KR101092003B1 - Anthracene derivative and organoelectroluminescent device employing the same - Google Patents

Abstract

The present invention relates to an anthracene derivative represented by the following formula (1) and an organic light emitting device using the anthracene derivative, wherein the organic light emitting device employing the anthracene derivative has excellent color purity, power efficiency, and luminous efficiency.

           (One)

Anthracene Derivatives, Organic Light Emitting Diodes

Description

Anthracene derivative and organic electroluminescent device employing the same {Anthracene derivative and organoelectroluminescent device employing the same}

The present invention relates to an anthracene derivative and an organic light emitting device using the anthracene derivative, and more particularly, to an anthracene derivative having excellent color purity, power efficiency and luminous efficiency, and an organic light emitting device employing the same.

Recently, as the size of the display device increases, the demand for a flat display device having less space is increasing. A liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT. However, the viewing angle is limited and the rear surface is limited. There were disadvantages such as the need for back light. On the contrary, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays that require self-luminous phenomena, and have a large viewing angle, are thinner and shorter than liquid crystal displays, and have a fast response speed. Has a vertex

Currently, organic light emitting diodes have excellent characteristics such as low driving voltage (eg, 10V or less), wide viewing angle, high-speed response, and high contrast compared to plasma display panel (PDP) or inorganic electroluminescent display. It can be used as a pixel of a graphic display, a pixel of a television image display or a surface light source. The device can be formed on a flexible transparent substrate, can be made very thin and light, and has good color, which is emerging as a device suitable for the next generation flat panel display (FPD).

Such an organic light emitting device has a hole from the anode and a cathode in an organic light emitting layer formed between a first electrode (anode), which is a hole injection electrode (anode), and a second electrode (cathode, cathode), which is an electron injection electrode. When electrons are injected, electrons and holes combine to form an exciton in the excited state as a pair, and the exciton in the excited state falls to the ground state and disappears and emits light. In recent years, full color ) Application to display is expected.

Representative organic electroluminescent devices of the early days have a single layer structure known by Gurnee in 1969 (US Patent No. 3,172,862 and US Patent No. 3,173,050), and are practically used because they require excessive driving voltage of 100 V or more. There was a problem that it is difficult to be. Therefore, in order to solve this problem, a multi-layered organic electroluminescent device having a significantly low driving voltage of about 6 to 14 V was developed by Tang of Eastman Kodak Co. in 1987 (CW Tang et al. ., Appl. Phys. Lett ., 51, 913 (1987); J. Applied Phys ., 65, 3610 (1989); US 4,356, 429), currently a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer, etc. Organic electroluminescent devices having the same various functional stacking structures are continuously being developed.

Anthracene and its derivatives have been employed in various conventional organic electroluminescent devices, and 9,10-di (2-naphthyl) anthracene (US Pat. No. 5,935,721), 9, well known by the abbreviation "ADN", 9 Naphthyl-10-phenylanthracene derivatives (US Patent Publication No. 2006/0014046) and 9-biphenyl-10-naphthylanthracene derivatives (International Patent Publication No. 2005/080527) are used as hosts for the light emitting layer. In addition, a technique of improving the life of an organic light emitting device using bis-anthracene as a light emitting layer has been disclosed (US Patent No. 6,534,199). In addition, a technique using an anthracene derivative in the hole transport layer (HTL) has also been disclosed (US Pat. No. 6,465,115 and US Pat. No. 5,759,444), and anthracene and its derivatives are employed in organic electroluminescent devices for various purposes. It has been.

As the dopant material of the green light emitting layer, there are C545T and gutacridone derivatives of the following formulas, which are one of coumarin derivatives, and among them, coumarin derivative C545T is most widely used.

               C545T Quinacridone Derivatives

Meanwhile, US Patent No. 6,951,693 discloses an anthracene derivative of the following structural formula in which various ligands are introduced at 2,6 or 9,10 positions, wherein an amine ligand of the following structural formula is represented at the 9,10 or 2,6 position of the anthracene structure. By introducing, as a dopant, a material having higher efficiency and longer life than existing materials is known. Patents using a similar structure include European Patent Publication No. 1,775,334, Japanese Patent No. 7,109,449, and the like. However, all have problems with high driving voltage and color purity.

As described above, many studies have been made in which anthracene is employed in the organic light emitting display device, but until now, the present conditions have not sufficiently satisfied characteristics such as brightness, efficiency, driving stability, and lifespan. Various technological developments are urgently needed. In particular, in a host-guest system based on the principle of energy transfer in which a dopant is doped to a light emitting layer host, much research on a new anthracene derivative as a light emitting layer dopant material is required.

Therefore, the first technical problem to be achieved by the present invention is to provide an anthracene derivative excellent in color purity, power efficiency and luminous efficiency.

In addition, the second technical problem to be achieved by the present invention is to provide an organic light emitting device employing the anthracene derivative.

In order to achieve the above technical problem, the present invention provides an anthracene derivative represented by the following formula (1):

Wherein D is deuterium, A ₁ and A ₂ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 19 carbon atoms Group;

When A ₁ and A ₂ are a substituted alkyl group, a substituted aryl group or a substituted heteroaryl group, the substituent is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, Cyano group, substituted or unsubstituted substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, halogen group, substituted or unsubstituted aryl group having 6 to 10 carbon atoms , Substituted or unsubstituted aryloxy group having 6 to 10 carbon atoms, substituted or unsubstituted arylamino group having 6 to 10 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 10 carbon atoms, substituted or unsubstituted C 3 to One or more selected from the group consisting of 19 heteroaryl groups, deuterium and hydrogen.

According to one embodiment of the invention, the anthracene derivative according to formula (1) may be any one compound selected from the group represented by the following formula:

          (2) (3)

          (4) (5)

          (6) (7)

          (8) (9)

    (10) (11)

           (12) (13)

           (14) (15)

          (16) (17)

          (18) (19)

          (20) (21)

           (22) (23)

           (24) (25)

           (26) (27)

           (28) (29)

           (30) (31)

           (32) (33)

According to another embodiment of the present invention, the substituent of A ₁ or A ₂ of the anthracene derivative preferably includes at least one silyl group.

Further, according to another embodiment of the present invention, the substituent of A ₁ or A ₂ of the anthracene derivative preferably includes at least one deuterium.

In addition, according to another embodiment of the present invention, it is preferable that the substituent of A ₁ or A ₂ of the anthracene derivative includes at least one halogen group.

In addition, the present invention, in order to achieve the second technical problem, an anode; Cathode; And it provides an organic electroluminescent device having a layer comprising an anthracene derivative represented by the formula (1) interposed between the anode and the cathode.

According to an embodiment of the present invention, the anode and the cathode may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer The anthracene derivative is preferably included 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 Pa.

According to the present invention, it is possible to provide an organic light emitting device having excellent color purity, power efficiency, and luminous efficiency.

The present invention provides an anthracene derivative represented by Chemical Formula 1, as shown in Chemical Formula 1, phenyl is introduced into carbons 9 and 10 with anthracene as a basic skeleton, and deuterium, which isotopes instead of hydrogen of phenyl, is introduced. It is characterized by one. Deuterium introduced into the phenyl group in the anthracene derivative according to the present invention performs the same function as the hydrogen atom while preventing energy loss between hydrogen and carbon.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like. Halogen atoms, hydroxy groups, nitro groups, cyano groups, silyl groups (in this case referred to as "alkylsilyl groups"), substituted or unsubstituted amino groups (-NH ₂ , -NH (R), -N (R ') ( R ''), R 'and R "are each independently an alkyl group having 1 to 10 carbon atoms, in which case it is referred to as" alkylamino group "), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, carbon number 1 to 20 alkyl groups, halogenated alkyl groups of 1 to 20 carbon atoms, alkenyl groups of 1 to 20 carbon atoms, alkynyl groups of 1 to 20 carbon atoms, heteroalkyl groups of 1 to 20 carbon atoms, aryl groups of 6 to 20 carbon atoms, and 6 to 20 carbon atoms An arylalkyl group having 20, a heteroaryl group having 6 to 20 carbon atoms or having 6 carbon atoms It may be substituted with a heteroarylalkyl group 20.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like. At least one hydrogen atom of the alkoxy group may be substituted with the same substituent as in the alkyl group.

The aryl group, which is a substituent used in the compound of the present invention, means a cyclic aromatic system including one or more rings, and the rings may be attached or fused together in a pendant manner. Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like, and one or more hydrogen atoms of the aryl group may be substituted with the same substituents as in the case of the alkyl group (for example, When substituted with an amino group, an "arylamino group", when substituted with a silyl group, an "arylsilyl group", and when substituted with an oxy group, "aryloxy group".

The heteroaryl group, which is a substituent used in the compound of the present invention, N, O, P means a ring aromatic system having 5 to 30 carbon atoms containing 1, 2 or 3 hetero atoms selected from S, and the remaining ring atoms are carbon, The rings may be attached or fused together in a pendant manner. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.

Anthracene compound according to the present invention may have a structure represented by the above formula. However, the above structural formulas only show an example of an anthracene compound according to the present invention and do not limit the present invention.

In addition, the present invention, in order to achieve the second technical problem, an anode; Tasos; And it provides an organic electroluminescent device having a layer comprising an anthracene derivative represented by Formula 2 to 33 interposed between the anode and the cathode.

Referring to the organic light emitting device according to the present invention in more detail, the organic light emitting device further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer between the anode and the cathode. The hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer serve to increase the probability of light emitting coupling in the light emitting polymer by efficiently transferring holes or electrons to the light emitting layer.

The hole injection layer and the hole transport layer are laminated to facilitate the injection of holes from the anode and the transport of the injected holes. As the material for the hole transport layer, electron donor molecules having small ionization potential are used. Diamine, triamine or tetraamine derivatives based on amines are frequently used. In the present invention, as the material of the hole transport layer, as long as it is commonly used in the art, various materials can be used without limitation, for example, N, N' -bis (3-methylphenyl) -N, N ' -Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) or N, N' -di (naphthalen-1-yl) -N, N' -diphenyl benzidine (α-NPD ) Can be used. In addition, a hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc or Starburst type amines such as TCTA, m-MTDATA, IDE406 (manufactured by Idemitsu Corp.) and the like can be used.

                   CuPc TCTA

                  m-MTDATA

An organic light emitting layer is stacked on the hole transport layer, and the organic light emitting layer may be made of a single material or may be made of a host / dopant.

In general, when the compound is used as a single material, a host / dopant-based light emitting layer is preferable, because an intermolecular interaction causes a mound peak at long wavelengths, resulting in poor color purity, and poor efficiency due to a light emission decay effect. The anthracene derivative may be used as a dopant material in the host / dopant light emitting layer. The host material in the host / dopant light emitting layer is not particularly limited as long as it is generally used in the art.

The electron transport layer serves to increase the chance of recombination within the light emitting layer by smoothly transporting electrons supplied from the cathode to the light emitting layer and suppressing movement of holes that are not bonded in the light emitting layer. Such electron transport layer material is not particularly limited as long as it is a material used in the art, for example, tri-8-hydroxyquinoline aluminum (Alq3), PBD (2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole), TNF (2,4,7-trinitro fluorenone), BMD, BND and the like can be used.

Meanwhile, an electron injection layer (EIL) may be further stacked on the upper portion of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li ₂ O, BaO.

Furthermore, in addition to the above-described hole injection layer, hole transport layer, electron transport layer, and electron injection layer, the organic light emitting device according to the present invention may further include additional functional laminated structures such as a hole blocking layer or an electron blocking layer. . At this time, the hole blocking layer serves to prevent such a problem by using a material having a very low HOMO level because the life and efficiency of the device is reduced when holes are introduced into the cathode through the organic light emitting layer. The material constituting the hole blocking layer is not particularly limited, but must have an ionization potential higher than that of the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

More specifically, FIGS. 1A to 1E illustrate organic light emitting diodes having various types of stacked structures. Referring to this, the organic light emitting diode of FIG. 1A includes an anode / hole injection layer / light emitting layer / cathode. The organic electroluminescent device of FIG. 1B has a structure consisting of an anode / hole injection layer / light emitting layer / electron injection layer / cathode. In addition, the organic light emitting display device of FIG. 1c has a structure of an anode / hole injection layer / hole transporting layer / light emitting layer / cathode, and the organic light emitting device shown in FIG. 1d includes an anode / hole injection layer / hole transporting layer / light emitting layer / electron injection Has a structure of layers / cathodes. Finally, the organic light emitting display device of FIG. 1E has a structure of an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode.

The organic electroluminescent device according to the present invention may include the anthracene derivative in various laminated structures interposed between the anode and the cathode. Preferably, the anthracene derivative may be used as a light emitting material in the light emitting layer between the anode and the cathode. have.

In addition, the thickness of the light emitting layer including the anthracene derivative may be 50 to 2,000 kW, but when the thickness is less than 50 kW, the luminous efficiency is lowered, and when it exceeds 2,000 kW, the driving voltage is uneconomical.

A method of manufacturing an organic light emitting display device according to the present invention will be described with reference to FIGS. 1A to 1E.

First, an anode material is coated on the substrate. As the substrate, a substrate used in a conventional light emitting device is used. A glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, as the anode material, materials commonly used in the art such as transparent and conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), or zinc oxide (ZnO) may be used. Can be. The hole injection layer is selectively stacked on the anode by vacuum thermal deposition or spin coating, and then the hole transport layer is formed on the hole injection layer by vacuum thermal deposition or spin coating. .

Next, after the light emitting layer is laminated on the hole transport layer, a hole blocking layer is selectively formed thereon by vacuum thermal evaporation or spin coating. Finally, the electron transport layer is deposited on the hole blocking layer by vacuum thermal deposition or spin coating, and then an electron injection layer is selectively formed, and the cathode forming metal is vacuum-deposited on the electron injection layer. The organic electroluminescent device according to the present invention can be manufactured. On the other hand, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminium-lithium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), Magnesium-silver (Mg-Ag) or the like may be used, and a transmissive cathode using ITO or IZO may be used to obtain a front light emitting device.

Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.

Synthesis Example 1 2,6-bis [di ( p Tolyl) amino] -9,10-di (phenyl-d5) anthracene

Synthesis Example 1-1: Synthesis of 2,6-dibromo-9,10-dihydroxy-9,10-di (phenyl-d5) anthracene

60.9 ml (578 mmol) of bromobenzene-d5 and 1100 ml of THF were added to a 1000 ml round bottom flask, and then cooled to minus 78 ° C. Then 335.6 ml (537 mmol) of n-butyllithium were slowly added dropwise, stirred for 30 minutes at the same temperature, and then 75.6 g (201 mmol) of 2,6-dibromoanthraquinone were added. The reaction product was warmed to room temperature, stirred for 3 hours, and 260 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO ₄ , filtered and the filtrate was concentrated, followed by subsequent reaction.

Synthesis Example 1-2: Synthesis of 2,6-dibromo-9,10-di (phenyl-d5) anthracene

Into a 1000 ml round bottom flask, 2,6-dibromo-9,10-dihydroxy-9,10-di (phenyl-d5) anthracene obtained from Synthesis Example 1-1 was added, followed by KI 102.8 g (620 mmol), 109.0 g (1239 mmol) of NaH ₂ PO ₂ -H ₂ O, and 760 ml of acetic acid are added to reflux for 3 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The dried product was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 58.3 g of yellow solid 2,6-dibromo-9,10-di (phenyl-d5) anthracene (117 mmol, 56.8%).

Synthesis Example 1-3 Synthesis of 2,6-bis [di (p-tolyl) amino] -9,10-di (phenyl-d5) anthracene

1000 ml obtained in the above Synthesis Example 1-2 To a round bottom flask was added 2, 6-dibromo-9,10-di (phenyl -d5) anthracene 16.8 g (33.8 mmol), di-p-tolyl-amine (di- p - tolyl amine) 8.9 g (94.7 mmol), palladium acetate (palladium acetate) 0.38 g (1.7 mmol), BINAP 1.05 g (1.7 mmol), potassium tert- butoxide (potassium tert -butoxide) 13.3 g ( 118 mmol) 1650 ml of toluene was added and refluxed for 20 hours. When the reaction is complete, it is filtered while hot. After cooling to room temperature, the resulting solid is filtered and recrystallized three times with toluene. The resulting solid was filtered under reduced pressure and dried to give 14.0 g (19.1 mmol, 56.5%) of an orange solid 2,6-di [di-p-tolylamino] -9,10-di (phenyl-d5) anthracene. .

Synthesis Example 2 2,6-di ( N -methyl- N Preparation of -phenylamino) -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-dibromo-9,10-di (phenyl-d5) anthracene and N -methylaniline react to give 2,6-di ( N -methyl- N -phenylamino) -9,10-di (phenyl -d 5) 4.5 g of anthracene was obtained.

Synthesis Example 3 2,6-bis [ N , N -D( p Preparation of -trimethylsilylphenyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-dibromo-9,10-di (phenyl-d5) anthracene is reacted with N, N -di ( p -trimethylsilylphenyl) amine to give 2,6-bis [ N , N -di ( p- 6.0 g of trimethylsilylphenyl) amino] -9,10-di (phenyl-d5) anthracene was obtained.

Synthesis Example 4 2,6-bis [ N , N Preparation of -di (4'-biphenyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-bis [ N , N -di (4'-) by reacting 2,6-dibromo-9,10-di (phenyl-d5) anthracene with N, N -di (4-biphenyl) amine 3.2 g of biphenyl) amino] -9,10-di (phenyl-d5) anthracene was obtained.

Synthesis Example 5 2,6-bis [ N , N Preparation of -di (4'-fluorophenyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-bis [ N , N -di (4 ') by reacting 2,6-dibromo-9,10-di (phenyl-d5) anthracene with N, N -di (4-fluorophenyl) amine 4.3 g of -fluorophenyl) amino] -9,10-di (phenyl-d5) anthracene was obtained.

Synthesis Example 6 2,6-bis [ N , N Preparation of -di (3 ', 5'-dimethylphenyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-bis [ N , N -di (3) by reacting 2,6-dibromo-9,10-di (phenyl-d5) anthracene with N, N -di (3,5-dimethylphenyl) amine 2.7 g of ', 5'-dimethylphenyl) amino] -9,10-di (phenyl-d5) anthracene was obtained.

Synthesis Example 7 2,6-bis [ N- (4'- tert -Butylphenyl)- N- Preparation of (2 "-naphthyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-bis [ N-] was reacted by reacting 2,6-dibromo-9,10-di (phenyl-d5) anthracene with N- (4- tert -butylphenyl) -N- 2'-naphthylamine. (4'- tert - butylphenyl) - N - (2 "- naphthyl) amino] -9,10-di (phenyl -d5) anthracene was obtained 2.3 g.

Synthesis Example 8 2,6-bis [ N -(4'-cyanocyphenyl)- N Preparation of-(3 ", 5" -dimethylphenyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-dibromo-9,10-di (phenyl -d5) anthracene and N - (4- cyanophenyl) - N - (3 ', 5'- dimethyl-phenyl) reacting an amine 2,6 di [N - (4'- cyano-shi phenyl) - N - (3 ", 5" - dimethylphenyl) amino] -9,10-di (phenyl -d5) anthracene was obtained 3.2 g.

Synthesis Example 9: 2,6-bis [ N -(4-cyanophenyl)- N Preparation of -cyclohexylamino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 Reaction of 2,6-dibromo-9,10-di (phenyl-d5) anthracene with N- (4-cyanophenyl) -N -cyclohexylamine to give 2,6-bis [ N- (4-sia 3.9 g of nophenyl) -N -cyclohexylamino] -9,10-di (phenyl-d5) anthracene were obtained.

Synthesis Example 10 2,6-bis [ N, N Preparation of -di (4'-methoxyphenyl) amino] -9,10-di (phenyl-d5) anthracene

In the same manner as in Synthesis example 1 2,6-dibromo-9,10-di (phenyl-d5) anthracene reacts with N, N -di (4-methoxyphenyl) amine to give 2,6-bis [ N, N -di (4 ' 4.9 g of -methoxyphenyl) amino] -9,10-di (phenyl-d5) anthracene was obtained.

Example 1 Fabrication of Organic Electroluminescent Device According to the Present Invention

The ITO glass was patterned on the substrate so as to have a light emitting area of 2 mm x 2 mm, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ⁻⁶ torr and then CuPC (200 kPa), NPD (400 kPa), 9,10- on the ITO glass, using a known method. di (2'- naphthyl) anthracene (200Å) + the compounds prepared according to synthesis example 1 (3%) (200Å) , Alq 3 (350Å), LiF (5Å), it was formed in the order of Al (1000Å). The light emission characteristic of the manufactured organic light emitting display device was 2354 Cd / m ² (5.65 V) at 0.4 mA.

Example 2 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 2 instead of the compound. The luminescence properties of the manufactured organic light emitting diode showed 2172 Cd / m ² (5.71 V) at 0.4 mA.

Example 3 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 3 instead of the compound. The luminescence properties of the manufactured organic electroluminescent device showed 2284 Cd / m ² (5.42 V) at 0.4 mA.

Example 4 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 4 instead of the compound. The luminescence properties of the manufactured organic electroluminescent device showed 2458 Cd / m ² (5.76 V) at 0.4 mA.

Example 5 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 5 instead of the compound. The luminescence properties of the prepared organic light emitting device showed 2254 Cd / m ² (5.16 V) at 0.4 mA.

Example 6 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 6 instead of the compound. The luminescence properties of the manufactured organic light emitting diode showed 2229 Cd / m ² (5.52 V) at 0.4 mA.

Example 7 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 7 instead of the compound. The luminescence properties of the prepared organic light emitting diode showed 2241 Cd / m ² (5.73 V) at 0.4 mA.

Example 8 Fabrication of Organic Electroluminescent Device According to the Present Invention

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound prepared in Synthesis Example 8 instead of the compound. The luminescence properties of the manufactured organic electroluminescent device showed 1663 Cd / m ² (5.76 V) at 0.4 mA.

Comparative Example 1: Fabrication of organic light emitting diode according to the prior art

Of Synthesis Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using C545T instead of the compound. The luminescence properties of the prepared organic light emitting diode showed 1150 Cd / m ² (6.09 V) at 0.4 mA.

Table 1 summarizes various characteristics of the organic light emitting display device according to Examples 1, 2 and Comparative Example 1.

Classification Dopant Driving voltage
(V) Efficiency (Cd / A) Power efficiency (lm / W) Color purity
CIE (x, y) Example 1 15 5.65 23.5 13.06 (0.27, 0.65) Example 2 3 5.71 21.7 11.09 (0.26, 0.65) Example 3 12 5.42 22.8 13.21 (0.25, 0.65) Example 4 13 5.76 24.6 13.41 (0.29, 0.66) Example 5 17 5.16 22.54 13.72 (0.26, 0.66) Example 6 18 5.52 22.3 12.69 (0.28, 0.66) Example 7 20 5.73 22.4 12.28 (0.27, 0.66) Example 8 24 5.76 16.6 9.05 (0.24, 0.64) Comparative Example 1 C545T 6.09 11.5 5.93 (0.35, 0.60)

Referring to Table 1, it can be seen that the organic light emitting display device according to Examples 1 and 2 has better power efficiency and luminous efficiency than the organic light emitting display device according to Comparative Example 1.

1A to 1E are cross-sectional views illustrating a lamination structure of an organic light emitting display device according to a preferred embodiment of the present invention.

Claims (9)

delete Anthracene derivative, which is any one compound selected from compounds represented by the following formula:

                 (12) (13)

                 (15) (17)

                 (18) (20)

                 (24) (32) delete delete delete Anode; Cathode; And a layer comprising the anthracene derivative according to claim 2 interposed between the anode and the cathode. The organic material of claim 6, further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron blocking layer between the anode and the cathode. Electroluminescent element. The organic light emitting device of claim 6, wherein the anthracene derivative is included in a light emitting layer between the anode and the cathode. The organic light emitting device of claim 6, wherein the light emitting layer has a thickness of 50 to 2,000 μm.

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