KR101560028B1 - New hetero-cyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present invention provides a novel compound capable of greatly improving the lifetime, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, and an organic light emitting device in which the compound is contained in an organic compound layer.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel heterocyclic compound and an organic light-

The present invention relates to a novel compound and an organic light emitting device using the same. Specifically, the present invention relates to a novel compound capable of greatly improving lifetime, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, and an organic light emitting device in which such a compound is contained in an organic compound layer.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between an anode and a cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic layer are recombined to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

In addition to the above, it is preferable that the material used in the organic light emitting device further has the following properties.

First, the material used in the organic light emitting device is preferably excellent in thermal stability. This is because joule heating occurs due to the movement of charges in the organic light emitting device. Currently, NPB, which is mainly used as a hole transport layer material, has a glass transition temperature of 100 ^° C or less, which is difficult to use in an organic light emitting device requiring a high current.

Secondly, in order to obtain a highly efficient organic light emitting device capable of driving at a low voltage, holes or electrons injected into the organic light emitting element should be smoothly transferred to the light emitting layer, and injected holes and electrons should not escape from the light emitting layer. For this purpose, the material used in the organic light emitting device should have an appropriate band gap and a HOMO or LUMO energy level. In the case of PEDOT: PSS used as a hole transport material in the organic light emitting device manufactured by the solution coating method, since the LUMO energy level is lower than the LUMO energy level of the organic material used as the light emitting layer material, There is a difficulty.

In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface characteristics with electrodes or adjacent layers. That is, the material used in the organic light emitting device should have little deformation of the material due to moisture or oxygen. In addition, by having appropriate hole or electron mobility, it is necessary to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. And, for the stability of the device, the interface with the electrode including the metal or the metal oxide should be good. Accordingly, there is a need in the art to develop organic materials having the above-mentioned requirements.

Accordingly, the present inventors have found that a compound capable of satisfying the conditions required for a material usable in an organic light emitting device, for example, an appropriate energy level, electrochemical stability, and thermal stability, Structure and an organic light emitting device comprising the same.

The present invention provides a compound of formula (1).

In Formula 1,

X is - (A) _m - (B) _n ,

Y is - (B ') _p ,

Ar is an arylene group having 6 to 40 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, alkyl group, alkoxy group and amino group; Or a divalent heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of nitro, nitrile, halogen, alkyl group, alkoxy group and amino group,

A represents a halogen atom, an alkyl group, an alkenyl group alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A substituted or unsubstituted arylene group having at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group,

B and B 'independently represent a halogen group, an alkyl group, an alkenyl group alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkene An arylamine group substituted or unsubstituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group, a nitrile group and an acetylene group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group containing at least one substituent selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group, a heterocyclic group containing O, N or S as a hetero atom,

m is an integer of 1 to 10, n is an integer of 0 to 10, p is an integer of 1 to 10,

R 1 to R 5 are each independently hydrogen; heavy hydrogen; A halogen atom, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, An alkyl group substituted or unsubstituted with at least one substituent selected from the group consisting of A halogen atom, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, An alkoxy group substituted or unsubstituted with at least one substituent selected from the group consisting of A substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group, an alkenyl group alkoxy group, a substituted or unsubstituted aryl group, An alkenyl group substituted or unsubstituted with at least one substituent selected from the group A substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group, an alkenyl group alkoxy group, a substituted or unsubstituted aryl group, An aryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of A silicon group substituted with a substituted or unsubstituted aryl group; A boron group substituted with a substituted or unsubstituted aryl group; A halogen atom, an alkyl group, an alkenyl group alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A heterocyclic group which is substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen group, a nitrile group and an acetylene group, a heterocyclic group containing O, N or S as a hetero atom; An amino group substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group-substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, and a substituted or unsubstituted arylalkenyl group; A nitrile group; A nitro group; A halogen group; Amide group; And an ester group.

Also, the present invention provides an organic light emitting device comprising a first electrode, at least one organic material layer, and at least one second electrode in a laminated form, wherein at least one of the organic material layers includes the compound of Formula 1 Lt; / RTI >

The compound of the present invention can be used as an organic material layer material, particularly a hole injecting material and / or a hole transporting material in an organic light emitting device. When the compound is used in an organic light emitting device, the driving voltage of the device is lowered, The lifetime characteristics of the device can be improved by the thermal stability of the device.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element made up of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

The substituents of Formula 1 will be described in detail as follows.

In the above formula (1), the number of carbon atoms is not particularly limited, but is preferably 1 to 20 carbon atoms, and may be linear or branched.

The length of the alkyl group contained in the compound does not affect the conjugation length of the compound, but may additionally affect the application of the compound to an organic light emitting device, for example, a vacuum deposition method or a solution coating method.

In the above formula (1), the aryl group preferably has 6 to 40 carbon atoms, more preferably 6 to 20 carbon atoms. Specific examples of the aryl group include monocyclic aromatic and naphthyl groups such as phenyl group, biphenyl group, terphenyl group and stilbene, polycyclic aromatic rings such as anthracenyl group, phenanthrene group, pyrenyl group and perylenyl group, But is not limited thereto

In the above formula (1), the heterocyclic group preferably has 2 to 40 carbon atoms including S, O or N, more preferably 3 to 20 carbon atoms. Specific examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a pyrazinyl group, a quinolinyl group, an isoquinoline group, And a chrysidyl group, but the present invention is not limited thereto.

In the general formula (1), as the arylamine group, an amine group substituted with one or more of the above-exemplified aryl groups may be used.

The divalent arylene group and divalent heterocyclic group in the above formula (1) may be divalent groups having the same structures as the structures exemplified above for the monovalent aryl group and the heterocyclic group.

As the arylene group, A is preferably a monocyclic aromatic or naphthylene group such as a phenylene group, a biphenylene group, a terphenylene group or a stilbene group, an anthracenylene group, a phenanthrenylene group, a pyrenylene group, But are not limited to, aromatic rings.

When B or B 'in formula (1) is a heterocyclic group, it is preferably a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, An isoquinoline group, an acridyl group, and a carbazole group, but the present invention is not limited thereto.

When B or B 'in the general formula (1) is an arylamine group, there are preferably the following groups, but the groups are not limited thereto.

In the above formula (1), Ar is more preferably a phenylene group.

In the above formula (1), R 1 and R 2 are preferably phenyl groups, and R 3 to R 5 are preferably hydrogen.

The term "substituted or unsubstituted" as used herein refers to a substituent such as a halogen group, an alkyl group, an alkoxy group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, a nitrile group, Substituted or unsubstituted with one or more substituents selected from the group consisting of an amino group and an acetylene group. The substituents may be further substituted as necessary.

The compound of Formula 1 is preferably a compound represented by the following Chemical Formulas 2 to 8, but is not limited thereto.

The compound represented by Chemical Formula 1 has a core structure represented by Chemical Formula 1, that is, a structure in which an arylene or a divalent heterocyclic group as a substituent Ar is substituted at a carbon position between R3 and R4 of the indole as a core structure, Substituents R 1 to R 5 are hydrogen; heavy hydrogen; A substituted or unsubstituted aliphatic hydrocarbon; Substituted or unsubstituted aromatic hydrocarbons; A silicon group substituted with a substituted or unsubstituted aryl group; A boron group substituted with a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; An amino group; A nitrile group; A nitro group; A halogen group; Amide group; And an ester group, it can have properties suitable for being used as an organic material layer used in an organic light emitting device.

Generally, the conjugation length of a compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap. As described above, since the core of the compound of Formula 1 contains limited conjugation, it has a large energy band gap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituent groups at positions R1 to R5, X and Y in the above formula (1) having a large energy bandgap. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents at the R1 to R5, X and Y positions of the above formula (1) having a large energy bandgap.

Further, it is possible to synthesize a compound having the intrinsic property of a substituent introduced by introducing various substituent groups into the core structure represented by the above-described Higgs type 1. For example, by introducing a substituent mainly used for a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting element into the core structure, a material that satisfies the conditions required in each organic layer is synthesized can do.

In particular, the compound of Formula 1 may include an arylamine structure in the core structure, and thus may have an appropriate energy level as a hole injecting and / or hole transporting material in the organic light emitting device. In the present invention, a compound having an appropriate energy level according to the substituent among the compounds of the formula (1) is selected and used in an organic light emitting device, thereby realizing a device having a low driving voltage and a high light efficiency.

Further, by introducing various substituent groups into the core structure, it is possible to finely control the energy band gap, and the characteristics at the interface between the organic materials can be improved and the use of the materials can be diversified.

In particular, by controlling the number of amines including substituents B and B ', it is possible to finely control the HOMO, LUMO energy level and energy bandgap, while improving the properties at the interface between the organic materials, I can do it

On the other hand, the compound of formula (1) has a high glass transition temperature (Tg) and is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic electronic device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

A specific method for preparing the compound of formula (1) according to the present invention is described in the examples, and those skilled in the art can prepare the compounds according to the present invention based on the examples.

The present invention also provides an organic electroluminescent device comprising a first electrode, at least one organic material layer, and a second electrode in a laminated form, wherein at least one of the organic material layers contains a compound represented by the following formula Lt; / RTI >

The organic electronic device of the present invention can be produced by a conventional method and materials for producing an organic electronic device, except that one or more organic material layers are formed using the above-described compounds.

Hereinafter, the organic light emitting device will be described.

The compounds of the present invention can act as a hole injecting, hole transporting, electron injecting, electron transporting, or luminescent material in an organic light emitting device. When the compounds of the present invention are used as luminescent materials, But can also act as a luminescent dopant together with a suitable luminescent dopant as well as a luminescent host or a suitable luminescent host. In particular, the compounds of the present invention are preferably used as a hole transport material in an organic light emitting device.

In the organic light emitting device according to the present invention, the organic material layer includes a hole transporting layer, and the hole transporting layer contains the compound of Formula 1 can do.

In the organic light-emitting device according to the present invention, the organic compound layer may include a hole injection layer, and the hole injection layer may be formed of the compound of Formula 1 . ≪ / RTI >

In the organic light emitting device according to the present invention, the organic material layer includes a layer which simultaneously injects holes and transports holes. The organic material layer includes a hole injecting layer and a hole injecting layer. The layer simultaneously transporting the hole may include the compound of the above formula (1).

In the organic light emitting device according to the present invention, the organic material layer may include an electron injection or electron transport layer, and the electron injection or electron transport layer may be formed on the first electrode, (1). ≪ / RTI >

In the organic light emitting device according to the present invention, the organic layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1 In one embodiment of the present invention, the organic light emitting device may have a structure including a first electrode, a second electrode, and an organic material layer interposed therebetween, and the above- The organic EL device can be manufactured by using a conventional method and materials for manufacturing an organic light emitting device, except that the organic EL device is used for at least one layer of the organic material layer. The structure of the organic light emitting device according to the present invention is illustrated in FIGS. 1 and 2. FIG. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. However, the scope of the present invention is not limited to the structure shown in Fig. 1 or Fig.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, A hole transporting layer, a light emitting layer, and an electron transporting layer, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate (see International Patent Application Publication No. 2003/012890).

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The method for preparing the compound of Formula 1 and the preparation of the organic light emitting device using the same will be specifically described in the following Production Examples and Examples. However, the following Preparation Examples and Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

The method of synthesizing an organic compound represented by Formula 1 and the production of an organic electroluminescent device using the same will be described in more detail with reference to the following Examples and Comparative Examples. However, these embodiments are for illustrating the present invention, but the scope of the present invention is not limited thereto.

PREPARATION EXAMPLE 1 Synthesis of Compound of Formula 1-A

[Chemical Formula 1-A]

Benzyl phenyl ketone (36.6 g, 186 mmol), 4-bromohydrazine hydrochloride (50.0 g, 223 mmol) and 4M hydrochloric acid (diluted in 1,4-dioxane, 14 mL, 0.3 eq.) Were suspended in 300 mL of ethanol . The resulting mixture was stirred and refluxed for about 18 hours and cooled to room temperature. The mixture was diluted with water (200 mL) and extracted with dichloromethane (3 x 100 mL). The organic extract was dried over magnesium sulfate and distilled under reduced pressure. The product was recrystallized using hexane to give the compound of formula 1-A (61.8 g, 95%).

MS: [M] < + > = 348

PREPARATION EXAMPLE 2 Synthesis of Compound of Formula 1-B

[Chemical Formula 1-B]

4-Bromo-iodobenzene (3.4 g, 12 mmol) and bisdiphenylamine (3.86 g, 12 mmol) were dissolved in 50 ml of N, N- dimethylacetamide and copper chloride (CuCl) mmol) and 2,2'-bipyridyl (187 mg, 1.2 mmol) were added thereto, and the mixture was refluxed in a nitrogen stream for 12 hours. After cooling to room temperature, distilled water (200 mL) was added to the reaction solution, and the reaction was terminated and extracted with chloroform (3 x 100 mL). The organic layer was dried over magnesium sulfate and distilled under reduced pressure. The product was recrystallized from ethyl ether and hexane to give the compound of formula 1-B (3.7 g, 65%).

MS: [M] < + > = 476

PREPARATION EXAMPLE 3 Synthesis of Compound of Formula 1-C shown below

[Chemical Formula 1-C]

4-Bromo-iodobenzene (3.4 g, 12 mmol) and bisdiphenylamine (3.86 g, 12 mmol) were dissolved in 50 ml of N, N- dimethylacetamide and copper chloride (CuCl) mmol) and 2,2'-bipyridyl (187 mg, 1.2 mmol) were added thereto, and the mixture was refluxed in a nitrogen stream for 12 hours. After cooling to room temperature, distilled water (200 mL) was added to the reaction solution, and the reaction was terminated and extracted with chloroform (3 x 100 mL). The organic layer was dried over magnesium sulfate and distilled under reduced pressure. The product was recrystallized from ethyl ether and hexane to give the compound of formula 1-B (3.7 g, 65%).

MS: [M] < + > = 476

PREPARATION EXAMPLE 4 Synthesis of Compound of Formula 1-D

[Chemical Formula 1-D]

In the same manner as in the preparation of the compound of formula (1-B), except that naphthylphenylamine was used instead of bisdiphenylamine in the preparation of the compound of formula (1-B) Lt; / RTI >

MS: [M] < + > = 375

PREPARATION EXAMPLE 5 Synthesis of Compound of Formula 1-E shown below

[Chemical Formula 1-E]

In the same manner as in the preparation of the compound of the formula 1-C, except for using the compound of the formula 1-D instead of the compound of the formula 1-B in the process for the preparation of the compound of the formula 1-C, The compound of formula I-E was prepared.

MS: [M] < + > = 339

PREPARATION EXAMPLE 6 Synthesis of Compound of Formula 1-F

[Chemical Formula 1-F]

The method for preparing the compound of the formula 1-C, except that 3-bromo-N-phenylcarbazole was used instead of the compound of the formula 1-B in the process for the preparation of the compound of the formula 1-C of Preparation Example 3 The compound of the above formula 1-F was prepared in the same manner.

MS: [M] < + > = 287

PREPARATION EXAMPLE 7 Synthesis of Compound of Formula 1-G

[Chemical Formula 1-G]

The compound of Formula 1-A (5 g, 14.3 mmol) and the compound of Formula 1-C (6.3 g, 14.3 mmol) were completely dissolved in tetrahydrofuran (50 mL), and 2M aqueous potassium carbonate solution (20 mL) And tetrakistriphenylphosphinopalladium (495 mg, 3 mol%) were added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare the compound of Formula 1-G (6.64 g, 70%).

MS: [M] ^< ⁺ & gt ^; = 664

PREPARATION EXAMPLE 8 Synthesis of Compound of Formula 1-H

[Chemical Formula 1-H]

In the same manner as in the preparation of the compound of the formula 1-C, except for using the compound of the formula 1-E instead of the compound of the formula 1-C in the preparation of the compound of the formula 1-G of Preparation Example 7, The compound of formula 1-H was prepared.

MS: [M] ^< ⁺ & gt ^; = 562

PREPARATION EXAMPLE 9 Synthesis of Compound of Formula I-I

                                                   [Formula I-I]

A solution of 2M potassium carbonate aqueous solution (20 mL) was added to the compound of the formula 1-A (5 g, 14.3 mmol) and the amine compound (7.23 g, 14.3 mmol) in tetrahydrofuran Phosphino palladium (495 mg, 3 mol%) was added and the mixture was heated with stirring for 5 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare a compound represented by the above formula (I-I) (6.77 g, 65%).

MS: [M] ^< ⁺ & gt ^; = 729

≪ Example 1 > Preparation of a compound represented by the formula (2)

(2)

The compound of Formula 1-G (2 g, 3 mmol) and iodobenzene (1.22 g, 6 mmol) were dissolved in 20 mL of xylene and sodium-tertiary-butoxide (578 mg, t-Bu) ₃ ] ₂ (46 mg, 3 mol%) was added thereto, and the mixture was refluxed in a nitrogen stream for 5 hours. Distilled water was added to the reaction solution, and the reaction was terminated and the organic layer was extracted. The residue was subjected to column separation using a solvent of normal hexane / tetrahydrofuran = 10/1 to obtain the compound of the above formula (2) (1.2 g, 54%).

MS: [M] ^< ⁺ & gt ^; = 740

Example 2 Synthesis of Compound of Formula 3

(3)

The compound of formula 3 was prepared in the same manner as in the preparation of the compound of formula 2, except that 4-bromobiphenyl compound was used instead of iodobenzene compound in the preparation of compound of formula 2 Respectively.

MS: [M] ^< ⁺ & gt ^; = 817

Example 3 Synthesis of Compound of Formula 4

[Chemical Formula 4]

The same procedure as in the preparation of the compound of Formula 2, except that 2- (3-bromophenyl) -5-phenylthiophene compound was used in place of the iodobenzene compound in the preparation of the compound of Formula 2 in Example 1 The compound of the above formula (4) was prepared.

MS: [M] ^< ⁺ & gt ^; = 899

Example 4 Synthesis of Compound of Formula 5

[Chemical Formula 5]

The same procedure as in the preparation of the compound of Formula 2, except that 2- (4-bromophenyl) -5-phenylthiophene compound was used in place of the iodobenzene compound in the preparation of the compound of Formula 2 in Example 1 The compound of formula 5 was prepared.

MS: [M] ^< ⁺ & gt ^; = 899

≪ Example 5 > Preparation of the compound represented by the formula (6)

[Chemical Formula 6]

(1.69 g, 3 mmol) and iodobenzene (1.22 g, 6 mmol) were dissolved in 20 mL of xylene and sodium-tertiary-butoxide (578 mg, 6 mmol) and Pd [P (t-Bu) ₃ ] ₂ (46 mg, 3 mol%) was added thereto, and the mixture was refluxed in a nitrogen atmosphere for 5 hours. Distilled water was added to the reaction solution, and the reaction was terminated and the organic layer was extracted. The residue was subjected to column separation using a solvent of normal hexane / tetrahydrofuran = 10/1 to obtain the compound of Formula 6 (1.15 g, 60%).

MS: [M] ^< ⁺ & gt ^; = 638

Example 6 Synthesis of Compound of Formula 7

(7)

The compound of formula (7) was prepared in the same manner as the compound of formula (6) except that 4-bromobiphenyl compound was used instead of iodobenzene compound in the preparation of compound of formula (6) Respectively.

MS: [M] ^< ⁺ & gt ^; = 714

Example 7 Synthesis of Compound of Formula 8

[Chemical Formula 8]

In the same manner as in the preparation of the compound of Formula 2, except that the compound of Formula 1-I was used instead of the compound of Formula 1-G in the preparation of the compound of Formula 2 of Example 1, the compound of Formula 8 .

MS: [M] ^< ⁺ & gt ^; = 806

<Experimental Example 1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) thin film with a thickness of 1000 Å was immersed in distilled water containing dissolved dispersant and ultrasonically cleaned. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. (400 ANGSTROM) synthesized in the above preparation example, which is a hole transport material, was vacuum deposited, and a host H1 and a dopant D1 compound were vacuum deposited to a thickness of 300 ANGSTROM as a light emitting layer. The E1 compound (300 ANGSTROM) was then thermally vacuum deposited sequentially by electron injection and transport layer. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

In the above procedure, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was maintained at 0.2 Å / sec, and the deposition rate of aluminum was maintained at 3 to 7 Å / sec.

[Hexanitrile hexaazatriphenylgylene] [NPB]

      [H1] [D1] [E1]

<Experimental Example 2>

The same experiment was carried out except that the hole transport layer in Example 1 was replaced by the hole transport layer 3 in place of the hole transport layer 2 synthesized in Production Example.

<Experimental Example 3>

The same experiment was carried out except that the hole transport layer in Example 1 was replaced with the hole transport layer in Chemical Formula 4, which was synthesized in Production Example.

<Experimental Example 4>

The same experiment was carried out except that the hole transport layer in Example 1 was replaced with the hole transport layer in Formula 5 instead of Formula 2 synthesized in Production Example.

<Experimental Example 5>

The same experiment was conducted except that the hole transport layer in Example 1 was replaced with the hole transport layer 6 in place of the hole transport layer 2 synthesized in Production Example.

<Experimental Example 6>

The same experiment was conducted as in Example 1, except that the hole transport layer was replaced with the hole transport layer represented by Chemical Formula 7, which was synthesized in the Production Example.

<Experimental Example 7>

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced by the hole transport layer represented by the formula 8 instead of the hole transport layer 2 synthesized in the Production Example.

<Comparative Example>

In the same manner as in Example 1 except that NPB was used in place of Formula 2 synthesized in Production Example as a hole transport layer.

Table 1 shows the results of an experiment of an organic light emitting device manufactured using each compound as a hole transporting layer material as in the above examples.

The compound represented by the formula according to the present invention can act as a hole injecting, hole transporting, electron injecting and transporting or light emitting material in an organic electric device including an organic light emitting device. And exhibits excellent properties in terms of surface area.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7:
8: Electron transport layer

Claims (14)

A compound of formula
[Chemical Formula 1]

In Formula 1,
X is - (A) _m - (B) _n ,
Y is - (B ') _p ,
Ar is an arylene group having 6 to 40 carbon atoms,
A is an arylene group,
B is a substituted or unsubstituted heterocyclic group containing O, N or S as a hetero atom,
B 'is an arylamine group substituted or unsubstituted with an aryl group,
m is an integer of 1 to 10, n is an integer of 1 to 10, p is an integer of 1 to 10,
R1 and R2 are each independently an aryl group,
R3 to R5 are hydrogen. [2] The compound according to claim 1, wherein A in Formula 1 is a group selected from the group consisting of phenylene, biphenylene, terphenylene, stilbene, naphthylene, &Lt; / RTI &gt; The heterocyclic group of claim 1, wherein the heterocyclic group of Formula 1 is selected from the group consisting of a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a pyrazine group, An isoquinoline group, an acrylyl group, and a carbazole group. The compound according to claim 1, wherein B 'in the above formula (1) is one of the following groups:

delete 2. The compound according to claim 1, wherein Ar in formula (1) is a phenylene group. The compound according to claim 1, wherein R 1 and R 2 in the formula (1) are phenyl groups, and R 3 to R 5 are hydrogen. The compound according to claim 1, wherein the compound of formula 1 is a compound of formula 4 or 5:
[Chemical Formula 4]

[Chemical Formula 5]

The organic light-emitting device according to any one of claims 1 to 4 and 6 to 8, wherein the organic material layer includes a hole-transporting layer, Wherein the organic compound contains one of the compounds of the present invention. delete delete delete delete delete

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