KR20160048577A - Display device using a composition for organic electronic element, and an organic electronic element thereof - Google Patents

Abstract

The present invention provides an organic electronic element, a display device, and an electronic device comprising the same. The organic electronic element has improved light-emitting efficiency, stability and lifespan properties by using a composition consisting of two or more compounds which have different structures as a hole transport layer.

Description

TECHNICAL FIELD [0001] The present invention relates to a display device and an organic electroluminescent device using a composition for an organic electroluminescent device,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device, a display device, and an electronic device using the composition of organic electroluminescent compound. More particularly, the present invention relates to a display device including an organic electroluminescent layer And an organic electric device.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electroluminescence device using an organic light emitting phenomenon is a self-luminous device using a principle that a light emitting material emits light by a recombination energy of holes injected from an anode and electrons injected from a cathode by applying a current.

The organic electroluminescent device may have a structure in which an anode is formed on a substrate, and a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are sequentially formed on the anode. Here, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer are organic thin films made of organic compounds.

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is an important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues as well as drive voltage issues are critical issues to be solved.

Particularly, in the case of driving voltage problem and lifetime problem, there are many problems associated with the thermal deterioration problem of the hole injecting material and the hole transporting material. For example, a method of forming a multilayer structure of a hole transporting layer (US Patent No. 5256945) and a method of using a material having a high glass transition temperature (U.S. Patent No. 5061569) have been proposed.

In addition, when a material having a good hole transport function is used to reduce the driving voltage, although the driving voltage of the device is greatly reduced, the efficiency and lifetime of the device are degraded due to excessive charge injection. There was an attempt.

However, there is a problem that the power consumption of the organic electronic device is increased and the lifetime is lowered due to the increase of the driving voltage of the progressive driving voltage of the blue organic electronic device such as red, green, and blue. In order to solve this problem, a buffer layer is formed between the anode and the hole transporting layer Technology was proposed

(Korean Patent Publication 2006-0032099)

In the present invention, two or more hole transporting materials having different band gaps are mixed in the hole transporting layer to reduce the thermal deterioration occurring at the interface between the hole transporting layer and the hole transporting layer and at the interface between the hole transporting layer and the light emitting layer, And an object of the present invention is to provide an organic electroluminescent device having an excellent luminous efficiency by efficiently controlling the amount of injected charges and increasing the efficiency.

The present invention provides a light emitting device comprising: a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer including at least one hole transport layer and a light emitting compound, wherein the hole transport layer has a different chemical structure And a display device including the organic electronic device.

The present invention also relates to an organic electronic device and an electronic device using the same, and more particularly, to an organic electronic device using the composition of the present invention, An organic electronic device is provided using a composition in which two or more hole transporting materials having different structures are mixed, and an electronic device including the same is provided.

The organic electroluminescent device and the display device including the organic electroluminescent device provided in the present invention have the advantages that the thermal deterioration occurring at the interface between the hole injection layer and the hole transporting layer and the interface between the hole transporting layer and the light emitting layer is reduced and the lifetime is prolonged, Is efficiently controlled to provide excellent luminous efficiency.

1 is an exemplary view of an organic electronic device according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

As used in this specification and the appended claims, unless stated otherwise, the following terms have the following meanings:

The term " halo "or" halogen ", as used herein, unless otherwise indicated, is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

The term "alkenyl group "," alkenyl group ", or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups , But is not limited thereto.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxyl group "," alkoxy group ", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

As used herein, the term "aryloxyl group" or "aryloxy group" refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

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

Also, if prefixes are named consecutively, it means that the substituents are listed in the order listed first. For example, the arylalkoxy group means an alkoxy group substituted with an aryl group, the alkoxycarbonyl group means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, an alkenyl group substituted with an arylcarbonyl group means Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise specified, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, Aromatic rings. Adjacent functional groups may be combined and formed.

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

The "heterocyclic group" may also include a ring including SO2 instead of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

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

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring of 3 to 60 carbon atoms or an aromatic ring of 6 to 60 carbon atoms or a heterocycle of 2 to 60 carbon atoms, or combinations thereof, Saturated or unsaturated ring.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term "carbonyl" as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise indicated, the term "ether" used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group having 1 to 20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of 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 Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. At this time, the electronic device may be a current or a future wired or 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 controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, a display device and an organic electroluminescent device according to aspects of the present invention will be described.

The present invention relates to a plasma display panel comprising a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode and including a hole transport layer and a light emitting layer, wherein the hole transport layer comprises two kinds of compounds having different structures from each other, Wherein the organic compound layer is formed by a sublimation process, a vapor deposition process, a spin coating process, a nozzle printing process, an inkjet process, and an inkjet process, wherein the weight ratio of the compound of each of the different structural formulas is selected from 5: 5 to 9: A printing process, a slot coating process, a dip coating process, or a roll-to-roll process.

According to a specific example of the present invention, A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer including at least one hole transport layer and a light emitting compound, wherein the hole transport layer comprises a compound represented by Formula 1 below, And a compound represented by the following general formula (2) are mixed together, and a display device including the same.

Wherein Ar ¹ to Ar ³ are selected from the group consisting of an aryl group having _{6 to 60} carbon atoms, a heteroaryl group having _{2 to 60} carbon atoms, and a fluorenyl group; L ¹ ~ L ³ 2 of a single bond, C _{6 ~ 60} aryl group, a group a heterocyclic of the divalent C _{2 ~ 60,} a fluorenyl group, an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the Is selected from the group consisting of fused ring groups; Ar ^{4 to 6} are a C _{6 to} C ₆₀ aryl group, a C _{2 to} C ₆₀ heteroaryl group, or a fluorenyl group; L ⁴ represents a single bond, C _{6 ~ 60} arylene group, a divalent C _{2 ~ 60} of the heterocyclic group, fluorenyl group, a divalent fused ring of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 to 60} of ≪ / RTI > m is an integer of 0 to 4, and n is an integer of 0 to 3; R ^{1 and} R ² are the same as or different from each other, and are independently selected from the group consisting of deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and 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 ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R _a ) (R _b ); wherein L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene 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 ; And a C ₂ to C ₆₀ heterocyclic group, wherein R _a and R _b are independently of each other a C ₆ to C ₆₀ aryl group; A 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; or R ^{1 to} R ² are each selected from the group consisting of And a plurality of R ^{1 s} or a plurality of R ^{2 s} may be bonded to each other to form a ring. A halogen group, a silyl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a -L _{'-N (R a) (R} b); C 1 ~ Import alkylthio of C _20; C ₁ ~ alkoxy group of C _20; C ₁ ~ alkyl group of C _20; C ₂ ~ C ₂₀ alkenyl group a; ₂ C ~ alkynyl of C _20; an aryl group of C ₆ - C ₂₀ substituted with heavy hydrogen;; C ₆ ~ C ₂₀ aryl group, a fluorenyl group; C ₂ - heterocyclic group of C _20; C of ₃ ~ C ₂₀ cycloalkyl An alkyl group, an arylalkyl group having ₇ to ₂₀ carbon atoms, and an arylalkenyl group having ₈ to ₂₀ carbon atoms, and these substituents may be further bonded to each other to form a ring, wherein The term " ring " means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof Refers to a luer binary fused ring, a saturated or unsaturated ring.)}

In another specific example of the present invention, at least one of the two compounds represented by Formula 1 is represented by the following Formulas 1-2, 1-3, and 1-4.

(In the formula 1-2, 1-3, 1-4, wherein ^{Ar 2, Ar 3, L 1} ~ L 3 are the same and, X, Y as defined above, Z is S, O, CR ', R R 'and R "are selected from the group consisting of C _6-24 aryl, C _1-20 alkyl, C _2-20 alkenyl, C ₁ -C ₂₀ alkoxy, and R', R" And R ³ to R ⁸ may be selected from the group consisting of deuterium, tritium, cyano, nitro, halogen, aryl, alkenyl, alkylene, alkoxy and heterocyclic groups And R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 may} be bonded to each other to form a ring, l, b and p each represent an integer of 0-3, and a, o, q is an integer of 0-4.)

In another specific example of the present invention, the organic electroluminescent device is characterized in that the compound represented by Formula 2 is represented by the following Formulas 2-2 and 2-3.

R ² , Ar ⁵ , L ⁴ , m and n are as defined above, V and W are S, O, CR'R "and R ', R "is an aryl group of C6-24, an alkyl group of C1-20, an alkenyl of C2-20 or a C1-20 alkoxy group; R ⁹ and R ¹² may be the same or different and are each a group selected from the group consisting of deuterium, tritium, cyano group, nitro group, halogen group, aryl group, alkenyl group, alkylene group, alkoxy group or heterocyclic group R ⁹ , R ¹⁰ , R ¹¹ and R ^{12 may} be bonded to each other to form a ring, c and e are integers of 0-3, and d and f are integers of 0-4.

According to a specific example of the present invention, the compound of formula (1) includes a compound represented by the following formula, and provides an organic electronic device containing such a compound.

As another specific example, the compound of formula (2) includes those represented by the following compounds, and provides an organic electric device including the same.

In one embodiment of the present invention, there is provided an organic electroluminescent device comprising a compound wherein Ar ¹ , Ar ² , and Ar ³ of the compound represented by Formula 1 are all C _{6 to} C ₂₄ aryl groups, Wherein Ar < ⁴ > and Ar < ⁵ > each represent an aryl group having _{6 to 24} carbon atoms. Preferably, Ar ¹ , Ar ² , and Ar ³ of the compound represented by Formula 1 are all C _{6 to} C ₂₄ aryl groups; A compound represented by the formula 2 Ar ^4, Ar ⁵ of at least one dibenzothiophene, or an organic electrical device comprising a composition as dibenzofuran combination, more preferably of Ar ^1, Ar compound represented by the formula (1) ² , Ar ³ is dibenzothiophene or dibenzofuran; And Ar ⁴ and Ar ⁵ of the compound represented by the formula (2) are aryl groups of C _{6 to 24} .

As another preferred example, at least one of Ar ¹ , Ar ² and Ar ³ of the compound represented by Formula 1 is dibenzothiophene or dibenzofuran; Wherein at least one of Ar ⁴ and Ar ⁵ of the compound represented by the general formula (2) is dibenzothiophene or dibenzofuran.

According to another aspect of the present invention, there is provided a composition comprising a compound represented by the formula (1) and a compound represented by the formula (2), wherein the composition comprises 10% to 90% of the compound represented by the formula An organic electric device and a display device are provided. As a preferable example, in a composition in which the compound represented by the formula (1) and the compound represented by the formula (2) are mixed, at least one of a mixing ratio of 5: 5 or 6: 4 or 7: 3 or 8: 2 or 9: Composition.

As another specific example, the composition may further include at least one compound represented by the formula (1) in a composition in which the compound represented by the formula (1) and the compound represented by the formula (2) are mixed.

In another aspect of the present invention, a compound represented by the general formula (1) is further added between the hole transporting layer and the light emitting layer using the composition of the compound represented by the general formula (1) and the compound represented by the general formula Thereby forming an organic electric device and providing a display device including the same.

In addition, the organic electroluminescent device may be formed by forming a light efficiency improvement layer on at least one surface of the first electrode and the second electrode opposite to the organic material layer, and a display device including the first electrode and the second electrode may be provided.

The organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process.

The present invention provides an electronic device including a display device including the organic electronic devices of various examples described above and a control unit for driving the display device. The organic electroluminescent device may be an organic electroluminescent device, an organic photovoltaic cell, an organophotoreceptor, an organic transistor, or an element for monochromatic or white illumination.

Hereinafter, the synthesis examples of the compound represented by the formula (1) and the production example of the organic electroluminescent device of the present invention included in the organic electroluminescent device of the present invention will be specifically described. It is not.

[Synthesis Example]

The final product of Formula 1 according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.

<Reaction Scheme 1>

Sub 1

Synthetic example of Sub 2

Sub 2 of Reaction Scheme 1 can be synthesized by the following Reaction Scheme 2 or Reaction Scheme 3, but is not limited thereto.

<Reaction Scheme 2>

<Reaction Scheme 3>

[Example of Sub 2-1]

To a round bottom flask was added Aniline (15 g, 161.1 mmol) , 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd 2 (dba) 3 (7.37 g, 8.05 mmol), P (t-Bu) 3 (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol) and toluene (1690 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 25.2 g of Sub 2-1. (Yield: 72%).

[Examples of Sub 2-26]

(15 g, 88.6 mmol), 2- (4-bromophenyl) -9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd ₂ (dba) ₃ (4.06 g, 4.43 mmol), P (t-Bu) ₃ (1.8 g, 8.86 mmol), NaOt-Bu (28.1 g, 292.5 mmol) And 34.9 g of Sub 2-26 was obtained.

(Yield: 70%).

[Examples of Sub 2-40]

To a round bottom flask was added naphthalen-1-amine (15 g, 104.8 mmol), 2-bromodibenzo [b, d] thiophene (30.3 g, 115.2 mmol), Pd ₂ (dba) ₃ (4.8 g, 5.24 mmol) t-Bu) ₃ (2.12 g, 10.48 mmol), NaOt-Bu (33.22 g, 345.7 mmol) and toluene (1100 mL) were tested in the same manner as Sub 2-1 to obtain 24.9 g of Sub 2-40.

(Yield: 73%)

[Example of Sub 2-51]

Dibenzo [b, d] furan-2-yl) aniline (15 g, 57.85 mmol), 2-bromodibenzo [b, d] furan (15.7 g, 63.63 mmol), Pd ₂ (dba) a _{3 (2.65 g, 2.89 mmol)} , P (t-Bu) 3 (1.17 g, 5.78 mmol), NaOt-Bu (18.35 g, 190.9 mmol), toluene (607 mL) in the same manner as in the Sub 2-1 17.2 g of Sub 2-51 was obtained.

(Yield: 70%).

The following Sub2-1 to Sub2-52 were synthesized in the same manner as in the synthesis method, but Sub2 is not limited thereto.

compound FD-MS compound FD-MS Sub 2-1 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 2-2 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-3 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 2-4 m / z = 169.09 (C ₁₂ H ₁₁ N = 169.22) Sub 2-5 _{m / z = 245.12 (C 18} H 15 N = 245.32) Sub 2-6 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-7 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 2-8 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 2-9 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 2-10 m / z = 325.18 (C ₂₄ H ₂₃ N = 325.45) Sub 2-11 _{m / z = 397.18 (C 30} H 23 N = 397.51) Sub 2-12 _{m / z = 447.20 (C 34} H 25 N = 447.57) Sub 2-13 _{m / z = 371.17 (C 28} H 21 N = 371.47) Sub 2-14 m / z = 421.18 (C ₃₂ H ₂₃ N = 421.53) Sub 2-15 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 2-16 _{m / z = 397.18 (C 30} H 23 N = 397.51) Sub 2-17 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-18 _{m / z = 245.12 (C 18} H 15 N = 245.32) Sub 2-19 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-20 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 2-21 _{m / z = 371.17 (C 28} H 21 N = 371.47) Sub 2-22 m / z = 421.18 (C ₃₂ H ₂₃ N = 421.53) Sub 2-23 _{m / z = 395.17 (C 30} H 21 N = 395.49) Sub 2-24 m / z = 473.21 (C ₃₆ H ₂₇ N = 473.61) Sub 2-25 _{m / z = 369.15 (C 28} H 19 N = 369.46) Sub 2-26 m / z = 561.25 (C ₄₃ H ₃₁ N = 561.71) Sub 2-27 m / z = 411.20 (C ₃₁ H ₂₅ N = 411.54) Sub 2-28 _{m / z = 459.20 (C 35} H 25 N = 459.58) Sub 2-29 _{m / z = 483.20 (C 37} H 25 N = 483.60) Sub 2-30 m / z = 375.16 (C ₂₇ H ₂₁ NO = 375.46) Sub 2-31 _{m / z = 475.19 (C 35} H 25 NO = 475.58) Sub 2-32 m / z = 575.22 (C ₄₃ H ₂₉ NO = 575.70) Sub 2-33 m / z = 533.21 (C ₄₁ H ₂₇ N = 533.66) Sub 2-34 _{m / z = 485.21 (C 37} H 27 N = 485.62) Sub 2-35 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 2-36 _{m / z = 485.21 (C 37} H 27 N = 485.62) Sub 2-37 _{m / z = 499.19 (C 37} H 25 NO = 499.60) Sub 2-38 m / z = 439.19 (C ₃₂ H ₂₅ NO = 439.55) Sub 2-39 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 2-40 _{m / z = 325.09 (C 22} H 15 NS = 325.43) Sub 2-41 _{m / z = 427.14 (C 30} H 21 NS = 427.56) Sub 2-42 _{m / z = 461.18 (C 34} H 23 NO = 461.55) Sub 2-43 m / z = 349.11 (C ₂₄ H ₁₅ NO ₂ = 349.38) Sub 2-44 m / z = 381.06 (C ₂₄ H ₁₅ NS ₂ = 381.51) Sub 2-45 m / z = 457.10 (C ₃₀ H ₁₉ NS ₂ = 457.61) Sub 2-46 m / z = 533.13 (C ₃₆ H ₂₃ NS ₂ = 533.70) Sub 2-47 _{m / z = 353.10 (C 22} H 15 N 3 S = 353.44) Sub 2-48 _{m / z = 327.0 (C 20} H 13 N 3 S = 327.40) Sub 2-49 m / z = 375.11 (C ₂₆ H ₁₇ NS = 375.48) Sub 2-50 _{m / z = 411.16 (C 30} H 21 NO = 411.49) Sub 2-51 _{m / z = 425.14 (C 30} H 19 NO 2 = 425.48) Sub 2-52 m / z = 475.16 (C ₃₄ H ₂₁ NO ₂ = 475.54)

Synthesis of the final product of formula (1)

Sub 2 (1 eq.) And Sub 1 (1.1 eq.) Were dissolved in toluene and then Pd ₂ (dba) ₃ (0.05 eq.), PPh ₃ (0.1 eq.) And NaO t- Bu (3 eq.) Were added to a round bottom flask After the addition, the mixture is refluxed at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain a final product.

Example of Final Product Synthesis

Synthesis of 1-1 '

4-yl) amine (10 g, 31.1 mmol), 4-bromo-1,1'-biphenyl (8 g, 34.2 mmol), Pd ₂ (dba ), ₃ (1.42 g, 1.56 mmol), P (t-Bu) ₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol) and toluene (330 mL) do. After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 11.1 g of Product 1-1 '. (Yield: 77%)

Synthesis of 1-4 '

(10 g, 23.7 mmol), 1- (4-bromophenyl) naphthalene (7.4 g, 26.1 mmol), Pd ₂ (dba) ₃ (1.09 g, 1.19 mmol), P (t-Bu) ₃ (0.5 g, 2.4 mmol), NaOt-Bu (7.52 g, 78.3 mmol) and toluene (250 mL) To obtain 11.5 g of 1-4 '. (Yield: 78%).

Synthesis of 1-10 '

To a round bottom flask was added N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 3', 1 "-terphenyl] -5'-amine (10 g, 25.2 mmol) P (t-Bu) ₃ (0.51 g, 1.27 mmol), Pd ₂ (dba) ₃ (1.15 g, 1.26 mmol) 2.52 mmol), NaOt-Bu (7.98 g, 83.02 mmol) and toluene (264 mL) were tested in the same manner as in 1-1 'to obtain 11.8 g of Product 1-10'. (Yield: 75%).

Synthesis of 1-19 '

(10 g, 33.6 mmol), 2-bromodibenzo [b, d] thiophene (9.8 g, 37.2 mmol) was added to a round bottom flask, _{Pd 2 (dba) 3 (1.55} g, 1.7 mmol), P (t-Bu) 3 (0.68 g, 3.38 mmol), NaOt-Bu (10.76 g, 112 mmol), toluene (355 mL) to the 1-1 'To obtain 12.3 g of Product 1-19'. (Yield: 76%).

Synthesis of 1-20 '

(10 g, 31.1 mmol), 2-bromodibenzo [b, d] thiophene (9 g, 34.2 mmol), Pd ₂ (dba) a _{3 (1.42 g, 1.56 mmol)} , P (t-Bu) 3 (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (327 mL) in the same manner as 1-1, 12.2 g of Product 1-20 'was obtained. (Yield: 78%).

Synthesis of 1-23 '

(Naphthalen-1-yl) -9,9-diphenyl-9H-fluoren-2-amine (10 g, 21.8 mmol), 2-bromodibenzo [b, d] thiophene (6.3 g, 23.9 mmol ), Pd ₂ (dba) ₃ (1 g, 1.09 mmol), P (t-Bu) ₃ (0.44 g, 2.2 mmol), NaOt-Bu (6.9 g, 71.8 mmol) -1 'to obtain 10.2 g of Product 1-23'. (Yield: 73%)

Synthesis of 1-24 '

2-amine (10 g, 20.7 mmol), 2-bromodibenzo [b, d] thiophene- P (t-Bu) ₃ (0.42 g, 2.07 mmol), NaOt-Bu (6.55 g, 68.2 mmol), Pd ₂ (dba) ₃ (0.95 g, 1.03 mmol) (220 mL) were tested in the same manner as in 1-1 'above to give 10.2 g of Product 1-24'. (Yield: 74%).

Synthesis of 1-29 '

Dibenzo [b, d] thiophen-2-amine (10 g, 30.7 mmol), 2- (4-bromophenyl) dibenzo [b, d] thiophene (11.5 g, P (t-Bu) ₃ (0.62 g, 3.07 mmol), NaOt-Bu (9.75 g, 101.4 mmol), toluene (325 mL), Pd ₂ (dBA) ₃ (1.41 g, 1.54 mmol) 12.9 g of Product 1-29 'was obtained in the same manner as in 1-1' above. (Yield: 72%).

Synthesis of 1-30 '

(10 g, 31.1 mmol), 2- (3-bromophenyl) dibenzo [1, 1'- b, d] thiophene (11.6 g , 34.2 mmol), Pd 2 (dba) 3 (1.42 g, 1.55 mmol), P (t-Bu) 3 (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103 mmol) and toluene (330 mL) were tested in the same manner as in 1-1 'above to obtain 12.8 g of Product 1-30'. (Yield: 71%).

Synthesis of 1-36 '

Dibenzo [b, d] thiophen-2-yl) amine (10 g, 26.2 mmol), 2-bromodibenzo [b, d] thiophene (7.59 g, 28.8 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.31 mmol), P (t-Bu) 3 (0.53 g, 2.62 mmol), NaOt-Bu (8.31 g, 86.5 mmol), the experiment toluene (275 mL) in the same manner as 1-1, To obtain 11.4 g of Product 1-36 '. (Yield: 77%)

Synthesis of 1-49 '

Dibenzo [b, d] furan (11.1 g, 34.2 mmol) was added to a round bottom flask and a solution of di ((1,1'-biphenyl) _{Pd 2 (dba) 3 (1.42} g, 1.56 mmol), P (t-Bu) 3 (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103 mmol), toluene (330 mL) to the 1-1 'To obtain 13.3 g of Product 1-49'. (Yield: 76%).

Synthesis of 1-51 '

A solution of N- (4- (naphthalen-1-yl) phenyl) naphthalen-2-amine (10 g, 28.9 mmol), 2- (7- yl) dibenzo [b, d] furan (14 g, 32 mmol), Pd 2 (dba) 3 (1.33 g, 1.45 mmol), P (t-Bu) 3 (0.59 g, 2.9 mmol), NaOt-Bu ( 9.2 g, 95.5 mmol) and toluene (310 mL) were tested in the same manner as in 1-1 above to give 14.5 g of Product 1-51 '. (Yield: 71%).

Synthesis of 1-59 '

4-yl) benzo [4,5] thieno [3,2-d] pyrimidin-2-amine (10 g, 28.3 mmol), 4- 4-bromophenyl) dibenzo [b, d] furan (10.1 g, 31.1 mmol), Pd 2 (dba) 3 (1.3 g, 1.41 mmol), P (t-Bu) 3 (0.57 g, 2.83 mmol), NaOt- Bu (8.98 g, 93.4 mmol) and toluene (300 mL) were tested in the same manner as in 1-1 'above to give 12.3 g of Product 1-59'. (Yield: 73%)

Synthesis of 1-71 '

(10.1 g, 31.1 mmol), 2- (4-bromophenyl) -9,9'-spirobi [fluorene] (16.1 g, 34.2 mmol) was added to a round bottom flask. wherein an _{mmol), Pd 2 (dba)} 3 (1.42 g, 1.56 mmol), P (t-Bu) 3 (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (330 mL) 1-1 '' to obtain 15.5 g of Product 1-71 '. (Yield: 70%).

Synthesis of 1-75 '

4-amine (10 g, 17.8 mmol), 3-bromo (4-methylphenyl) -9,9-diphenyl-9H-fluorene ( 7.78 g, 19.6 mmol), Pd 2 (dba) 3 (0.82 g, 0.89 mmol), P (t-Bu) 3 (0.36 g, 1.78 mmol), NaOt-Bu (5.65 g, 58.75 mmol) and toluene (190 mL) were tested in the same manner as in 1-1 'above to obtain 11.3 g of Product 1-75'. (Yield: 72%).

compound FD-MS compound FD-MS 1-1 ' m / z = 473.21 (C ₃₆ H ₂₇ N = 473.61) 1-2 ' m / z = 523.23 (C ₄₀ H ₂₉ N = 523.66) 1-3 ' m / z = 573.25 (C ₄₄ H ₃₁ N = 573.72) 1-4 ' m / z = 623.26 (C ₄₈ H ₃₃ N = 623.78) 1-5 ' _{m / z = 447.20 (C 34} H 25 N = 447.57) 1-6 ' _{m / z = 371.17 (C 28} H 21 N = 371.47) 1-7 ' m / z = 471.20 (C ₃₆ H ₂₅ N = 471.59) 1-8 ' m / z = 521.21 (C ₄₀ H ₂₇ N = 521.65) 1-9 ' m / z = 549.25 (C ₄₂ H ₃₁ N = 549.70) 1-10 ' m / z = 625.28 (C ₄₈ H ₃₅ N = 625.80) 1-11 ' m / z = 675.29 (C ₅₂ H ₃₇ N = 675.86) 1-12 ' m / z = 473.21 (C ₃₆ H ₂₇ N = 473.61) 1-13 ' m / z = 523.23 (C ₄₀ H ₂₉ N = 523.66) 1-14 ' m / z = 623.26 (C ₄₈ H ₃₃ N = 623.78) 1-15 ' m / z = 549.25 (C ₄₂ H ₃₁ N = 549.70) 1-16 ' m / z = 625.28 (C ₄₈ H ₃₅ N = 625.80) 1-17 ' m / z = 503.17 (C ₃₆ H ₂₅ NS = 503.66) 1-18 ' m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 1-19 ' m / z = 477.16 (C ₃₄ H ₂₃ NS = 477.62) 1-20 ' m / z = 503.17 (C ₃₆ H ₂₅ NS = 503.66) 1-21 ' m / z = 451.14 (C ₃₂ H ₂₁ NS = 451.58) 1-22 ' m / z = 593.22 (C ₄₃ H ₃₁ NS = 593.78) 1-23 ' m / z = 641.22 (C ₄₇ H ₃₁ NS = 641.82) 1-24 ' m / z = 665.22 (C ₄₉ H ₃₁ NS = 665.84) 1-25 ' m / z = 503.17 (C ₃₆ H ₂₅ NS = 503.66) 1-26 ' m / z = 655.23 (C ₄₈ H ₃₃ NS = 655.85) 1-27 ' m / z = 695.26 (C ₅₁ H ₃₇ NS = 695.91) 1-28 ' m / z = 593.18 (C ₄₂ H ₂₇ NOS = 593.73) 1-29 ' m / z = 583.14 (C ₄₀ H ₂₅ NS ₂ = 583.76) 1-30 ' m / z = 579.20 (C ₄₂ H ₂₉ NS = 579.75) 1-31 ' m / z = 685.19 (C ₄₈ H ₃₁ NS ₂ = 685.90) 1-32 ' m / z = 719.23 (C ₅₂ H ₃₃ NOS = 719.89) 1-33 ' m / z = 629.22 (C ₄₆ H ₃₁ NS = 629.81) 1-34 ' m / z = 629.22 (C ₄₆ H ₃₁ NS = 629.81) 1-35 ' m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 1-36 ' m / z = 563.08 (C ₃₆ H ₂₁ NS ₃ = 563.75) 1-37 ' m / z = 639.11 (C ₄₂ H ₂₅ NS ₃ = 639.85) 1-38 ' m / z = 715.15 (C ₄₈ H ₂₉ NS ₃ = 715.95) 1-39 ' m / z = 791.18 (C ₅₄ H ₃₃ NS ₃ = 792.04) 1-40 ' m / z = 607.16 (C ₄₂ H ₂₅ NO ₂ S = 607.72) 1-41 ' m / z = 633.21 (C ₄₅ H ₃₁ NOS = 633.80) 1-42 ' m / z = 733.24 (C ₅₃ H ₃₅ NOS = 733.92) 1-43 ' m / z = 883.29 (C ₆₅ H ₄₁ NOS = 884.09) 1-44 ' m / z = 585.13 (C ₃₈ H ₂₃ N ₃ S ₂ = 585.74) 1-45 ' m / z = 553.19 (C ₄₀ H ₂₇ NS = 553.71) 1-46 ' m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 1-47 ' m / z = 841.28 (C ₆₃ H ₃₉ NS = 842.06) 1-48 ' m / z = 563.22 (C ₄₂ H ₂₉ NO = 563.69) 1-49 ' m / z = 563.22 (C ₄₂ H ₂₉ NO = 563.69) 1-50 ' m / z = 613.24 (C ₄₆ H ₃₁ NO = 613.74) 1-51 ' m / z = 703.29 (C ₅₃ H ₃₇ NO = 703.87) 1-52 ' m / z = 587.22 (C ₄₄ H ₂₉ NO = 587.71) 1-53 ' m / z = 639.26 (C ₄₈ H ₃₃ NO = 639.78) 1-54 ' m / z = 639.26 (C ₄₈ H ₃₃ NO = 639.78) 1-55 ' m / z = 653.24 (C ₄₈ H ₃₁ NO ₂ = 653.77) 1-56 ' m / z = 603.26 (C ₄₅ H ₃₃ NO = 603.75) 1-57 ' m / z = 727.29 (C ₅₅ H ₃₇ NO = 727.89) 1-58 ' m / z = 725.27 (C ₅₅ H ₃₅ NO = 725.87) 1-59 ' m / z = 595.17 (C ₄₀ H ₂₅ N ₃ OS = 595.71) 1-60 ' m / z = 567.26 (C ₄₂ H ₃₃ NO = 567.72) 1-61 ' m / z = 611.22 (C ₄₆ H ₂₉ NO = 611.73) 1-62 ' m / z = 617.18 (C ₄₄ H ₂₇ NOS = 617.76) 1-63 ' m / z = 637.24 (C ₄₈ H ₃₁ NO = 637.77) 1-64 ' m / z = 667.21 (C ₄₈ H ₂₉ NO ₃ = 667.75) 1-65 ' m / z = 767.25 (C ₅₆ H ₃₃ NO ₃ = 767.87) 1-66 ' m / z = 681.27 (C ₅₀ H ₃₅ NO ₂ = 681.82) 1-67 ' m / z = 713.31 (C ₅₅ H ₃₉ N = 713.90) 1-68 ' m / z = 589.28 (C ₄₅ H ₃₅ N = 589.77) 1-69 ' m / z = 639.29 (C ₄₉ H ₃₇ N = 639.82) 1-70 ' m / z = 613.28 (C ₄₇ H ₃₅ N = 613.79) 1-71 ' m / z = 711.29 (C ₅₆ H ₃₇ N = 711.89) 1-72 ' m / z = 637.28 (C ₄₉ H ₃₅ N = 637.81) 1-73 ' m / z = 761.31 (C ₅₉ H ₃₉ N = 761.95) 1-74 ' m / z = 637.28 (C ₄₉ H ₃₅ N = 637.81) 1-75 ' m / z = 877.37 (C ₆₈ H ₄₇ N = 878.11) 1-76 ' m / z = 875.36 (C ₆₈ H ₄₅ N = 876.09) 1-77 ' m / z = 813.30 (C ₆₂ H ₃₉ NO = 813.98)

The final product of Formula 2 according to the present invention is prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 4 below.

<Reaction Scheme 4>

Synthesis example of Sub 3 (when L 4 is not a single bond)

1) M3-2-1 Synthesis Example

After dissolving 2-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in 980 mL of DMF, bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol) 41.3 g, 420 mmol) were added in this order, followed by stirring for 24 hours to synthesize a borate compound. The resulting compound was separated by silicagel column and recrystallization to obtain 36.2 g (70%) of a borate compound.

2) Synthesis example of M3-2-2

43.6 g (67%) was obtained through the same experimental procedure as M3-2-1.

3) Sub 3-1-1 Synthesis Example

M3-2-1 (29.5 g, 80 mmol) was dissolved in THF 360 mL, 4-bromo- 4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3) 4 ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL), and the mixture is refluxed with stirring. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 26.95 g (70%) of the product

4) Sub 3-1-2 Synthesis Example

M3-2-1 (29.5 g, 80 mmol) , THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd (PPh 3) 4 (2.8 g, 2.4 mmol), NaOH (9.6 g , 240 mmol) and 180 mL of water, 23.26 g (73%) of the product was obtained through the same experimental procedure as Sub 3-1-1

5) Sub 3-1-3 Synthesis Example

M3-2-1 (29.5 g, 80 mmol) was dissolved in THF 360 mL, 4'-bromo- 3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd (PPh 3) 4 ( 2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL) were added, and 25.8 g (68%) of the product was obtained through the same experimental procedure as Sub 3-1-1.

6) Sub 3-1-4 Synthetic Example

After dissolving M3-2-2 (35.63 g, 80 mmol) obtained in the above synthesis in 360 mL of THF, 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL), and the mixture is refluxed with stirring. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 30.4 g (69%) of the product.

 Synthetic example of Sub 4

Sub 4 of Scheme 1 can be synthesized by the reaction path of Scheme 5 below.

<Reaction Scheme 5>

Synthetic example of Sub 4-28

4-bromo-1,1'-biphenyl ( 5.6g, 24mmol) was dissolved in toluene, [1,1'-biphenyl] -4- amine (3.4 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P ( t-Bu) 3 (0.2 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol), toluene (300 mL) then was added to each, stirred for 24 hours at 100 ℃ Reflux. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resultant organic material was purified by silicagel column and recrystallized to obtain 6.2 g (yield: 80%) of final compound.

Examples of Sub 4 include, but are not limited to, the following.

compound FD-MS compound FD-MS Sub 4-1 m / z = 169.09 (C ₁₂ H ₁₁ N = 169.22) Sub 4-2 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 4-3 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 4-4 _{m / z = 245.12 (C 18} H 15 N = 245.32) Sub 4-5 m / z = 170.08 (C ₁₁ H ₁₀ N ₂ = 170.21) Sub 4-6 _{m / z = 199.10 (C 10} H 13 NO = 199.25) Sub 4-7 m / z = 225.15 (C ₁₆ H ₁₉ N = 225.33) Sub 4-8 _{m / z = 285.15 (C 21} H 19 N = 285.38) Sub 4-9 m / z = 409.18 (C ₃₁ H ₂₃ N = 409.52) Sub 4-10 m / z = 407.17 (C ₃₁ H ₂₁ N = 407.51) Sub 4-11 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 4-12 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 4-13 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 4-14 _{m / z = 220.10 (C 15} H 12 N 2 = 220.27) Sub 4-15 _{m / z = 249.12 (C 17} H 12 NO = 249.31) Sub 4-16 m / z = 275.17 (C ₂₀ H ₂₁ N = 275.39) Sub 4-17 _{m / z = 335.17 (C 25} H 21 N = 335.44) Sub 4-18 _{m / z = 459.20 (C 35} H 25 N = 459.58) Sub 4-19 _{m / z = 457.18 (C 35} H 23 N = 457.56) Sub 4-20 _{m / z = 269.12 (C 20} H 15 N = 269.34) Sub 4-21 _{m / z = 295.14 (C 22} H 17 N = 295.38) Sub 4-22 _{m / z = 220.10 (C 15} H 2 N 2 = 220.27) Sub 4-23 _{m / z = 249.12 (C 17} H 15 NO = 249.31) Sub 4-24 m / z = 275.17 (C ₂₀ H ₂₁ N = 275.39) Sub 4-25 _{m / z = 335.17 (C 25} H 21 N = 335.44) Sub 4-26 _{m / z = 459.20 (C 35} H 25 N = 459.58) Sub 4-27 _{m / z = 457.18 (C 35} H 23 N = 457.56) Sub 4-28 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 4-29 _{m / z = 246.12 (C 17} H 14 N 2 = 246.31) Sub 4-30 _{m / z = 275.13 (C 19} H 17 NO = 275.34) Sub 4-31 _{m / z = 301.18 (C 22} H 23 N = 301.42) Sub 4-32 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 4-33 _{m / z = 485.21 (C 37} H 27 N = 485.62) Sub 4-34 _{m / z = 483.20 (C 37} H 25 N = 483.60) Sub 4-35 _{m / z = 171.08 (C 10} H 09 N 3 = 171.20) Sub 4-36 m / z = 200.09 (C ₁₂ H ₁₂ N ₂ O = 200.24) Sub 4-37 _{m / z = 226.15 (C 15} H 18 N 2 = 226.32) Sub 4-38 _{m / z = 286.15 (C 20} H 18 N 2 = 286.37) Sub 4-39 _{m / z = 410.18 (C 30} H 22 N 2 = 410.51) Sub 4-40 _{m / z = 408.16 (C 30} H 20 N 2 = 408.49) Sub 4-41 _{m / z = 229.11 (C 14} H 15 NO 2 = 229.27) Sub 4-42 _{m / z = 255.16 (C 17} H 21 NO = 255.35) Sub 4-43 _{m / z = 315.16 (C 22} H 21 NO = 315.41) Sub 4-44 m / z = 439.19 (C ₃₂ H ₂₅ NO = 439.55) Sub 4-45 m / z = 437.18 (C ₃₂ H ₂₃ NO = 437.53) Sub 4-46 m / z = 281.21 (C ₂₀ H ₂₇ N = 281.44) Sub 4-47 _{m / z = 341.21 (C 25} H 27 N = 341.49) Sub 4-48 _{m / z = 465.25 (C 35} H 31 N = 465.63) Sub 4-49 _{m / z = 463.23 (C 35} H 29 N = 463.61) Sub 4-50 _{m / z = 401.21 (C 30} H 27 N = 401.54) Sub 4-51 m / z = 525.25 (C ₄₀ H ₃₁ N = 525.68) Sub 4-52 m / z = 523.23 (C ₄₀ H ₂₉ N = 523.66) Sub 4-53 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 4-54 _{m / z = 401.12 (C 28} H 19 NS = 401.52) Sub 4-55 m / z = 357.11 (C ₂₆ H ₁₇ NS = 375.48) Sub 4-56 _{m / z = 427.14 (C 30} H 21 NS = 427.56) Sub 4-57 m / z = 335.13 (C ₂₄ H ₁₇ NO = 335.40) Sub 4-58 _{m / z = 385.15 (C 28} H 19 NO = 385.46) Sub 4-59 m / z = 349.11 (C ₂₄ H ₁₅ NO ₂ = 349.38) Sub 4-60 m / z = 381.06 (C ₂₄ H ₁₅ NS ₂ = 381.51) Sub 4-61 m / z = 365.09 (C ₂₄ H ₁₅ NOS = 365.45) Sub 4-62 m / z = 533.13 (C ₃₆ H ₂₃ NS ₂ = 533.70) Sub 4-63 _{m / z = 501.17 (C 36} H 23 NO 2 = 501.57) Sub 4-64 m / z = 517.15 (C ₃₆ H ₂₃ NOS = 349.38)

Synthesis of Final Product 2 of Formula (2)

Synthetic example of 2-5 '

Sub 3-1-2 (9.6 g, 24 mmol) was dissolved in toluene followed by Sub 4-32 (7.2 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, Bu) ₃ (0.2 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (300 mL) were added to the solution, and the mixture was refluxed at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 13.2 g (yield: 81%) of final compound.

Synthetic examples of 2-10 '

Sub 3-1-5 (9.6 g, 24 mmol) was dissolved in toluene followed by Sub 4-28 (6.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, ), ₃ (0.2 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (300 mL) were added, 78%).

Synthesis example of 2-14 '

Sub 3-1-4 (11.4 g, 24 mmol) was dissolved in toluene followed by Sub 4-13 (5.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, _{Bu) 3 (0.2 g, 2} mmol), NaO t -Bu (5.8 g, 60 mmol), toluene (300 mL) after the addition of each of the 2-5 '13.7g of the final compound using the synthetic method (yield : 83%).

Synthesis Example of 2-36 '

Sub 3-1-2 (9.6 g, 24 mmol) was dissolved in toluene followed by Sub 4-53 (7.0 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, _{Bu) 3 (0.2 g, 2} mmol), NaO t -Bu (5.8 g, 60 mmol), toluene (300 mL) after the addition of each of the 2-5 '12.5g of the final compound using the synthetic method (yield : 78%).

Synthesis Example of 2-46 '

Sub 3-1-5 (7.7 g, 24 mmol) was dissolved in toluene followed by Sub 4-58 (7.7 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, After the addition of ₃ (0.2 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (300 mL), the final compound was obtained in a yield of 12.2 g : 81%).

Synthetic example of 2-56 '

Sub 3-1-6 (9.6 g, 24 mmol) was dissolved in toluene followed by Sub 4-61 (7.3 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, After the addition of ₃ (0.2 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (300 mL), the final compound was obtained in a yield of 12.3 g : 75%).

The obtained product was confirmed by Mass Data as follows.

compound FD-MS compound FD-MS 2-1 ' m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.70) 2-2 ' m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) 2-3 ' m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.70) 2-4 ' m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 2-5 ' m / z = 678.30 (C ₄₂ H ₃₈ N ₂ = 678.86) 2-6 ' m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.00) 2-7 ' m / z = 800.32 (C ₆₁ H ₄₀ N ₂ = 800.98) 2-8 ' m / z = 602.27 (C ₄₅ H ₃₄ N ₂ = 602.76) 2-9 ' m / z = 774.30 (C ₅₉ H ₃₈ N ₂ = 774.95) 2-10 ' m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 2-11 ' m / z = 678.30 (C ₅₁ H ₃₈ N ₂ = 678.86) 2-12 ' m / z = 802.33 (C ₆₁ H ₄₂ N ₂ = 803.00) 2-13 ' m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 2-14 ' m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 2-15 ' m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86)) 2-16 ' m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.89) 2-17 ' m / z = 754.33 (C ₅₇ H ₄₂ N ₂ = 754.96) 2-18 ' m / z = 878.37 (C ₆₇ H ₄₆ N ₂ = 879.10) 2-19 ' m / z = 876.35 (C ₆₇ H ₄₄ N ₂ = 877.08) 2-20 ' m / z = 744.26 (C ₅₄ H ₃₆ N ₂ S = 744.94) 2-21 ' m / z = 638.27 (C ₄₈ H ₃₄ N ₂ = 638.80) 2-22 ' m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 2-23 ' m / z = 688.29 (C ₅₂ H ₃₆ N ₂ = 688.86) 2-24 ' m / z = 714.30 (C ₅₄ H ₃₈ N ₂ = 714.89) 2-25 ' m / z = 652.29 (C ₄₉ H ₃₆ N ₂ = 652.82) 2-26 ' m / z = 602.27 (C ₄₅ H ₃₄ N ₂ = 602.76) 2-27 ' m / z = 612.26 (C ₄₆ H ₃₂ N ₂ = 612.76) 2-28 ' m / z = 562.24 (C ₄₂ H ₃₀ N ₂ = 562.70) 2-29 ' m / z = 762.30 (C ₅₈ H ₃₈ N ₂ = 762.94) 2-30 ' m / z = 662.27 (C ₅₀ H ₃₄ N ₂ = 662.82) 2-31 ' m / z = 686.27 (C ₅₂ H ₃₄ N ₂ = 686.84) 2-32 ' m / z = 762.30 (C ₅₈ H ₃₈ N ₂ = 762.94) 2-33 ' m / z = 592.20 (C ₄₂ H ₂₈ N ₂ S = 592.75) 2-34 ' m / z = 642.21 (C ₄₆ H ₃₀ N ₂ S = 642.81) 2-35 ' m / z = 642.21 (C ₄₆ H ₃₀ N ₂ S = 642.81) 2-36 ' m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.85) 2-37 ' m / z = 668.23 (C ₄₈ H ₃₂ N ₂ S = 668.85) 2-38 ' m / z = 642.21 (C ₄₆ H ₃₀ N ₂ S = 642.81) 2-39 ' m / z = 692.23 (C ₅₀ H ₃₂ N ₂ S = 692.87) 2-40 ' m / z = 744.26 (C ₅₄ H ₃₆ N ₂ S = 744.94) 2-41 ' m / z = 576.22 (C ₄₂ H ₂₈ N ₂ O = 576.22) 2-42 ' m / z = 702.27 (C ₅₂ H ₃₄ N ₂ O = 702.84) 2-43 ' m / z = 702.27 (C ₅₂ H ₃₄ N ₂ O = 702.84) 2-44 ' m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.78) 2-45 ' m / z = 652.25 (C ₄₈ H ₃₂ N ₂ O = 652.78) 2-46 ' m / z = 626.24 (C ₄₆ H ₃₀ N ₂ O = 626.74) 2-47 ' m / z = 676.25 (C ₅₀ H ₃₂ N ₂ O = 676.80) 2-48 ' m / z = 728.28 (C ₅₄ H ₃₆ N ₂ O = 728.88) 2-49 ' m / z = 622.15 (C ₄₂ H ₂₆ N ₂ S ₂ = 622.80) 2-50 ' m / z = 698.19 (C ₄₈ H ₃₀ N ₂ S ₂ = 698.90) 2-51 ' m / z = 850.25 (C ₆₀ H ₃₈ N ₂ S ₂ = 851.09) 2-52 ' m / z = 804.17 (C ₅₄ H ₃₂ N ₂ S ₃ = 805.04) 2-53 ' m / z = 606.18 (C ₄₂ H ₂₆ N ₂ OS = 606.73) 2-54 ' m / z = 682.21 (C ₄₈ H ₃₀ N ₂ OS = 682.83) 2-55 ' m / z = 834.27 (C ₆₀ H ₃₈ N ₂ OS = 835.02) 2-56 ' m / z = 683.20 (C ₄₇ H ₂₉ N ₃ OS = 683.82)

Evaluation of manufacturing of organic electric device

[Example I-1] Blue organic electroluminescent device (hole transport layer)

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as a hole transport layer material. First, 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ") was vacuum deposited on the ITO layer (anode) To form a hole injection layer, and then the mixture of the present invention was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Subsequently, a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping 9,10-di (naphthalen-2-yl) anthracene on the hole transport layer and BD-052X (Idemitsukosan) as a dopant. Subsequently, aluminum (1,1-bisphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum forming a blocking layer, and a tris (8-quinolinol) aluminum (hereinafter referred to as "Alq _3" abbreviated as) on the hole blocking layer to form an electron transport layer was vacuum deposited to a thickness of 40 nm. Thereafter, LiF as 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. Thus, an organic electroluminescent device was manufactured.

[Comparative Example 1]

An organic electroluminescence device was fabricated in the same manner as in Example I-1, except that the following Comparative Compound 1 was used instead of the mixture of the present invention as the hole transport layer material.

[Comparative Example 2]

An organic electroluminescent device was fabricated in the same manner as in Example I-1, except that the compound of the present invention was used alone as the hole transport layer material instead of the compound of the present invention.

[Comparative Example 3]

An organic electroluminescent device was fabricated in the same manner as in Example I-1, except that the compound of the invention 2-5 'was used alone as a hole transport layer material instead of the mixture of the present invention.

The electroluminescence (EL) characteristics of the organic electroluminescent devices manufactured according to Examples and Comparative Examples 1 to 3 were measured by applying a forward bias DC voltage to PR-650 of a photoresearch company, The measured T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a luminance of 500 cd / m 2. The following table shows the results of device fabrication and evaluation.

Mixing ratio Compound A Compound B Driving
Voltage electric current
(mA / cm 2) Luminance
(cd / m &lt; 2 & efficiency
(cd / A) Luminous color T (95) Comparative Example (1) Single compound Comparative Compound (1) none 4.5 15.2 500.0 3.3 blue 83 Comparative Example (2) Single compound Compound 1-1 none 4.6 11.4 500.0 4.4 blue 90 Comparative Example (3 Single compound Compound 1-17 none 4.7 11.9 500.0 4.2 blue 93 Comparative Example (4) Single compound Compound 2-5 none 4.1 9.8 500.0 4.9 blue 97 Example (1) A (2): B (8) Compound 1-1 ' Compound 2-4 ' 4.0 84.7 5000.0 5.9 blue 126.0 Example (2) A (2): B (8) Compound 1-1 ' Compound 2-5 ' 4.1 86.4 5000.0 5.8 blue 120.9 Example (3) A (2): B (8) Compound 1-1 ' Compound 2-6 ' 4.0 83.9 5000.0 6.0 blue 127.4 Example (4) A (2): B (8) Compound 1-1 ' Compound 2-7 ' 4.0 87.0 5000.0 5.7 blue 119.6 Example (5) A (2): B (8) Compound 1-1 ' Compound 2-11 ' 4.1 92.3 5000.0 5.4 blue 128.9 Example (6) A (2): B (8) Compound 1-1 ' Compound 2-28 ' 4.0 90.0 5000.0 5.6 blue 120.3 Example (7) A (2): B (8) Compound 1-1 ' Compound 2-36 ' 4.1 86.3 5000.0 5.8 blue 113.7 Example (8) A (2): B (8) Compound 1-1 ' Compound 2-48 ' 4.1 94.0 5000.0 5.3 blue 106.4 Example (9) A (2): B (8) Compound 1-1 ' Compound 2-50 ' 4.1 85.5 5000.0 5.8 blue 100.3 Example (10) A (2): B (8) Compound 1-1 ' Compound 2-54 ' 4.1 84.6 5000.0 5.9 blue 115.5 Example (11) A (3): B (7) Compound 1-1 ' Compound 2-4 ' 4.0 89.4 5000.0 5.6 blue 109.5 Example (12) A (3): B (7) Compound 1-1 ' Compound 2-5 ' 4.0 88.9 5000.0 5.6 blue 122.6 Example (13) A (3): B (7) Compound 1-1 ' Compound 2-6 ' 4.1 87.5 5000.0 5.7 blue 109.9 Example (14) A (3): B (7) Compound 1-1 ' Compound 2-7 ' 4.0 84.5 5000.0 5.9 blue 101.1 Example (15) A (3): B (7) Compound 1-1 ' Compound 2-11 ' 4.0 91.8 5000.0 5.4 blue 119.5 Example (16) A (3): B (7) Compound 1-1 ' Compound 2-28 ' 4.1 85.2 5000.0 5.9 blue 108.6 Example (17) A (3): B (7) Compound 1-1 ' Compound 2-36 ' 4.0 85.5 5000.0 5.8 blue 118.5 Example (18) A (3): B (7) Compound 1-1 ' Compound 2-48 ' 4.0 88.5 5000.0 5.6 blue 117.4 Example (19) A (3): B (7) Compound 1-1 ' Compound 2-50 ' 4.1 83.4 5000.0 6.0 blue 109.5 Example (20) A (3): B (7) Compound 1-1 ' Compound 2-54 ' 4.1 91.3 5000.0 5.5 blue 101.0 Example (21) A (4): B (6) Compound 1-1 ' Compound 2-4 ' 4.1 83.7 5000.0 6.0 blue 124.4 Example (22) A (4): B (6) Compound 1-1 ' Compound 2-5 ' 4.0 85.4 5000.0 5.9 blue 111.6 Example (23) A (4): B (6) Compound 1-1 ' Compound 2-6 ' 4.0 90.0 5000.0 5.6 blue 128.2 Example (24) A (4): B (6) Compound 1-1 ' Compound 2-7 ' 4.1 83.6 5000.0 6.0 blue 127.6 Example (25) A (4): B (6) Compound 1-1 ' Compound 2-11 ' 4.1 84.7 5000.0 5.9 blue 109.8 Example (26) A (4): B (6) Compound 1-1 ' Compound 2-28 ' 4.1 88.9 5000.0 5.6 blue 116.9 Example (27) A (4): B (6) Compound 1-1 ' Compound 2-36 ' 4.1 86.4 5000.0 5.8 blue 129.8 Example (28) A (4): B (6) Compound 1-1 ' Compound 2-48 ' 4.1 87.8 5000.0 5.7 blue 104.7 Example (29) A (4): B (6) Compound 1-1 ' Compound 2-50 ' 4.1 86.1 5000.0 5.8 blue 128.8 Example (30) A (4): B (6) Compound 1-1 ' Compound 2-54 ' 4.1 87.5 5000.0 5.7 blue 115.4 Example (31) A (5): B (5) Compound 1-1 ' Compound 2-4 ' 4.2 82.1 5000.0 6.1 blue 130.3 Example (32) A (5): B (5) Compound 1-1 ' Compound 2-5 ' 4.3 73.0 5000.0 6.8 blue 133.2 Example (33) A (5): B (5) Compound 1-1 ' Compound 2-6 ' 4.3 75.4 5000.0 6.6 blue 130.0 Example (34) A (5): B (5) Compound 1-1 ' Compound 2-7 ' 4.2 79.1 5000.0 6.3 blue 132.7 Example (35) A (5): B (5) Compound 1-1 ' Compound 2-11 ' 4.2 81.4 5000.0 6.1 blue 131.1 Example (36) A (5): B (5) Compound 1-1 ' Compound 2-28 ' 4.3 72.8 5000.0 6.9 blue 130.8 Example (37) A (5): B (5) Compound 1-1 ' Compound 2-36 ' 4.3 82.1 5000.0 6.1 blue 133.1 Example (38) A (5): B (5) Compound 1-1 ' Compound 2-48 ' 4.3 71.8 5000.0 7.0 blue 131.7 Example (39) A (5): B (5) Compound 1-1 ' Compound 2-50 ' 4.2 75.7 5000.0 6.6 blue 132.7 Example (40) A (5): B (5) Compound 1-1 ' Compound 2-54 ' 4.3 82.0 5000.0 6.1 blue 130.1 Example (41) A (7): B (3) Compound 1-1 ' Compound 2-4 ' 4.6 5.4 300.0 5.6 blue 120.9 Example (42) A (7): B (3) Compound 1-1 ' Compound 2-5 ' 4.4 5.1 300.0 5.8 blue 121.2 Example (43) A (7): B (3) Compound 1-1 ' Compound 2-6 ' 4.5 5.3 300.0 5.7 blue 111.7 Example (44) A (7): B (3) Compound 1-1 ' Compound 2-7 ' 4.5 5.0 300.0 6.0 blue 100.8 Example (45) A (7): B (3) Compound 1-1 ' Compound 2-11 ' 4.4 5.2 300.0 5.7 blue 101.5 Example (46) A (7): B (3) Compound 1-1 ' Compound 2-28 ' 4.6 5.1 300.0 5.9 blue 113.2 Example (47) A (7): B (3) Compound 1-1 ' Compound 2-36 ' 4.4 5.4 300.0 5.6 blue 107.9 Example (48) A (7): B (3) Compound 1-1 ' Compound 2-48 ' 4.5 5.5 300.0 5.5 blue 109.4 Example (49) A (7): B (3) Compound 1-1 ' Compound 2-50 ' 4.5 5.5 300.0 5.5 blue 123.6 Example (50) A (7): B (3) Compound 1-1 ' Compound 2-54 ' 4.5 5.1 300.0 5.9 blue 101.0 Example (51) A (5): B (5) Compound 1-17 ' Compound 2-4 ' 4.2 4.3 300.0 7.1 blue 147.0 Example (52) A (5): B (5) Compound 1-17 ' Compound 2-5 ' 4.0 4.2 300.0 7.1 blue 143.5 Example (53) A (5): B (5) Compound 1-17 ' Compound 2-6 ' 4.0 4.2 300.0 7.2 blue 137.2 Example (54) A (5): B (5) Compound 1-17 ' Compound 2-7 ' 4.0 4.1 300.0 7.3 blue 139.6 Example (55) A (5): B (5) Compound 1-17 ' Compound 2-11 ' 4.1 4.1 300.0 7.3 blue 146.8 Example (56) A (5): B (5) Compound 1-17 ' Compound 2-28 ' 4.2 4.2 300.0 7.2 blue 147.8 Example (57) A (5): B (5) Compound 1-17 ' Compound 2-36 ' 4.2 4.1 300.0 7.4 blue 135.5 Example (58) A (5): B (5) Compound 1-17 ' Compound 2-48 ' 4.1 4.3 300.0 7.0 blue 145.9 Example (59) A (5): B (5) Compound 1-17 ' Compound 2-50 ' 4.0 4.2 300.0 7.2 blue 142.1 Example (60) A (5): B (5) Compound 1-17 ' Compound 2-54 ' 4.1 4.1 300.0 7.2 blue 140.4 Example (61) A (5): B (5) Compound 1-52 ' Compound 2-4 ' 4.0 4.1 300.0 7.4 blue 146.9 Example (62) A (5): B (5) Compound 1-52 ' Compound 2-5 ' 4.2 4.1 300.0 7.3 blue 137.6 Example (63) A (5): B (5) Compound 1-52 ' Compound 2-6 ' 4.1 4.0 300.0 7.4 blue 143.8 Example (64) A (5): B (5) Compound 1-52 ' Compound 2-7 ' 4.2 4.2 300.0 7.2 blue 141.7 Example (65) A (5): B (5) Compound 1-52 ' Compound 2-11 ' 4.1 4.0 300.0 7.5 blue 135.6 Example (66) A (5): B (5) Compound 1-52 ' Compound 2-28 ' 4.1 4.1 300.0 7.4 blue 143.0 Example (67) A (5): B (5) Compound 1-52 ' Compound 2-36 ' 4.1 4.0 300.0 7.5 blue 144.7 Example (68) A (5): B (5) Compound 1-52 ' Compound 2-48 ' 4.1 4.1 300.0 7.4 blue 139.4 Example (69) A (5): B (5) Compound 1-52 ' Compound 2-50 ' 4.1 4.0 300.0 7.5 blue 142.9 Example (70) A (5): B (5) Compound 1-52 ' Compound 2-54 ' 4.1 4.3 300.0 7.0 blue 150.0

As can be seen from the results of the above table, when the mixture of the present invention is used as a hole transporting layer, it can be confirmed that the compound of the present invention exhibits higher efficiency and longer lifetime than Comparative Compounds 1 to 4 using a single compound.

Compound 1-1, which is a tertiary amine substituted with an aryl group (biphenyl), and compound (2-4 ', 2-5 (Mixing ratio) of 2: 8, 2-6 ', 2-7', 2-11 ', 2-28', 2-36 ', 2-48', 2-50 ', 2-54' And the results of Examples 1 to 10, which were measured as a hole transporting layer, showed an increase in efficiency and lifetime and a decrease in driving voltage as compared with Comparative Examples 1 to 4 in which a single compound was used as a hole transporting layer. In particular, when comparing the results with Comparative Example 2 using 1-1 'as a single compound, it is confirmed that the efficiency is increased by about 134% when the compound containing carbazole represented by Formula 2 is mixed and used as a hole transport layer , And life span also increased by 140%.

As a result of proceeding from Examples 1 to 70, it was confirmed that when the mixing ratio was 5: 5, the highest efficiency increase and the lifetime increase were observed. Therefore, when 1-17 'and 1-52' in which the mixing ratio is limited to 5: 5 and the heterocyclic group of the compound represented by Compound 1 is substituted are mixed with the compound represented by Formula 2, and the device is measured, It is confirmed that the results obtained by mixing 1-17 'and 1-52' in which Dibenzofuran or Dibenzothiophen is substituted with the compound represented by the general formula (2) are more excellent in terms of efficiency and life I could.

That is, as a result of using the compound represented by the formula (1) and the compound represented by the formula (2) in the hole transport layer, it was confirmed that the lifetime and the efficiency were better than those using the single compound. It was confirmed that the results were slightly different. Among them, the device result with the mixing ratio of 5: 5 was the best. This proves that the present invention is more advanced than an example using a conventional single compound as a hole transport layer.

The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all techniques within the scope of the same should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: First electrode (anode) 130: Hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode (cathode)

Claims (19)

A first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a hole transport layer and a light emitting layer including a light emitting compound,
Wherein the hole transporting layer is composed of a composition in which an arylamine-based compound and a carbazole-based compound are mixed as two kinds of compounds having different structures from each other, and the weight ratio of the compounds of the different structural formulas is selected from 5: 5 to 9: 1, A dip coating process, a roll-to-roll process, or a sublimation process, a deposition process, a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process,
A first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer including at least one hole transport layer and a light emitting compound, wherein the hole transport layer comprises a compound represented by the following Formula 1 And a compound represented by the following general formula (2)

Wherein Ar ¹ to Ar ³ are selected from the group consisting of an aryl group having _{6 to 60} carbon atoms, a heteroaryl group having _{2 to 60} carbon atoms, and a fluorenyl group; L ¹ ~ L ³ 2 of a single bond, C _{6 ~ 60} aryl group, a group a heterocyclic of the divalent C _{2 ~ 60,} a fluorenyl group, an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 ~ 60} of the Is selected from the group consisting of fused ring groups; Ar ^{4 to 6} are a C _{6 to} C ₆₀ aryl group, a C _{2 to} C ₆₀ heteroaryl group, or a fluorenyl group; L ⁴ represents a single bond, C _{6 ~ 60} arylene group, a divalent C _{2 ~ 60} of the heterocyclic group, fluorenyl group, a divalent fused ring of an aromatic ring of C _{3 ~ 60} alicyclic and C _{6 to 60} of &Lt; / RTI &gt; m is an integer of 0 to 4, and n is an integer of 0 to 3;
R ^{1 and} R ² are the same as or different from each other, and are independently selected from the group consisting of deuterium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and 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 ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R _a ) (R _b ); wherein L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene 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 ; And a C ₂ to C ₆₀ heterocyclic group, wherein R _a and R _b are independently of each other a C ₆ to C ₆₀ aryl group; A 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 ; And a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; R ¹ and R ² are each a group selected from the group consisting of A plurality of R ^{1 s} or a plurality of R ^{2 s} may be bonded to each other to form a ring.
A halogen group, a silyl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a -L _{'-N (R a) (R} b); C 1 ~ Import alkylthio of C _20; C ₁ ~ alkoxy group of C _20; C ₁ ~ alkyl group of C _20; C ₂ ~ C ₂₀ alkenyl group a; ₂ C ~ alkynyl of C _20; an aryl group of C ₆ - C ₂₀ substituted with heavy hydrogen;; C ₆ ~ C ₂₀ aryl group, a fluorenyl group; C ₂ - heterocyclic group of C _20; C of ₃ ~ C ₂₀ cycloalkyl An alkyl group, an arylalkyl group having ₇ to ₂₀ carbon atoms, and an arylalkenyl group having ₈ to ₂₀ carbon atoms, and these substituents may be further bonded to each other to form a ring, wherein The term &quot; ring &quot; means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof Refers to a luer binary fused ring, a saturated or unsaturated ring.)} 3. The organic electroluminescent device according to claim 2, wherein at least one of the two compounds represented by the formula (1) is represented by the following formulas (1-2), (1-3)

(In the formula 1-2, 1-3, 1-4, wherein ^{Ar 2, Ar 3, L 1} ~ L 3 are the same, X, Y, and Z is S, O, CR 'as defined in claim 2, R "and R" are selected from the group consisting of C _6-24 aryl, C _1-20 alkyl, C _2-20 alkenyl, C ₁ -C ₂₀ alkoxy, and R ', R May be combined to form a spy group and R ³ to R ⁸ may be bonded to each other in the group consisting of deuterium, tritium, cyano group, nitro group, halogen group, aryl group, alkenyl group, alkylene group, alkoxy group and heterocyclic group And R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 may} be bonded to each other to form a ring, l, b and p each represent an integer of 0 to 3, a , o and q are integers of 0-4). The organic electroluminescent device according to claim 2, wherein the compound represented by Formula 2 is represented by Formula 2-2 or 2-3.

(Wherein R ¹ , ² , Ar ⁵ , ⁶ , L ⁴ , m and n are the same as defined in claim 2, V and W are S, O, CR'R " , R 'and R "are C6-24 aryl group, C1-20 alkyl group, C2-20 alkenyl or C1-20 alkoxy group, R' and R" may combine to form a spy, R ^9-12 is deuterium, tritium, a cyano group, a nitro group, a halogen group, an aryl group, an alkenyl group, an alkylene group, an alkoxy group or a heterocyclic group; each other among R ^9, R ¹⁰ together, R ^11, R ¹² C and e are integers of 0 to 3, d and f are integers of 0 to 4, The organic electroluminescent device according to claim 2, wherein the compound represented by Formula 1 is represented by the following formula

The organic electroluminescent device according to claim 2, wherein the compound of formula (2) is represented by the following formula

The organic electroluminescent device according to claim 2, wherein Ar ¹ , Ar ² , and Ar ³ of the compound represented by Formula 1 are all C _{6 to} C ₂₄ aryl groups. The organic electroluminescent device according to claim 2, wherein Ar ⁴ and Ar ⁵ of the compound represented by Formula 2 are all C _{6 to} C ₂₄ aryl groups. The compound according to claim 2, wherein Ar ¹ , Ar ² , and Ar ³ of the compound represented by Formula 1 are all C _{6 to} C ₂₄ aryl groups; Wherein at least one of Ar ⁴ and Ar ⁵ of the compound represented by the general formula (2) is dibenzothiophene or dibenzofuran. The compound according to claim 2, wherein at least one of Ar ¹ , Ar ² , and Ar ³ of the compound represented by Formula 1 is dibenzothiophene or dibenzofuran; Wherein Ar ⁴ and Ar ⁵ of the compound represented by the general formula (2) are aryl groups having _{6 to 24} carbon atoms, The compound according to claim 2, wherein at least one of Ar ¹ , Ar ² and Ar ³ of the compound represented by Formula (1) is dibenzothiophene or dibenzofuran; Wherein at least one of Ar ⁴ and Ar ⁵ of the compound represented by the general formula (2) is dibenzothiophene or dibenzofuran. The organic electroluminescent device according to claim 2, wherein the ratio of the compound represented by the general formula (1) is 10% to 90% when the compound represented by the general formula (1) is mixed with the compound represented by the general formula The method according to claim 2, wherein, when the compound represented by the formula (1) and the compound represented by the formula (2) are mixed, at least one of the mixing ratio is 5: 5 or 6: 4 or 7: 3 or 8: 2 or 9: And an organic electroluminescent device. The organic electroluminescent device according to claim 2, further comprising at least one compound represented by the formula (1) in a mixture of the compound represented by the formula (1) and the compound represented by the formula (2). 3. The organic electroluminescent device according to claim 2, wherein a compound represented by the general formula (1) is used as a luminescent auxiliary layer between the hole transporting layer and the light emitting layer in which the compound having the structure represented by the general formula (1) Electric device. The organic electroluminescent device according to claim 2, 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. The organic electroluminescent device according to claim 2, wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device including the organic electroluminescent device of claim 2; And a controller for driving the display device. &Lt; / RTI &gt; 19. The electronic device according to claim 18, wherein the organic electric device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor and an element for monochromatic or white illumination.

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