KR20090132352A - Organic light emitting material and organic light emitting diode having the same - Google Patents

Abstract

PURPOSE: An organic light emitting material is provided to produce an organic light emitting diode with excellent thermal stability, long lifetime, and good luminescent brightness and luminous efficiency by using a triphenylene derivative as a hole transport material. CONSTITUTION: An organic light emitting material is used as a light emitting material of an organic electroluminescent device and comprises a triphenylene derivative represented by the following chemical formula I. In chemical formula I, R1 and R2 are substituted or unsubstituted aryl group having 6-30 nucleus carbon atoms; R1 is has a unit of the following chemical formula b01; and R2 has a unit of the following chemical formula b01, b02, b03 or b09.

Description

Organic electroluminescent composition and organic electroluminescent device comprising same {Organic Light Emitting Material and Organic Light Emitting Diode Having The Same}

The present invention relates to an organic electroluminescent device, and more particularly, to a triphenylene derivative used as a light emitting material of an organic electroluminescent device, and more particularly, to produce a triphenylene derivative having a high glass transition temperature and to produce the organic electroluminescent device. By using it as a luminescent material of a light emitting element, it is providing the organic electroluminescent element which has the outstanding thermal stability, increases the lifetime of an element, and is excellent in luminescence brightness and luminous efficiency.

Organic electroluminescent devices with various advantages such as low voltage driving, self-luminous, light weight, wide viewing angle and fast response speed are one of the most researched fields as one of the next generation flat panel displays to replace LCD.

In US Pat. No. 4,356,429, Tang et al. Disclosed a two-layered organic electroluminescent device comprising two organic layers (hole transport layer and light emitting layer) sandwiched between an anode and a cathode. That is, the hole transport layer adjacent to the anode contains a hole transport material and has a function of transferring only holes to the light emitting layer mainly in the organic electroluminescent device.

Similarly, the electron transport layer adjacent to the cathode contains an electron transport material, and the organic electroluminescent device device having a two-layer structure selected to mainly transmit only electrons within the organic electroluminescent device device achieves high luminous efficiency and thus substantially organic electroluminescence. The technology of the device was improved. Therefore, in terms of luminous efficiency, a multilayer structure including a hole transport layer such as a hole injection layer and a hole transporting layer, an electron transporting layer, a hole blocking layer, and the like ( Without the multilayer system, it is impossible to expect high efficiency and high luminance.

In order to realize the organic electroluminescent device device, in addition to configuring the device in the above multilayer structure, the device material, in particular, the hole transport material must have thermal and electrical stability. Because of the heat generated by the device when the voltage is applied, molecules with low thermal stability have low crystal stability, resulting in rearrangement. Finally, if localization occurs and an inhomogeneous part exists, the electric field concentrates on this part. This is because it is accepted to bring about deterioration and destruction of the device. Therefore, the organic layer is usually used in an amorphous state. Furthermore, since the organic electroluminescent device is a current injection type device, if the material used has a low glass transition temperature (Tg), the heat generated during use causes the organic electroluminescent device to deteriorate and shorten the life of the device. Let's go. In this respect, materials having a high glass transition temperature are preferred.

Representative examples of hole-transfer materials used in the past include CuPC [copper phthalocyanine], m-MTDATA [4,4 ′, 4 ”-tris ( N- 3-methylphenyl- N -phenylamino) -triphenylamine], 2-TNATA [4,4 ', 4 "-tris ( N- (naphthylene-2-yl) -N -phenylamino) -triphenylamine] of 1, TPD [ N, N' -diphenyl- N, N' -di (3-methylphenyl) -4,4'-diaminobiphenyl] and NPB [ N, N' -di (naphthalen-1-yl) -N, N' -diphenylbenzidine] Etc.

[Formula 1] [Formula 2]

Since CuPC is a metal complex compound, it is widely used because it has excellent adhesion to ITO substrate and is the most stable. However, since absorption occurs in the visible light region, it is difficult to realize a total natural color. Not only low as ℃ and 108 ℃ but also a lot of problems in the process of mass production, there is also a problem in realizing the total color. In addition, TPD or NPB also has a fatal disadvantage of shortening the life of the device for the same reason because the glass transition temperature (Tg) as low as 60 ℃ and 96 ℃, respectively.

As described above, the hole transport material used in the conventional organic electroluminescent device still contains many problems, and there is a demand for improved performance having excellent physical properties. Therefore, there is an urgent need for development of an excellent material having an improved luminous efficiency of an organic electroluminescent device and having high thermal stability and high glass transition temperature.

An object of the present invention is to provide a triphenylene compound derivative having a high glass transition temperature, an organic electroluminescent composition comprising the same, and an organic electroluminescent device to solve the above problems. Another object of the present invention is to provide a hole transport material for an organic electroluminescent device having excellent thermal stability and a method of manufacturing the same, which can improve the luminous efficiency of the organic electroluminescent device and increase the lifetime of the device. Still another object of the present invention is to provide an organic electroluminescent device exhibiting high luminous efficiency. Another object of the present invention is to provide an organic electroluminescent device having an extended lifetime.

First, the present invention is an organic electroluminescent composition, which is used as a light emitting material of an organic electroluminescent device and comprises a triphenylene derivative represented by the following general formula (I).

[Formula I]

(In [Formula I], R1 and R2 each represent a substituted or unsubstituted aryl group having 6 to 30 nuclear carbon atoms.)

Herein, R1 and R2 of [Formula I] are preferably connected to each other by a single bond, a methylene group, an ethylene group or a vinyl group.

In addition, R1 of [Formula I] may have a unit structure of b01 below, and R2 may have a unit structure of b01, b02, b03, or b09.

[b01] [b02] [b03] [b09]

In addition, R1 of [Formula I] may have a unit structure of b02 below, and R2 may have a unit structure of b02, b03 or b04 below.

[b02] [b03] [b04]

Furthermore, the organic electroluminescent composition according to the present invention preferably has the structure of [Formula I] below [Formula I-091] or [Formula I-092].

[Formula I-091] [Formula I-092]

Another embodiment of the present invention is an organic electroluminescent device comprising at least one organic layer comprising the organic light emitting composition described above. Here, the organic electroluminescent device includes an organic light emitting diode, an organic field-effect transistor, an organic thin film transistor, an organic laser diode, an organic solar cell, an organic light emitting electrochemical cell, or an organic integrated circuit. It is apparent to those skilled in the art that various applications such as diodes can be made.

Other embodiments are described in the detailed description and drawings below.

Since the triphenylene derivative according to the present invention has a high glass transition temperature and a high pyrolysis temperature of 140 ° C. or higher, the thermal stability is excellent, and the composition including the same can be used as a hole transporting material for organic electroluminescent devices. As a result, the present invention showed better luminescence properties in terms of current density, luminance, highest luminance, and luminous efficiency than conventional hole transport materials, 2-TNATA (Formula 1) or NPB (Formula 2).

Accordingly, when the organic electroluminescent device is manufactured by using the triphenylene derivative according to the present invention as a hole transporting material, the problem of low luminous brightness and low luminous efficiency, which is the biggest disadvantage of the conventional organic electroluminescent device, is simultaneously solved. In addition to the high glass transition temperature, the thermal stability of the organic electroluminescent device is excellent, making it possible not only to manufacture a high performance organic electroluminescent device but also to commercialize a full-color organic electroluminescent device requiring high efficiency, high brightness and long life. Can contribute significantly.

The present invention is a triphenylene derivative represented by the following general formula (I) which is useful for use as a hole transport material or an organic electroluminescent material in an organic electroluminescent device. Since the organic electroluminescent device is manufactured using the same as a hole transport material, the light emitting efficiency can be increased and the life of the device can be increased.

[Formula I]

(In formula (I), R1 and R2 each represent an aryl group having 6 to 30 nuclear carbon atoms which is substituted or unsubstituted.)

The present invention may be an organic light emitting composition or an organic light emitting material or a triphenylene derivative which can be used as a light emitting material of the organic electroluminescent device as described above.

In Formula I, R1 and R2 are each substituted by a specific functional group or unsubstituted by any functional group, and may be an aryl group having 6 to 30 nuclear carbon atoms, and examples of such aryl groups include phenyl group and naphthyl group. , Phenanthryl group, anthryl group, biphenyl group, terphenyl group, fluorene group and the like.

A process for producing a triphenylene derivative that enables high luminous efficiency and long life organic electroluminescent device according to the present invention will be described below.

The process for preparing Formula I consists of the following steps. The present inventors were able to prepare a compound having the general structural formula of Formula I from phenanthrenequinone (I-a) by the synthetic route as in Scheme 1 below.

Scheme 1

In Scheme 1, R1 and R2 represent aryl groups having 6 to 30 nuclear carbon atoms which are substituted or unsubstituted.

First, phenanthrenequinone (1-a) and 1,3-bis (4-bromophenyl) acetone are reacted with alcoholic potassium hydroxide to prepare a dihalofenecyclone compound represented by 1-b. This intermediate (1-b compound) was reacted with bis (4-bromophenyl) acetylene in a xylene solvent to prepare a tetrahalo triphenylene compound represented by 1-c. A material of the organic electroluminescent device represented by the general formula (I), which is a triphenyl derivative according to the present invention, was finally prepared through amination reaction with various amine compounds in this core intermediate.

There are two main methods for the amination reaction used in the final step of synthesizing the general formula (I) in the manufacturing process.

The first method is the Ulnamm reaction using a copper catalyst, although not particularly limited, copper powder or copper sulfate (CuSO ₄ ) is suitable for the reaction, and potassium carbonate or sodium carbonate is most suitable. N, N -dimethylsulfoxide, nitrobenzene, or decalin is used, which is not used or has a high boiling point. Sometimes crown ethers or poly (ethylene glycol) are used to make the reaction smoother.

The second method is to use a palladium catalyst, which performs an amination reaction using a palladium catalyst, a phosphine catalyst and a base under a suitable reaction solvent. The palladium catalyst used in the reaction is not particularly limited, but mainly palladium acetate or tris (Dibenzylideneacetone) dipalladium (0) and the phosphine catalyst is not particularly limited, and tri- ( o -tolyl) phosphine, 2,2'-bis (diphenylphosphino) -1,1 ' -Vinaphthyl, tri- (n-butyl) phosphine or tri- (t-butyl) phosphine or the like is used. As the reaction base, metal alkoxides such as sodium t-butoxide or potassium th-butoxide are used. The reaction solvent is not particularly limited and may be non-reactive with the reagents used and have a solubility that allows the reaction to proceed smoothly. Specific examples include benzene, toluene, xylene, N, N -dimethylformamide, N, N -dimethylsulfoxide , and the like. The reagent or reaction solvent used in the reaction is not particularly limited thereto.

In the above formula (I), preferred examples of R 1 and R 2 are the same as those of the chemical structure shown in Table 1 below. Each unit structure is named by a delimiter b01 to b20 to distinguish it.

TABLE 1

In Table 1, R in b20 represents hydrogen or an alkyl group.

Based on Table 1 above, specific examples of the triphenylene derivative having the structure of [Formula I] to finally enable the organic electroluminescent device of high luminous efficiency and long life are shown in Tables 2 to 4 below. Compound of Formula I-001 to Formula I-090.

TABLE 2

Chemical formula R1 R2 I-001 b01 b01 I-002 b01 b02 I-003 b01 b03 I-004 b01 b04 I-005 b01 b05 I-006 b01 b06 I-007 b01 b07 I-008 b01 b08 I-009 b01 b09 I-010 b01 b10 I-011 b01 b11 I-012 b01 b12 I-013 b01 b13 I-014 b01 b14 I-015 b01 b15 I-016 b01 b16 I-017 b01 b17 I-018 b01 b18 I-019 b01 b19 I-020 b01 b20 I-021 b02 b02 I-022 b02 b03 I-023 b02 b04 I-024 b02 b05 I-025 b02 b06 I-026 b02 b07 I-027 b02 b09 I-028 b02 b10 I-029 b02 b12 I-030 b02 b13

TABLE 3

Chemical formula R1 E I-031 b02 b15 I-032 b02 b16 I-033 b02 b19 I-034 b02 b20 I-035 b03 b03 I-036 b03 b04 I-037 b03 b05 I-038 b03 b10 I-039 b03 b12 I-040 b03 b13 I-041 b03 b16 I-042 b03 b20 I-043 b04 b04 I-044 b04 b05 I-045 b04 b07 I-046 b04 b09 I-047 b04 b10 I-048 b04 b12 I-049 b04 b13 I-050 b04 b19 I-051 b04 b20 I-052 b05 b05 I-053 b05 b07 I-054 b05 b10 I-055 b05 b12 I-056 b05 b13 I-057 b05 b20 I-058 b06 b06 I-059 b06 b10 I-060 b06 b13

TABLE 4

Chemical formula R1 E I-061 b07 b07 I-062 b07 b10 I-063 b07 b12 I-064 b07 b13 I-065 b07 b16 I-066 b08 b08 I-067 b08 b10 I-068 b09 b09 I-069 b09 b10 I-070 b09 b13 I-071 b09 b20 I-072 b10 b10 I-073 b10 b12 I-074 b10 b13 I-075 b11 b11 I-076 b11 b12 I-077 b12 b12 I-078 b12 b13 I-079 b12 b20 I-080 b13 b13 I-081 b13 b14 I-082 b14 b14 I-083 b15 b15 I-084 b15 b20 I-085 b16 b16 I-086 b16 b17 I-087 b16 b20 I-088 b17 b17 I-089 b19 b19 I-090 b20 b20

In the above [Formula I], R1 and R2 represent an aryl group having 6 to 30 nuclear carbon atoms substituted or unsubstituted, and R1 and R2 may be connected to each other by a single bond, methylene group, ethylene group or vinyl group. have. Compounds of formula (I-091) and formula (I-92) are specific examples in which R1 and R2 are linked to each other. However, the present invention is not limited to these.

[Formula I-091] [Formula I-092]

According to the present invention, the triphenylene derivative represented by [Formula I] may be prepared by the above method, and the present invention may be a material or composition for an organic electroluminescent device including the same. When such a material or composition is used as a hole transporting material of an organic electroluminescent device, high luminous efficiency can be obtained, and a device having excellent durability can be manufactured because the glass transition temperature of the triphenylene derivative is high. Here, the hole transport material refers to a material used for the hole injection layer or the hole transport layer, in some cases may be a material used for the light emitting layer.

Triphenylene derivatives represented by Chemical Formula I of the present invention synthesized as described above were purified using recrystallization and sublimation in view of the characteristics of organic electroluminescent devices requiring high purity.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. The invention can be better understood by the following examples and comparative examples, the following examples are intended to illustrate the invention and are not intended to limit the scope of protection defined by the appended claims.

Example 1 Preparation of Chemical Formula I-001

1-1. 1,3-bis- (4-bromophenyl) -cyclopenta [ l ] Production of Phenanthrene-2-one

This synthesis example is to prepare the formula 1-b from 1-a according to the above Scheme 1.

37.7 g (0.18 mol) of phenanthrenequinone (Formula 1-a), 70 g of 1,3-bis (4-bromophenyl) acetone and 600 ml of ethanol were added to a 1000-ml, four-necked round bottom flask and stirred. 9.65 g of potassium hydroxide was added to this solution, and the mixture was stirred at 50 ° C for 1 hour. After cooling the reaction solution to room temperature, the resulting solid was filtered and washed well with methanol. The obtained solid was dried in vacuo to give 89.5 g (yield 92%) of the title compound.

¹ H NMR (500 MHz, CDCl ₃ ): δ 8.81 (d, J = 8.36 Hz, 2H), 7.63-7.59 (m, 6H), 7.54-7.50 (m, 8H).

MALDI-TOF mass (M + H ⁺ ): C29H16Br2O: 538.9752 (538.9568)

1-2. Preparation of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene (formula 1-c)

This synthesis example is to prepare 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene of formula 1-c from formula 1-b of Example 1-1 according to Scheme 1 described above It is for.

50 g (0.09 mol) of 1,3-bis- (4-bromophenyl) -cyclopenta [ l ] phenanthrene-2-one prepared in Example 1-1 in a 1000-ml, four-necked round bottom flask under nitrogen atmosphere ) Was diluted with 500 ml of o-xylene and 28.3 g of bis (4-bromophenyl) acetylene was added thereto. The mixture was refluxed for 15 hours, cooled to room temperature and poured into excess methanol to precipitate a solid. The precipitated solid was filtered, washed with methanol and dried in vacuo to give 62 g (yield 81%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C42H24Br4: 844.9052 (844.8611)

1-3. Preparation of Formula (I-001) (ELM405)

This synthesis example induces an amination reaction with amines to 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2, according to the present invention As one of the preferred embodiments of the triphenylene derivative represented by the present invention relates to a synthesis example for preparing the formula (I-001).

500.ml, 3-necked round bottom flask, 26,33 g of diphenylamine in 30 g (0.035 mol) of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2 0.31 g of palladium acetate (II), 0.57 g of tri- (t-butyl) phosphine, 16.3 g of sodium t-butoxide and 300 ml of toluene were added thereto. The reaction solution was refluxed for 10 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried under vacuum to obtain 37 g (yield 88%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C90H64N4: 1201.5546 (1201.5131)

UV (λ _max ): 335 nm PL: 446 nm (see FIG. 1)

Melting point (mp): 307 ° C Glass transition temperature (measured by Tg, DSC): 169 ° C (see Fig. 2)

1-4. Other Preparations of Formula I-001

This example relates to an example of preparing Chemical Formula I-001 as in Examples 1-3, but in this example, the Ulman reaction using a copper catalyst instead of a palladium catalyst was used as the condition for the amination reaction.

In a 250-ml, three-necked round bottom flask, 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene 28g (0.033mol) prepared in Example 1-2, 25g of diphenylamine Add 13.7 g of potassium carbonate and 0.31 g of copper powder. After heating the reaction vessel for 20 hours at 220 ° C. to 230 ° C., the reaction solution was cooled to 60 ° C. while adding an appropriate amount of N, N -dimethylformamide to prevent the reaction solution from hardening. Tetrahydrofuran was added to the suspension and filtered to remove insoluble matters. The filtrate was concentrated appropriately and excess methanol was added to precipitate the target compound as a solid. The obtained solid was filtered, washed sequentially with distilled water and methanol, and then dried in vacuo to give 32.5 g (yield 82%) of the title compound.

Example 2 Preparation of Chemical Formula I-002 (ELM405)

This synthesis example relates to a synthesis example of preparing Chemical Formula I-002 from 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2.

N -phenyl-1 in 30 g (0.035 mol) of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2 in a 500-ml, three-necked round bottom flask 34.1 g of naphthylamine, 0.31 g of palladium acetate (II), 0.57 g of tri- (t-butyl) phosphine, 16.3 g of sodium t-butoxide and 300 ml of toluene were added. The reaction solution was refluxed for 12 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried in vacuo to give 47 g (yield 96%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C106H72N4: 1401.5982 (1401.5757)

Example 3 Preparation of Chemical Formula I-003

This synthesis example relates to a synthesis example of preparing Chemical Formula I-003 from the 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2.

N -phenyl-2 in 30 g (0.035 mol) of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2 in a 500-ml, three-necked round bottom flask 34.1 g of naphthylamine, 0.31 g of palladium acetate (II), 0.57 g of tri- (t-butyl) phosphine, 16.3 g of sodium t-butoxide and 300 ml of toluene were added. The reaction solution was refluxed for 12 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried in vacuo to give 46 g (yield 93%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C106H72N4: 1401.5991 (1401.5757)

Example 4 Preparation of Chemical Formula I-009

This synthesis example relates to a synthesis example of preparing Chemical Formula I-009 from 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2.

Phenanthrene-9- in 30 g (0.035 mol) of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2 in a 500-ml, three-neck round bottom flask. 41.5 g of mono-phenylamine, 0.31 g of palladium acetate (II), 0.57 g of tri- (t-butyl) phosphine, 16.3 g of sodium t-butoxide and 300 ml of o-xylene were added. The reaction solution was refluxed for 15 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried in vacuo to give 54 g (yield 95%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C122H80N4: 1601.6093 (1601.6383)

Example 5 Preparation of Chemical Formula I-020

This Synthesis Example relates to a synthesis example of preparing Chemical Formula I-034 from 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2. This is the case when R in b20 of 1 is a methyl group.

500-ml, 3-necked round bottom flask was prepared in Example 1-2 in 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene 30g (0.035 mol) in (9,9- 42.4 g dimethyl-9H-fluoren-2-yl) -phenyl-amine, 0.31 g palladium acetate (II), 0.57 g tri- (t-butyl) phosphine, 16.3 g sodium t-butoxide and o-xylene 300 ml were added. The reaction solution was refluxed for 12 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried in vacuo to give 47 g (yield 96%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C126H96N4: 1665.9927 (1665.7635)

Example 6 Preparation of Chemical Formula I-022

This synthesis example relates to a synthesis example of preparing Chemical Formula I-022 from 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2.

Naphthalen-1-yl in 30 g (0.035 mol) of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2 in a 500-ml, three-necked round bottom flask 41.5 g of naphthalen-2-yl-amine, 0.31 g of palladium acetate (II), 0.57 g of tri- (t-butyl) phosphine, 16.3 g of sodium t-butoxide and 300 ml of o-xylene were added. The reaction solution was refluxed for 15 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried in vacuo to give 49 g (yield 87%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C122H80N4: 1601.7538 (1601.6383)

Example 7 Preparation of Chemical Formula I-091

This synthesis example relates to a synthesis example of preparing Chemical Formula I-091 from 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2.

24.8 g of carbazole in 30 g (0.035 mol) of 1,2,3,4-tetrakis (4-bromophenyl) -triphenylene prepared in Example 1-2 in a 500-ml, three-necked round bottom flask; 0.31 g of palladium acetate (II), 0.57 g of tri- (t-butyl) phosphine, 16.3 g of sodium t-butoxide and 230 ml of o-xylene were added. The reaction solution was refluxed for 15 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered and dried under vacuum to obtain 35 g (yield 83%) of the title compound.

MALDI-TOF mass (M + H ⁺ ): C90H56N4: 1193.6851 (1193.4505)

Example 8

Formula I-001 Hole injection layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

A transparent anode of indium tin oxide (ITO) having a thickness of 750 kPa was formed on a glass substrate having a size of 25 mm x 75 mm x 1.1 mm. The glass substrate was placed in a vacuum deposition apparatus to reduce the pressure to about 10 ⁻⁷ torr. Subsequently, the chemical formula I-001 of the present invention was deposited to a thickness of 500 kPa to form a hole injection layer. Subsequently, NPB of Chemical Formula 2 was deposited to have a thickness of 300 GPa to form a hole transport layer. Alq ₃ of Formula 3 was deposited to a thickness of 400 kPa to form a light emitting layer. Finally, aluminum and lithium were simultaneously deposited to form a cathode having a thickness of 1000 m 3 (see FIG. 3). Luminescence test was performed by applying a voltage of 0 ~ 17V to the organic electroluminescent device manufactured as described above. At 9V applied voltage, the current density was 13.5mA / cm ² , the luminance was 346cd / m ^2, and the luminous efficiency was 2.56cd / A.

[Formula 2] [Formula 3]

Example 9

Formula I-002 Hole injection layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

In the present Example, the organic electroluminescent device was manufactured and evaluated in the same manner as in Example 8, except that Formula I-002 was used instead of Formula I-001 in Example 8. At 9V applied voltage, the current density was 89.2mA / cm ² , the luminance was 2829cd / m ^2, and the luminous efficiency was 3.17cd / A.

Example 10

Formula I-003 Hole injection layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

In the present Example, the organic electroluminescent device was manufactured and evaluated in the same manner as in Example 8, except that Formula I-003 was used instead of Formula I-001 in Example 8. At 9V applied voltage, the current density was 41.5mA / cm ² , the luminance was 1219cd / m ^2, and the luminous efficiency was 2.94cd / A.

Example 11

Formula I-009 Hole injection layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

In the present Example, the organic electroluminescent device was manufactured and evaluated in the same manner as in Example 8, except that Formula I-009 was used instead of Formula I-001 in Example 8. At 9V applied voltage, the current density was 38.5mA / cm ² , the luminance was 1248cd / m ^2, and the luminous efficiency was 3.24cd / A.

Example 12

Formula I-020 Hole injection layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

In the present Example, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 8, except that Formula I-020 was used instead of Formula I-001 in Example 8. At 9V applied voltage, the current density was 50.2mA / cm ² , the luminance was 1406cd / m ^2, and the luminous efficiency was 2.80cd / A.

Example 13

Formula I-022 Hole injection layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

In the present Example, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 8, except that Formula I-022 was used instead of Formula I-001 in Example 8. At 9V applied voltage, the current density was 74.5mA / cm ² , the luminance was 2258cd / m ^2, and the luminous efficiency was 3.03cd / A.

Example 14

Formula I- 091 Hole transport layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

A transparent anode of indium tin oxide (ITO) having a thickness of 750 kPa was formed on a glass substrate having a size of 25 mm x 75 mm x 1.1 mm. The glass substrate was placed in a vacuum deposition apparatus to reduce the pressure to about 10 ⁻⁷ torr. Subsequently, 2-TNATA of Chemical Formula 1 was deposited to have a thickness of 500 kPa, thereby forming a hole injection layer. Subsequently, the chemical formula I-091 of the present invention was deposited to have a thickness of 300 GPa to form a hole transport layer. Alq ₃ of Formula 3 was deposited to a thickness of 400 kPa to form a light emitting layer. Finally, aluminum and lithium were simultaneously deposited to form a cathode having a thickness of 1000 mW. Luminescence test was performed by applying a voltage of 0 ~ 17V to the organic electroluminescent device manufactured as described above. At 9V applied voltage, the current density was 19.2mA / cm ² , the luminance was 512cd / m ^2, and the luminous efficiency was 2.67cd / A.

[Formula 1]

Comparative Example 1

2- TNATA To Hole injection layer  material, NPB To Hole transport layer  Fabrication of Green Organic Electroluminescent Devices Using Materials

In the present Comparative Example, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 1, except that 2-TNATA of Chemical Formula 1, which is well known in the art, was used instead of Chemical Formula I-001 in Example 1. At 9V applied voltage, the current density was 10.1A / cm ² , the luminance was 258cd / m ^2, and the luminous efficiency was 2.55cd / A.

Simple modifications or changes of the present invention can be easily made by those skilled in the art, and all such modifications or changes can be included in the scope of the present invention.

The organic light emitting composition and the organic electroluminescent device including the same according to the present invention are not only organic light emitting diodes but also organic field-effect transistors, organic thin film transistors, organic laser diodes, organic solar cells, organic light emitting electrochemical cells, and organic integrated circuits. Can also be used in the field.

1 is a UV / Vis. For the triphenylene derivative of formula I-001 according to the present invention. And fluorescence spectral graph 405-PL.

Figure 2 is a differential scanning calorimetry (DSC) curve graph (405-DSC) for the triphenylene derivative of formula I-001 according to the present invention.

3 is a diagram showing a multilayer structure of an organic electroluminescent device manufactured using the triphenylene derivative according to the present invention.

Claims (6)

An organic electroluminescent composition, which is used as a light emitting material of an organic electroluminescent device, comprises a triphenylene derivative represented by the following general formula (I). [Formula I]

(In formula (I), R1 and R2 each represent an aryl group having 6 to 30 nuclear carbon atoms which is substituted or unsubstituted.) The organic electroluminescent composition according to claim 1, wherein R1 in [Formula I] has a unit structure of b01, and R2 has a unit structure of b01, b02, b03 or b09. [b01] [b02] [b03] [b09]

The organic electroluminescent composition according to claim 1, wherein R1 in Formula [I] has a unit structure of b02, and R2 has a unit structure of b02, b03 or b04. [b02] [b03] [b04]

The organic electroluminescent composition of claim 1, wherein R1 and R2 of [Formula I] are connected to each other by a single bond, a methylene group, an ethylene group, or a vinyl group. The organic electroluminescent composition according to claim 4, wherein [Formula I] has a structure of Formula I-091 or Formula I-092. [Formula I-091] [Formula I-092]

An organic electroluminescent device comprising at least one organic layer comprising the organic light emitting composition according to any one of claims 1 to 5.

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