KR20210061574A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability and lifespan of a device, an organic electric device using the compound, and an electronic apparatus thereof. By using the compound according to the present invention, it is possible to achieve high luminous efficiency, low driving voltage, and high heat resistance of the device, and it is possible to greatly improve and color purity and lifespan of the device.

Description

Compound for organic electric device, organic electric device using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN 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 emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic electric device using the organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electronic device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

Materials used as an organic material layer in an organic electronic device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become large-area, such efficiency and lifetime problems must be resolved. Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan.

However, the efficiency cannot be maximized simply by improving the organic material layer. This is because the long life and high efficiency can be achieved at the same time 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.

In particular, in a phosphorescent organic electronic device using a phosphorescent dopant material, the LUMO and HOMO levels of the host material are factors that have a very large influence on the effectiveness and lifetime of the organic electronic device, which enables efficient control of electron and hole injection in the emission layer. This is because it is possible to prevent reduction in efficiency and lifespan due to light emission at the interface of the hole transport layer, such as controlling charge balance in the light emitting layer, quenching dopants, and depending on whether or not.

In the case of host materials for fluorescence and phosphorescence emission, we are researching to increase the efficiency and lifespan of organic electronic devices using TADF (Thermal Activated Delayed Fluorescent) and Exciplex. There is a lot of research in progress.

There are several methods for determining the energy transfer in the emission layer for thermal activated delayed fluorescent (TADF) and exciplex, but it can be easily confirmed by measuring the PL lifetime (TRTP).

The TRTP (Time resolved transient PL) measurement method is a method of observing the decay time of the spectrum over time after irradiating a pulsed light source onto the host thin film. This is a measurement method. The TRTP measurement is a measurement method capable of distinguishing fluorescence and phosphorescence, and an energy transfer method, an exciplex energy transfer method, and a TADF energy transfer method in a mixed host material.

As such, there are various factors affecting the efficiency and lifespan depending on the way energy is transferred from the host material to the dopant material, and the energy transfer method is different depending on the material, so the development of a stable and efficient host material for organic electric devices. This is a state that hasn't been done enough. Therefore, development of new materials is continuously required, and in particular, development of a host material for a light emitting layer is urgently required.

In addition, in order to solve the problem of light emission in the hole transport layer in recent organic electroluminescent devices, an emission auxiliary layer must exist between the hole transport layer and the emission layer, and different emission auxiliary layers according to each emission layer (R, G, B). This is the time when layer development is necessary.

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

However, in the case of a material used for the hole transport layer, since it must have a low HOMO value, most have a low T1 value, and this causes excitons generated in the emission layer to pass to the hole transport layer, resulting in charge unbalance in the emission layer. This results 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 deteriorated, and the lifespan is shortened. Therefore, development of a light emission auxiliary layer having a high T1 value and having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer is urgently required.

On the other hand, while delaying penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of organic electronic devices, stable characteristics against Joule heating generated when the device is driven, that is, high glass transition. There is a need to develop a material for a hole injection layer having a temperature. The low glass transition temperature of the hole transport layer material has a property of lowering the uniformity of the surface of the thin film when the device is driven, and it is reported that it has a great influence on the life of the device. In addition, OLED devices are mainly formed by a vapor deposition method, and it is necessary to develop a material that can withstand a long time during deposition, that is, a material having strong heat resistance.

In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials, are stable and efficient. Supported by the material must precede, but the development of a stable and efficient organic material layer material for an organic electric device has not been made sufficiently. Therefore, the development of new materials continues to be required.

KR 1020130076842 A

In order to solve the problems of the background art described above, the present invention has revealed a compound having a novel structure, and when the compound is applied to an organic electronic device, the luminous efficiency, stability and lifespan of the device can be greatly improved. Revealed.

Accordingly, an object of the present invention is to provide a novel compound, an organic electric device using the same, and an electronic device thereof.

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In another aspect, the present invention provides an organic electric device including the compound represented by Formula 1 and an electronic device thereof.

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

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
4 shows a chemical formula according to an aspect of the present invention.

Hereinafter, it will be described in detail with reference to an embodiment of the present invention. In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof will be omitted.

In addition, in describing the constituent elements of the present invention, terms such as first, second, A, B, (a) and (b) may be used. These terms are for distinguishing the constituent element from other constituent elements, and the nature, order, or order of the constituent element is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected or connected to that other component, but another component between each component It will be understood that elements may be “connected”, “coupled” or “connected”.

As used in the specification and appended claims, unless stated otherwise, the meaning of the following terms is as follows:

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

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms unless otherwise specified, and is a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo It means a radical of a saturated aliphatic functional group including an alkyl group and a cycloalkyl-substituted alkyl group.

The terms "alkenyl group", "alkenyl group" or "alkynyl group" as used in the present invention each have a double bond or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include a straight or branched chain group, , It is not limited to this.

The term "cycloalkyl" as used in the present invention means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

The terms "alkoxyl group", "alkoxy group", or "alkyloxy group" as used herein refers to an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.

The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms, and is not limited thereto.

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatics, and includes an aromatic ring formed by neighboring substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has the number of carbon atoms described herein.

In addition, when the prefixes are named consecutively, it means that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group. And the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heterocyclic group" as used in the present invention includes one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, unless otherwise specified, heteroaliphatic ring and hetero It contains an aromatic ring. It may be formed by combining adjacent functional groups.

As used herein, the term "heteroatom" refers to N, O, S, P or Si unless otherwise specified.

In addition, the "heterocyclic group" may also include a ring including _{SO 2 instead of carbon forming the ring.} For example, "heterocyclic group" includes the following compounds.

The terms "fluorenyl group" or "fluorenylene group" as used in the present invention mean a monovalent or divalent functional group in which R, R'and R" are all hydrogen in each of the following structures, unless otherwise specified, " Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R'are bonded to each other and the carbon to which they are bonded It includes the case of forming a compound with a spy together.

The term "spyro compound" used in the present invention has a'spiro union', and the spiro linkage refers to a connection made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spyro atoms', and depending on the number of spyro atoms in one compound, these are respectively referred to as'monospiro-','dispiro-', and'trispyro-'. 'It is called a compound.

Unless otherwise specified, the term "aliphatic" as used herein refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" used in the present invention refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms, or a combination thereof, Contains saturated or unsaturated rings.

Other hetero compounds or hetero radicals other than the aforementioned hetero compounds include one or more heteroatoms, but are not limited thereto.

In addition, unless expressly stated, the term "substituted or unsubstituted" used in the present invention means "substituted" deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkylamine group, C ₁ to C ₂₀ alkylthiophene group, C ₆ to C ₂₀ arylthiophene group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ ~ C _{20 heterocyclic group, and is not limited to these substituents.}

In addition, unless explicitly stated, the chemical formula used in the present invention is applied in the same manner as the definition of the substituent by the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming a benzene ring, and a is an integer of 2 or 3. Each is bonded as follows, wherein R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is indicated. Is omitted.

Hereinafter, a compound according to an aspect of the present invention and an organic electric device including the same will be described.

The present invention provides a compound represented by the following formula (1).

[Formula 1] [Formula 2]

{In Formulas 1 and 2,

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; Alkynyl group of C ₂ ~ C _60; An alkoxyl group of C ₁ to C _60; C ₆ ~ C ₆₀ aryloxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; And -L'-N (R ^c ) (R ^d ); is selected from the group consisting of,

Or wherein a, b, c, d and e is 2, the same or different, a plurality each or more, a plurality of R ₁ each other or a plurality of R ₂ to each other or a plurality of R ₃ to each other or a plurality of R ₄ or a plurality of each other R ₅ can be bonded to each other to form a ring,

Where L'is a single bond; C ₆ ~ C ₆₀ arylene group; And C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of, wherein R ^c and R ^d are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,

a, c and d are each independently an integer of 0 to 3, b and e are each independently an integer of 0 to 4,

X is CR'R", O or S,

Wherein the R'and R" are independently of each other C ₁ ~ C ₆₀ alkyl group; C ₆ ~ C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C including at least one heteroatom of P _{A heterocyclic group of 60} ; And -L'-N(R ^c )(R ^d ); is selected from the group consisting of, R'and R" may be bonded to each other to form a ring with a spy

Y is NAr ³ , O, S or CR ^a R ^b ,

Here, Ar ³ is a C ₆ ~C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Or a fluorenyl group; and,

R ^a and R ^b are each independently hydrogen; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; Alkynyl group of C ₂ ~ C _60; An alkoxyl group of C ₁ to C _60; C ₆ ~ C ₆₀ aryloxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ fused ring group of the aromatic ring, and selected from the group consisting of, R ^a and R ^b may form a ring in spy bonded to each other,

At least one pair of two adjacent * in Formula 1 is combined with * in Formula 2 to form a condensed ring,

Here, the aryl group, heterocyclic group, fluorenyl group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C _20; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; Alkynyl group of C ₂ -C _20; C ₆ -C ₂₀ aryl group; _{A C 6} -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be bonded to each other to form a ring, wherein'ring' refers to C ₃ -C ₆₀ It refers to a fused ring consisting of an aliphatic ring of or a C ₆ -C ₆₀ aromatic ring or a C ₂ -C ₆₀ hetero ring or a combination thereof, and includes a saturated or unsaturated ring.}

In addition, the present invention includes a compound represented by any one of Formula 1 to Formula 1-4 below.

[Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4]

{In Formulas 1-1 to 1-4, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , X, Y, a, b, c, d and e are defined in Formulas 1 and 2 It is the same as before.}

In addition, the present invention includes the compound represented by any one of Formula 1 to Formula 1-5 to Formula 1-16 below.

[Formula 1-5] [Formula 1-6] [Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10] [Formula 1-11] [Formula 1-12]

[Formula 1-13] [Formula 1-14] [Formula 1-15] [Formula 1-16]

{In Formula 1-5 to Formula 1-16, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , Y, R', R", a, b, c, d and e are represented by Formula 1 and It is the same as defined in Formula 2.}

In addition, the present invention includes _{a compound wherein any one of R 1} , R ₂ , R ₃ , R ₄ and R ₅ is represented by the following Formula 3, Formula 4 or Formula 5.

[Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5]

{In Formulas 3 to 5,

Ar ¹ and Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; C ₆ ~ C ₆₀ aryloxy group; And -N (R ^c ) (R ^d ); is selected from the group consisting of,

L ¹ , L ² , L ³ and L ₁ are each independently a single bond; C ₆ -C ₆₀ arylene group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,

Z ¹ to Z ⁸ are each independently N or CR ₆ ,

R ₆ is hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; Alkynyl group of C ₂ ~ C _60; An alkoxyl group of C ₁ to C _60; And C ₆ ~ C ₆₀ aryloxy group; is selected from the group consisting of,

C ring is a C ₆ ~ C ₆₀ aryl group; Or a heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; and,

* Indicates the position to be combined.}

In addition, the present invention includes a compound represented by any one of the following Chemical Formula 5 to Chemical Formula 5-6.

[Chemical Formula 5-1] [Chemical Formula 5-2] [Chemical Formula 5-3]

[Chemical Formula 5-4] [Chemical Formula 5-5] [Chemical Formula 5-6]

{In Formula 5-1 to Formula 5-6,

R ₇ is a C ₆ ~ C ₆₀ aryl group; _{Or a C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; and,

A and B are each independently a direct bond, O or S,

f is 0 to 4, g is 0 to 6, h is an integer of 0 to 8,

i and j are each independently 0 or 1,

L ₁ is a single bond; C ₆ -C ₆₀ arylene group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,

Z ⁶ , Z ⁷ and Z ⁸ are the same as defined in Chemical Formula 5,

* Indicates the position to be combined.}

Specifically, the compound represented by Formula 1 may be a compound represented by any one of the following compounds P-1 to P-72, but is not limited thereto.

Referring to FIG. 1, the organic electric device 100 according to the present invention has a formula 1 between the first electrode 110, the second electrode 170, and the first electrode 110 and the second electrode 170. A single compound represented by or an organic material layer including two or more compounds is provided. At this time, the first electrode 110 may be an anode or an anode, and the second electrode 170 may be a cathode or a 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 sequentially include a hole injection layer 120, a hole transport layer 130, an emission layer 140, an electron transport layer 150, and an electron injection layer 160 on the first electrode 110. In this case, other layers other than the emission layer 140 may not be formed. A hole blocking layer, an electron blocking layer, a light emission auxiliary layer 220, a buffer layer 210, etc. may be further included, and the electron transport layer 150 may serve as a hole blocking layer. (See Fig. 2)

In addition, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improvement layer 180. The light efficiency improvement layer may be formed on a surface not in contact with the organic material layer among both surfaces of the first electrode or on a surface not in contact with the organic material layer among both surfaces of the second electrode. The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 120, a hole transport layer 130, a light emission auxiliary layer 220, an electron transport auxiliary layer, an electron transport layer 150, an electron injection layer ( 160), a host or a dopant of the light emitting layer 140, or a material for a light efficiency improvement layer. Preferably, for example, the compound according to Formula 1 of the present invention may be used as a host of a light emitting layer or/and a material of a light emitting auxiliary layer.

The organic material layer may include two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks (see FIG. 3 ). )

On the other hand, even with the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is bonded to any position, so the selection of the core and the combination of sub-substituents bonded thereto are also very It is important, and in particular, long life and high efficiency can be achieved at the same time 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.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150 and After forming an organic material layer including the electron injection layer 160, it may be manufactured by depositing a material that can be used as a cathode thereon.

In addition, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic material layer includes the compound as an electron transport material. It provides an organic electric device characterized in that.

As another specific example, the present invention provides an organic electric device, characterized in that the organic material layer is used by mixing the same or different compounds of the compound represented by Formula 1 above.

In addition, the present invention provides a light-emitting auxiliary layer composition comprising the compound represented by Formula 1, and provides an organic electric device including the light-emitting auxiliary layer.

In addition, the present invention provides a light emitting layer composition comprising the compound represented by Formula 1, and provides an organic electric device comprising the light emitting layer.

In addition, the present invention is a display device including the organic electric device; And a control unit for driving the display device.

In another aspect, the present invention provides an electronic device, characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a single color or white lighting device. At this time, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

Hereinafter, examples for synthesizing the compound represented by Chemical Formula 1 of the present invention and examples for preparing the organic electric device of the present invention will be described in detail, but are not limited to the following examples of the present invention.

[ Synthesis example ]

The compound (final product) represented by Formula 1 according to the present invention may be synthesized by reacting Sub1 to Sub3 with Sub4 or Sub5 as shown in Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

In Scheme 1, 1) Z ₁ to Z ₄ of Sub1 to Sub3 are all hydrogen or at least one is Br, Cl or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

I. Sub1 To Sub3 synthesis

Sub1 to Sub3 of Reaction Scheme 1 may be synthesized by the reaction route of Scheme 2 to Scheme 5 below, but is not limited thereto.

<Reaction Scheme 2>

<Reaction Scheme 3>

<Reaction Scheme 4>

<Reaction Scheme 5>

In Reaction Schemes 2 to 5, as an example, "Sub2(a), Sub3(a)" means "Sub2(a) or Sub3(a)", and the coupling reaction is performed only in the case of Sub2,

1) _{At least one of Z 1} to Z ₅ of Sub2 is Cl, Z ₁ to Z ₅ of Sub3 is H, and 2) _{At least one of Z 1} to Z ₅ of Sub1 is 4,4,5,5-tetramethyl- 1,3,2-dioxaborolane.

Specific synthesis examples of the compounds belonging to Sub1 to Sub3 of Scheme 1 are as follows, but are not limited thereto.

One. Sub1 -One Synthesis example

(One) Sub1 -1b synthesis

Sub1-1a (40 g, 0.20 mol), 7-bromo-6-chloro-12-phenyl-12H-benzofuro[2,3-a]carbazole (88.6 g, 0.20 mol), Pd ₂ (dba) ₃ (5.5 g, 0.006 mol), 50% P( t- Bu) ₃ (4.8 g, 0.012 mol), and NaO t- Bu (57.2 g, 0.60 mol) were added to toluene (398 ml) and stirred at 90°C. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Then, the concentrated reaction product was separated using a silicagel column or a recrystallization method to obtain 95 g (84.4%) of the product Sub1-1b.

(2) Sub1 -1c synthesis

Sub1-1b (90 g, 0.16 mol) in Pd(OAc) ₂ (1.07 g, 0.005 mol), P(t-Bu) ₃ (3.9 g, 0.009 mol), K ₂ CO ₃ (65.8 g, 0.48 mol) , DMA (320 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 39.5 g (46.9%) of the product Sub1-1c was obtained using the above-described separation method of Sub1-1b.

(3) Sub1 -1 synthesis

4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (21.5 in Sub1-1c (48 g, 0.08 mol) g, 0.08 mol), Pd ₂ (dba) ₃ (2.3 g, 0.0025 mol), AcOK (24.9 g, 0.25 mol), and DMF (170 ml) were added and stirred at 170° C. for 24 hours. When the reaction was completed, 43 g (81.6%) of the product Sub1-1 was obtained using the above-described separation method of Sub1-1b.

2. Sub1 -6 Synthesis example

(One) Sub1 -6b synthesis

Sub1-6a (34 g, 0.20 mol), 1-bromo-3,12-dichlorospiro[benzo[b]fluoreno[3,2-d]thiophene-7,9'-fluorene] (116 g, 0.20 mol), Add Pd ₂ (dba) ₃ (5.6 g, 0.006 mol), 50% P( t -Bu) ₃ (4.9 g, 0.012 mol), NaO t -Bu (58.8 g, 0.61 mol) to toluene (410 ml) And stirred at 90°C. When the reaction was completed, 117 g (87.6%) of the product Sub1-6b was obtained using the above-described separation method of Sub1-1b.

(2) Sub1 -6c synthesis

_{Pd(OAc) 2} (0.51 g, 0.002 mol), P(t-Bu) ₃ (1.9 g, 0.005 mol), K ₂ CO ₃ (31.6 g, 0.23 mol) in Sub1-6b (50 g, 0.08 mol) , DMA (150 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 40 g (84.6%) of the product Sub1-6c was obtained using the above-described separation method of Sub1-1b.

(3) Sub1 -6 synthesis

Sub1-6c (30 g, 0.05 mol) in 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (12.3 g, 0.05 mol), Pd ₂ (dba) ₃ (1.3 g, 0.0015 mol), AcOK (14.2 g, 0.15 mol), and DMF (100 ml) were added and stirred at 170° C. for 24 hours. When the reaction was completed, 31 g (90%) of the product Sub1-6 was obtained using the above-described separation method of Sub1-1b.

3. Sub1 -8 Synthesis example

(One) Sub1 -8b synthesis

Sub1-8a (50 g, 0.10 mol), 13-chloro-9H-carbazole (21 g, 0.20 mol), Pd ₂ (dba) ₃ (2.9 g, 0.003 mol), 50% P( t- Bu) ₃ ( 2.5 g, 0.006 mol), NaO t -Bu (30 g, 0.31 mol) was added to toluene (210 ml) and stirred at 90°C. When the reaction was completed, 50 g (79.8%) of the product Sub1-8b was obtained using the above-described separation method of Sub1-1b.

(2) Sub1 -8c synthesis

_{Pd(OAc) 2} (0.55 g, 0.002 mol), P(t-Bu) ₃ (2.0 g, 0.005 mol), K ₂ CO ₃ (34 g, 0.25 mol) in Sub1-8b (50 g, 0.08 mol) , DMA (166 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 25 g (54.9%) of the product Sub1-8c was obtained using the above-described separation method of Sub1-1b.

(3) Sub1 -8 synthesis

4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (22.4 in Sub1-8c (50 g, 0.09 mol) g, 0.09 mol), Pd ₂ (dba) ₃ (2.4 g, 0.003 mol), AcOK (26.1 g, 0.27 mol), and DMF (180 ml) were added and stirred at 170° C. for 24 hours. When the reaction was completed, 51 g (87.8%) of the product Sub1-8 was obtained using the above-described separation method of Sub1-1b.

4. Sub1 -19 Synthesis example

(One) Sub1 -19b synthesis

Sub1-19a (30 g, 0.10 mol), 1-bromo-9-chlorodibenzo[b,d]thiophene (30.6 g, 0.10 mol), Pd ₂ (dba) ₃ (2.8 g, 0.003 mol), 50% P( t -Bu) ₃ (2.5 g, 0.006 mol), NaO t -Bu (29.7 g, 0.31 mol) was added to toluene (210 ml) and stirred at 90°C. When the reaction was completed, 45 g (85.9%) of the product Sub1-19b was obtained using the above-described separation method of Sub1-1b.

(2) Sub1 -19c synthesis

Sub1-19b (45 g, 0.15 mol) in Pd(OAc) ₂ (1 g, 0.005 mol), P(t-Bu) ₃ (3.7 g, 0.009 mol), K ₂ CO ₃ (62.8 g, 0.45 mol) , DMA (305 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 40 g (55.9%) of the product Sub1-19c was obtained using the above-described separation method of Sub1-1b.

(3) Sub1 -19 synthesis

Sub1-19c (40 g, 0.08 mol) 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (21.4 g, 0.08 mol), Pd ₂ (dba) ₃ (2.3 g, 0.003 mol), AcOK (25 g, 0.25 mol), and DMF (170 ml) were added and stirred at 170° C. for 24 hours. When the reaction was completed, 42 g (88%) of the product Sub1-19 was obtained using the above-described separation method of Sub1-1b.

5. Sub1 -26 Synthesis example

(One) Sub1 -26b synthesis

Sub1-26a (30 g, 0.10 mol), 6-bromo-7-chloronaphtho[1,2-b]benzofuran (34 g, 0.10 mol), Pd ₂ (dba) ₃ (2.8 g, 0.003 mol), 50% P( t -Bu) ₃ (2.5 g, 0.006 mol), NaO t -Bu (29.7 g, 0.31 mol) was added to toluene (210 ml) and stirred at 90°C. When the reaction was completed, the product Sub1-26b 49 g (87.7%) was obtained using the above-described separation method of Sub1-1b.

(2) Sub1 -26c synthesis

_{Pd(OAc) 2} (0.65 g, 0.003 mol), P(t-Bu) ₃ (2.3 g, 0.006 mol), K ₂ CO ₃ (40 g, 0.29 mol) in Sub1-26b (52 g, 0.10 mol) , DMA (190 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 24 g (49.5%) of the product Sub1-26c was obtained using the above-described separation method of Sub1-1b.

(3) Sub1 -26 synthesis

Sub1-26c (20 g, 0.04 mol) in 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (10 g, 0.04 mol), Pd ₂ (dba) ₃ (1.1 g, 0.0012 mol), AcOK (11.7 g, 0.12 mol), and DMF (80 ml) were added and stirred at 170° C. for 24 hours. When the reaction was completed, 19 g (80.4%) of the product Sub1-26 was obtained using the above-described separation method of Sub1-1b.

6. Sub2 -2 Synthesis example

(One) Sub2 -2b synthesis

Sub2-2a (25 g, 0.05 mol), 9H-carbazole (9.1 g, 0.07 mol), Pd ₂ (dba) ₃ (1.5 g, 0.0016 mol), 50% P( t- Bu) ₃ (1.3 g, 0.0033 mol), NaO t -Bu (15.7 g, 0.16 mol) was added to toluene (110ml) and stirred at 90°C. When the reaction was completed, the product Sub2-2b 26 g (87.5%) was obtained using the above-described separation method of Sub1-1b.

(2) Sub2 -2 synthesis

Sub2-2b (25 g, 0.05 mol) in Pd(OAc) ₂ (0.31 g, 0.001 mol), P(t-Bu) ₃ (1.1 g, 0.003 mol), K ₂ CO ₃ (19.1 g, 0.14 mol) , DMA (92 ml) was added and stirred at 170°C for 12 hours. When the reaction was completed, 20 g (85.7%) of the product Sub2-2 was obtained using the above-described separation method of Sub1-1b.

7. Sub2 -12 Synthesis example

(One) Sub2 -12b synthesis

Sub2-12a (50 g, 0.16 mol), 4-bromo-5-chloro-9,9-dimethyl-9H-fluorene (50 g, 0.16 mol), Pd ₂ (dba) ₃ (4.5 g, 0.0016 mol), 50% P( t- Bu) ₃ (4 g, 0.01 mol), NaO t- Bu (47 g, 0.49 mol) was added to toluene (325ml) and stirred at 90°C. When the reaction was completed, 80 g (92%) of the product Sub2-12b was obtained using the above-described separation method of Sub1-1b.

(2) Sub2 -12 synthesis

_{Pd(OAc) 2} (0.38 g, 0.002 mol), P(t-Bu) ₃ (1.4 g, 0.003 mol), K ₂ CO ₃ (23.3 g, 0.17 mol) in Sub2-12b (30 g, 0.06 mol) , DMA (120 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, the product Sub2-12 14 g (50%) was obtained using the above-described separation method of Sub1-1b.

8. Sub3 -One Synthesis example

(One) Sub3 -1b synthesis

Sub3-1a (30 g, 0.08 mol), 9H-carbazole (26 g, 0.16 mol), Pd ₂ (dba) ₃ (2.1 g, 0.0023 mol), 50% P( t -Bu) ₃ (1.9 g, 0.005 mol), NaO t -Bu (22.4 g, 0.23 mol) was added to toluene (155ml) and stirred at 90°C. When the reaction was completed, 30 g (81.8%) of the product Sub3-1b was obtained using the above-described separation method of Sub1-1b.

(2) Sub3 -1 synthesis

Sub3-1b (30 g, 0.06 mol) in Pd(OAc) ₂ (0.43 g, 0.02 mol), P(t-Bu) ₃ (1.5 g, 0.004 mol), K ₂ CO ₃ (26.4 g, 0.19 mol) , DMA (130 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 18 g (65%) of the product Sub3-1 was obtained using the above-described separation method of Sub1-1b.

9. Sub3 -6 Synthesis example

(One) Sub3 -6b synthesis

Sub3-6a (50 g, 0.20 mol), 1-bromo-9-chlorodibenzo[b,d]furan (54.9 g, 0.20 mol), Pd ₂ (dba) ₃ (5.4 g, 0.006 mol), 50% P( t -Bu) ₃ (4.7 g, 0.012 mol), NaO t -Bu (56.3 g, 0.59 mol) was added to toluene (390 ml) and stirred at 90°C. When the reaction was completed, 80 g (89.8%) of the product Sub3-6b was obtained using the above-described separation method of Sub1-1b.

(2) Sub3 -6 synthesis

_{Pd(OAc) 2} (0.59 g, 0.003 mol), P(t-Bu) ₃ (2.1 g, 0.005 mol), K ₂ CO ₃ (36.4 g, 0.26 mol) in Sub3-6b (40 g, 0.09 mol) , DMA (175 ml) was added and stirred at 170° C. for 12 hours. When the reaction was completed, 20 g (54.3%) of the product Sub3-6 was obtained using the above-described separation method of Sub1-1b.

Meanwhile, the compounds belonging to Sub1 to Sub3 may be the following compounds, but are not limited thereto, and Tables 1 to 3 below show the FD-MS values of the compounds belonging to Sub1 to Sub3.

compound FD-MS compound FD-MS Sub1-1 m/z=622.24 (C ₄₂ H ₃₁ BN ₂ O ₃ =622.53) Sub1-2 m/z=789.29 (C ₅₅ H ₄₀ BNO ₂ S=789.8) Sub1-3 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5) Sub1-4 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5) Sub1-5 m/z=563.17 (C ₃₆ H ₂₆ BNO ₃ S=563.48) Sub1-6 m/z=711.24 (C ₄₉ H ₃₄ BNO ₂ S=711.69) Sub1-7 m/z=547.2 (C ₃₆ H ₂₆ BNO ₄ =547.42) Sub1-8 m/z=655.18 (C ₄₂ H ₃₀ BNO ₂ S ₂ =655.64) Sub1-9 m/z=563.17 (C ₃₆ H ₂₆ BNO ₃ S=563.48) Sub1-10 m/z=589.22 (C ₃₉ H ₃₂ BNO ₂ S=589.56) Sub1-11 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5) Sub1-12 m/z=613.19 (C ₄₀ H ₂₈ BNO ₃ S=613.54) Sub1-13 m/z=614.22 (C ₄₀ H ₃₁ BN ₂ O ₂ S=614.57) Sub1-14 m/z=599.3 (C ₄₂ H ₃₈ BNO ₂ =599.58) Sub1-15 m/z=622.24 (C ₄₂ H ₃₁ BN ₂ O ₃ =622.53) Sub1-16 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5) Sub1-17 m/z=563.17 (C ₃₆ H ₂₆ BNO ₃ S=563.48) Sub1-18 m/z=589.22 (C ₃₉ H ₃₂ BNO ₂ S=589.56) Sub1-19 m/z=563.17 (C ₃₆ H ₂₆ BNO ₃ S=563.48) Sub1-20 m/z=761.26 (C ₅₃ H ₃₆ BNO ₂ S=761.75) Sub1-21 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5) Sub1-22 m/z=563.17 (C ₃₆ H ₂₆ BNO ₃ S=563.48) Sub1-23 m/z=723.33 (C ₅₂ H ₄₂ BNO ₂ =723.72) Sub1-24 m/z=563.17 (C ₃₆ H ₂₆ BNO ₃ S=563.48) Sub1-25 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5) Sub1-26 m/z=597.21 (C ₄₀ H ₂₈ BNO ₄ =597.48) Sub1-27 m/z=579.15 (C ₃₆ H ₂₆ BNO ₂ S ₂ =579.54) Sub1-28 m/z=613.19 (C ₄₀ H ₂₈ BNO ₃ S=613.54) Sub1-29 m/z=589.22 (C ₃₉ H ₃₂ BNO ₂ S=589.56) Sub1-30 m/z=547.2 (C ₃₆ H ₂₆ BNO ₄ =547.42) Sub1-31 m/z=599.3 (C ₄₂ H ₃₈ BNO ₂ =599.58) Sub1-32 m/z=651.24 (C ₄₄ H ₃₄ BNO ₂ S=651.63) Sub1-33 m/z=573.25 (C ₃₉ H ₃₂ BNO ₃ =573.5)

compound FD-MS compound FD-MS Sub2-1 m/z=471.05 (C ₃₀ H ₁₄ ClNOS=471.96) Sub2-2 m/z=507.18 (C ₃₆ H ₂₆ ClN=508.06) Sub2-3 m/z=481.12 (C ₃₃ H ₂₀ ClNO=481.98) Sub2-4 m/z=455.07 (C ₃₀ H ₁₄ ClNO ₂ =455.9) Sub2-5 m/z=487.03 (C ₃₀ H ₁₄ ClNS ₂ =488.02) Sub2-6 m/z=471.05 (C ₃₀ H ₁₄ ClNOS=471.96) Sub2-7 m/z=497.1 (C ₃₃ H ₂₀ ClNS=498.04) Sub2-8 m/z=481.12 (C ₃₃ H ₂₀ ClNO=481.98) Sub2-9 m/z=546.1 (C ₃₆ H ₁₉ ClN ₂ S=547.07) Sub2-10 m/z=621.13 (C ₄₃ H ₂₄ ClNS=622.18) Sub2-11 m/z=481.12 (C ₃₃ H ₂₀ ClNO=481.98) Sub2-12 m/z=497.1 (C ₃₃ H ₂₀ ClNS=498.04) Sub2-13 m/z=455.07 (C ₃₀ H ₁₄ ClNO ₂ =455.9) Sub2-14 m/z=487.03 (C ₃₀ H ₁₄ ClNS ₂ =488.02) Sub2-15 m/z=481.12 (C ₃₃ H ₂₀ ClNO=481.98) Sub2-16 m/z=597.1 (C ₄₀ H ₂₀ ClNOS=598.12) Sub2-17 m/z=650.16 (C ₄₄ H ₂₇ ClN ₂ S=651.22) Sub2-18 m/z=531.06 (C ₃₃ H ₁₉ Cl ₂ NS=532.48) Sub2-19 m/z=762.15 (C ₅₂ H ₂₇ ClN ₂ OS=763.31) Sub2-20 m/z=481.12 (C ₃₃ H ₂₀ ClNO=481.98) Sub2-21 m/z=521.06 (C ₃₄ H ₁₆ ClNOS=522.02) Sub2-22 m/z=487.03 (C ₃₀ H ₁₄ ClNS ₂ =488.02) Sub2-23 m/z=471.05 (C ₃₀ H ₁₄ ClNOS=471.96)

compound FD-MS compound FD-MS Sub3-1 m/z=436.1 (C ₃₀ H ₁₆ N ₂ S=436.53) Sub3-2 m/z=446.18 (C ₃₃ H ₂₂ N ₂ =446.55) Sub3-3 m/z=682.33 (C ₅₁ H ₄₂ N ₂ =682.91) Sub3-4 m/z=436.1 (C ₃₀ H ₁₆ N ₂ S=436.53) Sub3-5 m/z=420.13 (C ₃₀ H ₁₆ N ₂ O=420.47) Sub3-6 m/z=420.13 (C ₃₀ H ₁₆ N ₂ O=420.47) Sub3-7 m/z=436.1 (C ₃₀ H ₁₆ N ₂ S=436.53) Sub3-8 m/z=420.13 (C ₃₀ H ₁₆ N ₂ O=420.47) Sub3-9 m/z=446.18 (C ₃₃ H ₂₂ N ₂ =446.55) Sub3-10 m/z=436.1 (C ₃₀ H ₁₆ N ₂ S=436.53) Sub3-11 m/z=557.21 (C ₄₃ H ₂₇ N=557.7) Sub3-12 m/z=420.13 (C ₃₀ H ₁₆ N ₂ O=420.47) Sub3-13 m/z=570.21 (C ₄₃ H ₂₆ N ₂ =570.7) Sub3-14 m/z=420.13 (C ₃₀ H ₁₆ N ₂ O=420.47)

Meanwhile, the compounds belonging to Sub4 and Sub5 may be the following compounds, but are not limited thereto, and Tables 4 and 5 below show the FD-MS values of the compounds belonging to Sub4 and Sub5.

compound FD-MS compound FD-MS Sub4-1 m/z=112.01 (C ₆ H ₅ Cl=112.56) Sub4-2 m/z=277.07 (C ₁₈ H ₁₂ ClN=277.75) Sub4-3 m/z=162.02 (C ₁₀ H ₇ Cl=162.62) Sub4-4 m/z=202.02 (C ₁₂ H ₇ ClO=202.64) Sub4-5 m/z=279.08 (C ₁₈ H ₁₄ ClN=279.77) Sub4-6 m/z=138.02 (C ₈ H ₇ Cl=138.59) Sub4-7 m/z=188.04 (C ₁₂ H ₉ Cl=188.65) Sub4-8 m/z=117.04 (C ₆ D ₅ Cl=117.59) Sub4-9 m/z=327.08 (C ₂₂ H ₁₄ ClN=327.81) Sub4-10 m/z=264.07 (C ₁₈ H ₁₃ Cl=264.75) Sub4-11 m/z=369.09 (C ₂₄ H ₁₆ ClNO=369.85) Sub4-12 m/z=279.08 (C ₁₈ H ₁₄ ClN=279.77) Sub4-13 m/z=218.99 (C ₁₁ H ₆ ClNS=219.69) Sub4-14 m/z=113 (C ₅ H ₄ ClN=113.54) Sub4-15 m/z=189.03 (C ₁₁ H ₈ ClN=189.64) Sub4-16 m/z=289.07 (C ₁₉ H ₁₂ ClN=289.76) Sub4-17 m/z=240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub4-18 m/z=342.09 (C ₂₂ H ₁₅ ClN ₂ =342.83) Sub4-19 m/z=296.02 (C ₁₆ H ₉ ClN ₂ S=296.77) Sub4-20 m/z=290.06 (C ₁₈ H ₁₁ ClN ₂ =290.75) Sub4-21 m/z=290.06 (C ₁₈ H ₁₁ ClN ₂ =290.75) Sub4-22 m/z=240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub4-23 m/z=266.06 (C ₁₆ H ₁₁ ClN ₂ =266.73) Sub4-24 m/z=240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub4-25 m/z=302.04 (C ₁₆ H ₉ ClF ₂ N ₂ =302.71) Sub4-26 m/z=208.02 (C ₁₀ H ₆ ClFN ₂ =208.62) Sub4-27 m/z=266.06 (C ₁₆ H ₁₁ ClN ₂ =266.73) Sub4-28 m/z=330.06 (C ₂₀ H ₁₁ ClN ₂ O=330.77) Sub4-29 m/z=316.08 (C ₂₀ H ₁₃ ClN ₂ =316.79) Sub4-30 m/z=280.04 (C ₁₆ H ₉ ClN ₂ O=280.71) Sub4-31 m/z=258.04 (C ₁₄ H ₈ ClFN ₂ =258.68) Sub4-32 m/z=317.07 (C ₁₉ H ₁₂ ClN ₃ =317.78) Sub4-33 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub4-34 m/z=521.13 (C ₃₄ H ₂₀ ClN ₃ O=522) Sub4-35 m/z=267.06 (C ₁₅ H ₁₀ ClN ₃ =267.72) Sub4-36 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86) Sub4-37 m/z=291.06 (C ₁₇ H ₁₀ ClN ₃ =291.74) Sub4-38 m/z=407.08 (C ₂₅ H ₁₄ ClN ₃ O=407.86) Sub4-39 m/z=348.12 (C ₂₁ H ₉ D ₅ ClN ₃ =348.84) Sub4-40 m/z=343.09 (C ₂₁ H ₁₄ ClN ₃ =343.81) Sub4-41 m/z=373.04 (C ₂₁ H ₁₂ ClN ₃ S=373.86)

compound FD-MS compound FD-MS Sub5-1 m/z=169.09 (C ₁₂ H ₁₁ N=169.23) Sub5-2 m/z=245.12 (C ₁₈ H ₁₅ N=245.33) Sub5-3 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub5-4 m/z=321.15 (C ₂₄ H ₁₉ N=321.42) Sub5-5 m/z=295.14 (C ₂₂ H ₁₇ N=295.39) Sub5-6 m/z=179.15 (C ₁₂ HD ₁₀ N=179.29) Sub5-7 m/z=285.15 (C ₂₁ H ₁₉ N=285.39) Sub5-8 m/z=336.16 (C ₂₄ H ₂₀ N ₂ =336.44) Sub5-9 m/z=167.07 (C ₁₂ H ₉ N=167.21) Sub5-10 m/z=334.15 (C ₂₄ H ₁₈ N ₂ =334.42) Sub5-11 m/z=275.08 (C ₁₈ H ₁₃ NS=275.37) Sub5-12 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub5-13 m/z=325.09 (C ₂₂ H ₁₅ NS=325.43) Sub5-14 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31) Sub5-15 m/z=362.14 (C ₂₅ H ₁₈ N ₂ O=362.43) Sub5-16 m/z=259.1 (C ₁₈ H ₁₃ NO=259.31)

II. Product synthesis

1.P-1 Synthesis example

Sub1-1 (35 g, 0.06 mol) to Sub4-35 (15 g, 0.06 mol), Pd(PPh ₃ ) ₄ (2 g, 0.002 mol), NaOH (6.8 g, 0.17 mol), THF (120 mL), Water (30 mL) was added and reacted for 6 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Then, the concentrated reaction product was separated using a silicagel column or a recrystallization method to obtain 37 g (90.4%) of the product P-1.

2. P-4 Synthesis example

Sub1-3 (30 g, 0.05 mol) to Sub4-2 (14.5 g, 0.05 mol), Pd(PPh ₃ ) ₄ (1.8 g, 0.002 mol), NaOH (6.3 g, 0.16 mol), THF (110 mL), Water (28 mL) was added and reacted for 6 hours. When the reaction was completed, 30 g (83.3%) of the product P-4 was obtained using the above-described separation method of P-1.

3. P-5 synthesis

Sub3-1 (18 g, 0.04 mol) to Sub4-22 (9.9 g, 0.04 mol), Pd ₂ (dba) ₃ (1.1 g, 0.0012 mol), 50% P( t- Bu) ₃ (1.0 g, 0.0025 mol), NaO t -Bu (11.9 g, 0.12 mol), and toluene (85ml) were added, followed by stirring at 90°C. When the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Subsequently, the concentrated reactant was separated using a silicagel column or a recrystallization method to obtain 23 g (87%) of the product P-5.

4. P-12 Synthesis example

Sub2-2 (18 g, 0.04 mol) to Sub5-2 (8.7 g, 0.04 mol), Pd ₂ (dba) ₃ (1 g, 0.0011 mol), 50% P( t- Bu) ₃ (0.9 g, 0.0021 mol), NaO t -Bu (10.2 g, 0.11 mol), and toluene (70ml) were added and stirred at 90°C. When the reaction was completed, 22 g (86.7%) of the product P-12 was obtained using the above-described separation method of P-5.

5. P-13 Synthesis example

Sub3-5 (20 g, 0.05 mol) to Sub4-18 (16.3 g, 0.05 mol), Pd ₂ (dba) ₃ (1.3 g, 0.0014 mol), 50% P( t- Bu) ₃ (1.2 g, 0.0029 mol), NaO t -Bu (13.7 g, 0.14 mol), and toluene (95ml) were added, followed by stirring at 90°C. When the reaction was completed, 31 g (89.7%) of the product P-13 was obtained using the above-described separation method of P-5.

6. P-26 Synthesis example

Sub2-6 (25 g, 0.05 mol) to Sub5-12 (18.6 g, 0.05 mol), Pd ₂ (dba) ₃ (1.5 g, 0.0016 mol), 50% P( t- Bu) ₃ (1.5 g, 0.0016 mol), NaO t -Bu (15.3 g, 0.16 mol), and toluene (106ml) were added, followed by stirring at 90°C. When the reaction was completed, 34 g (81.5%) of the product P-26 was obtained using the above-described separation method of P-5.

7. P-37 Synthesis example

Sub3-7 (23 g, 0.05 mol) to Sub4-7 (9.9 g, 0.05 mol), Pd ₂ (dba) ₃ (1.4 g, 0.0016 mol), 50% P( t- Bu) ₃ (1.3 g, 0.0016 mol), NaO t -Bu (15.2 g, 0.16 mol), and toluene (105ml) were added and stirred at 90°C. When the reaction was completed, 28 g (90.3%) of the product P-37 was obtained using the above-described separation method of P-5.

8. P-49 Synthesis example

Sub3-10 (30 g, 0.07 mol) to Sub4-33 (23.9 g, 0.07 mol), Pd ₂ (dba) ₃ (1.9 g, 0.0021 mol), 50% P( t- Bu) ₃ (1.7 g, 0.0041 mol), NaO t -Bu (19.9 g, 0.21 mol), and toluene (140ml) were added, followed by stirring at 90°C. When the reaction was completed, 45 g (87.4%) of the product P-49 was obtained using the above-described separation method of P-5.

9. P-59 Synthesis example

Sub2-18 (31 g, 0.06 mol) to Sub5-1 (20 g, 0.12 mol), Pd ₂ (dba) ₃ (1.6 g, 0.0017 mol), 50% P( t- Bu) ₃ (1.4 g, 0.0035 mol), NaO t -Bu (16.8 g, 0.17 mol), and toluene (120ml) were added and stirred at 90°C. When the reaction was completed, 40 g (86%) of the product P-59 was obtained using the above-described separation method of P-5.

10. P-65 Synthesis example

Sub3-13 (30 g, 0.05 mol) to Sub4-32 (16.7 g, 0.05 mol), Pd ₂ (dba) ₃ (1.4 g, 0.0016 mol), 50% P( t- Bu) ₃ (1.3 g, 0.0032 mol), NaO t -Bu (15.2 g, 0.16 mol), and toluene (110ml) were added, followed by stirring at 90°C. When the reaction was completed, 40 g (89.2%) of the product P-65 was obtained using the above-described separation method of P-5.

11.P-69 Synthesis example

Sub3-14 (20 g, 0.05 mol) to Sub4-34 (16.3 g, 0.05 mol), Pd ₂ (dba) ₃ (1.3 g, 0.0016 mol), 50% P( t- Bu) ₃ (1.2 g, 0.0032 mol), NaO t -Bu (13.7 g, 0.14 mol), and toluene (100ml) were added and stirred at 90°C. When the reaction was completed, 28 g (80.9%) of the product P-69 was obtained using the above-described separation method of P-5.

12. P-70 Synthesis example

Sub2-23 (18 g, 0.04 mol) to Sub5-8 (12.8 g, 0.04 mol), Pd ₂ (dba) ₃ (1.1 g, 0.0011 mol), 50% P( t- Bu) ₃ (0.9 g, 0.0023 mol), NaO t -Bu (11 g, 0.11 mol), and toluene (80ml) were added and stirred at 90°C. When the reaction was completed, 24 g (81.3%) of the product P-70 was obtained using the above-described separation method of P-5.

Meanwhile, the FD-MS values of the compounds P-1 to P-72 of the present invention prepared according to the Synthesis Example are shown in Table 6 below.

compound FD-MS compound FD-MS P-1 m/z=727.24 (C ₅₁ H ₂₉ N ₅ O=727.83) P-2 m/z=604.16 (C ₄₂ H ₂₄ N ₂ OS=604.73) P-3 m/z=739.23 (C ₅₅ H ₃₃ NS=739.94) P-4 m/z=688.25 (C ₅₁ H ₃₂ N ₂ O=688.83) P-5 m/z=640.17 (C ₄₄ H ₂₄ N ₄ S=640.76) P-6 m/z=678.24 (C ₄₈ H ₃₀ N ₄ O=678.8) P-7 m/z=603.13 (C ₄₂ H ₂₁ NO ₂ S=603.7) P-8 m/z=1070.31 (C ₇₇ H ₄₂ N ₄ OS=1071.27) P-9 m/z=677.26 (C ₄₈ H ₃₁ N ₅ =677.81) P-10 m/z=604.12 (C ₄₁ H ₂₀ N ₂ O ₂ S=604.68) P-11 m/z=605.13 (C ₄₂ H ₂₃ NS ₂ =605.77) P-12 m/z=716.32 (C ₅₄ H ₄₀ N ₂ =716.93) P-13 m/z=726.24 (C ₅₂ H ₃₀ N ₄ O=726.84) P-14 m/z=697.13 (C ₄₆ H ₂₃ N ₃ OS ₂ =697.83) P-15 m/z=694.22 (C ₄₈ H ₃₀ N ₄ S=694.86) P-16 m/z=704.25 (C ₅₁ H ₃₂ N ₂ O ₂ =704.83) P-17 m/z=690.19 (C ₄₈ H ₂₆ N ₄ S=690.82) P-18 m/z=523.19 (C ₃₉ H ₂₅ NO=523.64) P-19 m/z=505.09 (C ₃₄ H ₁₆ FNOS=505.57) P-20 m/z=742.22 (C ₅₂ H ₃₀ N ₄ S=742.9) P-21 m/z=784.38 (C ₅₉ H ₄₈ N ₂ =785.05) P-22 m/z=740.25 (C ₅₄ H ₃₂ N ₂ O ₂ =740.86) P-23 m/z=726.13 (C ₄₈ H ₂₆ N ₂ S ₃ =726.93) P-24 m/z=716.32 (C ₅₄ H ₄₀ N ₂ =716.93) P-25 m/z=777.25 (C ₅₅ H ₃₁ N ₅ O=777.89) P-26 m/z=786.18 (C ₅₄ H ₃₀ N ₂ OS ₂ =786.97) P-27 m/z=640.28 (C ₄₅ H ₂₀ D ₁₀ N ₂ S=640.87) P-28 m/z=768.25 (C ₅₄ H ₃₂ N ₄ O ₂ =768.88) P-29 m/z=805.26 (C ₅₈ H ₃₅ N ₃ S=806) P-30 m/z=573.21 (C ₄₃ H ₂₇ NO=573.7) P-31 m/z=514.11 (C ₃₅ H ₁₈ N ₂ OS=514.6) P-32 m/z=693.22 (C ₄₉ H ₃₁ N ₃ S=693.87) P-33 m/z=624.2 (C ₄₄ H ₂₄ N ₄ O=624.7) P-34 m/z=703.15 (C ₄₆ H ₂₃ F ₂ N ₃ OS=703.77) P-35 m/z=754.24 (C ₅₅ H ₃₄ N ₂ S=754.95) P-36 m/z=730.3 (C ₅₄ H ₃₈ N ₂ O=730.91) P-37 m/z=588.17 (C ₄₂ H ₂₄ N ₂ S=588.73) P-38 m/z=784.23 (C ₅₄ H ₃₂ N ₄ OS=784.94) P-39 m/z=609.13 (C ₄₀ H ₂₀ FN ₃ OS=609.68) P-40 m/z=716.23 (C ₅₃ H ₂₄ D ₅ NS=716.91) P-41 m/z=676.26 (C ₄₉ H ₃₂ N ₄ =676.82) P-42 m/z=781.24 (C ₅₅ H ₃₁ N ₃ O ₃ =781.87) P-43 m/z=696.17 (C ₄₈ H ₂₈ N ₂ S ₂ =696.89) P-44 m/z=852.33 (C ₆₃ H ₄₀ N ₄ =853.04) P-45 m/z=714.21 (C ₅₀ H ₂₆ N ₄ O ₂ =714.78) P-46 m/z=717.19 (C ₅₀ H ₂₇ N ₃ OS=717.85) P-47 m/z=756.26 (C ₅₅ H ₃₆ N ₂ S=756.97) P-48 m/z=738.27 (C ₅₅ H ₃₄ N ₂ O=738.89) P-49 m/z=748.25 (C ₅₁ H ₂₄ D ₅ N ₅ S=748.92) P-50 m/z=704.25 (C ₅₁ H ₃₂ N ₂ O ₂ =704.83) P-51 m/z=728.19 (C ₅₂ H ₂₈ N ₂ OS=728.87) P-52 m/z=783.27 (C ₅₆ H ₃₇ N ₃ S=783.99) P-53 m/z=646.24 (C ₄₉ H ₃₀ N ₂ =646.79) P-54 m/z=675.19 (C ₄₈ H ₂₅ N ₃ O ₂ =675.75) P-55 m/z=681.16 (C ₄₈ H ₂₇ NS ₂ =681.87) P-56 m/z=673.28 (C ₅₂ H ₃₅ N=673.86) P-57 m/z=573.18 (C ₄₁ H ₂₃ N ₃ O=573.66) P-58 m/z=858.21 (C ₅₉ H ₃₀ N ₄ O ₂ S=858.98) P-59 m/z=797.29 (C ₅₇ H ₃₉ N ₃ S=798.02) P-60 m/z=599.22 (C ₄₅ H ₂₉ NO=599.73) P-61 m/z=895.27 (C ₆₄ H ₃₇ N ₃ OS=896.08) P-62 m/z=770.24 (C ₅₅ H ₃₄ N ₂ OS=770.95) P-63 m/z=740.19 (C ₅₃ H ₂₈ N ₂ OS=740.88) P-64 m/z=706.24 (C ₅₁ H ₃₄ N ₂ S=706.91) P-65 m/z=851.3 (C ₆₂ H ₃₇ N ₅ =852.01) P-66 m/z=651.19 (C ₄₆ H ₂₅ N ₃ O ₂ =651.73) P-67 m/z=785.2 (C ₅₄ H ₃₁ N ₃ S ₂ =785.98) P-68 m/z=810.28 (C ₅₇ H ₃₈ N ₄ S=811.02) P-69 m/z=727.24 (C ₅₁ H ₂₉ N ₅ O=727.83) P-70 m/z=771.23 (C ₅₄ H ₃₃ N ₃ OS=771.94) P-71 m/z=769.22 (C ₅₄ H ₃₁ N ₃ OS=769.92) P-72 m/z=669.22 (C ₄₇ H ₂₈ FN ₃ O=669.76)

Manufacturing evaluation of organic electric devices

[ Example One] Red organic light emitting device ( Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured according to a conventional method by using the compound obtained through the synthesis as a light emitting auxiliary layer material. ^{First, N 1} -(naphthalen-2-yl)-N ⁴ , N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl as a hole injection layer on the ITO layer (anode) formed on the glass substrate. )-N ¹ -phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Then, N, N'-Bis(1-naphthalenyl)-N, N'-bis-phenyl-(1, 1'-Biphenyl)-4, 4'-diamine (hereinafter abbreviated as NPB) to a thickness of 60 nm The hole transport layer was formed by vacuum evaporation. Subsequently, compound P-2 represented by Formula 1 as a material for a light emission auxiliary layer was vacuum-deposited to a thickness of 20 nm to form a light emission auxiliary layer. After forming the light-emitting auxiliary layer, CBP[4,4'-N,N'-dicarbazole-biphenyl] was used as a host on the light-emitting auxiliary layer, and (piq) ₂ Ir(acac) [bis-( 1-phenyl isoquinolyl)iridium(III)acetylacetonate] was doped with a weight of 95:5 to deposit a light emitting layer having a thickness of 30 nm on the auxiliary light emitting layer. As a hole blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and the electron transport layer As a result, tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, as an electron injection layer, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to be used as a cathode, thereby manufacturing an organic light emitting diode.

[ Example 2] to [ Example 18]

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 7 below was used instead of the compound P-2 of the present invention as the light emitting auxiliary layer material.

[ Comparative example One]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light emission auxiliary layer was not used.

[ Comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P-2 of the present invention as the light emitting auxiliary layer material.

Comparative compound A

By applying a forward bias DC voltage to the organic electric devices manufactured according to Examples 1 to 18 and Comparative Examples 1 to 2 of the present invention, electroluminescence (EL) characteristics were obtained with PR-650 of photoresearch. As a result of the measurement, the T95 life was measured using a life measurement equipment manufactured by McScience at a reference luminance of ^{2500 cd/m 2, and the measurement results are shown in Table 7 below.}

compound Driving voltage electric current
(mA/cm ² ) Luminance
(cd/m ² ) efficiency
(cd/A) T(95) CIE x y Comparative Example (1) - 6.3 32.9 2500 7.6 70.4 0.62 0.32 Comparative Example (2) Comparative compound A 6.1 14.0 2500 17.8 93.4 0.63 0.35 Example (1) P-2 5.0 9.3 2500 26.8 118.5 0.61 0.32 Example (2) P-4 5.6 10.2 2500 24.4 104.4 0.62 0.35 Example (3) P-7 5.4 10.5 2500 23.9 115.9 0.63 0.32 Example (4) P-11 5.5 10.4 2500 24.0 114.1 0.63 0.33 Example (5) P-12 5.1 9.4 2500 26.6 106.2 0.61 0.31 Example (6) P-16 5.0 9.6 2500 25.9 111.5 0.60 0.31 Example (7) P-22 4.8 9.7 2500 25.7 119.4 0.63 0.31 Example (8) P-23 4.8 10.0 2500 25.1 109.7 0.65 0.34 Example (9) P-24 5.3 9.3 2500 27.0 107.8 0.63 0.33 Example (10) P-26 4.7 10.1 2500 24.8 108.8 0.65 0.34 Example (11) P-29 5.3 9.8 2500 25.5 112.3 0.62 0.33 Example (12) P-35 5.2 9.1 2500 27.4 113.2 0.60 0.33 Example (13) P-36 5.1 9.6 2500 26.1 110.6 0.64 0.32 Example (14) P-37 5.5 10.3 2500 24.3 115.0 0.63 0.35 Example (15) P-43 4.9 9.9 2500 25.3 116.8 0.64 0.33 Example (16) P-48 5.6 10.2 2500 24.6 105.3 0.60 0.32 Example (17) P-59 5.2 9.2 2500 27.2 107.2 0.64 0.33 Example (18) P-70 4.9 9.5 2500 26.3 117.6 0.63 0.31

As can be seen from the results of Table 7 above, when a red organic electric device is manufactured using the material for an organic electric device of the present invention as a light emitting auxiliary layer material, the organic light emitting diode is not used or compared to the comparative example using the comparative compound A. It can be seen that not only can the driving voltage of the electroluminescent device be lowered, but also the luminous efficiency and lifespan are remarkably improved.

Comparing Comparative Example 1 and Comparative Example 2, the device result of Comparative Example 2 using Comparative Compound A was superior to Comparative Example 1 in which the light-emitting auxiliary layer was not used. In addition, the device result of the specific core compound of the present invention was better than that of Comparative Example 2.

Comparing the results of Comparative Example 2 and Examples 1 to 18, it can be seen that the difference in mobility appears large depending on the structure of the core core, and this difference in mobility affects the overall device. In addition, since the structure of this patent has a plate-like structure and exhibits a high refractive index and a high Tg value, it can be seen that luminous efficiency and thermal safety are improved, thereby increasing the lifespan. In addition, by using the compound of the present invention as a light emitting auxiliary layer, the HOMO or LUMO energy level of the compound of the present invention has an appropriate value between the hole transport layer and the light emitting layer. ), and it can be seen that the efficiency and lifespan are maximized by emitting light inside the light emitting layer, not the interface of the hole transport layer.

On the other hand, comparing the results of the embodiments of the present invention, there is a difference in driving voltage and luminous efficiency according to the presence or absence of an element and an amino group in the central core and the substitution position, and different lifetime results depending on the type of the element of the core core. I can see that. The plate shape of the central core caused a difference in hole mobility, thereby affecting the overall device.

In the case of the light-emitting auxiliary layer, it is necessary to grasp the correlation between the hole transport layer and the light-emitting layer (host). Even if a similar core is used, it is possible for a person skilled in the art to infer the characteristics of the light-emitting auxiliary layer in which the compound of the present invention is used. It will be very difficult.

The device characteristics in which the compound of the present invention was applied to only one of the light-emitting auxiliary layers were described in the evaluation results of the device fabrication described above, but it can be applied even when the compound of the present invention is formed of a hole transport layer or both a hole transport layer and a light emission auxiliary layer. will be.

[ Example 19] Red organic light emitting device (Phosphorescent host)

The compound obtained through the synthesis was used as a light emitting host material of the light emitting layer, and an organic light emitting device was manufactured according to a conventional method. First, on the 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) film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and then 4,4-bis[N-(1-naphthyl) as a hole transport compound on the hole injection layer. )-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Compound P-1 represented by Formula 1 was used as a host on the hole transport layer, and (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] was used as a dopant material in a 95:5 weight ratio. By doping, a light emitting layer was deposited to a thickness of 30 nm. Subsequently, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and the electron Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed as a transport layer to a thickness of 40 nm. Thereafter, as an electron injection layer, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to be used as a cathode, thereby manufacturing an organic light emitting diode.

[ Example 20] to [ Example 35]

An organic electroluminescent device was manufactured in the same manner as in Example 19, except that the compound of the present invention described in Table 8 was used instead of the compound P-1 of the present invention as the host material of the emission layer.

[ Comparative example 3] and [ Comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 19, except that Comparative Compounds B to C were used as host materials for the emission layer.

<Comparative Compound B> <Comparative Compound C>

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electric devices manufactured according to Examples 19 to 35 and Comparative Examples 3 to 4 thus prepared as described above with PR-650 of photoresearch Was measured, and as a result of the measurement, the T95 life was measured using a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m ^2. Table 8 below shows the results of device fabrication and evaluation.

compound Driving voltage electric current
(mA/cm ² ) Luminance
(cd/m ² ) efficiency
(cd/A) T(95) CIE x y Comparative Example (3) Comparative compound B 5.8 11.2 2500 22.4 98.7 0.61 0.33 Comparative Example (4) Comparative compound C 6.2 12.1 2500 20.7 100.2 0.65 0.32 Example (19) P-1 5.1 9.5 2500 26.3 116.4 0.65 0.32 Example (20) P-5 5.4 8.8 2500 28.4 110.1 0.62 0.32 Example (21) P-6 4.9 9.1 2500 27.5 118.8 0.62 0.35 Example (22) P-9 5.0 9.1 2500 27.5 119.6 0.64 0.33 Example (23) P-13 5.7 9.4 2500 26.7 121.2 0.63 0.31 Example (24) P-14 5.2 10.0 2500 25.1 110.0 0.60 0.34 Example (25) P-15 5.0 9.2 2500 27.3 112.4 0.65 0.34 Example (26) P-25 4.8 9.7 2500 25.9 114.7 0.63 0.31 Example (27) P-28 4.7 9.6 2500 26.1 118.0 0.61 0.31 Example (28) P-38 5.2 9.0 2500 27.9 117.1 0.63 0.35 Example (29) P-39 5.7 9.5 2500 26.5 109.3 0.64 0.35 Example (30) P-41 5.5 9.3 2500 26.9 122.0 0.64 0.31 Example (31) P-45 5.3 8.9 2500 28.1 111.7 0.64 0.31 Example (32) P-46 5.6 9.2 2500 27.2 115.6 0.65 0.34 Example (33) P-58 4.6 9.8 2500 25.5 113.2 0.65 0.31 Example (34) P-66 5.4 9.9 2500 25.3 120.4 0.60 0.33 Example (35) P-69 4.7 9.7 2500 25.7 114.0 0.63 0.30

As can be seen from the results of Table 8, it can be seen that when the compound of the present invention is used as the light emitting layer material, the driving voltage is lowered and the efficiency and lifespan are significantly improved compared to the case of using Comparative Compound B and Comparative Compound C.

That is, in the case of Comparative Compound B having a similar basic skeleton to Formula 1 of the present invention, the result was improved in the driving voltage and efficiency of the organic electroluminescent device compared to the case in which Comparative Compound C was used as a host material. It is shown as a result according to. When the compound of the present invention is used as a host material, driving voltage, efficiency, and lifespan are significantly improved compared to Comparative Compounds B to C.

In more detail, the compound of the present invention exhibits a higher refractive index and higher Tg value than the comparative compound by containing the S, O or C element in the structure of Formula 1, and has an LUMO level that maximizes the energy transfer effect, resulting in light emission. It can be seen that the efficiency is greatly improved and the lifespan is also significantly improved due to high thermal stability. In addition, the overall plate structure of the core has an effect on the hole mobility in the overall device, thus affecting the driving and efficiency life. In addition, in fact, the difference in device characteristics according to the type of substituents of Comparative Compound B and Comparative Compound C was confirmed in the structure of this patent, and it was shown that the device result is improved according to the substitution position, and the core of this patent is also the location of the heterocyclic group. Depending on the device results are significantly different. These results show that the energy level or thin film properties of the compound are significantly different depending on the type of hetero element or specific substituent as well as physical properties, and this difference is a major factor in improving the device performance during device deposition (e.g., energy balance, stability). Etc.), suggesting that such unpredictable device results may be derived.

In the above, the present invention has been exemplarily described, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted 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: pore layer 150: electron transport layer
160: electron injection layer 170: second electrode
160: electron transport layer 170: electron injection layer
180: light efficiency improvement layer 210: buffer layer
220: light emission auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first emission 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 emission layer
450: second electron transport layer CGL: charge generation layer
ST1: 1st stack ST2: 2nd stack

Claims (13)

Compound represented by the following formula (1)
[Formula 1] [Formula 2]

{In Formulas 1 and 2,
R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; Alkynyl group of C ₂ ~ C _60; An alkoxyl group of C ₁ to C _60; C ₆ ~ C ₆₀ aryloxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; And -L'-N (R ^c ) (R ^d ); is selected from the group consisting of,
Or wherein a, b, c, d and e is 2, the same or different, a plurality each or more, a plurality of R ₁ each other or a plurality of R ₂ to each other or a plurality of R ₃ to each other or a plurality of R ₄ or a plurality of each other R ₅ can be bonded to each other to form a ring,
Where L'is a single bond; C ₆ ~ C ₆₀ arylene group; And C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of, wherein R ^c and R ^d are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And fused ring groups of the aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; is selected from the group consisting of,
a, c and d are each independently an integer of 0 to 3, b and e are each independently an integer of 0 to 4,
X is CR'R", O or S,
Wherein the R'and R" are independently of each other C ₁ ~ C ₆₀ alkyl group; C ₆ ~ C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C including at least one heteroatom of P _{A heterocyclic group of 60} ; And -L'-N(R ^c )(R ^d ); is selected from the group consisting of, R'and R" may be bonded to each other to form a ring with a spy
Y is NAr ³ , O, S or CR ^a R ^b ,
Here, Ar ³ is a C ₆ ~C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Or a fluorenyl group; and,
R ^a and R ^b are each independently hydrogen; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; Alkynyl group of C ₂ ~ C _60; An alkoxyl group of C ₁ to C _60; C ₆ ~ C ₆₀ aryloxy group; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; And C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ fused ring group of the aromatic ring, and selected from the group consisting of, R ^a and R ^b may form a ring in spy bonded to each other,
At least one pair of two adjacent * in Formula 1 combines with * in Formula 2 to form a condensed ring
Here, the aryl group, heterocyclic group, fluorenyl group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio group; An alkoxyl group of C ₁ -C _20; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C _20; Alkynyl group of C ₂ -C _20; C ₆ -C ₂₀ aryl group; _{A C 6} -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group; A C ₃ -C ₂₀ cycloalkyl group; A C ₇ -C ₂₀ arylalkyl group; And C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be bonded to each other to form a ring, wherein'ring' refers to C ₃ -C ₆₀ It refers to a fused ring consisting of an aliphatic ring of or a C ₆ -C ₆₀ aromatic ring or a C ₂ -C ₆₀ hetero ring or a combination thereof, and includes a saturated or unsaturated ring.}
The compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4.
[Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4]

{In Formulas 1-1 to 1-4, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , X, Y, a, b, c, d and e are the same as defined in claim 1 Do.}
The compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 1-5 to 1-16.
[Formula 1-5] [Formula 1-6] [Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10] [Formula 1-11] [Formula 1-12]

[Formula 1-13] [Formula 1-14] [Formula 1-15] [Formula 1-16]

{In Formulas 1-5 to 1-16, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , Y, R', R'', a, b, c, d and e are the claims 1 It is the same as defined in.}
The compound according to claim 1, wherein _{any one of R 1} , R ₂ , R ₃ , R ₄ and R ₅ is represented by the following Formula 3, Formula 4 or Formula 5.
[Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5]

{In Formulas 3 to 5,
Ar ¹ and Ar ² are each independently a C ₆ ~ C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; C ₆ ~ C ₆₀ aryloxy group; And -N (R ^c ) (R ^d ); is selected from the group consisting of,
L ¹ , L ² , L ³ and L ₁ are each independently a single bond; C ₆ -C ₆₀ arylene group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,
Z ¹ to Z ⁸ are each independently N or CR ₆ ,
R ₆ is hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₆₀ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C _{60 and an aromatic ring of C 6} to C _60; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; Alkynyl group of C ₂ ~ C _60; An alkoxyl group of C ₁ to C _60; And C ₆ ~ C ₆₀ aryloxy group; is selected from the group consisting of,
C ring is a C ₆ ~ C ₆₀ aryl group; Or a heterocyclic group containing at least one heteroatom of O, N, S, Si, and P; and,
* Indicates the position to be combined.}
The compound of claim 4, wherein the formula 5 is represented by any one of the following formulas 5-1 to 5-6
[Chemical Formula 5-1] [Chemical Formula 5-2] [Chemical Formula 5-3]

[Chemical Formula 5-4] [Chemical Formula 5-5] [Chemical Formula 5-6]

{In Formula 5-1 to Formula 5-6,
R ₇ is a C ₆ ~ C ₆₀ aryl group; _{Or a C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; and,
A and B are each independently a direct bond, O or S,
f is 0 to 4, g is 0 to 6, h is an integer of 0 to 8,
i and j are each independently 0 or 1,
L ₁ is a single bond; C ₆ -C ₆₀ arylene group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ heterocyclic group; is selected from the group consisting of,
Z ⁶ , Z ⁷ and Z ⁸ are the same as defined in claim 4,
* Indicates the position to be combined.}
The compound according to claim 1, wherein the formula 1 is represented by any one of the following P-1 to P-72

An organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a single compound represented by Formula 1 of claim 1 or two or more compounds.
The organic electric device of claim 7, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.
The organic electric device of claim 7, wherein the organic material layer is a phosphorescent emission layer.
The organic electric device of claim 7, wherein the organic material layer is a light emission auxiliary layer.
The organic electric device of claim 7, further comprising a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
A display device including the organic electric device of claim 7; And a control unit for driving the display device.
The method of claim 12, wherein the organic electric device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or white lighting device. Electronic device

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