KR101815909B1 - Indolocarbazole derivatives and organoelectroluminescent device using the same - Google Patents

Abstract

(상기 [화학식 1]에 있어서, X1 내지 X3, R1 내지 R3는 발명의 상세한 설명 및 청구항에 정의된 바와 같다.)The present invention relates to an indolocarbazole derivative represented by the following formula (1) and an organic electroluminescent device including the same, wherein the organic electroluminescent device comprising an indolocarbazole derivative according to the present invention has a low driving voltage and a high luminous efficiency It has excellent effect.
[Chemical Formula 1]

(Wherein X1 to X3 and R1 to R3 are as defined in the description and claims of the present invention).

Description

[Technical Field] The present invention relates to indolocarbazole derivatives, and to organic electroluminescent devices using the same. BACKGROUND ART [0002] Indolocarbazole derivatives and organoelectroluminescent devices using the same

The present invention relates to an indolocarbazole derivative and an organic electroluminescent device including the same, and an organic electroluminescent device including the indolocarbazole derivative according to the present invention has a low driving voltage and excellent luminous efficiency.

Organic electroluminescent devices have been increasingly applied to display and illumination fields of various electronic products. However, efficiency and lifetime characteristics are limiting the expansion of application fields. In order to improve efficiency and lifetime characteristics, Many studies are under way. A host-dopant system is mainly adopted as a method for maximizing luminous efficiency from the viewpoint of materials, a phosphorescent dopant as a light emitting material, and a host capable of maximizing the luminescent characteristics of a dopant include CBP (4, 4'-N, N'-dicarbazolb pheny) and carbazole (Japanese Patent Application Laid-Open No. 2008-214244 and Japanese Patent Application Laid-Open No. 2003-133075). However, further improvement is required in terms of efficiency and life span.

A first object of the present invention is to provide a novel indolocarbazole derivative having a low driving voltage and a high luminous efficiency of an organic electroluminescent device.

Another object of the present invention is to provide an organic electroluminescent device improved in characteristics by employing the indolocarbazole derivative.

In order to accomplish the first object, the present invention provides indolecarbazole derivatives of the following formula (1).

[Chemical Formula 1]

In the above formula (1)

The rings containing X1 to X3 are each independently a substituted or unsubstituted aromatic group having 6 to 40 carbon atoms,

R 1 to R 3 are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 40 aromatic, substituted or unsubstituted C 3 -C 40 heteroaromatic ≪ / RTI >

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The present invention, in order to achieve the second technical object, Cathode; And a layer comprising an indolocarbazole derivative represented by the formula (1) interposed between the anode and the cathode.

According to an embodiment of the present invention, at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode And the indolocarbazole derivative is contained in the light emitting layer between the anode and the cathode, and the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

The use of the indolocarbazole derivative according to the present invention can provide an organic electroluminescent device having a low driving voltage and an excellent luminous efficiency.

1A to 1F are cross-sectional views illustrating a stacked structure of organic electroluminescent devices according to a preferred embodiment of the present invention.
2 is a representative view showing the structure of indolocarbazole according to the present invention.

The present invention relates to indolecarbazole derivatives represented by the above formula (1), which can be effectively used in all layers of organic electroluminescent devices. In particular, when used as a light emitting layer host, It is possible to maximize the formation of excitons in the light emitting layer.

The indolocarbazole derivative according to the present invention can be represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1)

The rings containing X1 to X3 are each independently a substituted or unsubstituted aromatic group having 6 to 40 carbon atoms,

R 1 to R 3 are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 40 aromatic, substituted or unsubstituted C 3 -C 40 heteroaromatic ≪ / RTI >

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Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. (R '), -N (R') (R '), a substituted or unsubstituted amino group (in this case, , A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, A halogenated alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 6 to 20 carbon atoms, A heteroaryl group having 6 to 20 carbon atoms or a heteroaryl group having 6 to 20 carbon atoms It may be substituted with an alkyl group Le.

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, hexyloxy, At least one hydrogen atom of the alkoxy group may be substituted with the same substituent as the alkyl group.

The aryl group used in the compounds of the present invention means an aromatic system comprising at least one ring, which rings may be attached together or fused together by a pendant method. The aryl group also includes a non-condensed aromatic group. Specific examples of the aryl group include phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, chrysenyl and fluoranthenyl, biphenyl, terphenyl and the like. At least one hydrogen atom of the aryl group may be substituted with the same substituent as the alkyl group (for example, an "arylamino group" when it is substituted with an amino group, an "arylsilyl group" when it is substituted with a silyl group, Quot; aryloxy group "when it is substituted with a group).

The heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 3 to 30 carbon atoms in which the remaining ring atoms are carbon atoms containing 1, 2 or 3 hetero atoms selected from N, O or S, Can be attached together in a pendant manner. When the heteroaryl group is fused with an aryl group or another heteroaryl group, it is a condensed aromatic heterocycle, and the heteroaryl group includes a condensed aromatic heterocycle. Specific examples of the heteroaryl group include a pyrrolyl group, a furane group, a thiophene group, a bithiophene group, a thiophene group, a pyrazole group, an imidazole group, a triazole group, an isoxazole group, an oxazole group, an oxadiazole group, A pyridyl group, a pyrimidyl group, a pyrazine group, a triazine group, an indole group, a carbazole group, a dibenzoazepin group, an azaindole group, an indolocarbazole group, a benzofurane group, a dibenzofurane group, Thienaphthone, thienaphthone, dibenzothiophene, indazole, benzimidazole, imidazopyridine, benzotriazole, benzothiazole, benzothiadiazole, triazolopyrimidine, purine, quinoline , Benzoquinoline group, acridine group, isoquinoline group, phenanthroline group, phthalazine group, quinazoline group, phenoxaline group, phenazine group, phenanthroline group, phenoxazine group and the like.

And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the alkyl group.

Specific examples of the indolocarbazole derivative according to one embodiment of the present invention may be any one compound selected from the group consisting of the following formulas [SPH1] to [SPH93], but the present invention is not limited thereto.

[SPH1] [SPH2] [SPH3]

[SPH4] [SPH5]

[SPH6] [SPH7] [SPH8]

[SPH9] [SPH10]

[SPH11] [SPH12] [SPH13]

[SPH14] [SPH15] [SPH16]

[SPH17] [SPH18] [SPH19]

[SPH20] [SPH21] [SPH22]

[SPH23] [SPH24] [SPH25]

[SPH26] [SPH27] [SPH28]

[SPH29] [SPH30] [SPH31]

[SPH32] [SPH33] [SPH34]

[SPH35] [SPH36] [SPH37]

[SPH38] [SPH39] [SPH40]

[SPH41] [SPH42] [SPH43]

[SPH44] [SPH45] [SPH46]

[SPH47] [SPH48] [SPH49]

[SPH50] [SPH51] [SPH52]

[SPH53] [SPH54] [SPH55]

[SPH56] [SPH57] [SPH58]

[SPH59] [SPH60] [SPH61]

[SPH62] [SPH63] [SPH64]

[SPH65] [SPH66] [SPH67]

[SPH68] [SPH69] [SPH70]

[SPH71] [SPH72] [SPH73]

[SPH74] [SPH75] [SPH76]

[SPH77] [SPH78]

[SPH79] [SPH80] [SPH81]

[SPH82] [SPH83] [SPH84]

[SPH85] [SPH86]

[SPH87] [SPH88]

[SPH89] [SPH90]

[SPH91] [SPH92] [SPH93]

According to another aspect of the present invention, there is provided a plasma display panel comprising: an anode; Cathode; And a layer comprising an indolocarbazole derivative represented by the formula (1) interposed between the anode and the cathode.

The organic electroluminescent device according to the present invention may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer between the anode and the cathode The hole injecting layer, the hole transporting layer, the electron transporting layer, and the electron injecting layer efficiently transport holes or electrons to the light emitting layer, thereby enhancing the probability of light emitting coupling in the light emitting layer.

The hole injecting layer and the hole transporting layer are laminated in order to inject holes from the anode and transport the injected holes. As the material for the hole transporting layer, electron donating molecules having a small ionization potential are used. Diamine, triamine or tetraamine derivatives having an amine as a basic skeleton are widely used. In the present invention, as the material of the hole transport layer, various materials can be used without limitation as long as they are commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (? -NPD ) Can be used. In addition, 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, CuPc or starburst type amines such as TCTA, m-MTDATA, and IDE406 (manufactured by Idemitsu) can be used.

       CuPc TCTA

      m-MTDATA

An organic light emitting layer is laminated on the hole transport layer. The organic light emitting layer may be formed of a single material or a host / dopant.

In general, when such a compound is used as a single substance, a host / dopant luminescent layer is preferable because a mound peak in a long wavelength is generated due to intermolecular interaction, the color purity drops, The indolocarbazole derivative may be used as a host material in a host / dopant emitting layer. In general, CBP (4,4'-dicarbazolyl-1,1'-biphenyl) is used as a host material in the host / dopant emission layer and Ir (ppy) 3 is used as a dopant material. Is not particularly limited as long as it is used as the " The electron transporting layer serves to smoothly transport electrons supplied from the cathode to the light emitting layer and to suppress the movement of holes that are not coupled in the light emitting layer, thereby increasing the chance of recombination in the light emitting layer. The material of the electron transport layer is not particularly limited as long as it is a material used in the art, and examples thereof include Alq3 (tri-8-hydroxyquinoline aluminum), PBD (2- (4- 4-t-butylphenyl) -1,3,4-oxadiazole), TNF (2,4,7-trinitrofluorenone), BMD, BND and the like.

On the other hand, 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. May be used without any particular limitation as long as it is commonly used in the art. For example, materials such as LiF, NaCl, CsF, Li2O, and BaO may be used.

Furthermore, the organic electroluminescent device according to the present invention may further include additional functional laminated structures such as a hole blocking layer or an electron blocking layer in addition to the above-mentioned hole injecting layer, hole transporting layer, electron transporting layer and electron injecting layer . In this case, when the holes are injected into the cathode through the organic light emitting layer, the hole blocking layer reduces the lifetime and the efficiency of the device. Therefore, the use of a material having a very low HOMO level prevents the problem. The material forming the hole blocking layer is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having an electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

1A to 1F illustrate organic electroluminescent devices having various laminated structures. Referring to FIG. 1A, the organic electroluminescent device of FIG. 1A includes an anode, a hole injection layer, a light emitting layer, and a cathode And the organic electroluminescent device of FIG. 1B has a structure composed of an anode / a hole injection layer / a light emitting layer / an electron injection layer / a cathode. 1C has the structure of anode / hole injection layer / hole transporting layer / light emitting layer / cathode, and the organic electroluminescent element shown in FIG. 1D has an anode / hole injection layer / hole transporting layer / light emitting layer / electron injection 1E has a structure of anode / hole injection layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode, and finally the organic electroluminescent device of FIG. / Hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode structure.

The organic electroluminescent device according to the present invention may comprise the indolocarbazole derivative in various laminated structures interposed between the anode and the cathode, but preferably the indolocarbazole derivative has a structure in which the light-emitting layer between the anode and the cathode Can be used as a host material.

In addition, the thickness of the light emitting layer including the indolocarbazole derivative may be 50 to 2,000 ANGSTROM. When the thickness is less than 50 ANGSTROM, the luminous efficiency is decreased. When the thickness is more than 2,000 ANGSTROM, .

A method of manufacturing an organic electroluminescent device according to the present invention will be described with reference to Figs. 1A to 1F.

First, the anode material is coated on the substrate. As the substrate, a substrate used in a conventional light emitting device is used, and a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the anode material, materials commonly used in the art such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2) or zinc oxide (ZnO) which are transparent and excellent in conductivity can be used . A hole injection layer is stacked on the anode, and then a hole transport layer is formed on the hole injection layer.

Next, a light emitting layer is laminated on the hole transporting layer, and a hole blocking layer is selectively formed thereon. Finally, an organic electroluminescent device according to the present invention can be manufactured by selectively forming an electron injecting layer after laminating an electron transporting layer on the hole blocking layer, and vacuum depositing a cathode forming metal on the electron injecting layer . The lamination of the organic layers is performed by one or more methods selected from the methods of vacuum thermal deposition, spin coating or ink jet printing.

On the other hand, examples of the cathode forming metal include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium- Magnesium-silver (Mg-Ag) or the like may be used. In order to obtain a top-emitting device, a transmissive cathode using ITO or IZO may be used.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further illustrating the present invention and that the scope of the present invention is not limited thereby.

<Examples>

Synthesis Example 1 Synthesis of a compound represented by [SPH3]

(1) Synthesis of Compound Represented by Formula (1-a)

A compound represented by the formula (1-a) was synthesized by the following Reaction Scheme 1.

[Reaction Scheme 1]

[Chemical Formula 1-a]

50 g (0.45 mol) of 1,2-cyclohexanedione, 135 g (0.92 mol) of phenylhydrazine-hydrochloride and 1500 ml of ethyl alcohol are placed in a 2 L round bottom flask. After stirring for 30 minutes, 5 ml of concentrated sulfuric acid was added to the reaction solution. The mixture was stirred at 65 ° C for 10 hours. After completion of the reaction, the reaction mixture was filtered, washed with ethyl alcohol, and dried under reduced pressure at room temperature. To the filtrate was added filtrate, 1200 ml of acetic acid and 120 ml of trifluoroacetic acid to a 2 L round bottom flask, Lt; / RTI &gt; After completion of the reaction, the reaction mixture was filtered, washed with ethyl alcohol and hexane, and dried under reduced pressure at room temperature to obtain 80 g of a compound represented by the formula (I-a). (Yield: 76.8%)

(2) Synthesis of Compound Represented by Formula (1-b)

A compound represented by the formula (1-b) was synthesized by the following reaction scheme (2).

[Reaction Scheme 2]

[Chemical Formula 1-b]

30 g (0.117 mol) of iodobenzene, 71.6 g (0.351 mol) of iodobenzene, 14.9 g (0.234 mol) of copper powder, 9.3 g (0.035 mol) of 18-crown- (0.468 mol) were added in this order, 300 ml of ortho-dichlorobenzene was added, and the mixture was refluxed at 180 ° C for 24 hours. When the reaction was completed, 300 ml of methylene chloride and 300 ml of distilled water were used for extraction. After repeating 2 times, the organic layer was concentrated under reduced pressure, and the residue was subjected to column chromatography using hexane as a developing solvent to obtain 42.1 g of a compound represented by the formula (1-b). (Yield: 88%).

(3) Synthesis of Compound Represented by Formula (1-c)

The compound represented by the formula (1-c) was synthesized by the following reaction scheme [3].

[Reaction Scheme 3]

[Chemical Formula 1-c]

40 g (0.098 mol) of [Formula 1-b] and 500 ml of dimethylformamide were dissolved in a 1000 ml round-bottomed flask. 15.7 g (0.088 mol) of N-bromosuccinimide was dissolved in 200 ml of dimethylformamide and the mixture was stirred for 4 hours. When the reaction was completed, 1000 ml of distilled water was added to the reaction solution to precipitate a solid. The solid was filtered and the residue was subjected to column chromatography using hexane as a developing solvent to obtain 36.5 g of a compound represented by the formula (1-c). (Yield: 76.5%).

(4) Synthesis of a compound represented by the formula (1-d)

[Chemical formula 1-d] was synthesized by the following reaction scheme [4].

[Reaction Scheme 4]

[Chemical formula 1-d]

36.5 g (0.075 mol) of 4,4,5,5-tetramethyl-2- (2-nitrophenyl) -1,3,2-dioxaborane 28.0 were placed g (0.112 mol), Pd ( PPh 3) 4 1.7 g (0.001mol), potassium carbonate and 20.7g (0.150mol), 180ml tetrahydrofuran, 1,4- dioxide-old 180ml, 60ml water. 80 C &lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with 800 ml of ethyl acetate and 200 ml of distilled water. The organic layer was concentrated under reduced pressure, and the residue was subjected to column chromatography using ethyl acetate and hexane as eluent to obtain 30.0 g of a compound represented by the formula 1-d. (Yield: 75.6%).

(5) Synthesis of Compound Represented by Formula (1-e)

[Chemical Formula 1-e] was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

[Formula 1-e]

10.0 g (0.019 mol) of [Formula 1-d], 9.9 g (0.038 mol) of triphenylphosphine and 100 ml of dichlorobenzene were added to a 250 ml round bottom flask, and the mixture was refluxed at 180 ° C for 24 hours. After completion of the reaction, the reaction mixture was filtered under a hot condition and extracted with methylene chloride and distilled water. The organic layer was concentrated under reduced pressure, and the residue was subjected to column chromatography using methylene chloride and hexane as eluent to obtain 5.0 g &Lt; / RTI &gt; (Yield: 53.2%).

(6) Synthesis of a compound represented by [SPH3]

A compound represented by [SPH3] was synthesized by the following reaction scheme [6].

[Reaction Scheme 6]

[SPH3]

0.45 g (0.012 mol) of sodium hydride and 10 ml of dimethylformamide were stirred in a 250 ml round bottom flask under a nitrogen stream. After the temperature of the reactor was lowered to 0 占 폚, 5.0 g (0.010 mol) of [Formula 1-e] was dispersed in 100 ml of dimethylformamide and added dropwise to the reactor. After 30 minutes, 3.2 g (0.012 mol) of chlorodiphenyltriazine was dissolved in 30 ml of dimethylformamide and added dropwise. After the temperature was raised to room temperature, the mixture was stirred for 4 hours. When the reaction was completed, distilled water was added to form a solid, and recrystallization was performed several times to obtain 6.0 g of a compound represented by [SPH3]. (Yield: 81.9%)

MS (MALDI-TOF): m / z = 728.3 [M] ^&lt; ^{+ &}

EA (Elemental analysis): Theoretical value - C. 84.01%; H 4.43%; N, 11.53%

Actual value - C. 84.51%; H 4.28%; N, 11.18%

Synthesis Example 2 Synthesis of Compound Represented by [SPH5]

(1) Synthesis of Compound Represented by Formula (2-a)

A compound represented by the formula (2-a) was synthesized by the following reaction scheme (7).

[Reaction Scheme 7]

[Chemical Formula 2-a]

(0.030 mol) of 3-bromoiodobenzene, 3.8 g (0.060 mol) of copper powder and 2.4 g (0.009 mol) of 18-crown-6 in a 500 ml round- ) And 16.7 g (0.121 mol) of potassium carbonate were added in this order, 150 ml of ortho-dichlorobenzene was added, and the mixture was refluxed at 180 캜 for 12 hours. When the reaction was completed, 500 ml of methylene chloride and 300 ml of distilled water were used for extraction. After repeating 2 times, the organic layer was concentrated under reduced pressure, and the residue was subjected to column chromatography using hexane as a developing solvent to obtain 14.3 g of a compound represented by the following formula (2-a). (Yield: 72.7%).

(2) Synthesis of a compound represented by the formula (2-b)

[Chemical Formula 2-b] was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

[Formula 2-b]

(0.001 mol) of PdCl ₂ (dppf) and 4.5 g (0.001 mol) of PdCl ₂ (dppf) were added to a 250 mL round-bottomed flask equipped with a stirrer, 0.060 mol) and 130 ml of toluene were placed, and the mixture was stirred for 6 hours. When the reaction was completed, the reaction mixture was filtered under a hot condition, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography using methylene chloride and hexane as eluent to obtain 11.2 g of a compound represented by the formula (2-b). (Yield: 80.4%).

(3) Synthesis of a compound represented by [SPH5]

A compound represented by [SPH5] was synthesized by the following Reaction Scheme 9.

[Reaction Scheme 9]

[SPH5]

250mL round bottom flask Formula 2-b] 10.0g (0.019 mol ), dichloro-phenyl-triazine 2.4g (0.009mol), Pd (PPh 3) 4 0.9g (0.001 mol), 10.3g (0.075 mol) of potassium carbonate , 60 ml of tetrahydrofuran, 60 ml of 1,4-dioxane and 20 ml of water were added and refluxed. After completion of the reaction, the reaction mixture was extracted with methylene chloride and water, and the organic layer was concentrated under reduced pressure. The residue was subjected to column chromatography using methylene chloride and hexane as developing solvents and recrystallized several times to obtain 9.5 g of a compound represented by [SPH5]. (Yield: 63.1%).

MS (MALDI-TOF): m / z = 804.3 [M] ^&lt; ^{+ &}

EA (Elemental analysis): theoretical value - C 85.05%; H 4.51%; N, 10.44%

Actual value - C. 85.07%; H 4.40%; N, 10.53%

Synthesis Example 3 Synthesis of a compound represented by [SPH18]

(1) Synthesis of Compound Represented by Formula 3-a

A compound represented by the general formula [3-a] was synthesized by the following scheme [Reaction formula 10].

[Reaction Scheme 10]

[Formula 3-a]

In a 500 ml round bottom flask, 24.2 g (0.094 mol) of iodobenzene, 0.104 mol of iodobenzene, 9.7 g (0.189 mol) of copper powder, 7.5 g (0.028 mol) of 18- 52.2 g (0.378 mol) of potassium were placed in this order, 300 ml of ortho-dichlorobenzene was added, and the mixture was refluxed at 180 ° C for 1 day. When the reaction was completed, 500 ml of methylene chloride and 200 ml of distilled water were used for extraction. After repeating 2 times, the organic layer was concentrated under reduced pressure, and hexane was filtered with developing solvent to remove olso-dichlorobenzene. An excess of methylene chloride was added to obtain an impure product, which was subjected to column chromatography using methylene chloride: hexane = 1: 10 to obtain 17.9 g of a compound represented by the formula (3-a). (Yield: 56%)

(2) Synthesis of Compound Represented by Formula 3-b

[Chemical Formula 3-b] was synthesized by the following Reaction Scheme 11.

[Reaction Scheme 11]

[Formula 3-b]

1.8 g (0.054 mol) of sodium hydride and 20 ml of dimethylformamide were stirred in a 500 ml round bottom flask under a nitrogen stream. After the temperature of the reactor was lowered to 0 占 폚, 15.0 g (0.045 mol) of [Formula 3-a] was dispersed in 200 ml of dimethylformamide and added dropwise to the reactor. After 1 hour, 14.5 g (0.054 mol) of chlorodiphenyltriazine was dissolved in 100 ml of dimethylformamide and added dropwise. After the temperature was raised to room temperature, the mixture was stirred for 6 hours. When the reaction was completed, distilled water was added to form a solid, and recrystallization was performed several times to obtain 22.1 g of a compound represented by the formula (3-b). (Yield: 86.9%).

(3) Synthesis of compound represented by [SPH18]

Except that iodobenzene was used in place of chlorodiphenyltriazine in Reaction Scheme 6 of Synthesis Example 1 except that [Formula 3-b] was used instead of [Formula 1-b] in [Reaction Scheme 3] [SPH18] was obtained in the same manner as in Synthesis Example 1 in which [SPH3] was synthesized.

MS (MALDI-TOF): m / z = 728.3 [M] ^&lt; ^{+ &}

EA (Elemental analysis): theoretical value - C 84.04%; H 4.43%; N, 11.53%

Actual value - C. 84.11%; H 4.43%; N, 11.46%

Synthesis Example 4 Synthesis of Compound Represented by [SPH22]

Except that 9- (4-chloro-6-phenyl-1,3,5-triazin-2-yl) -carbazole was used in place of chlorodiphenyltriazine in [Reaction Scheme 6] [SPH22] was obtained in the same manner as in Synthesis Example 1 in which [SPH3] was synthesized.

MS (MALDI-TOF): m / z = 817.3 [M] ^&lt; ^{+ &}

EA (Elemental analysis): theoretical value - C 83.70%; H 4.31%; N, 11.99%

Actual value - C. 82.80%; H 4.53%; N, 12.87%

Synthesis Example 5 Synthesis of a compound represented by [SPH28]

[SPH28] was obtained in the same manner as in Synthesis Example 1 for synthesizing [SPH3] except that 4-iodobiphenyl was used in place of chlorodiphenyltriazine in [Reaction Scheme 2] in Synthesis Example 3.

MS (MALDI-TOF): m / z = 804.3 [M] ^&lt; ^{+ &}

EA (Elemental analysis): theoretical value - C 85.05%; H 4.51%; N, 10.44%

Actual value - C. 85.03%; H 4.54%; N, 10.43%

Examples 1 to 5 Production of an organic electroluminescent device including the compound synthesized by Synthesis Examples 1 to 5

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, an organic material was added to the ITO using DNTPD (700 Å), NPD (300 Å), each compound prepared in Synthesis Examples 1 to 5 + Ir (ppy) ₃ (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å) and Al (1,000 Å).

[DNTPD]

[NPD]

[Ir (ppy) ₃ ]

[Alq ₃ ]

&Lt; Comparative Example 1 &

The organic electroluminescent device for the comparative example was fabricated in the same manner except that CBP was used instead of the compound prepared by the present invention as a host material in the device structure of the above example.

[CBP]

division Host Dopant Doping concentration (%) ETL V ㏅ / A COLOR Comparative Example 1 CBP Ir (ppy) ₃ 10 Alq ₃ 7.2 36.24 green Example 1 SPH3 Ir (ppy) ₃ 10 Alq ₃ 3.11 40.8 green Example 2 SPH5 Ir (ppy) ₃ 10 Alq ₃ 3.32 39.91 green Example 3 SPH18 Ir (ppy) ₃ 10 Alq ₃ 3.58 41.96 green Example 4 SPH22 Ir (ppy) ₃ 10 Alq ₃ 4.52 40.06 green Example 5 SPH28 Ir (ppy) ₃ 10 Alq ₃ 4.87 38.46 green

From the results of Examples 1 to 5, Comparative Example 1 and Table 1, it can be seen that the organic electroluminescent device comprising the indolocarbazole derivative according to the present invention as a host material has an organic electric field of CBP It can be seen that the organic EL device of the present invention can be used effectively for a display device, a display device, an illumination, and the like because the organic EL device exhibits a low driving voltage and a high luminous efficiency such as current efficiency.

Claims (11)

delete delete delete delete delete delete An indolecarbazole derivative which is any one selected from the group consisting of compounds represented by the following formulas [SPH1] to [SPH93]

[SPH1] [SPH2] [SPH3]

[SPH4] [SPH5]

[SPH6] [SPH7] [SPH8]

[SPH9] [SPH10]

[SPH11] [SPH12] [SPH13]

[SPH14] [SPH15] [SPH16]

[SPH17] [SPH18] [SPH19]

[SPH20] [SPH21] [SPH22]

[SPH23] [SPH24] [SPH25]

[SPH26] [SPH27] [SPH28]

[SPH29] [SPH30] [SPH31]

[SPH32] [SPH33] [SPH34]

[SPH35] [SPH36] [SPH37]

[SPH38] [SPH39] [SPH40]

[SPH41] [SPH42] [SPH43]

[SPH44] [SPH45] [SPH46]

[SPH47] [SPH48] [SPH49]

[SPH50] [SPH51] [SPH52]

[SPH53] [SPH54] [SPH55]

[SPH56] [SPH57] [SPH58]

[SPH59] [SPH60] [SPH61]

[SPH62] [SPH63] [SPH64]

[SPH65] [SPH66] [SPH67]

[SPH68] [SPH69] [SPH70]

[SPH71] [SPH72] [SPH73]

[SPH74] [SPH75] [SPH76]

[SPH77] [SPH78]

[SPH79] [SPH80] [SPH81]

[SPH82] [SPH83] [SPH84]

[SPH85] [SPH86]

[SPH87] [SPH88]

[SPH89] [SPH90]

[SPH91] [SPH92] [SPH93] Anode;
Cathode; And
And a layer containing the indolocarbazole derivative according to claim 7 interposed between the anode and the cathode. 9. The method of claim 8,
Further comprising at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, a light emitting layer, an electron transporting layer, an electron injecting layer and an electron blocking layer between the anode and the cathode. 10. The method of claim 9,
Wherein the indolocarbazole derivative is contained in the light emitting layer between the anode and the cathode. 11. The method of claim 10,
Wherein the thickness of the light emitting layer is 50 to 2,000 ANGSTROM.

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