KR101794557B1 - Amine-based compound and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention relates to a novel amine compound and an organic electroluminescent device including the same, and an organic electroluminescent device including the amine compound according to the present invention has an excellent effect on luminance, color purity and lifetime characteristics.

Description

(AMINE-BASED COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME)

The present invention relates to an amine compound and an organic electroluminescent device including the same, and more particularly, to an amine compound having excellent luminance, color purity and lifetime, and an organic electroluminescent device including the same.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. On the other hand, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminous phenomenon, has a large viewing angle, is slimmer and smaller than a liquid crystal display, And in recent years, application to a full-color display or illumination is expected.

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 electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials.

SUMMARY OF THE INVENTION The present invention provides an amine compound having excellent light emission luminance and color purity and long life.

A second object of the present invention is to provide an organic electroluminescent device including the amine compound.

In order to accomplish the first technical object, the present invention provides an amine compound represented by the following general formula (1-1) or (1-2).

[Formula 1-1]

[Formula 1-2]

In the above Formulas 1-1 and 1-2,

Each of R 1 to R 11 independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted group having 3 to 50 carbon atoms A substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C20 alkylsulfinyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C1- Or a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a cyano group, a halogen group, a medium-small water group, and hydrogen, and one of R 1 to R 11 Adjacent groups may combine with each other to form a condensed ring of a substituted or unsubstituted aliphatic, aromatic, heteroaliphatic or heteroaromatic ring,

L 1 and L 2 are each independently a direct bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms A substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a heterocycloalkylene group having 2 to 60 carbon atoms containing at least one selected from N, O and S, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms , And a substituted or unsubstituted divalent linking group selected from the group consisting of heteroarylene groups having 3 to 50 carbon atoms,

P1 and P2 are each independently selected from the group consisting of a substituted or unsubstituted anthracene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted triphenylene group, and a substituted or unsubstituted phenanthroline group,

X 1 and X 2 are each independently a direct bond or a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms,

X3 each independently represents a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms,

m and p are each independently an integer of 1 to 4,

n, q and r are each independently an integer of 0 to 10, and when n, q or r is an integer of 2 or more, two or more R5, R10 or R11 may be the same or different from each other.

In order to solve the second technical problem, the present invention provides a semiconductor device comprising: an anode; Cathode; And a layer containing an amine compound represented by Formula 1-1 or Formula 1-2 interposed between the anode and the cathode.

The organic electroluminescent device comprising the organic compound layer represented by Formula 1-1 or Formula 1-2 according to the present invention has excellent brightness, color purity, and lifetime characteristics, and thus can be used for display and illumination.

1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.
Description of the Related Art
10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

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

The amine compound according to the present invention is characterized by being represented by Formula 1-1 or Formula 1-2.

In the amine compound according to the present invention, the substituents of the above-mentioned formulas (1-1) and (1-2) will be described in more detail as follows.

delete

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " alkylsilyl group "hereinafter), a substituted or unsubstituted amino group _{(-NH 2, -NH (R)} , -N (R ') (R''), where R, R' and R" are each independently a carbon number A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms (for example, an alkyl group having 1 to 24 carbon atoms , An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, An aryl group having from 5 to 24 carbon atoms, an aryl group having from 5 to 24 carbon atoms, an arylalkyl group having from 6 to 24 carbon atoms, a heteroaryl group having from 3 to 24 carbon atoms, or a heteroarylalkyl group having from 3 to 24 carbon atoms.

Specific examples of the cycloalkyl group as the substituent used in the compound of the present invention include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and an adamantyl group. And can be substituted with the same substituent.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And can be substituted with substituents similar to those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.

In the present invention, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heteroaryl, Substituted or unsubstituted with at least one substituent selected from the group consisting of an acetylene group, a nitrile group and an acetylene group.

Specifically, the amine compound according to the present invention may be any one of the compounds represented by Chemical Formulas (2) to (216) shown in Table 1 below.

[Table 1]

The method for producing an amine compound according to the present invention is specifically shown in the following Examples.

The present invention also relates to a fuel cell comprising an anode; Cathode; And a layer containing an amine compound represented by Formula 1-1 or Formula 1-2 interposed between the anode and the cathode.

In this case, the layer containing the amine compound is preferably a light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, ≪ RTI ID = 0.0 > and / or < / RTI >

In addition, according to another embodiment of the present invention, the thickness of the light emitting layer is preferably 0.5 nm to 500 nm, and the light emitting layer may further include an ADN having the following structural formula.

[ADN]

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the hole transport layer. It is widely used.

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).

A HIL (Hole Injection Layer) may be additionally deposited on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30. A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited thereto.

< Example >

< Synthetic example  1> Preparation of the compound represented by the formula (15)

1) Synthesis of the compound represented by the formula (1-b)

The compound represented by the formula 1-b was synthesized according to the following Reaction Scheme 1.

[Reaction Scheme 1]

44.3 g (0.282 mol) of bromobenzene and 250 ml of THF were placed in a 1 L round bottom flask, and then cooled to -78 ° C. Subsequently, 163 ml (0.2613 mol) of n-butyllithium was slowly added dropwise, and the mixture was stirred at the same temperature for 1 hour, and then 30 g (0.1045 mol) of 2-bromoanthraquinone was added. The reaction product was warmed to room temperature, stirred for 12 hours, and 300 ml of 2N hydrochloric acid was added to the reaction mixture. The resultant was separated, the organic layer was dried over MgSO ₄ , and the filtrate and filtrate were concentrated to prepare a compound represented by the formula 1-a.

After adding the compound represented by the formula 1-a to a 1 L round bottom flask, 52 g (0.3135 mol) of KI, 66.5 g (0.627 mol) of NaH ₂ PO ₂ -H ₂ O and 600 ml of acetic acid were added and the mixture was refluxed for 5 hours . The resultant was cooled to room temperature, filtered, and washed with excess water and methanol. The washed product was dried and then recrystallized with toluene. The resulting solid was filtered and dried under reduced pressure to give 19 g (45%) of a compound represented by the formula 1-b

2) Synthesis of the compound represented by the formula (1-c)

The compound represented by the formula 1-c was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

Compound 500ml round bottom flask of the formula 1-b obtained from the Reaction Scheme 1 15g (0.0366mol), 4- bromo-phenyl-1-boronic acid 8.8g (0.044mol), potassium carbonate (K ₂ CO ₃₎ 10.1 g (0.0732mol), tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} 0.8g (0.732mmol), added 120mL of water, 60ml of toluene and 60mL of tetrahydrofuran and refluxed for 12 hours. After completion of the reaction, the reaction product was separated to remove the water layer, and the organic layer was separated, concentrated under reduced pressure, and then subjected to column chromatography using hexane and ethyl acetate as eluent to give the compound represented by the formula 1-c (10 g, 57%).

3) Synthesis of Compound Represented by Formula 15

The compound represented by the formula (15) was synthesized according to the following reaction formula (3).

[Reaction Scheme 3]

7 g (0.0144 mol) of the compound represented by the formula 1-c, 0.0 g (0.0173 mol) of 2-methylindoline, 0.06 g (0.288 mmol) of palladium acetate and 0.18 g 2.8 g (0.0288 mol) of sodium alginate butoxide and 60 ml of toluene were placed, and the mixture was refluxed for 12 hours. Upon completion of the reaction, celite was placed on a Buchner funnel under a hot condition, and the mixture was filtered. The filtrate was concentrated and recrystallized with toluene. The recrystallization method was repeated several times to obtain 2.7 g (35%) of a yellow solid compound (15).

MS (MALDI-TOF): m / z 537.25 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₄₁ H ₃₁ N : C, 91.58; H, 5.81; N, 2.60. Found: C, 91.63; H, 5.71; N, 2.65

< Synthetic example  2> Preparation of the compound represented by the formula (9)

1) Synthesis of the compound represented by the formula 2-a

A compound represented by the formula 2-a was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

2,3,3-trimethylindole (30 g, 0.2066 mol) and 150 ml of acetic acid were added to a 250 ml reactor and stirred. After the external temperature was lowered to 0 ° C, sodium cyanoborohydride (NaCNBH ₃ , 38.9 g, 0.6198 mol) was slowly added to the above solution in five divided portions. After completion of the addition, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 100 ml of water was added, and then NaOH was added to make the reaction solution basic. Ethyl acetate and water were added to neutralize. The organic layer was dried over anhydrous, concentrated under reduced pressure, and purified by column chromatography using hexane and ethyl acetate as eluent to give 24.3 g (80%) of the compound represented by the formula 2-a.

2) Synthesis of Compound Represented by Formula 9

The compound represented by the formula (9) was synthesized by the following Reaction Scheme (5).

[Reaction Scheme 5]

Except that 2-methylindoline used in Reaction Scheme 4 was used instead of the compound represented by Formula 2-a, 4.3 g (40%) of the compound represented by Formula 9 was prepared.

MS (MALDI-TOF): m / z 565.28 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₄₃ H ₃₅ N : C, 91.29; H, 6.24; N, 2.46. Found: C, 91.33; H, 6.21; N, 2.45

< Synthetic example  3> Preparation of the compound represented by the formula (23)

1) Synthesis of Compound Represented by Formula 3-a

A compound represented by the general formula (3-a) was synthesized by the following Reaction Scheme (6).

[Reaction Scheme 6]

Except that 2-phenylindole was used in place of 2,3,3-trimethylindole used in Reaction Scheme 3, 14 g (78%) of the compound represented by Formula 3-a was prepared.

2) Synthesis of compound represented by formula (23)

The compound represented by the formula (23) was synthesized by the following Reaction Scheme 7.

[Reaction Scheme 7]

Except that 2-methylindoline used in Reaction Scheme 3 was used instead of the compound represented by Formula 3-a, 2.3 g (32%) of the compound represented by Formula 23 was prepared.

MS (MALDI-TOF): m / z 599.26 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₄₆ H ₃₃ N : C, 92.12; H, 5.55; N, 2.34. Found: C, 92.23; H, 5.41; N, 2.36

< Synthetic example  4> Preparation of the compound represented by the formula (33)

1) Synthesis of the compound represented by the formula 4-b

The compound represented by the formula 4-b was synthesized according to the following Reaction Scheme 8.

[Reaction Scheme 8]

17 g (48%) of the compound represented by the formula 4-b was prepared, except that 2,6-dibromoanthraquinone was used instead of the 2-bromoanthraquinone used in the reaction scheme 1.

2) Synthesis of the compound represented by the formula 4-c

The compound represented by the formula 4-c was synthesized according to the following Reaction Scheme 9.

[Reaction Scheme 9]

7 g (35%) of the compound represented by the formula 4-c was prepared, except that phenylboronic acid was used in place of 4-bromo-phenyl-1-boronic acid used in the reaction scheme 2.

3) Synthesis of the compound represented by the formula 4-d

The compound represented by the formula 4-d was synthesized according to the following Reaction Scheme 10.

[Reaction Scheme 10]

5 g (61%) of a compound represented by the formula (4-d) was prepared by the same method except that the compound represented by the formula (4-c) was used in place of the compound represented by the formula (1-b) .

4) Synthesis of the compound represented by the formula (33)

The compound represented by the formula (33) was synthesized according to the following reaction scheme (11).

[Reaction Scheme 11]

(33%) was synthesized in the same manner as in the synthesis of the compound represented by the formula (33) except that the compound represented by the formula (4-d) was used instead of the compound represented by the formula (1-c) used in the reaction formula (7).

MS (MALDI-TOF): m / z 675.29 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₅₂ H ₃₇ N : C, 92.41; H, 5.52; N, 2.07. Found: C, 92.45; H, 5.48; N, 2.07

< Synthetic example  5> Preparation of the compound represented by the general formula (120)

1) Synthesis of Compound Represented by Formula 5-a

The compound represented by the formula 5-a was synthesized by the following Reaction Scheme 12.

[Reaction Scheme 12]

Except that bromodriphenylene was used instead of the compound represented by the formula 1-b used in the reaction scheme 2, 22 g (47%) of the compound represented by the formula 5-a was prepared.

2) Synthesis of compound represented by formula (120)

The compound represented by the general formula (120) was synthesized by the following Reaction Scheme (13).

[Reaction Scheme 13]

Except that 6-phenylindoline was used instead of 2-methylindoline, instead of the compound represented by the formula 1-c used in the reaction scheme 3, to obtain the compound represented by the formula 120 4.2 g (47%) of the compound was prepared.

MS (MALDI-TOF): m / z 497.21 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₃₈ H ₂₇ N : C, 91.72; H, 5.47; N, 2.81. Found: C, 91.68; H, 5.49; N, 2.83

< Synthetic example  6> Preparation of a compound represented by the formula (111)

1) Synthesis of the compound represented by the formula 6-a

A compound represented by the formula 6-a was synthesized by the following Reaction Scheme 14.

[Reaction Scheme 14]

Except that dibromotriphenylene was used instead of the compound represented by the formula 1-b used in the reaction scheme 2 and 3-bromo-phenyl-1-boronic acid was used instead of 4-bromo-phenyl- Synthesis was conducted in the same manner to prepare 7.5 g (53%) of the compound represented by the formula 6-a.

2) Synthesis of Compound Represented by Formula 111

A compound represented by Formula 111 was synthesized by the following Reaction Scheme 15.

[Reaction Scheme 15]

Except that 2-phenyl-6-cyanoindoline was used instead of 2-methylindoline, instead of the compound represented by the formula 1-c used in the reaction scheme 3 to obtain the compound represented by the formula 6-a, 2.3 g (34%) of a compound represented by 111 was prepared.

MS (MALDI-TOF): m / z 816.33 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₆₀ H ₄₀ N ₄ : C, 88.21; H, 4.93; N, 6.86. Found: C, 88.45; H, 4.76; N, 6.79

< Synthetic example  7> Preparation of the compound represented by the general formula (135)

The compound represented by the general formula (135) was synthesized by the following Reaction Scheme (16).

[Reaction Scheme 16]

Referring to Scheme 14 and Scheme 15, dibromopyrrole was used instead of dibromotriphenylene and 2,3,3-trimethylindoline was used in place of 2-phenyl-6-cyanoindoline to obtain the compound represented by Formula 135 (36%).

MS (MALDI-TOF): m / z 672.35 [M] ^&lt; ^{+ &}

Anal.Calcd for C ₅₀ H ₄₄ N ₂ : C, 89.25; H, 6.59; N, 4.16. Found: C, 89.31; H, 6.59; N, 4.12

< Synthetic example  8> Preparation of the compound represented by the formula 145

The compound represented by the general formula (145) was synthesized by the following Reaction Scheme (17).

[Reaction Scheme 17]

Referring to the reaction schemes 14 and 15, bromomethane was used instead of dibromotriphenylene and 2,3-dimethylindoline in place of 2-phenyl-6-cyanoindoline to obtain 3.9 g (36%).

MS (MALDI-TOF): m / z 423.2 [M] &lt; ⁺ & gt ^;

Anal.Calcd for C ₃₂ H ₂₅ N : C, 90.74; H, 5.95; N, 3.31. Found: C, 90.74; H, 7.27; N, 3.47

< Example  1 to 8> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, organic substances were injected onto the ITO by DNTPD (700 Å), NPD (300 Å), ADN + 300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å).

[DNTPD]

[NPD]

[ADN]

[Alq ₃ ]

< Comparative Example  1>

The organic electroluminescent device for the comparative example was fabricated in the same manner except that perylene of the following structural formula was used in place of the compound prepared by the invention in the device structures of Examples 1 to 8 above.

[perylene]

[Table 2]

The results of Examples 1 to 8, Comparative Examples 1 and 2 show that the compound represented by Formula 1-1 or Formula 1-2 according to the present invention has a lower driving voltage than Comparative Example 1, It can be seen that it can be used effectively for a display element, a display element, an illumination, and the like.

Claims (9)

An amine compound represented by any one of the chemical formulas (2) to (216) shown in Table 1 below:
[Table 1]

delete delete Anode;
Cathode; And
And a layer containing an amine compound according to claim 1 interposed between the anode and the cathode. 5. The method of claim 4,
Wherein the layer containing the amine compound is a light emitting layer between the anode and the cathode. 6. The method of claim 5,
And at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode. 6. The method of claim 5,
Wherein the thickness of the light emitting layer is 0.5 nm to 500 nm. The method according to claim 6,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process. 5. The method of claim 4,
Wherein the organic electroluminescent device is used in a display device, a display device, or a device for monochromatic or white illumination.

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