KR102464552B1 - Red phosphorescent host compound and Organic Light Emitting Device and Display Device using the same - Google Patents

Abstract

(상기 화학식 1에서, Ar₁은 헤테로방향족 그룹(heteroaromatic group) 또는 방향족 정공 수송 그룹(aromatic hole transporting group)으로 구성되고, Ar₂는 아릴 그룹(aryl group)이 작용기로 결합된 전자 수송 그룹(electron transporting group)으로 구성됨)
로 표현되는 유기 화합물로 이루어진 적색 인광 호스트 화합물에 관한 것이다. The present invention, the following formula 1:
[Formula 1]

(In Formula 1, Ar ₁ is composed of a heteroaromatic group or an aromatic hole transporting group, and Ar ₂ is an electron transporting group to which an aryl group is bonded as a functional group (electron) (consisting of a transporting group)
It relates to a red phosphorescent host compound consisting of an organic compound represented by

Description

Red phosphorescent host compound and organic light emitting device and display device using the same

The present invention relates to an organic light emitting device, and more particularly, to a host compound used in a red light emitting layer of the organic light emitting device.

The organic light emitting device has a structure in which a light emitting layer is formed between a cathode for injecting electrons and an anode for injecting holes, and electrons generated from the cathode and holes generated from the anode are inside the light emitting layer It is a device that emits light as the injected electrons and holes combine to generate an exciton, and the generated exciton falls from an excited state to a ground state.

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 from FIG. 1 , the organic light emitting diode according to an exemplary embodiment of the related art includes an anode 1 , a hole injection layer (HIL) 2 , a hole transport layer (HTL). (3), an Emitting Layer (EML) (4), and an Electron Transporting Layer (ETL) (5), an Electron Injecting Layer (EIL) (6), and a cathode (7) ) is included.

The organic light emitting device emits different colors depending on the material constituting the light emitting layer 4 , and thus an image of a desired color may be realized by appropriately adjusting a host material and a dopant material constituting the light emitting layer 4 . The luminous efficiency of such an organic light emitting device varies greatly depending on the material of the light emitting layer 4 .

The conventional light emitting layer 4 emitting red light mainly uses a CBP material as a host material and an iridium compound as a dopant. However, in this case, when high-purity red is displayed, there is a disadvantage in that luminous efficiency or luminance is deteriorated. Therefore, although research on a host material that can be used for a red light emitting layer having excellent luminance and luminous efficiency is in progress, it is still insufficient.

The present invention has been devised to solve the above-described problems in the prior art, and the present invention is to provide a red phosphorescent host compound that displays high purity red and excellent luminance and luminous efficiency, and an organic light emitting device and a display device using the same. do.

The present invention in order to achieve the above object, the following formula 1:

[Formula 1]

(In Formula 1, Ar ₁ is composed of a heteroaromatic group or an aromatic hole transporting group, and Ar ₂ is an electron transporting group to which an aryl group is bonded as a functional group (electron) (consisting of a transporting group)

It relates to a red phosphorescent host compound composed of an organic compound represented by and to an organic light emitting device and a display device using the same.

According to the present invention as described above, by using the red phosphorescent host compound represented by Chemical Formula 1 as a material for the red light emitting layer, high purity red is displayed, and luminance and luminous efficiency are excellent.

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 diode according to an embodiment of the present invention.
3 is a schematic cross-sectional view of a display device according to an embodiment of the present invention.

Advantages and features of the present invention and methods of achieving them will become apparent with reference to the embodiments described below in detail in conjunction with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below, but will be implemented in various different forms, and only these embodiments allow the disclosure of the present invention to be complete, and common knowledge in the technical field to which the present invention belongs It is provided to fully inform the possessor of the scope of the invention, and the present invention is only defined by the scope of the claims.

The shapes, sizes, proportions, angles, numbers, etc. disclosed in the drawings for explaining the embodiments of the present invention are illustrative and the present invention is not limited to the illustrated matters. Like reference numerals refer to like elements throughout. In addition, in describing the present invention, if it is determined that a detailed description of a related known technology may unnecessarily obscure the subject matter of the present invention, the detailed description thereof will be omitted. When 'including', 'having', 'consisting', etc. mentioned in this specification are used, other parts may be added unless 'only' is used. When a component is expressed in the singular, the case in which the plural is included is included unless specifically stated otherwise.

In interpreting the components, it is interpreted as including an error range even if there is no separate explicit description.

In the case of a description of the positional relationship, for example, when the positional relationship of two parts is described as 'on', 'on', 'on', 'beside', etc., 'right' Alternatively, one or more other parts may be positioned between the two parts unless 'directly' is used.

In the case of a description of a temporal relationship, for example, 'immediately' or 'directly' when a temporal relationship is described as 'after', 'following', 'after', 'before', etc. It may include cases that are not continuous unless this is used.

Although the first, second, etc. are used to describe various components, these components are not limited by these terms. These terms are only used to distinguish one component from another. Accordingly, the first component mentioned below may be the second component within the spirit of the present invention.

Each feature of the various embodiments of the present invention may be partially or wholly combined or combined with each other, technically various interlocking and driving are possible, and each of the embodiments may be implemented independently of each other or may be implemented together in a related relationship. may be

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

The red phosphorescent host compound according to an embodiment of the present invention consists of an organic compound represented by Formula 1 below.

[Formula 1]

In Formula 1 above, Ar ₁ is a heteroaromatic group or an aromatic hole transporting group.

또는

로 이루어질 수 있다.
The heteroaromatic group constituting Ar ₁ may include indole carbazole, and the indole carbazole includes dibenzofuran or dibenzothiophene. It can be bound to this functional group. The dibenzofuran may be made of dibenzo[b,d]furan, and the dibenzothiophene may be dibenzo[b,d]thiophene. ) can be made. The heteroaromatic group constituting Ar ₁ is

or

can be made with

,

,

, 또는

로 이루어질 수 있다.The aromatic hole transporting group constituting Ar ₁ may include indole carbazole having hole transporting ability, and the indole carbazole having hole transporting ability includes aryl An aryl group may be bonded to a functional group, and the aryl group bonded to the indole carbazole is phenyl, biphenyl, terphenyl, naphthalene, and phenane. It may be selected from the group consisting of threne (phenanthrene). An aromatic hole transporting group constituting the Ar ₁ is

,

,

, or

can be made with

In Formula 1 above, Ar ₂ is composed of an electron transporting group to which an aryl group is bonded as a functional group.

로 이루어질 수 있고, 여기서, 상기 Ar₃는 각각 독립적으로 페닐(phenyl), 바이페닐(biphenyl), 테르페닐(terphenyl), 나프탈렌(naphthalene), 및 페난트렌(phenanthrene)으로 이루어진 군에서 선택될 수 있다. An electron transporting group to which an aryl group constituting Ar ₂ is bonded to a functional group may include triazine to which an aryl group is bonded to a functional group, and the triazine) The aryl group bonded to may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene and phenanthrene. An electron transporting group to which an aryl group constituting the Ar ₂ is bonded as a functional group is

wherein Ar ₃ is each independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, and phenanthrene. .

In the case where Ar ₁ is composed of a heteroaromatic group, Chemical Formula 1 includes various compounds such as the following Chemical Formulas A1 to A54, but is not necessarily limited thereto.

(A1),

(A2),

(A3),

(A1),

(A2),

(A3),

(A4),

(A5),

(A4),

(A5),

(A6),

(A7),

(A6),

(A7),

(A8),

(A9),

(A8),

(A9),

(A10),

(A11),

(A10),

(A11),

(A12),

(A13),

(A12),

(A13),

(A14),

(A15),

(A14),

(A15),

(A16),

(A17),

(A16),

(A17),

(A18),

(A19),

(A18),

(A19),

(A20),

(A21),

(A20),

(A21),

(A22),

(A23),

(A22),

(A23),

(A24),

(A25),

(A24),

(A25),

(A26),

(A27),

(A26),

(A27),

(A28),

(A29),

(A28),

(A29),

(A30),

(A31),

(A30),

(A31),

(A32),

(A33),

(A32),

(A33),

(A34),

(A35),

(A34),

(A35),

(A36),

(A37),

(A36),

(A37),

(A38),

(A39),

(A38),

(A39),

(A40),

(A41),

(A40),

(A41),

(A42),

(A43),

(A42),

(A43),

(A44),

(A45),

(A44),

(A45),

(A46),

(A47),

(A46),

(A47),

(A48),

(A49),

(A48),

(A49),

(A50),

(A51),

(A50),

(A51),

(A52),

(A53),

(A52),

(A53),

(A54).

(A54).

When Ar ₁ is composed of an aromatic hole transporting group, Chemical Formula 1 includes various compounds such as Chemical Formulas B1 to B81, but is not necessarily limited thereto.

(B1),

(B2),

(B1),

(B2),

(B3),

(B4),

(B3),

(B4),

(B5),

(B6),

(B5),

(B6),

(B7),

(B8),

(B7),

(B8),

(B9),

(B10),

(B9),

(B10),

(B11),

(B12),

(B11),

(B12),

(B13),

(B14),

(B13),

(B14),

(B15),

(B16),

(B15),

(B16),

(B17),

(B18),

(B17),

(B18),

(B19),

(B20),

(B19),

(B20),

(B21),

(B22),

(B21),

(B22),

(B23),

(B24),

(B23),

(B24),

(B25),

(B26),

(B25),

(B26),

(B27),

(B28),

(B27),

(B28),

(B29),

(B30),

(B29),

(B30),

(B31),

(B32),

(B31),

(B32),

(B33),

(B34),

(B33),

(B34),

(B35),

(B36),

(B35),

(B36),

(B37),

(B38),

(B37),

(B38),

(B39),

(B40),

(B39),

(B40),

(B41),

(B42),

(B41),

(B42),

(B43),

(B44),

(B43),

(B44),

(B45),

(B46),

(B45),

(B46),

(B47),

(B48),

(B47),

(B48),

(B49),

(B50),

(B49),

(B50),

(B51),

(B52),

(B51),

(B52),

(B53),

(B54),

(B53),

(B54),

(B55),

(B56),

(B55),

(B56),

(B57),

(B58),

(B57),

(B58),

(B59),

(B60),

(B59),

(B60),

(B61),

(B62),

(B61),

(B62),

(B63),

(B64),

(B63),

(B64),

(B65),

(B66),

(B65),

(B66),

(B67),

(B68),

(B67),

(B68),

(B69),

(B70),

(B69),

(B70),

(B71),

(B72),

(B71),

(B72),

(B73),

(B74),

(B73),

(B74),

(B75),

(B76),

(B75),

(B76),

(B77),

(B78),

(B77),

(B78),

(B79),

(B80),

(B79),

(B80),

(B81)

(B81)

When the organic compound represented by Chemical Formula 1 as described above is used as a red phosphorescent host compound, there are advantages as follows.

First, since the organic compound represented by Chemical Formula 1 has a twisted core structure, the glass transition temperature (Tg) is high and the film morphology can be improved. In addition, since the organic compound represented by Formula 1 has high steric hindrance characteristics, solubility may be improved, and accordingly spin coating, slit coating, and inkjet printing The light emitting layer may be formed by a solution process such as inkjet printing and screen printing. In addition, when Ar ₁ has a dibenzofuran or dibenzothiophene-based moiety, it may have a high triplet energy characteristic. In addition, when Ar ₁ has a fused carbazole-based moiety, hole transport properties may be improved. In addition, since Ar ₂ may have a triazine moiety, it may have high electron transporting properties.

The organic compound represented by Formula 1 including A1 to A54 and B1 to B81 may be synthesized through various synthetic methods known in the art. Hereinafter, as an example, a method for synthesizing Compound A1, Compound A8, Compound B1, and Compound B19 will be sequentially described.

Schemes 1 to 9 below are methods for synthesizing Compound A1.

Scheme 1 (synthesis of 2-bromophenylacetylene)

As in Scheme 1 above, 2-bromoiodobenzene (20 g, 0.07 mol), PdCl ₂ (PPh ₃ ) (0.49 g, 0.7 mmol) and Cul (0.13) in a 2-round flask g, 0.7 mmol) was put in Et ₃ N and stirred. Trimethylsilylacetylene (8.3 g, 0.08 mmol) was slowly dropped and stirred at room temperature for 4 hours. After filtering with Celite, evaporating the solvent, and purification with a silica gel column (hexane:ethyl acetate=5:1) to 2-bromo Phenyltrimethylsilylacetylene (bromophenyltrimethylsilylacetylene) was obtained. Here K ₂ CO ₃ (1g, 7mmol) and 100mL of THF:MeOH (1:1) were added and stirred for 12 hours. After quenching with 1N HCl aqueous solution, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column 2- Bromophenylacetylene (bromophenylacetylene) (11.4 g, yield: 90%) was obtained.

Scheme 2 (synthesis of bis (bis) (2-bromophenyl) acetylene)

As in Scheme 2 above, 2-bromoiodobenzene (17.8 g, 0.06 mol), 2-bromophenylacetylene (11.4 g, 0.06 mol) in a 2-round flask , PdCl ₂ (PPh ₃ ) (0.44 g, 0.6 mmol) and Cul (0.12 g, 0.06 mmol) were put in Et ₃ N and stirred at room temperature for 15 hours. After quenching with 1N HCl aqueous solution, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column to bis ( bis) (2-bromophenyl) acetylene (17.7 g, yield: 84%) was obtained.

Scheme 3 (synthesis of bis (bis) (2-phenylboronic acid) acetylene)

As in Scheme 3 above, bis (bis) (2-bromophenyl) acetylene (15 g, 44.6 mmol) and 100 mL of ether were put in a 2-round flask. Stir. After lowering the temperature to -78°C in a dry-ice bath, 2.5M n-BuLi (37.5mL, 0.09mmol) was slowly dropped and stirred at room temperature for 1 hour. After lowering the temperature to -78 ℃ again in a dry-ice bath, triethylborate (19.5 g, 0.13 mol) is slowly dropped and stirred at room temperature for 6 hours. . 2N HCl 50mL was added, quenched, and the resulting solid was filtered and washed 3-4 times with distilled water and hexane, followed by bis(bis)(2-phenylboronic acid). (phenylboronic acid)) acetylene (8.3 g, yield: 70%) was obtained.

Scheme 4 (synthesis of bis (bis) (2- (4-bromophenyl) phenyl (phenyl)) acetylene)

As in Scheme 4 above, in a 2-round flask, bis (bis) (2-phenylboronic acid) acetylene (8 g, 0.03 mol), 1-bromo (bromo) )-4-iodobenzene (17g, 0.06mol), Pd(PPh ₃ ) ₄ (0.1g, 0.9mmol) and 2M-K ₂ CO ₃ /H ₂ O (1:1) were added and 12 hours while refluxed. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column, bis (2) -(4-bromophenyl) phenyl (phenyl)) acetylene (acetylene) (10.2 g, yield: 70%) was obtained.

Scheme 5 (synthesis of iodophenanthrene)

As in Scheme 5 above, in a 2-round flask, bis (bis) (2- (4-bromophenyl) phenyl (phenyl) acetylene 10 g, 0.02 mol) and 100 mL of methylene chloride, and then lowered the temperature to -78°C in a dry-ice bath. A 1.0M ICI solution (30 mL, 0.03 mol) was slowly dropped, followed by stirring for 4 hours. After raising the temperature to room temperature, quenching with sodium thiosulfate solution and extraction with methylene chloride, evaporating the solvent, and silica gel column (silica gel) column) to obtain iodophenanthrene (11 g, yield: 90%).

Scheme 6 (synthesis of 2,10-dibromodibenzo [g, p] chrysene)

As in Scheme 6 above, in a 2-round flask, iodophenanthrene (10 g, 0.016 mol), PdCl ₂ (PPh ₃ ) ₂ (0.6 g, 0.8 mmol), sodium acetate (sodium) acetate) (5.2 g, 0.064 mol) and DMAc (800 mL) were added and stirred at 120° C. for 4 hours. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column to 2,10-dibro Modibenzo (dibromodibenzo) [g, p] chrysene (chrysene) (5.4 g, yield: 70%) was obtained.

Scheme 7 (synthesis of 2-bromodibenzo[g,p]chrysene-10-(2-dibenzo[b,d]furan)

As in Scheme 7 above, 2,10-dibromodibenzo [g, p] chrysene (5 g, 0.01 mol), 2-dibenzo ( dibenzo)[b,d]furanboronic acid (2.2g, 0.01mol), Pd(PPh ₃ ) ₄ (0.01 g) and 2M-K ₂ CO ₃ /H ₂ O (1:1) and reflux for 12 hours. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column, 2-bromodibenzo ( Bromodibenzo) [g, p] chrysene-10- (2-dibenzo (dibenzo) [b, d] furan (furan) (4.1 g, yield: 70%) was obtained.

Scheme 8 (synthesis of 2-(dibenzo[b,d]furan)-10-dibenzo[g,p]chryseneboronic acid)

As in Scheme 8 above, 2-bromodibenzo [g,p] chrysene-10-(2-dibenzo [b,d] in a round flask ]Furan (4g, 7mmol) and 100mL of ether are added, stirred, and the temperature is lowered to -78℃ in a dry-ice bath, and then 2.5M n-BuLi ( 3.1mL, 7mmol) is slowly dropped and stirred for 1 hour at room temperature, then lowered to -78°C in a dry-ice bath, and then triethylborate (triethylborate) ( 3.1 g, 0.02 mol) is slowly dropped and stirred at room temperature for 6 hours, quenched by adding 50 mL of 2N HCl, filtered, distilled water and hexane (washing) 3-4 times with (hexane) 2- (dibenzo (dibenzo) [b, d] furan (furan))-10-dibenzo (dibenzo) [g, p] chryseneboronic acid (chryseneboronic) acid) (2.6 g, yield: 70%) was obtained.

Scheme 9 (synthesis of compound A1)

As in Scheme 9 above, 2-(dibenzo[b,d]furan)-10-dibenzo[g,p]chrysenbo in a 2-round flask Chryseneboronic acid (2.5 g, 4.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.3 g, 5 mmol), Pd (PPh ₃ ) ₄ (0.01 g) and 2M-K ₂ CO ₃ /H ₂ O (1:1) were added and refluxed for 12 hours. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column, Compound A1 (2.4 g, yield: 70%).

Scheme 10 below is a method for synthesizing Compound A8.

Scheme 10 (synthesis of compound A8)

As in Scheme 10 above, 2-(dibenzo[b,d]furan)-10-dibenzo[g,p]chrysenbo in a 2-round flask Chryseneboronic acid (2.5g, 4.6mmol), 2-chloro-4,6-terphenyl-1,3,5-triazine (2.9g, 5mmol), Pd (PPh ₃ ) ₄ (0.01 g) and 2M-K ₂ CO ₃ /H ₂ O (1:1) were added and refluxed for 12 hours. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column, Compound A8 (3.3 g, yield: 70%).

Schemes 11 to 13 below are methods for synthesizing Compound B1.

Scheme 11 (2-bromodibenzo [g,p] chrysene-7',7'-dimethyl-5',7'-dihydroindeno [2,1] -b] Synthesis of carbazole)

As in Scheme 11 above, 2,10-dibromodibenzo[g,p]chrysene (5g, 0.01mol), 7,7-dimethyl in a round flask (dimethyl)-5,7-dihydroindeno [2,1-b] carbazole (2.9 g, 0.01 mol), Pd ₂ (dba) ₃ (0.21 g, 0.023 mol%), P(t-Bu)3 (0.07 g, 0.035 mol%), NaOBu (1.7 g, 0.015 mol) and toluene were added and refluxed at 130° C. for 6 hours. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column, 2-bromodibenzo ( bromodibenzo) [g,p] chrysene-7',7'-dimethyl-5',7'-dihydroindeno[2,1-b]carbazole ( 5g, yield:70%) was obtained.

Scheme 12 (2-(7',7'-dimethyl)-5',7'-dihydroindeno[2,1-b]carbazole)-10-diibenzo ) [g,p] Synthesis of chryseneboronic acid)

As in Scheme 12 above, 2-bromodibenzo[g,p]chrysene-7',7'-dimethyl-5', in a 2-round flask 7'-dihydroindeno [2,1-b] carbazole (5 g, 7.3 mmol) and 100 mL of ether were added and stirred. After lowering the temperature to -78°C in a dry-ice bath, 2.5M n-BuLi (3.2mL, 8mmol) was slowly dropped and stirred at room temperature for 1 hour. After lowering the temperature to -78 ℃ again in a dry-ice bath, triethylborate (3.2 g, 0.02 mol) is slowly dropped and stirred at room temperature for 6 hours. . 2N HCl 50mL was added, quenched, and the resulting solid was filtered and washed 3-4 times with distilled water and hexane, followed by 2-(7',7'-dimethyl ( dimethyl)-5',7'-dihydroindeno[2,1-b]carbazole)-10-diibenzo[g,p]chryseneboronic acid (3.3 g, yield: 70%) was obtained.

Scheme 13 (synthesis of compound B1)

As in Scheme 13 above, 2-(7',7'-dimethyl-5',7'-dihydroindeno[2,1-b) in a 2-round flask ] Carbazole) -10-diibenzo (diibenzo) [g,p] chryseneboronic acid (3g, 4.6mmol), 2-chloro-4,6-diphenyl (diphenyl) )-1,3,5-triazine (1.3g, 5mmol), Pd(PPh ₃ ) ₄ (0.01 g) and 2M-K ₂ CO ₃ /H ₂ O (1:1) were added for 12 hours. while refluxed. After lowering the temperature to room temperature, extraction with methyl chloride (methylene chloride), evaporating the solvent, and purification with a silica gel column (silica gel column), compound B1 (2.7 g, yield: 70%).

Schemes 14 to 16 below are methods for synthesizing compound B19.

Scheme 14 (2-bromodibenzo [g,p] chrysene-10-(5-phenyl)-5,7-dihydroindolo [2,3-b] Synthesis of carbazole)

As in Scheme 14 above, 2,10-dibromodibenzo [g, p] chrysene (5 g, 0.01 mol), 5-phenyl in a round flask -5,7-dihydroindolo [2,3-b] carbazole (3.4 g, 0.01 mol), Pd ₂ (dba) ₃ (0.21 g, 0.023 mol%), P(t) -Bu) ₃ (0.07 g, 0.035 mol%), NaOBu (1.7 g, 0.015 mol) and toluene were added and refluxed at 130° C. for 6 hours. After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column, 2-bromodibenzo ( bromodibenzo) [g,p] chrysene-10- (5-phenyl)-5,7-dihydroindolo [2,3-b] carbazole) (3.5 g , yield :70%).

Scheme 15 (2-(5-phenyl)-5,7-dihydroindolo[2,3-b]carbazole)-10-dibenzo[g,p] Synthesis of chryseneboronic acid)

As in Scheme 15 above, 2-bromodibenzo [g,p] chrysene-10-(5-phenyl-5,7- in a round flask) Dihydroindolo [2,3-b] carbazole) (5 g, 6.8 mmol) and 100 mL of ether are added and stirred. After lowering the temperature to -78°C in a dry-ice bath, 2.5M n-BuLi (3.0mL, 7mmol) was slowly dropped and stirred at room temperature for 1 hour. After lowering the temperature to -78 ℃ again in a dry-ice bath, triethylborate (3.0 g, 0.02 mol) is slowly dropped and stirred at room temperature for 6 hours. . 2N HCl 50mL was added, quenched, and the resulting solid was filtered and washed 3-4 times with distilled water and hexane, followed by 2-(5-phenyl)-5 ,7-dihydroindolo [2,3-b] carbazole)-10-dibenzo [g, p] chryseneboronic acid (3.3 g, yield: 70%) was obtained.

Scheme 16 (synthesis of compound B19)

As in Scheme 16 above, 2-(5-phenyl)-5,7-dihydroindolo[2,3-b]carbazole in a round flask )-10-dibenzo (dibenzo) [g,p] chryseneboronic acid (3g, 4.3mmol), 2-chloro-4,6-diphenyl (diphenyl)-1,3, 5-triazine (1.3g, 4.7mmol), Pd(PPh ₃ ) ₄ (0.01 g) and 2M-K ₂ CO ₃ /H ₂ O (1:1) were added and refluxed for 12 hours. make it After lowering the temperature to room temperature, extraction with methylene chloride, evaporating the solvent, and purification with a silica gel column B19 compound (2.6 g, yield: 70%).

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

As can be seen from FIG. 2 , the organic light emitting device according to an embodiment of the present invention includes an anode 100 , a hole injection layer (HIL) 110 , a hole transport layer (HTL). ) 120 , an Emitting Layer (EML) (R) 130 , an Electron Transporting Layer (ETL) 140 , an Electron Injecting Layer (EIL) 150 , and a cathode ) (500).

The anode 100 may be made of a transparent conductive material having high conductivity and a work function, for example, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), SnO 2 , or ZnO, but is not necessarily limited thereto. not.

The hole injection layer (HIL) 110 is formed on the anode 100 . The hole injection layer (HIL) 110 is MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), CuPc (copper phthalocyanine), or PEDOT/PSS (poly(3,4-ethylenedioxythiphene, polystyrene sulfonate) ), but is not necessarily limited thereto.

The hole transport layer (HTL) 120 is formed on the hole injection layer (HIL) 110 . The hole transport layer (HTL) 120 is TPD (N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-bi-phenyl-4,4'-diamine), NPD ( N, N-dinaphthyl-N, N'-diphenyl benzidine), or NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), etc., but must be limited thereto it's not going to be

The emission layer (EML(R)) 130 is formed on the hole transport layer (HTL) 120 . The light-emitting layer (EML(R)) 130 is formed of a light-emitting layer that emits red light, and is formed by doping a host material with a dopant.

The host material constituting the red light emitting layer is made of a red phosphorescent host compound composed of the organic compound represented by Chemical Formula 1 described above. The dopant may be formed of a metal complex of iridium (Ir) or platinum (Pt).

The electron transport layer (ETL) 140 is formed on the emission layer (EML(R)) 130 . The electron transport layer (ETL) 140 may be made of Alq3, oxadiazole, triazole, phenanthroline, benzoxazole or benzthiazole, etc. It is not necessarily limited thereto.

The electron injection layer (EIL) 150 is formed on the electron transport layer (ETL) 140 . The electron injection layer (EIL) 150 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 . The negative electrode 500 may be made of a metal having a low work function, for example, aluminum (Al), silver (Ag), magnesium (Mg), lithium (Li) or calcium (Ca), but is not necessarily limited thereto. it is not

Although the organic light emitting device according to an embodiment of the present invention has been described above, the organic light emitting device according to the present invention may have various structures known in the art. For example, the present invention includes a white organic light emitting device having various structures known in the art having a red light emitting layer including the red phosphorescent host compound represented by Chemical Formula 1 described above. Such a white organic light emitting device may include a plurality of light emitting layers emitting light of different wavelengths and a charge generating layer (CGL) provided between the plurality of light emitting layers.

3 is a schematic cross-sectional view of a display device according to an embodiment of the present invention, which relates to a display device including the organic light emitting device according to FIG. 2 described above.

As can be seen from FIG. 3 , 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 element is electrically connected to the thin film transistor (TFT). , the organic light emitting device is driven by the thin film transistor TFT.

Specifically, the display device according to an embodiment of the present invention includes a substrate 10 , a gate electrode 20 , a gate insulating layer 25 , an active layer 30 , an etch stopper 35 , a source electrode 40a, It includes a drain electrode 40b, a passivation layer 50, 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 include molybdenum (Mo), aluminum (Al), chromium (Cr), gold (Au), titanium (Ti), nickel (Ni), neodium (Nd), or copper (Cu). It may be made of a 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. The channel region of the active layer 30 is prevented from being etched during the etching process for the patterning of . 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 face each other and are patterned on the etch stopper 30 . The source electrode 40a and the drain electrode 40b may include 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 passivation layer 50 is formed on the source electrode 40a and the drain electrode 40b,

The planarization layer 70 is formed on the passivation layer 50 . 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 the thin film transistor TFT, and a 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 , an organic light emitting unit 90 , and a cathode 500 . The structure of the organic light emitting part 90 formed between the anode 100 and the cathode 500 may be the structure shown in FIG. 2 described above. The organic light emitting unit 90 includes a hole injection layer (HIL) 110 , a hole transport layer (HTL) 120 , an emission layer (EML(R)) 130 , and an electron transport layer (ETL) 140 of FIG. 2 . ), and the electron injection layer (EIL) 150 , a repeated description thereof will be omitted.

Although the organic light emitting display device according to an embodiment to which the organic light emitting device according to the present invention is applied has been described above, the organic light emitting device according to the present invention can be applied to organic light emitting display devices having various structures. In addition, the organic light emitting device according to the present invention can be applied to various fields, for example, televisions, lighting, mobile phones, notebook computers, digital cameras, display devices for vehicles, display devices in fields such as food and clothing stores.

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

Example One

The ITO substrate was patterned to have a light emitting area of 3 mm × 3 mm and then washed. After the cleaned ITO substrate was mounted in a vacuum deposition chamber, organic materials were sequentially formed under a vacuum of 10 ^{to 6} torr.

Specifically, on an ITO substrate, CuPC (650 Å), NPB (400 Å), a red light emitting layer (EML) (200 Å) consisting of the aforementioned compounds A1 and RD-1 (5%) (200 Å), Alq3 (350 Å), LiF (5 Å), and An organic light emitting diode according to Example 1 was manufactured by sequentially depositing Al (1000 Å) into a film.

Example 2

In Example 1 above, a red light emitting layer (EML) (200 Å) consisting of compound A8 and RD-1 (5%) instead of a red light emitting layer (EML) (200 Å) consisting of compound A1 and RD-1 (5%) (200 Å) An organic light emitting diode according to Example 2 was manufactured in the same manner as in Example 1, except that a film was formed.

Example 3

The ITO substrate was patterned to have a light emitting area of 3 mm × 3 mm and then washed. After the cleaned ITO substrate was mounted in a vacuum deposition chamber, organic materials were sequentially formed under a vacuum of 10 ^{to 6} torr.

Specifically, after spin coating PEDOT:PSS (800Å) on an ITO substrate at 3000 rpm and baking at 120° C. for 1 hr, a red light-emitting layer (250Å) composed of compound A1 and RD-1 (5%) was spin-coated at 3000 rpm. After coating and baking at 100° C. for 30 minutes, Alq3 (350 Å), LiF (5 Å), and Al (1000 Å) were formed in this order to prepare an organic light emitting device according to Example 3.

Example 4

In Example 3 above, a red light emitting layer (EML) (250 Å) consisting of compound A8 and RD-1 (5%) instead of a red light emitting layer (EML) (250 Å) consisting of compound A1 and RD-1 (5%) An organic light emitting diode according to Example 4 was manufactured in the same manner as in Example 3, except that a film was formed.

Example 5

In Example 1 above, a red light emitting layer (EML) (200 Å) consisting of compound B1 and RD-1 (5%) instead of a red light emitting layer (EML) (200 Å) consisting of compound A1 and RD-1 (5%) (200 Å) An organic light emitting diode according to Example 5 was manufactured in the same manner as in Example 1, except that a film was formed.

Example 6

In Example 1 above, a red light emitting layer (EML) (200 Å) consisting of compound B19 and RD-1 (5%) instead of a red light emitting layer (EML) (200 Å) consisting of compound A1 and RD-1 (5%) An organic light emitting diode according to Example 6 was manufactured in the same manner as in Example 1, except that a film was formed.

Example 7

In Example 3 above, a red light emitting layer (EML) (250 Å) consisting of compound B1 and RD-1 (5%) instead of a red light emitting layer (EML) (250 Å) consisting of compound A1 and RD-1 (5%) An organic light emitting diode according to Example 7 was manufactured in the same manner as in Example 3, except that a film was formed.

Example 8

In Example 3 above, a red light emitting layer (EML) (250 Å) consisting of compound B19 and RD-1 (5%) instead of a red light emitting layer (EML) (250 Å) consisting of compound A1 and RD-1 (5%) An organic light emitting diode according to Example 8 was manufactured in the same manner as in Example 3, except that a film was formed.

comparative example

In Example 1 above, instead of the red light emitting layer (EML) (200 Å) composed of compound A1 and RD-1 (5%), a red light emitting layer (EML) (200 Å) composed of CBP and RD-1 (5%) was formed. Except for the above, an organic light emitting diode according to Comparative Example was manufactured in the same manner as in Example 1 above.

In Examples 1 to 8 and Comparative Examples above, CuPC, NPB, RD-1, Alq3, and CBP are compounds represented by the following formulas, respectively.

(CuPC),

(NPB),

(CuPC),

(NPB),

(RD-1),

(Alq3),

(CBP).

(RD-1),

(Alq3),

(CBP).

Experimental example

Driving voltage (V), current (mA), luminance (cd/m ² ), current efficiency (cd/A), and power efficiency (Im/W) for the organic light-emitting devices according to Examples 1 to 8 and Comparative Examples ), internal quantum efficiency (%), and CIE (X, Y) were measured, respectively, and the results are shown in Table 1 below.

Table 1

As can be seen from Table 1 above, the case of Examples 1 to 8 under the same driving voltage (V) and current (mA) and high purity red color coordinates CIE (X, Y) compared to Comparative Examples luminance (cd /m ² ), current efficiency (cd/A), power efficiency (Im/W), and internal quantum efficiency (%) are excellent.

Although the embodiments of the present invention have been described in more detail with reference to the accompanying drawings, the present invention is not necessarily limited to these embodiments, and various modifications may be made within the scope without departing from the technical spirit of the present invention. . Therefore, the embodiments disclosed in the present invention are not intended to limit the technical spirit of the present invention, but to explain, and the scope of the technical spirit of the present invention is not limited by these embodiments. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive. The protection scope of the present invention should be construed by the claims, and all technical ideas within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100: anode 110: hole injection layer
120: hole transport layer 130: light emitting layer
140: electron transport layer 150: electron injection layer
500: cathode

Claims (13)

Formula 1:
[Formula 1]

(In Formula 1, Ar ₁ is composed of a heteroaromatic group or an aromatic hole transporting group, and Ar ₂ is an electron transporting group to which an aryl group is bonded as a functional group (electron) (consisting of a transporting group)
Consists of an organic compound represented by
Wherein Ar ₁ is made to include indole carbazole,
The Ar ₂ is a red phosphorescent host compound comprising triazine to which the aryl group is bonded as a functional group. delete According to claim 1,
The indole carbazole is a red phosphorescent host compound in which dibenzofuran, dibenzothiophene, or an aryl group is bonded as a functional group. 4. The method of claim 3,
The dibenzofuran is made of dibenzo[b,d]furan, and the dibenzothiophene is dibenzo[b,d]thiophene. The aryl group is a red phosphorescent host compound selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene and phenanthrene. According to claim 1,
The Ar ₁ is

,

,

, and

is selected from the group consisting of
wherein Ar ₃ is a red phosphorescent host compound selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, and phenanthrene. delete According to claim 1,
The aryl group bonded to the triazine is a red phosphorescent host compound selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene and phenanthrene. According to claim 1,
The Ar ₂ is

wherein Ar ₃ is each independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, and phenanthrene. host compound. According to claim 1,
Formula 1 is a red phosphorescent host compound selected from the group consisting of Formulas B1 to B81:

(B1),

(B2),

(B3),

(B4),

(B5),

(B6),

(B7),

(B8),

(B9),

(B10),

(B11),

(B12),

(B13),

(B14),

(B15),

(B16),

(B17),

(B18),

(B19),

(B20),

(B21),

(B22),

(B23),

(B24),

(B25),

(B26),

(B27),

(B28),

(B29),

(B30),

(B31),

(B32),

(B33),

(B34),

(B35),

(B36),

(B37),

(B38),

(B39),

(B40),

(B41),

(B42),

(B43),

(B44),

(B45),

(B46),

(B47),

(B48),

(B49),

(B50),

(B51),

(B52),

(B53),

(B54),

(B55),

(B56),

(B57),

(B58),

(B59),

(B60),

(B61),

(B62),

(B63),

(B64),

(B65),

(B66),

(B67),

(B68),

(B69),

(B70),

(B71),

(B72),

(B73),

(B74),

(B75),

(B76),

(B77),

(B78),

(B79),

(B80),

(B81). delete delete Consists of an anode, a cathode, and a red light emitting layer provided between the anode and the cathode,
The red light emitting layer is an organic light emitting device comprising the red phosphorescent host compound according to any one of claims 1, 3 to 5, and claims 7 to 9. A display device comprising a thin film transistor and an organic light emitting device driven by the thin film transistor, wherein the organic light emitting device comprises the organic light emitting device according to claim 12 .

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