₄₄ N ₄ OS=965.19) P-65 m/z=1075.4 (C ₇₆ H ₄₉ N ₇ O=1076.28) P-66 m/z=681.24 (C ₄₈ H ₃₁ N ₃ O ₂ =681.8) P-67 m/z=647.24 (C ₄₅ H ₃₃ N ₃ S=647.84) P-68 m/z=813.28 (C ₅₇ H ₃₉ N ₃ OS=814.02) P-69 m/z=607.21 (C ₄₂ H ₂₉ N ₃ S=607.78)

Manufacturing evaluation of organic electric devices

( Example 1) Green organic light emitting device ( major transport floor )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a hole transport layer material.

First, on an ITO layer (anode) formed on a glass substrate, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1 ,4-diamine (hereinafter, abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.

On the hole injection layer, the compound P-3 of the present invention as a hole transport compound was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

4,4'-N,N'-dicarbazole-biphenyl (hereinafter, abbreviated as CBP) was used as a host on the hole transport layer, and as a dopant, tris(2-phenylpyridine)-iridium (hereinafter, Ir(ppy) ₃ ) was used to deposit a light emitting layer with a thickness of 30 nm by doping in a weight ratio of 95:5.

(1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 5 nm on the light emitting layer to form a hole blocking layer.

Tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

( Example 2) to ( Example 20)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-3 of the present invention as the hole transport layer material.

( comparative example One)

N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was used as the electron transport layer material. Except for the point, an organic electroluminescent device was manufactured in the same manner as in Example 1.

( comparative example 2) and ( comparative example 3)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 2 were used as the material for the hole transport layer.

<Comparative compound 1> <Comparative compound 2>

A forward bias DC voltage was applied to the organic electroluminescent devices manufactured according to Examples 1 to 20 and Comparative Examples 1 to 3, and electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, 5000 cd/ The T95 lifetime was measured using a lifetime measuring device manufactured by McScience at ^{m 2 standard luminance.} Table 4 below shows the manufactured devices and evaluation results.

compound drive voltage
(V) Current density (mA/cm ² ) Luminance (cd/m ² ) Efficiency (cd/A) T(95) CIE X Y Comparative Example (1) NPB 6.0 21.6 5000 23.1 57.9 0.31 0.60 Comparative Example (2) Comparative compound 1 5.7 17.4 5000 28.7 82.6 0.32 0.61 Comparative Example (3) Comparative compound 2 5.8 18.5 5000 27.1 79.4 0.32 0.60 Example (1) P-3 5.3 14.1 5000 35.4 100.7 0.32 0.61 Example (2) P-5 5.4 15.1 5000 33.2 96.8 0.32 0.61 Example (3) P-8 5.3 14.3 5000 35.0 100.3 0.33 0.61 Example (4) P-14 5.3 14.0 5000 35.8 101.5 0.33 0.61 Example (5) P-19 5.2 13.7 5000 36.4 102.9 0.33 0.60 Example (6) P-30 5.5 15.3 5000 32.7 96.1 0.33 0.61 Example (7) P-33 5.1 12.7 5000 39.3 108.6 0.33 0.60 Example (8) P-37 5.1 13.0 5000 38.5 106.8 0.33 0.61 Example (9) P-39 5.2 13.1 5000 38.3 106.2 0.33 0.62 Example (10) P-45 5.2 13.2 5000 37.9 105.7 0.33 0.62 Example (11) P-48 5.1 12.6 5000 39.6 109.0 0.33 0.63 Example (12) P-52 5.2 13.8 5000 36.2 102.1 0.33 0.63 Example (13) P-54 5.5 15.5 5000 32.2 95.4 0.33 0.63 Example (14) P-58 5.1 12.9 5000 38.9 108.2 0.33 0.62 Example (15) P-61 5.1 12.9 5000 38.7 107.5 0.33 0.63 Example (16) P-62 5.2 13.6 5000 36.8 103.4 0.33 0.62 Example (17) P-66 5.2 13.5 5000 37.1 104.0 0.33 0.63 Example (18) P-67 5.4 14.7 5000 34.0 98.7 0.33 0.63 Example (19) P-68 5.4 14.5 5000 34.6 99.4 0.33 0.63 Example (20) P-69 5.4 14.9 5000 33.6 97.6 0.33 0.63

From Table 4, it can be seen that the device using the compound represented by Formula 1 of the present invention as a hole transport layer material significantly improved the electrical properties of the device compared to the case where the comparative compounds were used.

That is, the device of Comparative Example 2 and Comparative Example 3 manufactured using a pentacyclic compound containing hetero elements such as N and S rather than the device of Comparative Example 1 manufactured using NPB mainly used as a hole transport layer material. Electrical properties (driving voltage, efficiency, and lifespan) were improved, and compared to Comparative Examples 2 and 3, when the compound according to Formula 1 of the present invention was used as a hole transport layer material, the luminous efficiency and lifespan of the organic electroluminescent device were increased. In addition, as the driving voltage was slightly lowered, the electrical characteristics of the device were improved.

More specifically, Comparative Compound 1 and Comparative Compound 2 are similar to the compound of the present invention in that an amine group is substituted on a polycyclic ring containing a hetero element, but the compound of the present invention is one of a pentacyclic condensed ring containing NO or SN. There is a difference in that the amine group is substituted on the 4-ring ring to which benzene is fused.

Accordingly, the compound's hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, electron blocking characteristics, etc. of the compound according to the fusion structure Physical properties may vary, and the device results suggest that the compound of the present invention is more suitable for the hole transport layer.

( Example 21) Red organic electroluminescent device ( light emitting layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a red host material of the emission layer.

First, on an ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene-1,4-diamine (hereinafter, 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.

On the hole injection layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) as a hole transport compound was vacuum deposited to a thickness of 60 nm to form a hole transport layer. formed.

On the hole transport layer, the compound P-3 of the present invention was vacuum-deposited to a thickness of 20 nm to form a light emitting auxiliary layer.

9,10-di(naphthalen-2-yl)anthracene was used as a host on the light emitting auxiliary layer, and BD-052X (manufactured by Idemitsu kosan) was used as a dopant and doped in a 96:4 weight ratio to form a thickness of 30 nm. A light emitting layer was deposited.

(1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed.

Tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

( Example 22) to ( Example 40)

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that the compound of the present invention described in Table 5 was used instead of the compound P-3 of the present invention as the material of the light emitting auxiliary layer.

( comparative example 4)

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that the light-emitting auxiliary layer was not formed.

( comparative example 5) and ( comparative example 6)

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that Comparative Compound 1 and Comparative Compound 2 were used as the light emitting auxiliary layer material, respectively.

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 21 to 40 and Comparative Examples 4 to 6, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, and 2500 cd / The T95 lifetime was measured using a lifetime measuring device manufactured by McScience at ^{m 2 standard luminance.} Table 5 below shows the manufactured devices and evaluation results.

compound drive voltage
(V) Current density (mA/cm ² ) Luminance (cd/m ² ) Efficiency (cd/A) T(95) CIE X Y Comparative Example (4) - 6.6 31.3 2500 8.0 64.7 0.66 0.32 Comparative Example (5) Comparative compound 1 6.2 15.8 2500 15.8 103.4 0.66 0.32 Comparative Example (6) Comparative compound 2 6.4 18.2 2500 13.7 100.2 0.66 0.33 Example (21) P-3 5.2 10.5 2500 23.8 134.1 0.66 0.33 Example (22) P-5 5.1 10.0 2500 24.9 142.1 0.66 0.33 Example (23) P-8 5.2 10.6 2500 23.5 133.6 0.66 0.32 Example (24) P-14 5.2 10.4 2500 24.0 136.4 0.66 0.32 Example (25) P-19 5.2 10.1 2500 24.7 140.7 0.66 0.33 Example (26) P-30 5.3 10.9 2500 22.9 128.6 0.66 0.32 Example (27) P-33 5.0 9.2 2500 27.2 155.7 0.66 0.32 Example (28) P-37 5.0 9.5 2500 26.3 151.2 0.66 0.32 Example (29) P-39 4.9 8.7 2500 28.7 167.2 0.66 0.33 Example (30) P-45 4.9 8.8 2500 28.4 166.5 0.66 0.32 Example (31) P-48 5.0 9.1 2500 27.5 157.3 0.66 0.33 Example (32) P-52 5.2 10.3 2500 24.3 138.2 0.66 0.33 Example (33) P-54 5.3 10.8 2500 23.2 131.9 0.66 0.32 Example (34) P-58 5.0 9.3 2500 26.9 155.0 0.66 0.32 Example (35) P-61 5.0 9.4 2500 26.6 153.4 0.66 0.32 Example (36) P-62 4.9 8.9 2500 28.0 164.8 0.66 0.32 Example (37) P-66 4.9 9.0 2500 27.8 160.9 0.66 0.33 Example (38) P-67 5.1 9.7 2500 25.7 146.7 0.66 0.33 Example (39) P-68 5.1 9.6 2500 26.0 148.6 0.66 0.33 Example (40) P-69 5.1 9.9 2500 25.2 144.3 0.66 0.32

It can be seen that the device characteristics of a green light-emitting device using the compound of the present invention as a hole transport layer material and a red light-emitting device using the light-emitting auxiliary layer material vary depending on the amine group substitution position of the compound of the present invention. That is, when the compound of the present invention is used as a hole transport layer, the compound when an amine group is substituted in the R group in Formula 1 of the present invention shows better device characteristics, whereas when used as a light emitting auxiliary layer, the compound of the present invention It can be seen that the compound in the case where an amine group is substituted for Ar, which is an N substituent in Formula 1, exhibits better device characteristics.

These results show that even if the core is the same compound, hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO level, T1 level), hole injection & mobility characteristics, electron blocking ( This suggests that the physical properties of the compound, such as electron blocking properties, may be changed, and this may lead to completely different device results.

In addition, in the evaluation result of the above-described device fabrication, the device characteristics in which the compound of the present invention is applied to the light emitting auxiliary layer or the hole transport layer has been described, but the compound of the present invention can be applied to one or more of the light emitting layer, the hole transport layer and the light emission auxiliary layer. have.

The above description is merely illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains may include a variety of methods for improving performance including other compounds within a range that does not depart from the essential characteristics of the present invention. transformation will be possible.

Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to limit the present invention, and the scope of the spirit of the present invention is not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: capping layer 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (13)

A compound represented by the following formula (1):
<Formula 1>

In Formula 1,
1) A is a thiophene ring or a furanyl ring,
2) Ar ¹ to Ar ⁸ are each independently a C ₆ to C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or C ₃ ~ C ₆₀ An aliphatic ring and a C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; -L'-N(R _a )(R _b ); or a combination thereof,
3) R _a ~ R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; Or C ₃ ~ C ₆₀ An aliphatic ring and a C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; or a combination thereof,
4) L' and L ¹ to L ⁴ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} or a combination thereof,
5) Ar _a ~ Ar _b are each independently a C ₆ ~ C ₆₀ arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} or a combination thereof,
6) e1 and e2 are each independently 0 or an integer of 1; e3 is an integer from 0 to 4; e4 is an integer from 0 to 2; provided that e1+e2+e3+e4 ≥ 1,
7) R ¹ to R ² are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; amino group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; or adjacent groups may combine to form a ring,
8) a is an integer from 0 to 4; b is an integer from 0 to 2,
9) R ^{1 to 2} , Ar ¹ to Ar ⁸ , R _a to R _b , L′, L ¹ to L ⁴ , Ar _a to Ar _b and the rings formed by bonding adjacent groups to each other are deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; boron group; germanium group; cyano group; amino group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ Aryl group; _{a C 6} -C ₂₀ aryl group substituted with deuterium; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof, and adjacent substituents may form a ring. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 5:
<Formula 2><Formula3>

<Formula 4><Formula5>

In Formulas 2 to 5, R ^{1 to 2} , L ¹ to L ⁴ , Ar ¹ to Ar ⁸ , Ar _a to Ar _b , a to b and e1 to e4 are the same as defined in Formula 1 of claim 1 . . The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 6 to 13:
<Formula 6><Formula7><Formula8>

<Formula 9><Formula10><Formula11>

<Formula 12><Formula13>

In Formulas 6 to 13,
1) X is S or O;
2) L ¹ to L ⁴ , Ar ¹ to Ar ⁸ , Ar _a to Ar _b and e1 to e4 are the same as defined in Formula 1 of claim 1. The compound according to claim 1, wherein Ar ¹ to Ar ⁸ are each independently represented by Formula A-1 or A-2:
<Formula A-1><FormulaA-2>

In Formulas A-1 and A-2,
1) Z is O, S, CR'R" or N-L'-Ar',
2) R _a to R _d , R′ and R” are the same as the definition ^{of R 1 in Formula 1 of claim 1,}
3) n is an integer from 0 to 3; m, o and p are each independently an integer from 0 to 4,
4) L' is the same as the definition ^{of L 1 in Formula 1 of Paragraph 1,}
5) Ar' is the same as the definition ^{of Ar 1 in Formula 1 of Paragraph 1.} The compound according to claim 1, wherein the compound represented by Formula 1 is one of the following P-1 to P-69:

a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device, characterized in that it comprises the compound represented by the formula (1) of claim 1 alone or in combination. a first electrode; a second electrode; an organic material layer formed between the first electrode and the second electrode; And in the organic electric device comprising a capping layer,
The capping layer is formed on one surface of both surfaces of the first electrode and the second electrode that is not in contact with the organic material layer,
The organic material layer or the capping layer is an organic electric device, characterized in that it comprises the compound represented by the formula (1) of claim 1 alone or in combination. 8. The method according to claim 6 or 7,
The organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. 9. The method of claim 8,
The organic material layer comprises at least one of the hole transport layer, the light emitting auxiliary layer and the light emitting layer. 8. The method according to claim 6 or 7,
The organic material layer comprises at least two stacks including a hole transport layer, a light emitting layer and an electron transport layer sequentially formed on the anode. 11. The method of claim 10,
The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 6 or 7; and a controller for driving the display device. 13. The method of claim 12,
The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.

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