KR102028503B1 - Phosphorescent material and organic light emitting diode device using the same - Google Patents

Abstract

은 하기 화학식2로 표시되며, 하기 화학식2에서 R1은 알콕시기, 트리메틸실릴기, 트리플루오르메틸기, 할로겐 중에서 선택되고 R2, R3, R4, R5 각각은 독립적으로 수소, C1~C6의 알킬기 또는 C1~C6의 알콕시기에서 선택되는 것을 특징으로 하는 인광 물질.
화학식1

화학식2

The present invention is represented by the following formula (1),

Is represented by the following formula (2), R1 in the formula (2) is selected from alkoxy group, trimethylsilyl group, trifluoromethyl group, halogen and each of R2, R3, R4, R5 is independently hydrogen, alkyl group of C1 ~ C6 or C1 ~ Phosphorescent material selected from alkoxy groups of C6.
Formula 1

Formula 2

Description

Phosphorescent material and organic light emitting diode device using the same

The present invention relates to a phosphor material used in an organic light emitting diode device, and more particularly to a phosphor material having a high color purity and efficiency and an organic light emitting diode device using the same.

Recently, as the size of a display device increases, the demand for a flat display device having less space is increasing. One of such flat display devices, an organic light emitting diode (OLED), also known as an organic electroluminescent device (OELD), has a high speed. It has been developed and several prototypes have already been announced.

An organic light emitting diode device is a device that emits light when electrons and holes are paired and then disappear when electrons are injected into a light emitting material layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode). Not only can the device be formed on a flexible transparent substrate such as plastic, but it can also be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic electroluminescent (EL) display. In addition, the power consumption is relatively low, there is an advantage that the color purity is excellent. In addition, the organic electroluminescent (EL) device can display three colors of green, blue, and red, and thus, has become a subject of much interest as a next-generation rich color display device. Here is a brief look at the process of manufacturing an organic light emitting diode device,

(1) First, a material such as indium tin oxide (ITO) is deposited on a transparent substrate to form an anode.

(2) forming a hole injecting layer (HIL) on the anode; The hole injection layer is mainly formed by depositing copper phthalocyanine (CuPc) represented by Chemical Formula 1-1 to a thickness of 10 nm to 30 nm.

(3) Next, a hole transport layer (HTL) is formed on the hole injection layer. This hole transport layer is formed by depositing about 30nm to 60nm 4,4'-bis [N- (1-naphtyl) -N-phenylamino] -biphenyl (NPB) represented by the following formula (1-2).

(4) Next, an emitting material layer (EML) is formed on the hole transport layer. In this case, a dopant may be added as necessary, and a red, green, and blue light emitting material layer may be formed to implement color. For example, Bis (N-carbazolyl) biphenyl (CBP), a host represented by Formula 1-3, is doped with an iridium complex dopant represented by Formula 1-4 or Formula 1-5 to form a light emitting material layer. .

(5) Next, an electron transport layer (ETL) and an electron injecting layer (EIL) are successively formed on the light emitting material layer.

(6) Next, a cathode is formed on the electron injection layer, and finally a protective film is formed on the cathode.

Formula 1 -One

Formula 1 -2

Formula 1 -3

Formula 1 -4

Formula 1 -5

Recently, more phosphors are used in the light emitting material layer than fluorescent materials. In the case of fluorescent materials, only about 25% of the singlet in the exciton formed in the light emitting layer is used to generate light, and 75% of the triplet is mostly lost by heat, while the phosphor converts both singlet and triplet into light. This is because it has a light emitting mechanism. Phosphorescent dopants generally contain heavy atoms such as Ir, Pt, and Eu at the center of the organic material, and have a high probability of electron transfer from triplet to singlet.

However, such a dopant has a rapid efficiency decrease due to concentration quenching, and thus the light emitting material layer cannot be formed alone. Therefore, the light emitting layer is formed together with the host having higher thermal stability and triplet energy than the dopant.

Looking at the light emitting process of the organic light emitting diode device including the phosphor, the holes injected from the anode and the electrons injected from the cathode meet at the host of the light emitting layer, and the singlet excitons formed at the host are the singlet or triplet of the dopant. Energy transfer occurs, and triplet excitons cause energy transfer to the triplet of the dopant. Since the excitons transferred to the singlet of the dopant are transferred back to the triplet of the dopant, the primary terminus of all excitons is the triplet level of the dopant. The exciton thus formed transitions to the ground state and generates light.

Since the light emitting material layer is greatly influenced by the dopant, there is a demand for a phosphorescent compound having advantages in terms of color purity, luminous efficiency, and lifetime.

The present invention seeks to provide a novel phosphor having improved properties in terms of color purity, luminous efficiency and lifetime.

로 표시되고,

은

로 표시되며, R1은 알콕시기, 트리메틸실릴기, 트리플루오르메틸기, 할로겐 중에서 선택되고 R2, R3, R4, R5 각각은 독립적으로 수소, C1~C6의 알킬기 또는 C1~C6의 알콕시기에서 선택되는 것을 특징으로 하는 인광 물질을 제공한다.In order to solve the above problems, the present invention

Is indicated by

silver

R 1 is selected from an alkoxy group, trimethylsilyl group, trifluoromethyl group or halogen and each of R 2, R 3, R 4 and R 5 is independently selected from hydrogen, an alkyl group of C 1 -C 6 or an alkoxy group of C 1 -C 6 It provides a phosphorescent material characterized by.

In the phosphor of the present invention, the alkoxy group, which is a substituent of R1, is selected from methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy. It is done.

In the phosphor of the present invention, the halogen is characterized in that selected from F, Cl, Br, I.

는 2,4-펜테인다이온, 2,2,6,6,-테트라메틸헵테인-3,5-다이온, 1,3-프로페인다이온, 1,3-부테인다이온, 3,5-헵테인다이온, 1,1,1-트라이플루오로-2,4-펜테인다이온, 1,1,1,5,5,5-헥사플루오로-2,4-펜테인다이온 및 2,2-다이메틸-3,5-헥세인다이온 중에서 선택되는 것을 특징으로 한다.
In the phosphor material of the present invention,

2,4-pentaneione, 2,2,6,6, -tetramethylheptane-3,5-dione, 1,3-propaneinone, 1,3-butaneinone, 3 , 5-heptanedionone, 1,1,1-trifluoro-2,4-pentaneione, 1,1,1,5,5,5-hexafluoro-2,4-pentane It is characterized in that it is selected from ions and 2,2-dimethyl-3,5-hexane ions.

로 표시되고,

은

로 표시되며, R1은 알콕시기, 트리메틸실릴기, 트리플루오르메틸기, 할로겐 중에서 선택되고 R2, R3, R4, R5 각각은 독립적으로 수소, C1~C6의 알킬기 또는 C1~C6의 알콕시기에서 선택되는 것을 특징으로 하는 인광 물질을 포함하여 이루어지는 유기발광다이오드소자를 제공한다.
In another aspect, the present invention comprises a first electrode; A second electrode facing the first electrode; And a light emitting material layer positioned between the first and second electrodes, wherein the light emitting material layer is

Is indicated by

silver

R 1 is selected from an alkoxy group, trimethylsilyl group, trifluoromethyl group or halogen and each of R 2, R 3, R 4 and R 5 is independently selected from hydrogen, an alkyl group of C 1 -C 6 or an alkoxy group of C 1 -C 6 An organic light emitting diode device comprising a phosphorescent material is provided.

In the iridium complex phosphor of the present invention, any one of an alkoxy group, trimethylsilyl group, trifluoromethyl group, and halogen is substituted for the quinoline moiety of the ligand, and an alkyl group or an alkoxy group is substituted for the phenyl moiety, thereby providing color purity, luminous efficiency and lifetime. Both have advantages.

In addition, the organic light emitting diode device using the phosphor has an effect that the display quality is improved and the low voltage driving is possible as the luminous efficiency is increased.

1 is a schematic cross-sectional view of an organic light emitting diode device according to an embodiment of the present invention.

Hereinafter, a structure of a phosphor, a synthesis example thereof, and an organic light emitting diode device using the same will be described.

은 하기 화학식3으로 표시된다.Phosphor material of the present invention is an iridium complex represented by the formula (2),

Is represented by the following formula (3).

Formula 2

Formula 3

That is, in the ligand of the iridium complex, any one of an alkoxy group, a trimethylsilyl group, a trifluoromethyl group, and a halogen is substituted at position 4 (based on nitrogen (N)) of the quinoline moiety, and an alkyl group having 1 to 6 carbon atoms in the benzene ring. Or alkoxy group of C1 ~ C6 may be substituted.

In other words, in Formula 3, R1 is selected from an alkoxy group, trimethylsilyl group, trifluoromethyl group, and halogen, and in Formula 4, each of R2, R3, R4, and R5 is independently hydrogen, an alkyl group of C1 ~ C6, or C1 ~. It is selected from the alkoxy group of C6. R2, E3, E4, R4 and R5 may be the same or different.

The alkoxy group may be selected from methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy and t-butoxy, wherein the halogen is selected from F, Cl, Br, I Can be selected.

는 2,4-펜테인다이온, 2,2,6,6,-테트라메틸헵테인-3,5-다이온, 1,3-프로페인다이온, 1,3-부테인다이온, 3,5-헵테인다이온, 1,1,1-트라이플루오로-2,4-펜테인다이온, 1,1,1,5,5,5-헥사플루오로-2,4-펜테인다이온 및 2,2-다이메틸-3,5-헥세인다이온 중에서 선택될 수 있다.In addition, in Formula 2

2,4-pentaneione, 2,2,6,6, -tetramethylheptane-3,5-dione, 1,3-propaneinone, 1,3-butaneinone, 3 , 5-heptanedionone, 1,1,1-trifluoro-2,4-pentaneione, 1,1,1,5,5,5-hexafluoro-2,4-pentane Ions and 2,2-dimethyl-3,5-hexane ions.

The ligand represented by Formula 3 may be any one of the substances represented by the following Formula 4.

Formula 4

In addition, the phosphor according to the embodiment of the present invention shown in the formula (2) is represented by the following formula (5).

Formula 5

The above-mentioned iridium complex phosphor has an improved characteristic in color purity, luminous efficiency and lifetime by replacing any one of an alkoxy group, trimethylsilyl group, trifluoromethyl group and halogen at the quinoline portion 4 position of the phenyl quinoline ligand.

In addition, by replacing the C1-C6 alkyl group or C1-C6 alkoxy group in the phenyl moiety, color purity, luminous efficiency and lifespan characteristics are further improved. If one is an alkyl group, the characteristic improvement is further increased.

Hereinafter, a synthesis example of a phosphor represented by A-04, A-10, A-16, A-22, and A-27 in Chemical Formula 5 in the phosphor according to the present invention will be described.

1.Synthesis of A-04

(1) Synthesis of 2- (3 ', 5'-dimethyphenyl) -7-trimethylsilylquinoline

Scheme 1

2-chloro-7-trimethylsilylquinoline (5g, 0.02mol), 3,5-dimethylbenzeneboronic acid (4.1g, 0.03mol), K2CO3 (8.3g) and a small amount of Pd (PPh3) 4 in THF / H2O (60 mL / 60 mL) and reflux for 18 h. After confirming the reaction by Thin-Layer Chromatography (TLC), it was cooled to room temperature and extracted with methylene chloride. The solvent was evaporated and purified by silica gel column to obtain 2- (3 ', 5'-dimethylphenyl) -7-trimethylsilylquinoline (5.0g, yield: 80%).

(2) Synthesis of Chloro-bridged Dimer Complex

Scheme 2

Iridium Chloride (5mmol) and 2- (3 ', 5-dimethylphenyl) -7-trimethylsilylquinoline (10mmol) were added to 2-ethoxyethanol: distilled H2O in a 3: 1 mixed solution (30ml) and refluxed for 24 hours. I was. The solid formed by adding water was filtered and then washed several times with distilled water to obtain a chloro bridged dimer complex.

(3) Synthesis of Iridium (III) (2- (3 ', 5'-dimethylphenyl) -7-trimethylsilylquinoline-N, C2') (2,4-pentanedionate-O, O) [A-04]

Scheme 3

Chloro-bridged dimer complex (1 mmol), 2,4-pentanedione (3 mmol) and Na2CO3 (6 mmol) were added to 2-ethoxyethanol (30 ml) and refluxed for 24 hours. After cooling to room temperature, distilled water was added to give a solid after filtration. The solid formed was dissolved in dichloromethane, filtered using silica gel, and recrystallized from dichloromethane / methanol to obtain a compound (A-04).

2. Synthesis of A-10

(1) Synthesis of 2- (3 ', 5'-dimethyphenyl) -7-trifluoromethylquinoline

Scheme 4

2-chloro-7-trifluoromethylquinoline (5g, 0.02mol), 3,5-dimethylbenzeneboronic acid (4.1g, 0.03mol), K2CO3 (8.3g) and a small amount of Pd (PPh3) 4 were added to THF / H2O in a two-necked round flask. (60mL / 60mL) and refluxed for 18 hours. After confirming the reaction by TLC, the mixture was cooled to room temperature and extracted with methylene chloride. The solvent was evaporated and purified by silica gel column to obtain 2- (3 ', 5'-dimethylphenyl) -7-trifluoromethylquinoline (4.5g, yield: 70%).

(2) Synthesis of Chloro-bridged dimer complex

Scheme 5

Iridium Chloride (5mmol) and 2- (3 ', 5-dimethylphenyl) -7-trifluoromethylquinoline (10mmol) were added to 2-ethoxyethanol: distilled sugar 3: 1 mixed solution (30ml) and refluxed for 24 hours. The solid formed by adding water was filtered and then washed several times with distilled water to obtain a chloro bridged dimer complex.

(3) Synthesis of Iridium (III) (2- (3 ', 5'-dimethylphenyl) -7-trifluoromethylquinoline-N, C2') (2,4-pentanedionate-O, O) [A-10]

Scheme 6

Chloro-bridged dimer complex (1 mmol), 2,4-pentanedione (3 mmol) and Na2CO3 (6 mmol) were added to 2-ethoxyethanol (30 ml) and refluxed for 24 hours. After cooling to room temperature, distilled water was added to give a solid after filtration. The solid formed was dissolved in dichloromethane, filtered through silica gel, and recrystallized from dichloromethane / methanol to obtain compound (A-10).

3. Synthesis of A-16

(1) Synthesis of 2- (3 ', 5'-dimethyphenyl) -7-fluoroquinoline

Scheme 7

2-chloro-7-fluoroquinoline (4.7 g, 0.02 mol), 3,5-dimethylbenzeneboronic acid (4.1 g, 0.03 mol), K2CO3 (8.3 g), and a small amount of Pd (PPh3) 4 in THF / It was placed in H 2 O (60 mL / 60 mL) and refluxed for 18 hours. After confirming the reaction by TLC, the mixture was cooled to room temperature and extracted with methylene chloride. The solvent was evaporated and purified by silica gel column to obtain 2- (3 ', 5'-dimethylphenyl) -7-fluoroquinoline (4.8, yield: 80%).

(2) Synthesis of Chloro-bridged dimer complex

Scheme 8

Iridium Chloride (5mmol) and 2- (3 ', 5-dimethylphenyl) -7-fluoroquinoline (10mmol) were added to 2-ethoxyethanol: distilled water 3: 1 mixed solution (30ml) and refluxed for 24 hours. The solid formed by adding water was filtered and then washed several times with distilled water to obtain a chloro bridged dimer complex.

(3) Synthesis of Iridium (III) (2- (3 ', 5'-dimethylphenyl) -7-fluoroquinoline-N, C2') (2,4-pentanedionate-O, O) [A-16]

Scheme 9

Chloro-bridged dimer complex (1 mmol), 2,4-pentanedione (3 mmol) and Na2CO3 (6 mmol) were added to 2-ethoxyethanol (30 ml) and refluxed for 24 hours. After cooling to room temperature, distilled water was added to give a solid after filtration. The solid formed was dissolved in dichloromethane, filtered through silica gel, and recrystallized from dichloromethane / methanol to obtain Compound (A-16).

4. Synthesis of A-22

(1) Synthesis of 2- (3 ', 5'-dimethyphenyl) -7-methoxyquinoline

Scheme 10

2-chloro-7-methoxyquinoline (4.8 g, 0.02 mol), 3,5-dimethylbenzeneboronic acid (4.0 g, 0.03 mol), K2CO3 (8.3 g), and a small amount of Pd (PPh3) 4 in THF / It was placed in H 2 O (60 mL / 60 mL) and refluxed for 18 hours. After confirming the reaction by TLC, the mixture was cooled to room temperature and extracted with methylene chloride. The solvent was evaporated and purified by silica gel column to obtain 2- (3 ', 5'-dimethylphenyl) -7-methoxyquinoline (4.7g, yield: 80%).

(2) Synthesis of Chloro-bridged dimer complex

Scheme 11

Iridium Chloride (5mmol) and 2- (3 ', 5-dimethylphenyl) -7-methoxyquinoline (10mmol) were added to 2-ethoxyethanol: distilled water 3: 1 mixed solution (30ml) and refluxed for 24 hours. The solid formed by adding water was filtered and then washed several times with distilled water to obtain a chloro bridged dimer complex.

(3) Synthesis of Iridium (III) (2- (3 ', 5'-dimethylphenyl) -7-methoxyquinoline-N, C2') (2,4-pentanedionate-O, O) [A-22]

Scheme 12

Chloro-bridged dimer complex (1 mmol), 2,4-pentanedione (3 mmol) and Na2CO3 (6 mmol) were added to 2-ethoxyethanol (30 ml) and refluxed for 24 hours. After cooling to room temperature, distilled water was added to give a solid after filtration. The solid formed was dissolved in dichloromethane, filtered through silica gel, and recrystallized from dichloromethane / methanol to obtain a compound (A-22).

5. Synthesis of A-27

Scheme 13

The chloro-bridged dimer complex (1mmol), 2,2,6,6-tetramethylheptanedione (3mmol) and Na2CO3 (6mmol) obtained through the reaction scheme 3 were added to 2-ethoxyethanol (30ml) and refluxed for 24 hours. After cooling to room temperature, distilled water was added to give a solid after filtration. The solid formed was dissolved in dichloromethane, filtered using silica gel, and recrystallized from dichloromethane / methanol to obtain a compound (A-27).

Hereinafter, the performance of the red material according to the present invention and the organic light emitting diode device using the same through Experimental Examples 1 to 5 and Comparative Examples 1 to 6 to fabricate the organic light emitting diode device using the phosphor of the present invention. To compare.

Experimental Example 1

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + A-04 (5%) (200 kPa), Alq3 (300 kPa), LiF (5 kPa) on the ITO layer with a vacuum chamber pressure of about 1 * 10 ^-6 torr. Film formation in the order of Al (1000 mW).

1950 cd / m2 (5.5 V) at 0.9 mA, where CIE x = 0.660 and y = 0.322. The lifetime (half the initial luminance) was 6000 hours at 2000 cd / m 2.

Experimental Example 2

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + A-10 (5%) (200 kPa), Alq3 (300 kPa), LiF () on the ITO layer with a vacuum chamber pressure of about 1 * 10 ^-6 torr. 5 mV) and Al (1000 mV) in this order.

At 0.9mA, 1750 cd / m2 (5.5V) was shown, with CIE x = 0.661 and y = 0.323. The lifetime (half the initial luminance) was 5500 hours at 2000 cd / m 2.

Experimental Example 3

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), Balq + A-16 (5%) (200 kPa), Alq3 (300 kPa), LiF (200 kPa) on the ITO layer with a vacuum chamber pressure of about 1 * 10 ^-6 torr. 5 mV) and Al (1000 mV) in this order.

At 0.9mA, 1732 cd / m2 (5.4V) was shown, with CIE x = 0.660 and y = 0.332. The lifetime (half the initial luminance) was 5500 hours at 2000 cd / m 2.

Experimental Example 4

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), Balq + A-22 (5%) (200 kPa), Alq3 (300 kPa), LiF () on the ITO layer with a vacuum chamber pressure of about 1 * 10 ^-6 torr. 5 mV) and Al (1000 mV) in this order.

1890 cd / m2 (5.4 V) at 0.9 mA, with CIE x = 0.662 and y = 0.331. The lifetime (half the initial luminance) was 6000 hours at 2000 cd / m 2.

Experimental Example 5

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), Balq + A-27 (5%) (200 kPa), Alq3 (300 kPa), LiF () on the ITO layer with a vacuum chamber pressure of about 1 * 10 ^-6 torr. 5 mV) and Al (1000 mV) in this order.

At 0.9 mA, 2001 cd / m2 (5.5 V) was shown, with CIE x = 0.662 and y = 0.323. The lifetime (half the initial luminance) was 6500 hours at 2000 cd / m 2.

Comparative Example 1

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 Pa), NPD (400 Pa), BAlq + (Material of Formula 1-4) (7%) (200 Pa), Alq3 (on the ITO layer) at a pressure of about 1 * 10 ^-6 torr Film formation in the order of 300 mV), LiF (5 mV) and Al (1000 mV).

1173 cd / m 2 (6.0 V) at 0.9 mA, where CIE x = 0.606 and y = 0.375. The lifetime (half the initial luminance) was 4000 hours at 2000 cd / m2.

Comparative Example 2

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + (substance of Formula 1-5) (7%) (200 kPa), Alq3 (on the ITO layer) at a vacuum chamber pressure of about 1 * 10 ^-6 torr. Film formation in the order of 300 mV), LiF (5 mV) and Al (1000 mV).

At 0.9mA, 780cd / m2 (7.5V) was shown, with CIE x = 0.659 and y = 0.329. The lifetime (half the initial luminance) was 2500 hours at 2000 cd / m2.

Comparative Example 3

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + (substance of formula 6-1) (7%) (200 kPa), Alq3 (on the ITO layer) at a pressure of about 1 * 10 ^-6 torr Film formation in the order of 300 mV), LiF (5 mV) and Al (1000 mV).

1190 cd / m2 (6.0 V) at 0.9 mA, where CIE x = 0.609 and y = 0.372. The lifetime (half the initial luminance) was 4000 hours at 2000 cd / m2.

Comparative Example 4

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + (substance of formula 6-2) (7%) (200 kPa), Alq3 (on the ITO layer) at a pressure of about 1 * 10 ^-6 torr Film formation in the order of 300 mV), LiF (5 mV) and Al (1000 mV).

1165 cd / m2 (6.1 V) at 0.9 mA, where CIE x = 0.605 and y = 0.376. The lifetime (half the initial luminance) was 3500 hours at 2000 cd / m 2.

Comparative Example 5

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + (material of formula 6-3) (7%) (200 kPa), Alq3 (300 kPa) on the ITO layer with a pressure of about 1 * 10-6torr ), LiF (5 kV) and Al (1000 kV) in this order.

At 0.9 mA, 1151 cd / m2 (5.9 V) was shown, with CIE x = 0.605 and y = 0.375. The lifetime (half the initial luminance) was 3000 hours at 2000 cd / m 2.

Comparative Example 6

The light emitting area of the indium tin oxide (ITO) layer was patterned to have a size of 3 mm x 3 mm and then washed. CuPC (200 kPa), NPD (400 kPa), BAlq + (substance of formula 6-4) (7%) (200 kPa), Alq3 (on the ITO layer) at a pressure of about 1 * 10 ^-6 torr Film formation in the order of 300 mV), LiF (5 mV) and Al (1000 mV).

1201cd / m2 (5.9V) at 0.9mA, where CIE x = 0.608 and y = 0.373. The lifetime (half the initial luminance) was 4000 hours at 2000 cd / m2.

Formula 6 -One

Formula 6 -2

Formula 6 -3

Formula 6 -4

The experimental results of the above Experimental Examples 1 to 5 and Comparative Examples 1 to 6 are shown in Table 1 below. Here, the unit of voltage is [V], the unit of current is [mA], the unit of brightness is [cd / m2], the unit of current efficiency is [cd / A], the unit of power efficiency is [lm / W], The unit of life is [hr].

Voltage electric current Luminance Current efficiency Power efficiency CIE (X) CIE (Y) life span Experimental Example 1 5.5 0.9 1950 19.5 11.1 0.660 0.322 6000 Experimental Example 2 5.5 0.9 1750 17.5 10.0 0.661 0.323 5500 Experimental Example 3 5.4 0.9 1732 17.3 10.1 0.660 0.332 5500 Experimental Example 4 5.5 0.9 1890 18.9 10.8 0.662 0.331 6000 Experimental Example 5 5.5 0.9 2001 20.0 11.4 0.662 0.323 6500 Comparative Example 1 6.0 0.9 1173 11.7 6.2 0.606 0.375 4000 Comparative Example 2 7.5 0.9 780 7.8 3.3 0.659 0.329 2500 Comparative Example 3 6.0 0.9 1190 11.9 6.2 0.609 0.372 4000 Comparative Example 4 6.1 0.9 1165 11.6 6.0 0.605 0.376 3500 Comparative Example 5 5.9 0.9 1151 11.5 6.1 0.605 0.375 3000 Comparative Example 6 5.9 0.9 1201 12.0 6.4 0.608 0.373 4000

As shown in Table 1, Experimental Examples 1 to 5 have improved luminance, current efficiency, power efficiency, and lifetime, and have excellent color sense (CIE (X), CIE (Y)).

Therefore, the organic light emitting diode device using the phosphor of the present invention has advantages in display quality, power consumption, and lifetime.

An embodiment of an organic light emitting diode device including the phosphorescent compound is shown in FIG. 1.

As illustrated, the organic light emitting diode device includes first and second substrates (not shown) facing each other, and an organic light emitting diode 130 formed between the first and second substrates (not shown). .

The organic light emitting diode 130 includes a first electrode 132 serving as an anode, a second electrode 138 serving as a cathode, and an organic light emitting layer formed between the first and second electrodes 132 and 138. .

The first electrode 132 is made of a material having a relatively high work function, for example, indium tin oxide (ITO), and the second electrode 138 is made of a material having a relatively low work function, for example For example, it is made of aluminum (Al) or aluminum alloy.

The organic light emitting layer has a multilayer structure, that is, a hole injection layer (HTL) 133 and a hole transporting layer (HIL) 134 sequentially from the first electrode 132 in order to maximize luminous efficiency. ), A light emitting material layer (EML) 135, an electron transporting layer (ETL) 136, and an electron injection layer (EIL) 137.

Here, the light emitting material layer 135 is made of a phosphorescent material of the present invention represented by the formula (2).

For example, the light emitting material layer 135 may be formed by doping the phosphor material of the present invention to a host material. The iridium complex phosphor used for the light emitting material layer 135 is substituted with any one of an alkoxy group, trimethylsilyl group, trifluoromethyl group, and halogen at the quinoline portion 4 position of the phenyl quinoline ligand, thereby resulting in color purity, luminous efficiency and lifetime. Has improved properties.

In addition, by replacing the C1-C6 alkyl group or C1-C6 alkoxy group in the phenyl moiety, color purity, luminous efficiency and lifespan characteristics are further improved. If one is an alkyl group, the characteristic improvement is further increased.

Although described above with reference to a preferred embodiment of the present invention, those skilled in the art various modifications and variations of the present invention without departing from the spirit and scope of the present invention described in the claims below I can understand that you can.

132: first electrode 133: hole injection layer
134: hole transport layer 135: light emitting material layer
136: electron transport layer 136: electron injection layer
138: second electrode

Claims (9)

It is represented by the following formula (1),

Is represented by the following Chemical Formula 2, in which R 1 is selected from trimethylsilyl and trifluoromethyl groups, each of R 2 and R 4 is independently selected from an alkyl group of C 1 to C 6, and R 3 and R 5 are hydrogen. matter.
Formula 1

Formula 2

delete delete The method of claim 1,
In Chemical Formula 1

2,4-pentaneione, 2,2,6,6, -tetramethylheptane-3,5-dione, 1,3-propaneinone, 1,3-butaneinone, 3 , 5-heptanedionone, 1,1,1-trifluoro-2,4-pentaneione, 1,1,1,5,5,5-hexafluoro-2,4-pentane A phosphor, selected from ions and 2,2-dimethyl-3,5-hexane ions.
A first electrode;
A second electrode facing the first electrode;
A light emitting material layer positioned between the first and second electrodes,
The organic light emitting diode device of claim 1, wherein the light emitting material layer comprises a phosphorescent material of claim 1.
The method of claim 1,
Wherein R 1 is a trimethylsilyl group, and R 2 and R 4 are methyl groups.
The method of claim 5,
R 1 is a trimethylsilyl group, and R 2 and R 4 are methyl groups.
The method of claim 1,
Phosphor substance selected from substances of the following formula.

The method of claim 5,
The phosphor is an organic light emitting diode device selected from the material of the following formula.

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