KR102274449B1 - Fluoranthene compound and organic light emitting element comprising the same - Google Patents

Abstract

The present invention relates to a fluoranthene compound and an organic light emitting device comprising the same. The organic light emitting diode of the present invention includes the fluoranthene compound of the present invention and exhibits excellent driving voltage and luminous efficiency characteristics.

Description

Derivatives of fluoranthene-based compounds and organic light emitting devices comprising the same {FLUORANTHENE COMPOUND AND ORGANIC LIGHT EMITTING ELEMENT COMPRISING THE SAME}

The present invention relates to a charge generating compound and an organic electroluminescent device including the same, and more particularly, to a charge generating compound capable of improving the luminous efficiency of an organic electroluminescent device and lowering a driving voltage, and a novel fluoran including the same It relates to ten derivatives.

A video display device that implements various information on a screen is a key technology in the information and communication era, which is developing in the direction of thinner, lighter, more portable and high-performance. With the recent development of the information society, as the demand for various types of display devices increases, LCD (Liquid Crystal Display), PDP (Plasma Display Panel), ELD (Electro Luminescent Display), FED (Field Emission Display), OLED ( Organic Light Emitting Diode) and other flat panel display devices are being actively researched. An organic light emitting device is a device for converting electrical energy into light energy using an organic material, and includes a structure in which a light emitting organic material layer is formed between an anode and a cathode. The organic light emitting device can be formed in various structures, and among them, a tandem type organic light emitting device in which a plurality of light emitting layers are stacked is being studied.

In a tandem type organic light emitting device, a plurality of light emitting units including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer are stacked between an anode and a cathode. In the tandem organic light emitting device, electrons are transferred to the charge generating layer and the electron injection layer between the light emitting units, and holes are transferred to the hole injection layer adjacent to the charge generating layer. At this time, the device efficiency is determined according to the difference in energy level and the interface characteristics between the charge generation layer and the charge generation layer and the interface characteristics and energy level between the charge generation layer and the doped alkali metal. As the energy level difference between the charge generation layers increases, charges are generated at the interface between the charge generation layer and the adjacent hole injection layer, making it difficult for electrons to be injected into the charge generation layer. Also, when the charge generation layer is doped with an alkali metal, the alkali metal diffuses into the charge generation layer and current leakage occurs. Current leakage reduces the lifetime of the device.

Patent Document 1: Korean Patent Registration No. 10-1645145

The present invention is to provide a novel fluoranthene derivative having superior luminous efficiency and excellent thermal stability than conventional materials, and the fluoranthene derivative is included in an organic film to lower the driving voltage of the device and improve luminous efficiency. To provide a light emitting device.

The object of the present invention can be achieved by a fluoranthene compound represented by the following formula (1).

[Formula 1]

Wherein Ar ₁ is hydrogen, a substituted or unsubstituted C 3 to C 60 aryl group, a substituted or unsubstituted C 3 to C 60 heteroaryl group including one or more heteroatoms selected from nitrogen, oxygen and sulfur, arylamine group and secondary amine groups.

Wherein Ar ₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted a pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenyl group Nyl group, substituted or unsubstituted perylenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or Unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofura nyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or Unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted an acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted carbazolyl group, And it may be selected from the group consisting of a substituted or unsubstituted spirobifluorenyl group.

In addition, an object of the present invention includes a first electrode, a second electrode, and at least one organic material layer positioned between the first electrode and the second electrode, wherein at least one of the organic material layers is fluoranthene according to the present invention It is achieved by an organic light emitting device comprising a compound.

The organic layer includes at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and the at least one layer is a fluoranthene compound according to the present invention may include.

The organic layer includes at least one layer selected from the group consisting of a light emitting layer, an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons, and the at least one layer is a fluoranthene compound according to the present invention may include.

The organic material layer may include at least one charge generation layer (CGL), and the at least one charge generation layer may include the fluoranthene compound according to the present invention.

The fluoranthene compound according to an embodiment of the present invention may be included in an organic film, preferably, a charge generating layer, a hole injection layer or a hole transport layer of an organic electroluminescent device to lower the driving voltage of the device and improve luminous efficiency. . In addition, the lifespan of the organic electroluminescent device can be improved by the thermal stability of the fluoranthene compound of the present invention.

1 is a cross-sectional view of an organic light emitting 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. However, the present invention is not limited to the embodiments disclosed below, but will be implemented in a variety of 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 size and thickness of each component shown in the drawings are illustrated for convenience of description, and the present invention is not necessarily limited to the size and thickness of the illustrated component.

Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.

The fluoranthene compound according to the present invention is represented by the following formula (1).

[Formula 1]

Wherein Ar ₁ is hydrogen, a substituted or unsubstituted C 3 to C 60 aryl group, a substituted or unsubstituted C 3 to C 60 heteroaryl group including one or more heteroatoms selected from nitrogen, oxygen and sulfur, arylamine group and secondary amine groups.

Wherein Ar ₁ is specifically a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or Unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted tree A phenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted A pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted A benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted A substituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted carbazolyl group group, a substituted or unsubstituted spirobifluorenyl group, or a combination thereof, but is not limited thereto. Preferably, Ar ₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted tree A phenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted phosphine oxide group , and combinations thereof.

Substituents that may be substituted for Ar ₁ are phenyl group, naphthyl group, anthracenyl group, phenanthryl group, naphthacenyl group, pyrenyl group, biphenylyl group, p-terphenyl group, m-terphenyl group, chrysenyl group, triphenyl Renyl group, perylenyl group, indenyl group, furanyl group, thiophenyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, oxazolyl group, thiazolyl group, oxadiazolyl group, thiadiazolyl group, pyri Diyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, benzofuranyl group, benzothiophenyl group, benzoimidazolyl group, indolyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group , from the group consisting of benzoxazinyl group, benzthiazinyl group, acridinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, phosphine oxide group, phenanthrolinyl group, carbazolyl group and spirobifluorenyl group can be chosen.

As a specific example, the fluoranthene compound according to the present invention may be a compound shown below.

The fluoranthene compound of the present invention was designed as a compound with increased conjugation for higher current efficiency and higher electron mobility than the conventionally used dimethylfluorene. As a result, the stability of the compound of the compound is improved and the band gap is reduced. In addition, the electrons move easily and the current efficiency increases during device fabrication. In particular, when a polycyclic compound containing N having an electron transport ability or a compound containing P is substituted, the stability of the charge generating ability and the electron transporting ability is secured.

1 is a cross-sectional view of an organic light emitting device according to an embodiment of the present invention. Referring to FIG. 1 , the organic light-emitting device 1 has a tandem-type structure, including a first electrode (anode, 110), a second electrode (cathode, 120), a first light-emitting unit 210, and a second light-emitting unit 220. , a third light emitting unit 230 , a first charge generating layer 240 , and a second charge generating layer 250 .

The first light emitting unit 210 , the second light emitting unit 220 , the third light emitting unit 230 , the first charge generating layer 240 , and the second charge generating layer 250 are organic material layers and the first electrode 110 . It is positioned between the second electrode 120 and the first charge generating layer 240 is positioned between the first light emitting part 210 and the second light emitting part 220, and the second charge generating layer 250 is the second It is positioned between the second light emitting unit 220 and the third light emitting unit 230 .

The first light emitting unit 210 includes a hole injection layer 211 , a first hole transport layer 212 , a first light emitting layer 213 , and a first electron transport layer 214 , and the second light emitting unit 220 is a second light emitting unit 220 . The second hole transport layer 221 , the second light emitting layer 222 and the second electron transport layer 223 are formed, and the third light emitting unit 230 includes a third hole transport layer 231 , a third light emitting layer 232 , and a third It consists of an electron transport layer 233 and an electron injection layer 234 .

The first charge generation layer 240 includes an n-type charge generation layer 241 and a p-type charge generation layer 242 , and the second charge generation layer 250 includes an n-type charge generation layer 251 and a p-type charge generation layer 251 . and a charge generation layer 252 . The n-type charge generation layers 241 and 251 may be doped with an alkali metal.

The fluoranthene compound according to the present invention includes a first electron transport layer 214, a second electron transport layer 223, a third electron transport layer 233, an electron injection layer 234, a first charge generation layer 240 and / Alternatively, it may be included in the second charge generation layer 250 , and in particular, may be used in the n-type charge generation layers 241 and 251 .

The described organic light emitting device 1 can be variously modified. Some organic layers may be omitted or added, may not be in a tandem form, and may be in a tandem form having two or four or more light emitting layers. In addition, the organic light emitting device 1 may include an organic layer including a layer that simultaneously transports and injects electrons, and even in this case, the fluoranthene compound according to the present invention may be used.

Hereinafter, Examples and Comparative Examples of the preparation of the fluoranthene compound and the organic light emitting device according to the present invention will be described. However, the Preparation Examples and Examples described below are only for specifically illustrating or explaining the present invention, and should not be construed as limiting the present invention by the Preparation Examples and Examples described below.

Example

Synthesis of compound 1-1

Intermediate A (2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) synthesis

After adding 4-bromo-9,9-dimethyl-9H-fluorene (20g, 73mmol) to a round bottom flask, bis(pinacolato)diboron (14g, 95mmol), potassium acetate (21g, 220mmol), PdCl ₂ (dppf) ( 1.6 g, 2.2 mmol) was added. 200 mL of 1,4-dioxane was added and refluxed for 12 hours. When the reaction was completed, it was precipitated with an excess of methanol, filtered and dried. After column purification with hexane and recrystallization with methanol, 11 g (48%) of Intermediate A was obtained. EI, MS m/z (%): 320 (100, M ⁺ )

Intermediate B (4-(8-bromonaphthalen-1-yl)-9,9-dimethyl-9H-fluorene) synthesis

Intermediate A (11 g, 34 mmol), 1,8-dibromonaphthalene (20 g, 69 mmol), and Pd (pph ₃ ) ₄ (1.2 g, 1.03 mmol) were added to a round-bottom flask, and then mixed well with 110 ml of toluene and 55 ml of ethanol. After dissolving potassium carbonate (14g, 103mmol) in 55ml of distilled water, it was added to the flask. After refluxing for 12 hours, the mixture was cooled to room temperature and extracted with methylene chloride. The organic layer was separated and dried _{over MgSO 4 .} The reaction product was purified by column with hexane to obtain 11.7 g (83%) of Intermediate B. EI, MS m/z (%): 398 (100, M ⁺ )

Synthesis of Intermediate C (6,6-dimethyl-6H-indeno[1,2-j]fluoranthene)

Dimethyformamide (Intermediate B (11 g, 27 mmol), Pd(pph ₃ ) ₂ Br ₂ (1 g, 1.38 mmol), 1,8-Diazabicyclo (5.4.0) undec-7-ene (42 g, 275 mmol) in a round bottom flask 110ml) and refluxed for 24 hours. Upon completion of the reaction, distilled water was added to precipitate, followed by filtering and drying. Column purification with hexane gave 6.7 g (77%) of Intermediate C. EI, MS m/z (%): 318 (100, M ⁺ )

Intermediate D (8-bromo-6,6-dimethyl-6H-indeno[1,2-j]fluoranthene) synthesis

Intermediate C (6.5g, 20mmol), N-bromosuccinimide (4g, 22mmol), and acetic acid (0.3ml) were added to a round bottom flask, and dissolved in chloroform (65ml). After stirring for 12 hours, it was cooled to room temperature. After extraction with methylene chloride, the organic layer was separated and dried _{over MgSO 4 .} It was used in the next reaction without purification. EI, MS m/z (%): 396 (100, M ⁺ )

Intermediate E 1-(4-(6,6-dimethyl-6H-indeno[1,2-j]fluoranthen-8-yl)phenyl)ethanone

After adding Intermediate D mixture (5g, 12.5mmol) to a round bottom flask, 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone (3.7g , 15mmol), Pd(pph ₃ ) ₄ (0.4g, 0.35mmol) was added, and then mixed well with 50ml of toluene and 25ml of ethanol. After dissolving potassium carbonate (5g, 38mmol) in 25ml of distilled water, it was added to the flask. After refluxing for 24 hours, the mixture was cooled to room temperature, precipitated with excess methanol, filtered and dried. Column purification with hexane gave 3 g (54%) of Intermediate E. EI, MS m/z (%): 436 (100, M ⁺ )

Compound 1-1 Synthesis of 2-(4-(6,6-dimethyl-6H-indeno[1,2-j]fluoranthen-8-yl)phenyl)-1,10-phenanthroline

Intermediate E (3g, 6.87mmol), 8-aminoquinoline-7-carbaldehyde (1.4g, 8.24mmol), and toluene (30ml) were added to a round bottom flask. After dissolving potassium hydroxide (1.16g, 20mmol) in ethanol (15ml), it was added to the reaction product and refluxed for 4 hours. When the reaction was completed, it was precipitated with excess water and methanol, filtered and dried. Column purification was performed with methylene chloride to obtain 2.4 g (61%) of compound 1-1. EI, MS m/z (%): 572 (100, M ⁺ )

Synthesis of compound 1-3

Intermediate F Synthesis of 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine

After adding 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10g, 25mmol) to a round bottom flask, bis(pinacolato)diboron (8.3g, 33mmol), potassium acetate (7.5g) , 77mmol), Pd(dppf)Cl ₂ (5.1g, 0.77mmol) was added. 100 mL of 1,4-dioxane was added and refluxed for 12 hours. When the reaction was completed, it was precipitated with an excess of methanol, filtered and dried. Column purification with hexane and recrystallization with methanol gave 9.8 g (90%) of Intermediate F. EI, MS m/z (%): 435 (100, M ⁺ )

Preparation of compound 1-3 2-(4-(6,6-dimethyl-6H-indeno[1,2-j]fluoranthen-8-yl)phenyl)-4,6-diphenyl-1,3,5-triazine

After adding Intermediate D mixture (5g, 12.5mmol) to a round bottom flask, Intermediate F (6.5g, 15mmol), Pd(Pph ₃ ) ₄ (0.4g, 0.35mmol) was added, and then mixed well with toluene 50ml and ethanol 25ml . After dissolving potassium carbonate (5g, 38mmol) in 25ml of distilled water, it was added to the flask. After refluxing for 24 hours, the mixture was cooled to room temperature, precipitated with excess methanol, filtered and dried. Column purification with hexane gave 5.4 g (70%) of compound 1-3. EI, MS m/z (%): 625 (100, M ⁺ )

Synthesis of compounds 1-5

Synthesis of intermediate G 2-(4-bromophenyl)-2,7a-dihydro-1H-benzo[d]imidazole

After adding o-Phenylenediamine (10 g, 92 mmol) to a round-bottom flask, ammonium acetate (27 g, 276 mmol) was dissolved in ethanol. After dissolving 4-bromobenzaldehyde (18.4 g, 101 mmol) in ethanol, it was slowly added to the reaction solution and refluxed. When the reaction was completed, 15 g (58%) of intermediate G was obtained by concentration and column purification with hexane. EI, MS m/z (%): 274 (100, M ⁺ )

Synthesis of intermediate H 2-(4-bromophenyl)-1-ethyl-2,7a-dihydro-1H-benzo[d]imidazole

Intermediate G (11g, 40mmol) was added to a round bottom flask, and sodium hydride (2.8g, 120mmol) was added thereto and dissolved in THF. Iodoethane (6.2g, 40mmol) was well dissolved in THF and then slowly added to the reaction solution and refluxed. When the reaction was completed, 11 g (91%) of intermediate H was obtained by concentration and column purification with hexane. EI, MS m/z (%): 302 (100, M ⁺ )

Intermediate I 1-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,7a-dihydro-1H-benzo[d]imidazole synthesis of

Intermediate H (10g, 33mmol) was added to a round bottom flask, and bis(pinacolato)diboron (9g, 36mmol), potassium acetate (9.7g, 99mmol), Pd(dppf)Cl ₂ (0.09g, 0.99mmol) was added thereto. . 100 mL of 1,4-dioxane was added and refluxed for 12 hours. When the reaction was completed, it was precipitated with an excess of methanol, filtered and dried. 8g (69%) of Intermediate I was obtained by column purification with hexane and recrystallization with methanol. EI, MS m/z (%): 350 (100, M+)

Compound 1-5 2-(4-(6,6-dimethyl-6H-indeno[1,2-j]fluoranthen-8-yl)phenyl)-1-ethyl-2,7a-dihydro-1H-benzo[d ]Preparation of imidazole

After adding Intermediate D mixture (5g, 12.5mmol) to a round bottom flask, Intermediate I (5.2g, 15mmol), Pd(Pph ₃ ) ₄ (0.4g, 0.35mmol) was added, and then mixed well with toluene 50ml and ethanol 25ml . After dissolving potassium carbonate (5g, 38mmol) in 25ml of distilled water, it was added to the flask. After refluxing for 24 hours, the mixture was cooled to room temperature, precipitated with excess methanol, filtered and dried. Column purification was performed with hexane to obtain 4.2 g (63%) of compound 1-5. EI, MS m/z (%): 540 (100, M+)

Compound 1-9 (4'-(4-(6,6-dimethyl-6H-indeno[1,2-j]fluoranthen-8-yl)phenyl)-3,2':6',3''-terpyridine ) synthesis

After adding the intermediate D mixture (5 g, 12.5 mmol) to a round bottom flask, 4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3, 2':6',3''-terpyridine (6.5g, 15mmol), Pd(Pph ₃ ) ₄ (0.4g, 0.35mmol) was added, and then mixed well with 50ml of toluene and 25ml of ethanol. After dissolving potassium carbonate (5g, 38mmol) in 25ml of distilled water, it was added to the flask. After refluxing for 24 hours, the mixture was cooled to room temperature, precipitated with excess methanol, filtered and dried. Column purification with methylene chloride gave 5.4 g (70%) of compound 1-9. EI, MS m/z (%): 626 (100, M+)

Synthesis of compound 1-10 ((4-(6,6-dimethyl-6H-indeno[1,2-j]fluoranthen-4-yl)phenyl)diphenylphosphine oxide)

Intermediate D mixture (5g, 12.5mmol) was added to a round bottom flask, and then diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (6.1g , 15mmol), Pd(Pph ₃ ) ₄ (0.4g, 0.35mmol) was added and mixed well with toluene 50ml and ethanol 25ml. After dissolving potassium carbonate (5g, 38mmol) in 25ml of distilled water, it was added to the flask. After refluxing for 24 hours, the mixture was cooled to room temperature, precipitated with excess methanol, filtered and dried. Column purification was performed with methylene chloride to obtain 9.2 g (74%) of compound 1-10. EI, MS m/z (%): 595 (100, M ⁺ )

Table 1 shows the ¹ H NMR and MASS / FAB of the composite material. The ¹ s of the abbreviation used in the H NMR analysis results of a singlet, d is doublet, t is triplet, g is quartet, m means multiplet.

[Manufacture of organic EL device]

1. Preparation Example of Comparative Example 1

After patterning the ITO substrate so that the emission area was 2 mm × 2 mm in size, washing was performed with isopropyl alcohol and UV ozone, respectively. Then, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus, and the pressure was applied so that ^{the degree of vacuum was 1×10 -7 torr.}

First, a HAT-CN compound was vacuum-deposited to form a thickness of 5 nm. This compound acts as the first hole injection layer. On this, an NPB material was formed to a thickness of 30 nm as a first hole transport layer. Then, an HT-1 material was formed to a thickness of 10 nm as a first electron blocking layer.

Thereafter, the YGH-1 material as a host and the YGD-1 material as a dopant were co-deposited to a thickness of 30 nm in a mass ratio of about 10% to form a yellow first light emitting layer.

A TmPyPB compound was formed on the light emitting layer to have a thickness of 25 nm and a first electron transport layer. Thereafter, a Li material was co-deposited to a thickness of 10 nm in a 2% mass ratio on the BPhen material to form an N-type charge generation layer. Thereafter, a HAT-CN compound was vacuum-deposited to a thickness of 5 nm as a P-type charge generation layer. The foreign material is also used as the second hole injection layer. On this, an NPB material was formed to a thickness of 60 nm as a second hole transport layer. Then, an HT-1 material was formed to a thickness of 10 nm as a second electron blocking layer.

Thereafter, the CPB material as a host and the Ir compound as a dopant were co-deposited to a thickness of 30 nm in a mass ratio of about 10% to form a yellow second emission layer. A TmPyPB compound was formed on the light emitting layer to have a thickness of 25 nm and a second electron transport layer. Thereafter, the LiF material was vacuum-deposited to a thickness of 1 nm as an electron injection layer. Finally, Al was deposited to a thickness of 100 nm to form a cathode to fabricate an organic EL device.

2. Preparation of Example 1

An organic light emitting diode was manufactured by changing only the N-type charge generation layer material to Compound 1-1, except that it was configured in the same manner as in the above-mentioned comparative example.

3. Preparation of Example 2

An organic light-emitting device was manufactured by changing only the N-type charge generation layer material to Compound 1-9, except that it was configured in the same manner as in the above-mentioned Comparative Example.

4. Preparation of Example 3

An organic light emitting diode was manufactured by changing only the N-type charge generation layer material to Compound 1-10, except that it was configured in the same manner as in the comparative example described above.

Hereinafter, the driving current, driving voltage, current efficiency and external quantum efficiency of the organic light emitting diodes of Examples 1 to 3 and Comparative Example 1 were measured and shown in Table 2 below.

It can be seen that the driving voltage, current efficiency, and external quantum efficiency of Examples 1 to 3 were significantly improved compared to Comparative Example 1.

5. Preparation Example of Comparative Example 2

After patterning the ITO substrate so that the emission area was 2mm × 2mm in size, washing was performed with isopropyl alcohol and UV ozone, respectively. Then, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus, and the pressure was applied so that ^{the degree of vacuum was 1×10 -7 torr.} Thereafter, plasma treatment was performed for 3 minutes under _{N 2 atmosphere.}

And first, a HAT-CN compound was vacuum-deposited to form a thickness of 5 nm. This compound acts as a hole injection layer. On this, an NPB material was formed to a thickness of 50 nm as a first hole transport layer. Then, an HT-1 material was formed to a thickness of 10 nm as a second hole transport layer.

Thereafter, the GH-1 material as the host and the GD-1 material as the dopant were co-deposited to a thickness of 30 nm in a mass ratio of about 10% to form a green light emitting layer.

An electron transport layer was formed on the light emitting layer with an ET-1 compound having a thickness of 35 nm. Then, a LiF material was deposited to form an electron injection layer to a thickness of 1 nm. Thereafter, Al was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic EL device.

6. Preparation Example of Comparative Example 3

An organic light emitting diode was manufactured by changing only the electron transport layer material ET-1 to ET-2, except that it was configured in the same manner as in Comparative Example 2 described above.

7. Preparation of Example 4

An organic light emitting device was manufactured in the same manner as in Comparative Example 2 described above, except that only the electron transport layer material ET-1 was replaced with Compound 1-1.

8. Preparation of Example 5

An organic light emitting device was fabricated in the same manner as in Comparative Example 2 described above, except that only the electron transport layer material ET-1 was replaced with Compound 1-9.

^{A constant current of 10 mA/cm 2} was applied to the organic light emitting diodes manufactured by Examples 4 and 5 and Comparative Examples 2 and 3 of the present invention, and luminescence characteristics were measured with a PR-670 manufactured by photoresearch.

Hereinafter, the driving current, driving voltage, current efficiency, and external quantum efficiency of the organic light emitting devices of Examples 4 and 5 and Comparative Examples 2 and 3 were measured and shown in Table 3 below.

It can be seen that the driving voltage, current efficiency, and external quantum efficiency of Examples 4 and 5 are significantly improved compared to Comparative Examples 2 and 3.

The present invention is not necessarily limited to these embodiments, and various modifications may be made 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 following claims, and all technical ideas within the equivalent range should be construed as being included in the scope of the present invention.

Claims (7)

A fluoranthene compound represented by the following formula (1):
[Formula 1]

Wherein Ar ₁ is hydrogen, a substituted or unsubstituted C 3 to C 60 aryl group, a substituted or unsubstituted C 3 to C 60 heteroaryl group including one or more heteroatoms selected from nitrogen, oxygen and sulfur, arylamine group and secondary amine groups. According to claim 1, wherein Ar _One is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or Unsubstituted triphenylenyl group, substituted or unsubstituted perylenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted Or an unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxa group Diazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted Or an unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted iso A quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group , substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazinyl group, substituted or unsubstituted phenothiazinyl group, substituted or unsubstituted phenoxazinyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted A fluoranthene compound selected from the group consisting of a cyclic carbazolyl group, and a substituted or unsubstituted spirobifluorenyl group. The fluoranthene compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

first electrode;
a second electrode, and
At least one organic material layer positioned between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic light emitting device comprising the fluoranthene compound according to claim 1. 5. The method of claim 4, wherein the organic material layer comprises at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and the at least one layer comprises a first An organic light emitting device comprising the fluoranthene compound according to claim. 5. The method of claim 4, wherein the organic material layer comprises at least one layer selected from the group consisting of a light emitting layer, an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons, and the at least one layer comprises a first An organic light emitting device comprising the fluoranthene compound according to claim. 5. The method of claim 4, wherein the organic material layer comprises at least one charge generation layer (CGL), and the at least one charge generation layer comprises the fluoranthene compound according to claim 1 . organic light emitting device.

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