KR102134715B1 - Organic Light Emitting Device and Display Device using the same - Google Patents

Abstract

로 표시되는 화합물을 포함하여 이루어진 것을 특징으로 하는 유기 발광 소자에 관한 것으로서,
본 발명에 따르면 유기 발광 소자의 구동 전압을 낮출 수 있다. The present invention comprises an anode, a cathode, and an organic layer formed between the anode and the cathode, wherein the organic layer has the following Chemical Formula 1:
[Formula 1]

It relates to an organic light-emitting device comprising a compound represented by,
According to the present invention, the driving voltage of the organic light emitting device can be lowered.

Description

Organic light emitting device and display device using the same{Organic Light Emitting Device and Display Device using the same}

The present invention relates to an organic light emitting device, and more particularly, to an organic light emitting device capable of lowering the driving voltage.

The organic light emitting device has a structure in which an organic light emitting part is formed between a cathode injecting electrons and an anode injecting holes, and electrons generated in the cathode and holes generated in the anode are organic. When injected into the light emitting part, injected electrons and holes are combined to generate an exciton, and the generated axitone falls from an excited state to a ground state to emit light.

Hereinafter, a conventional organic light emitting device will be described with reference to the drawings.

1 is a schematic cross-sectional view of an organic light emitting diode according to an exemplary embodiment.

As can be seen in Figure 1, the conventional organic light emitting device according to an embodiment, the anode (Anode) (1), a hole injection layer (HIL; Hole Injecting Layer) (2), a hole transport layer (HTL; Hole Transporting Layer) (3), Emitting Layer (EML) 4, and Electron Transporting Layer (ETL) 5, Electron Injecting Layer (EIL) 6, and Cathode 7 ).

When the driving voltage and current density are high in the organic light emitting device, strong stress is exerted on the material constituting the device, which affects material stability and life of the device. Accordingly, the energy levels of the organic layers such as the hole injection layer (HIL) 2, the hole transport layer (HTL) 3, the electron transport layer (ETL) 5, and the electron injection layer (EIL) 6 are adjusted. Many studies have been conducted to increase the efficiency of organic light-emitting devices and lower power consumption.

As part of such research, the development of materials capable of lowering the driving voltage of the organic light emitting device is steadily progressing, but it is still insufficient.

The present invention has been devised to solve the above-described conventional problems, and an object of the present invention is to provide an organic light emitting device capable of lowering a driving voltage by constructing an organic layer using a new material and a display device using the same.

Particularly, an object of the present invention is to provide a material having a deep LUMO (Lowest Unoccupied Molecular Orbital) property as an organic layer material of an organic light emitting device. When the material having the deep LUMO is adjacent to an organic hole transporting material (HTM) having excellent hole transport ability, electrons are received from the HTM to move electrons in the anode direction, and holes are moved to the emission layer direction. Therefore, when using such a deep LUMO material as a hole injection material, the driving voltage of the organic light emitting device can be lowered.

In order to achieve the above object, the present invention comprises an anode, a cathode, and an organic layer formed between the anode and the cathode, and the organic layer is represented by the following Chemical Formula 1:

[Formula 1]

(In the formula 1,

The M ₁ and M ₂ are each independently selected from the group consisting of O, S, NR ₃ , R ₄ CR ₅ , and C(=Z),

,

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로 이루어진 군에서 선택되고, X, Y, and Z are each independently

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Is selected from the group consisting of,

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로 이루어진 군에서 선택되고, A, B, C, and D are each independently

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,

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Is selected from the group consisting of,

R ₁ to R ₅ are each independently hydrogen, deuterium, hydroxyl group, halogen group, cyano group, fluoroalkyl group, C1 to C18 alkyl group, C1 to C18 alkoxy group, C6 or more substituted or unsubstituted aromatic group , C5 or more substituted or unsubstituted heteroaromatic group, C1 to C18 amine group group, C6 or more aromatic group substituted amine group, C5 or more heteroaromatic group substituted amine group, C1 to C18 alkyl group substituted A silyl group group, a silyl group group substituted with an aromatic group of C6 or more, and a silyl group group substituted with a hetero"‡ aromatic group of C5 or more,

R ₁₁ to R ₂₁ and R ₃₁ to R ₃₇ are each independently hydrogen, deuterium, hydroxyl group, C1 to C18 alkyl group, C1 to C18 alkoxy group, C6 or more substituted or unsubstituted aromatic group, and C5 Selected from the group consisting of the above substituted or unsubstituted heteroaromatic groups)

It provides an organic light emitting device comprising a compound represented by.

The present invention also provides a display device having the organic light emitting device.

According to the present invention as described above, the driving voltage of the organic light emitting device can be lowered by using the compound represented by Chemical Formula 1 as an organic layer material between the anode and the cathode.

1 is a schematic cross-sectional view of an organic light emitting diode according to an exemplary embodiment.
2 is a schematic cross-sectional view of an organic light emitting device according to an embodiment of the present invention.
3 is a schematic cross-sectional view of an organic light emitting device according to another embodiment of the present invention.
4 is a schematic cross-sectional view of an organic light emitting device according to another embodiment of the present invention.
5 is a schematic cross-sectional view of an organic light emitting device according to another embodiment of the present invention.
6 is a schematic cross-sectional view of a display device according to an exemplary embodiment of the present invention.
7 is a graph showing current-voltage characteristics of the organic light emitting diodes according to Examples 1 to 4 and Comparative Examples 1 to 2.

The term "on" described herein is meant to include not only the case where a certain component is formed on the upper surface of another component, but also when a third component is interposed between these components.

Modifiers such as “first” and “second” described in this specification are not meant to indicate the order of the corresponding components, but to distinguish the corresponding components from each other.

Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the drawings.

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

As can be seen in Figure 2, the organic light emitting device according to an embodiment of the present invention, the anode (Anode) 100, a hole injection layer (HIL; Hole Injecting Layer) 110, a hole transport layer (HTL; Hole Transporting Layer) ) 120, an emitting layer (EML; Emitting Layer) 130, and an electron transporting layer (ETL) 140, an electron injection layer (EIL) 150, and a cathode (Cathode) ( 500).

The positive electrode 100 may be made of a transparent conductive material having high conductivity and work function, such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), SnO2 or ZnO, but is not limited thereto. no.

The hole injection layer (HIL) 110 is formed on the anode 100, and is made of a compound represented by Formula 1 below. The compound represented by the following formula (1) is included in the organic light emitting device according to the present invention as a hole injection material.

Particularly, the hole injection layer (HIL) 110 may be formed of a compound represented by the following Chemical Formula 1, or a compound represented by the following Chemical Formula 1 may be doped. When the compound represented by the following Chemical Formula 1 is doped to form the hole injection layer (HIL) 110, the host material is MTDATA(4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc( Copper phthalocyanine) or PEDOT/PSS (poly(3,4-ethylenedioxythiphene, polystyrene sulfonate) may be used, but is not limited thereto.The doping amount of the compound represented by the following Chemical Formula 1 is the hole injection layer (HIL ) 110 to 0.1 to 50% by weight relative to the whole.

[Formula 1]

In Chemical Formula 1,

The M ₁ and M ₂ are each independently selected from the group consisting of O, S, NR ₃ , R ₄ CR ₅ , and C(=Z),

,

,

,

,

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,

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로 이루어진 군에서 선택되고, X, Y, and Z are each independently

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Is selected from the group consisting of,

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로 이루어진 군에서 선택되고, A, B, C, and D are each independently

,

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,

,

,

,

,

,

,

,

,

,

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Is selected from the group consisting of,

R ₁ to R ₅ are each independently hydrogen, deuterium, hydroxyl group, halogen group, cyano group, fluoroalkyl group, C1 to C18 alkyl group, C1 to C18 alkoxy group, C6 or more substituted or unsubstituted aromatic group , C5 or more substituted or unsubstituted heteroaromatic group, C1 to C18 amine group group, C6 or more aromatic group substituted amine group, C5 or more heteroaromatic group substituted amine group, C1 to C18 alkyl group substituted A silyl group group, a silyl group group substituted with an aromatic group of C6 or more, and a silyl group group substituted with a hetero"‡ aromatic group of C5 or more,

R ₁₁ to R ₂₁ and R ₃₁ to R ₃₇ are each independently hydrogen, deuterium, hydroxyl group, C1 to C18 alkyl group, C1 to C18 alkoxy group, C6 or more substituted or unsubstituted aromatic group, and C5 It is selected from the group consisting of the above substituted or unsubstituted heteroaromatic group.

In Chemical Formula 1, M ₁ and M ₂ may be made of the same material as each other, and R ₁ and R ₂ may be made of the same material, and in this case, Chemical Formula 1 may include various compounds such as the following Chemical Formulas A1 to A104. Includes.

(A1),

(A2),

(A3),

(A4),

(A5),

(A6),

(A7),

(A8),

(A9),

(A10),

(A11),

(A12),

(A13),

(A14),

(A15),

(A16),

(A17),

(A18),

(A19),

(A20),

(A21),

(A22),

(A23),

(A24),

(A25),

(A26),

(A27),

(A28),

(A29),

(A30),

(A31),

(A32),

(A33),

(A34),

(A35),

(A36),

(A37),

(A38),

(A39),

(A40),

(A41),

(A42),

(A43),

(A44),

(A45),

(A46),

(A47),

(A48),

(A49),

(A50),

(A51),

(A52),

(A53),

(A54),

(A55),

(A56),

(A57),

(A58),

(A59),

(A60),

(A61),

(A62),

(A63),

(A64),

(A65),

(A66),

(A67),

(A68),

(A69),

(A70),

(A71),

(A72),

(A73),

(A74),

(A75),

(A76),

(A77),

(A78),

(A79),

(A80),

(A81),

(A82),

(A83),

(A84),

(A85),

(A86),

(A87),

(A88),

(A89),

(A90),

(A91),

(A92),

(A93),

(A94),

(A95),

(A96),

(A97),

(A98),

(A99),

(A100),

(A101),

(A102),

(A103),

(A104).

(A1),

(A2),

(A3),

(A4),

(A5),

(A6),

(A7),

(A8),

(A9),

(A10),

(A11),

(A12),

(A13),

(A14),

(A15),

(A16),

(A17),

(A18),

(A19),

(A20),

(A21),

(A22),

(A23),

(A24),

(A25),

(A26),

(A27),

(A28),

(A29),

(A30),

(A31),

(A32),

(A33),

(A34),

(A35),

(A36),

(A37),

(A38),

(A39),

(A40),

(A41),

(A42),

(A43),

(A44),

(A45),

(A46),

(A47),

(A48),

(A49),

(A50),

(A51),

(A52),

(A53),

(A54),

(A55),

(A56),

(A57),

(A58),

(A59),

(A60),

(A61),

(A62),

(A63),

(A64),

(A65),

(A66),

(A67),

(A68),

(A69),

(A70),

(A71),

(A72),

(A73),

(A74),

(A75),

(A76),

(A77),

(A78),

(A79),

(A80),

(A81),

(A82),

(A83),

(A84),

(A85),

(A86),

(A87),

(A88),

(A89),

(A90),

(A91),

(A92),

(A93),

(A94),

(A95),

(A96),

(A97),

(A98),

(A99),

(A100),

(A101),

(A102),

(A103),

(A104).

Compounds represented by Chemical Formula 1 including A1 to A104 may be synthesized through various synthetic methods known in the art. Hereinafter, the synthesis method of the A25 compound and the A37 compound will be described as an example.

Scheme 1

As in Scheme 1 above, in a 100 ml round bottom flask, benzonitrile (10.00 g, 96.97 mmol), diisopropyl succinate (11.77 g, 58.18 mmol), and sodium tert-butylate (sodium tert-butylate) (15.47 g, 160.98 mmol) was added and stirred for 4 hours at 100° C. The isopropyl alcohol and tert-butyl alcohol produced during the reaction were distilled off. After off), further stirred at 120° C. for 30 minutes to obtain compound A.

Scheme 2

As in Scheme 2 above, for the hydrolysis reaction, methanol (80 ml) and acetic acid (0.5 g) were added to the 100 ml round bottom flask, and the mixture was refluxed with stirring for 2 hours. After the reaction was completed, the reaction was filtered around 50°C, washed with methanol and water, and dried in a vacuum oven at 80°C to obtain Compound B as a red solid compound (19.57g, 67.88mmol).

Scheme 3

As shown in Scheme 3 above, in a 250 ml round bottom flask, Compound B (5 g, 17.34 mmol), methyl iodide (9.85 g, 69.37 mmol), cesium carbonate (16.95 g, 52.03 mmol) ) Into dimethylformamide (DMF, 150ml) and stirred at room temperature for 24 hours. After completion of the reaction, after filtering the cesium carbonate, the filtrate is concentrated, and a short column is performed with a mixed solution of ethylacetate and methylene chloride. Then, it was concentrated again, and a precipitate was prepared using methyl chloride and methanol, followed by filtration to obtain compound C (5.21 g, 16.48 mmol).

Scheme 4-1

As in Scheme 4-1 above, in a 250 ml round bottom flask in ice water, Compound C (2.5 g, 17.34 mmol), malononitrile (5.22 g, 79.03 mmol), titanium chloride (29.98) g, 158.05mmol), pyridine (12.50g, 158.05mmol) was added to methylene chloride (MC, 100ml) and refluxed for 24 hours. After the reaction was completed by adding water, extraction was performed with MC and water, and concentrated to perform a column using ethyl acetate and hexane. The solution was concentrated again, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound A25 (1.04 g, 2.53 mmol).

Scheme 4-2

Compound C (2.5 g, 17.34 mmol), malononitrile (1.04 g, 15.81 mmol), titanium chloride (6.00 g, 31.61 mmol), pyridine in a 100 ml round bottom flask in ice water (2.50 g, 31.61 mmol) was added to methylene chloride (MC, 60 ml) and refluxed for 24 hours. After the reaction was completed by adding water, extraction was performed with MC and water, and concentrated to perform a column using ethyl acetate and hexane. The solution was concentrated again, a precipitate was prepared using methylene chloride and petroleum ether, and then filtered to obtain compound A37 (1.21 g, 3.32 mmol).

The hole transporting layer (HTL) 120 is formed on the hole injection layer (HIL) 110, and TPD (N,N'-diphenyl-N,N'-bis(3-methylphenyl)- 1,1'-bi-phenyl-4,4'-diamine) or NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine). It is not limited.

The light emitting layer (EML; Emitting Layer) 130 is formed on the hole transport layer (HTL) 120, and may be formed by doping a host material with a dopant. For example, when the light emitting layer (EML) 130 emits blue (B) light, the light emitting layer (EML) 130 includes an anthracene derivative, a pyrene derivative, and a perylene derivative A fluorescent blue (B) dopant may be doped on at least one fluorescent host material selected from the group consisting of. In addition, when the light emitting layer (EML) 130 emits green (G) light, the light emitting layer (EML) 130 is doped with a phosphorescent green (G) dopant in a phosphorescent host material made of a carbazole-based compound or a metal complex. Can be done. In addition, when the light emitting layer (EML) 130 emits red (R) light, the light emitting layer (EML) 130 is doped with a phosphorescent red (R) dopant in a phosphorescent host material made of a carbazole compound or a metal complex. Can be done.

The electron transport layer (ETL; Electron Transporting Layer) 140 is formed on the light emitting layer (EML) 130, oxadiazole, triazole, phenanthroline, benzoxazole ( benzoxazole) or benzthiazole, but is not limited thereto.

The electron injection layer (EIL: Electron Injecting Layer) 150 is formed on the electron transport layer (ETL) 140, and may be formed of LIF or lithium quinolate (LiQ), but is not limited thereto.

The cathode 500 is formed on the electron injection layer (EIL) 150, and has a low work function, for example, aluminum (Al), silver (Ag), magnesium (Mg), lithium (Li) or calcium (Ca), but it is not limited thereto.

3 is a schematic cross-sectional view of an organic light emitting device according to another embodiment of the present invention, which is a combination of the hole injection layer (HIL) 110 and the hole transport layer (HTL) 120 of FIG. 2 described above. It is the same as the organic light emitting device according to FIG. 2 described above, except that the compound represented by Chemical Formula 1 is changed to a hole transport layer (HTL) 125 formed by doping. Therefore, the same reference numerals are assigned to the same components, and repeated descriptions of the same components will be omitted.

As can be seen in Figure 3, according to another embodiment of the present invention, the positive electrode (Anode) 100 and the light emitting layer (EML) (130) between the hole represented by the compound represented by the formula (1) doped hole transport layer (HTL) ( 125) Bays are formed.

Since the compound represented by Chemical Formula 1 is the same as described above, repeated description will be omitted.

The hole transport layer (HTL) 125 uses the compound represented by Chemical Formula 1 as a dopant, MTDATA(4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc(copper phthalocyanine) or PEDOT/ A hole transport material such as poly(3,4-ethylenedioxythiphene, polystyrene sulfonate) (PSS) may be used as a host material, but the host material may be variously modified. In the hole transport layer (HTL) 125, Formula 1 The doping amount of the compound represented by may be 0.1 to 50% by weight relative to the entire hole injection layer (HTL) (125).

4 is a schematic cross-sectional view of an organic light emitting device according to another embodiment of the present invention, which relates to an organic light emitting device having a plurality of stacks to emit white light.

As can be seen in Figure 4, the organic light emitting device according to another embodiment of the present invention, the anode (Anode) (100), the first stack 200, a charge generating layer (CGL: Charge Generating Layer) (300), It comprises a second stack 400, and a cathode (Cathode) (500).

Since the anode 100 and the cathode 500 are the same as described above, repeated description will be omitted.

The first stack 200 is formed on the anode 100 to emit light of a first color, for example, blue (B) light.

The first stack 200 includes a hole injection layer (HIL) 210 sequentially formed on the anode 100, a first hole transport layer (HTL) 220, and a first light emitting layer (EML) 230. , And a first electron transport layer (ETL) 240.

The hole injection layer (HIL) 210 is MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc (copper phthalocyanine) or PEDOT/PSS (poly(3,4-ethylenedioxythiphene, polystyrene sulfonate) ), etc., but is not limited thereto. In addition, the hole injection layer (HIL) 210 may be formed of a compound represented by Formula 1 alone, or a compound represented by Formula 1 described above It can also be doped.

The first hole transport layer (HTL) 220 is TPD (N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-bi-phenyl-4,4'-diamine) or NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), and the like, but is not limited thereto.

On the other hand, although not shown, instead of the combination of the hole injection layer (HIL) 210 and the first hole transport layer (HTL) 220, the hole transport layer (HTL) made of a compound represented by the above formula (1) is doped It is also possible to form.

The first emission layer (EML) 230 is a layer that emits blue (B) light and may be formed by doping a blue (B) dopant in a host material. The first light emitting layer (EML) 230 is doped with a fluorescent blue (B) dopant in at least one fluorescent host material selected from the group consisting of an anthracene derivative, a pyrene derivative and a perylene derivative. Can be made, but is not necessarily limited thereto.

The first electron transport layer (ETL) 240 is oxadiazole (oxadiazole), triazole

(triazole), phenanthroline, benzoxazole or benzthiazole, but is not limited thereto.

The charge generating layer (CGL) 300 serves to balance charges between the first stack 200 and the second stack 400. Particularly, the charge generation layer (CGL) 300 generates an N-type charge generation layer 310 adjacent to the first stack 200 and a P-type charge generation adjacent to the second stack 400. It consists of layers (320). The N-type charge generation layer 310 injects electrons into the first stack 200, and the P-type charge generation layer 320 injects holes into the second stack 400. Do it.

The N-type charge generation layer 310 may be formed of an alkali metal such as Li, Na, K, or Cs, or an organic layer doped with an alkaline earth metal such as Mg, Sr, Ba, or Ra.

The P-type charge generating layer 320 may be formed of a compound represented by Formula 1 described above alone, or a compound represented by Formula 1 described above may be doped. When the compound represented by Chemical Formula 1 is doped to form the P-type charge generation layer 320, the host material is MTDATA(4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc( Copper phthalocyanine) or PEDOT/PSS (poly(3,4-ethylenedioxythiphene, polystyrene sulfonate), etc. may be used, but is not limited thereto.The doping amount of the compound represented by the following Chemical Formula 1 is the P-type charge generating layer It may be 0.1 to 50% by weight relative to the total (320).

The second stack 400 is formed on the charge generation layer (CGL) 300, and has a second color of light, particularly green (G) and yellow green corresponding to a longer wavelength than the blue (B). : YG) or orange light.

The second stack 400 is a second hole transport layer (HTL) 420, a second light emitting layer (EML) 430, and a second electron transport layer (ETL) sequentially formed on the charge generation layer (CGL) 300. 440, and an electron injection layer (EIL) 450.

The second hole transport layer (HTL) 420 may be made of the same material as the first hole transport layer (HTL) 220 described above, but is not limited thereto.

The second light emitting layer (EML) 430 is a layer that emits green (G), yellow green (YG), or orange (Orange) light, and is green (G), yellow green (YG), or orange in a phosphorescent host material. (Orange) The dopant may be doped. The phosphorescent host material may be formed of a carbazole-based compound or a metal complex.

The second electron transport layer (ETL) 440 may be made of the same material as the first electron transport layer (ETL) 240 described above, but is not limited thereto.

The electron injection layer (EIL) 450 may be formed of LIF or lithium quinolate (LiQ), but is not limited thereto.

5 is a schematic cross-sectional view of an organic light emitting device according to another embodiment of the present invention, which is a combination of the P-type charge generation layer 320 and the second hole transport layer (HTL) 420 of FIG. 4 described above. It is the same as the organic light emitting device according to FIG. 4 described above, except that the compound represented by Chemical Formula 1 is changed to a P-type charge generation layer 325 formed by doping. Therefore, the same reference numerals are assigned to the same components, and repeated descriptions of the same components will be omitted.

As can be seen in Figure 5, according to another embodiment of the present invention, the P-type charge formed by doping the compound represented by the formula (1) between the N-type charge generating layer 310 and the second light emitting layer (EML) 430 Only the production layer 325 is formed.

Since the compound represented by Chemical Formula 1 is the same as described above, repeated description will be omitted.

The P-type charge generating layer 325 uses a compound represented by Formula 1 as a dopant, MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc (copper phthalocyanine) or PEDOT/ A hole transport material such as PS(poly(3,4-ethylenedioxythiphene, polystyrene sulfonate), etc.) may be used as a host material, but the host material may be variously modified. In the P-type charge generating layer 325, the chemical formula 1 The doping amount of the compound represented by may be 0.1 to 50% by weight relative to the entire P-type charge generating layer 325.

The organic light emitting device according to FIGS. 4 and 5 described above emits white light through the first stack 200 emitting light of the first color and the second stack 400 emitting light of the second color. , The present invention is not necessarily limited thereto, and the present invention may further include a third stack emitting light of a third color in addition to the first stack 200 and the second stack 400. Accordingly, a stack of four or more stacks may be included.

6 is a schematic cross-sectional view of a display device according to an embodiment of the present invention, which relates to a display device having an organic light emitting device according to various embodiments described above.

As can be seen in FIG. 6, in the display device according to an embodiment of the present invention, a thin film transistor (TFT) is formed on a substrate 10, and an organic light emitting device is electrically connected to the thin film transistor (TFT). .

Specifically, the display device according to an embodiment of the present invention, the substrate 10, the gate electrode 20, the gate insulating film 25, the active layer 30, the etch stopper 35, the source electrode 40a, It comprises a drain electrode 40b, a protective film 50, a color filter 60, a planarization layer 70, a bank layer 80, and an organic light emitting device.

The gate electrode 20 is patterned on the substrate 10, and the gate insulating layer 25 is formed on the entire surface of the substrate including the gate electrode 20. The gate electrode 20 may be formed of molybdenum (Mo), aluminum (Al), chromium (Cr), gold (Au), titanium (Ti), nickel (Ni), neodium (Nd), or copper (Cu). It may be made of metal, and the gate insulating layer 25 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

The active layer 30 is patterned on the gate insulating layer 25, and the etch stopper 35 is patterned on the active layer 30 to form the source electrode 40a and the drain electrode 40b. During the etching process for patterning, the channel region of the active layer 30 is prevented from being etched. The active layer 30 may be formed of a silicon-based semiconductor or an oxide semiconductor such as ITZO, IZO, ZnO, or In-Ga-Zn-O (IGZO).

The source electrode 40a and the drain electrode 40b are patterned on the etch stopper 30 while facing each other. The source electrode 40a and the drain electrode 40b are molybdenum (Mo), aluminum (Al), chromium (Cr), gold (Au), titanium (Ti), nickel (Ni), neodium (Nd), or It may be made of a metal such as copper (Cu).

The protective film 50 is formed on the source electrode 40a and the drain electrode 40b, and the color filter 60 is patterned on the protective film 50. The protective layer 50 may be made of an inorganic insulating material such as silicon oxide or silicon nitride. The color filter 60 is formed to overlap the light emitting unit 90 of the organic light emitting device, so that light emitted from the light emitting unit 90 is emitted to the substrate 10 through the color filter 60 Can be. The color filter 60 may be formed of a red color filter, a green color filter, and a blue color filter that are distinctly formed for each pixel. The color filter 60 is applied when emitting white light in the organic light emitting device, and thus, the organic light emitting device emits colored light other than white light, for example, blue, green, or red light. In some cases, the color filter 60 may be omitted.

The planarization layer 70 is formed on the color filter 60. The planarization layer 70 may be made of an organic insulating material such as photo acryl or benzocyclobutene (BCB).

The bank layer 80 is formed on the planarization layer 70. Specifically, the bank layer 80 is patterned to overlap with the thin film transistor (TFT), and the light emitting region is defined by the bank layer 80. The bank layer 80 may be made of an organic insulating material, for example, polyimide, photo acryl, or benzocyclobutene (BCB).

The organic light emitting device includes an anode 100, a light emitting unit 90, and a cathode 500. The configuration of the light emitting unit 90 formed between the anode 100 and the cathode 500 may be variously changed as shown in FIGS. 2 to 5 described above, and repeated description thereof will be omitted.

The above has described the display device according to an embodiment to which the organic light emitting device according to the present invention is applied, but the organic light emitting device according to the present invention can be applied to a display device having various structures. Further, the organic light emitting device according to the present invention can be applied to display devices in various fields, for example, televisions, lighting, mobile phones, notebook computers, digital cameras, display devices for vehicles, display devices in food and clothing stores, and the like.

Hereinafter, specific examples and comparative examples according to the present invention will be described.

Example One

The ITO glass was patterned to have a light emitting area of 3 mm × 3 mm, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then the A25 compound (100 kPa), α-NPB (700 kPa), host MADN and dopant BD-1 on the ITO glass An organic light emitting device according to Example 1 was prepared by sequentially depositing (4 wt%) light emitting layer (300 kPa), Alq ₃ (200 kPa), LiF (10 kPa), and Al (1000 kPa) in this order.

Example 2

The ITO glass was patterned to have a light emitting area of 3 mm × 3 mm, and then washed. After mounting the substrate in the vacuum chamber, the base pressure was set to 1 × 10 ^-6 torr, and then the above-described A25 compound (20 wt%) doped α-NPB (100 Å), α-NPB on the ITO glass. (700 Å), the host MADN and the dopant BD-1 (4 wt%) of the light emitting layer (300 Å), Alq ₃ (200 Å), LiF (10 Å), and Al (1000 Å) in order of film deposition, in accordance with Example 2 An organic light emitting device was prepared.

Example 3

The ITO glass was patterned to have a light emitting area of 3 mm × 3 mm, and then washed. After mounting the substrate in the vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then the A37 compound (100 kPa), α-NPB (700 kPa), host MADN and dopant BD-1 on the ITO glass An organic light emitting device according to Example 3 was prepared by sequentially depositing (4% by weight) light emitting layer (300 Pa), Alq ₃ (200 Pa), LiF (10 Pa), and Al (1000 Pa) in this order.

Example 4

The ITO glass was patterned to have a light emitting area of 3 mm × 3 mm, and then washed. After mounting the substrate in the vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then the above-described A37 compound (20 wt%) doped α-NPB (100 Å), α-NPB on the ITO glass (700 Å), the host MADN and the dopant BD-1 (4 wt%) of the light emitting layer (300 Å), Alq ₃ (200 Å), LiF (10 Å), and Al (1000 Å) in order of film deposition, in accordance with Example 4 An organic light emitting device was prepared.

Comparative example One

The ITO glass was patterned to have a light emitting area of 3 mm × 3 mm, and then washed. After mounting the substrate in the vacuum chamber, make the base pressure to be 1 × 10 ^-6 torr, then DNTPD (100 kPa), α-NPB (700 kPa) on the ITO glass, host MADN and dopant BD-1 (4 wt. %) of the light emitting layer (300 Å), Alq ₃ (200 Å), LiF (10 Å), and Al (1000 Å) were sequentially formed in order, to prepare an organic light emitting device according to Comparative Example 1.

Comparative example 2

The ITO glass was patterned to have a light emitting area of 3 mm × 3 mm, and then washed. After mounting the substrate in the vacuum chamber, the base pressure was set to 1 × 10 ^-6 torr, and then α-NPB (800 kPa) on the ITO glass, the light emitting layer of host MADN and dopant BD-1 (4 wt%) ( 300 Å), Alq ₃ (200 Å), LiF (10 Å), and Al (1000 Å) were sequentially formed in order to prepare an organic light emitting device according to Comparative Example 2.

In Examples 1 to 4 and Comparative Examples 1 to 2, α-NPB, MADN, BD-1, DNTPD, and Alq ₃ are compounds represented by the following chemical formulas.

Current-voltage characteristics

Current-voltage characteristics of the organic light emitting devices according to Examples 1 to 4 and Comparative Examples 1 to 2 were measured, and the results are shown in FIG. 7.

As can be seen from FIG. 7, it can be seen that the driving voltages in Examples 1 to 4 are reduced compared to Comparative Examples 1 to 2. Specifically, with respect to the driving voltage at 10 mA/cm ² , Example 1 showed 3.87 V, Example 2 showed 4.19 V, Example 3 showed 4.76 V, and Example 4 showed 4.89. V is shown. On the other hand, in relation to the driving voltage at 10mA/cm ² , Comparative Example 1 showed 5.27V and Comparative Example 2 showed 6.1V.

100: anode 110: hole injection layer
120: hole transport layer 130: light emitting layer
140: electron transport layer 150: electron injection layer
200: first stack 300: charge generating layer
400: second stack 500: cathode

Claims (9)

It comprises an anode, a cathode, and an organic layer formed between the anode and the cathode,
The organic layer is the following formula 1:
[Formula 1]

(In the formula 1,
The M ₁ and M ₂ are each independently selected from the group consisting of O, S, NR ₃ , R ₄ CR ₅ , and C(=Z),
X, Y, and Z are each independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

, And

Is selected from the group consisting of,
A, B, C, and D are each independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

, And

Is selected from the group consisting of,
R ₁ to R ₅ are each independently hydrogen, deuterium, hydroxyl group, halogen group, cyano group, fluoroalkyl group, C1 to C18 alkyl group, C1 to C18 alkoxy group, C6 or more substituted or unsubstituted aromatic group , C5 or more substituted or unsubstituted heteroaromatic group, C1 to C18 amine group group, C6 or more aromatic group substituted amine group, C5 or more heteroaromatic group substituted amine group, C1 to C18 alkyl group substituted A silyl group group, a silyl group group substituted with an aromatic group of C6 or more, and a silyl group group substituted with a hetero"‡ aromatic group of C5 or more,
R ₁₁ to R ₂₁ and R ₃₁ to R ₃₇ are each independently hydrogen, deuterium, hydroxyl group, C1 to C18 alkyl group, C1 to C18 alkoxy group, C6 or more substituted or unsubstituted aromatic group, and C5 Selected from the group consisting of the above substituted or unsubstituted heteroaromatic groups)
It comprises a compound represented by,
The compound represented by Formula 1 is an organic light emitting device, characterized in that included in the organic layer as a hole injection material or a hole transport material. According to claim 1,
The M ₁ and M ₂ are made of the same material as each other, and the R ₁ and R ₂ are made of the same material as each other. According to claim 1,
Formula 1 is the following formula A1 to A104:

(A1),

(A2),

(A3),

(A4),

(A5),

(A6),

(A7),

(A8),

(A9),

(A10),

(A11),

(A12),

(A13),

(A14),

(A15),

(A16),

(A17),

(A18),

(A19),

(A20),

(A21),

(A22),

(A23),

(A24),

(A25),

(A26),

(A27),

(A28),

(A29),

(A30),

(A31),

(A32),

(A33),

(A34),

(A35),

(A36),

(A37),

(A38),

(A39),

(A40),

(A41),

(A42),

(A43),

(A44),

(A45),

(A46),

(A47),

(A48),

(A49),

(A50),

(A51),

(A52),

(A53),

(A54),

(A55),

(A56),

(A57),

(A58),

(A59),

(A60),

(A61),

(A62),

(A63),

(A64),

(A65),

(A66),

(A67),

(A68),

(A69),

(A70),

(A71),

(A72),

(A73),

(A74),

(A75),

(A76),

(A77),

(A78),

(A79),

(A80),

(A81),

(A82),

(A83),

(A84),

(A85),

(A86),

(A87),

(A88),

(A89),

(A90),

(A91),

(A92),

(A93),

(A94),

(A95),

(A96),

(A97),

(A98),

(A99),

(A100),

(A101),

(A102),

(A103),

(A104)
Organic light-emitting device selected from the group consisting of. delete According to claim 1,
Between the anode and the cathode, a hole injection layer, a hole transport layer, and a light emitting layer are formed,
The organic layer constitutes the hole injection layer,
The hole injection layer is made of a compound represented by the formula (1) alone or an organic light emitting device, characterized in that the compound represented by the formula (1) is doped. According to claim 1,
Between the anode and the cathode, a hole transport layer doped with an organic material, and a light emitting layer is formed,
The organic layer constitutes a hole transport layer doped with the organic material,
The organic light emitting device doped with the organic material is characterized in that the hole transport layer is doped with a compound represented by the formula (1). According to claim 1,
Between the anode and the cathode, a first stack that emits light of a first color, a second stack that emits light of a second color, and a charge generating layer that balances charge between the first stack and the second stack Is formed,
The charge generation layer is composed of an N type charge generation layer adjacent to the first stack and a P type charge generation layer adjacent to the second stack,
The organic layer constitutes the P-type charge generation layer,
The P-type charge generating layer is an organic light-emitting device, characterized in that the compound represented by the formula (1) alone or doped with the compound represented by the formula (1). According to claim 1,
Between the anode and the cathode, a first stack that emits light of a first color, a second stack that emits light of a second color, and a charge generating layer that balances charge between the first stack and the second stack Is formed,
The charge generation layer is composed of an N type charge generation layer adjacent to the first stack and a P type charge generation layer adjacent to the second stack,
The second stack comprises a light emitting layer in contact with the P-type charge generating layer,
The organic layer constitutes the P-type charge generation layer,
The P-type charge generating layer is an organic light emitting device, characterized in that the hole transporting material is made by doping the compound represented by the formula (1). A display device comprising the organic light emitting device according to any one of claims 1 to 3 and 5 to 8.

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