KR20180032294A - Phosphorescent compounds and light emitting diode and organic light emitting diode display device using the compound - Google Patents

Abstract

The present invention relates to a new structure of phosphorescent compound, and a light emitting diode and an organic light emitting diode display using the same. A light emitting element to which the phosphorescent compound is applied has improved life and light emitting efficiency thereof. The phosphorescent compound according to the present invention is applied to the light emitting diode to be used in a display apparatus and a lighting apparatus. The phosphorescent compound is represented by the following formula 1.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a phosphorescent compound and a light emitting diode and an organic light emitting diode (OLED)

TECHNICAL FIELD The present invention relates to a light emitting compound, and more particularly, to a compound having phosphorescence characteristics, a light emitting diode using the same, and an organic light emitting diode display device.

As display devices have become larger, there is a growing demand for flat display devices with less space occupancy. As one of such flat display devices, the technology of an organic light emitting diode device which is also called an organic electroluminescent device (OELD) is rapidly developing.

Organic light emitting diodes (OLEDs) are formed of thin organic thin films within 2000 Å, and it is possible to realize images in a single direction or in both directions depending on the configuration of the electrodes used. Further, in implementing a flexible or foldable display device, an organic light emitting diode display device can be formed on a flexible transparent substrate such as a plastic, can be driven at a low voltage, has excellent color purity , And a liquid crystal display device (LCD). In recent years, as materials having excellent charge mobility have been developed, the power consumption of display devices employing organic light emitting diodes is rapidly lowered. Therefore, organic light emitting diode (OLED) display devices are attracting much attention as next generation display devices to replace LCDs, and they are replacing LCDs in small display devices for actual mobile use.

The organic light emitting diode is a device that injects electric charge into a light emitting material layer formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode), and emits light while paired with electrons. A brief process of fabricating the organic light emitting diode device will be described.

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

(2) A hole injection layer (HIL) is formed on the anode. 4, 5, 8, 9, 12-hexaazatriphenylene hexacarbonitrile (HATCN) as a hole injection layer material to a thickness of 5 nm to 30 nm.

(3) Next, a hole transporting layer (HTL) is formed on the hole injection layer. The hole transport layer is formed by depositing 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB) at a thickness of 30 nm to 70 nm.

(4) Next, a light emitting material layer (EML) is formed on the hole transport layer. The light emitting material layer may include a dopant.

For example, a green light emitting layer can be formed by doping 8-hydroxyquinolatealuminum (Alq ₃ ) with N, N'-dimethylquinacridone (DMQA) as a dopant. In the case of a phosphorescent device, a green light emitting layer can be formed by using tris (2-phenylpyridine) iridium (III) (Ir (ppy) ₃ ) as a dopant in bis (N-carbazolyl) biphenyl (CBP).

(5) Next, an electron transport layer (ETL) and an electron injection layer (EIL) are formed on the light emitting material layer. For example, tris (8-hydroxy-quinolate) aluminum (Alq ₃ ) is used as the electron transport layer and LiF is used as the electron injection layer. In the case of a phosphorescent device, a hole blocking layer may be formed before the electron transport layer is formed in order to effectively confine the triplet exciton in the light emitting material layer.

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

The organic material used for the organic light emitting diode can be largely divided into a light emitting material and a charge transporting material. The charge transporting material can be classified into a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material. The light emitting material is classified into blue, red, and green light emitting materials according to the coloring light, and is used as a host or a dopant to increase the color purity as a coloring material and to increase the light emitting efficiency through energy transfer.

In recent years, a phosphorescent material is used more frequently than a fluorescent material in a luminescent material layer. In the case of a fluorescent material, only about 25% of the single excitons formed in the emitter layer are used to make light, and 75% of the triplet is mostly lost to heat, while the phosphors convert both singlet and triplet to light It has a luminescent mechanism.

In the case of the green phosphorescent dopant, an iridium complex is used, and a typical green phosphorescent dopant is Ir (ppy) ₃ Series. However, in the case of the Ir (ppy) ₃ series, since the quantum efficiency is low (about 20%), the luminous efficiency of the organic light emitting diode device is limited. In addition, currently commercially available green phosphorescent dopants have a very short life span of 3,000 cd / m2 to T90 = 62 hours (Sci. Rep. 2015, 5, 9855). A design method of iridium complex compounds for improving the lifetime is required. Particularly, in the case of a white organic light emitting diode device using a color filter, the necessity of a highly efficient light emitting material is further increased.

It is an object of the present invention to provide a phosphor which is excellent in luminous efficiency and can improve lifetime of a device, and a light emitting diode and an organic light emitting diode display device to which the phosphor is applied to an organic light emitting layer.

According to one aspect of the present invention, there is provided a phosphorescent compound in the form of an iridium complex having a structure in which a ligand connected to the main chain of iridium has a pyridine ring and a condensed ring of three 6-membered rings is connected to a pyridine ring.

When the phosphorescent compound according to the present invention is applied as a light emitting material of a light emitting diode, it exhibits excellent luminous efficiency and improves lifetime of the device.

According to another aspect of the present invention, there is provided a light emitting diode and an organic light emitting diode display device including the phosphor compound as a material of the organic light emitting layer.

The iridium complexes synthesized according to the present invention have a structure in which a vibration mode and a rotation mode of a ligand connected to the main chain of iridium are suppressed. When the iridium complex of the present invention is applied to the organic light emitting layer of the light emitting diode, excitons injected from the anode and the cathode emit light, respectively. In addition, the iridium complex of the present invention does not consume energy due to molecular vibration and rotation when emitting light, so that the lifetime of the material is excellent. Therefore, the lifetime of the device to which the iridium complex of the present invention is applied is improved and the luminous efficiency is increased.

The iridium complex according to the present invention can emit green light and can be used as a green dopant of a light emitting diode to realize excellent light emitting efficiency and to improve the lifetime of the device.

Accordingly, the phosphorescent compound according to the present invention can be utilized as an organic light emitting layer of a light emitting diode, for example, as a dopant of a light emitting material layer.

1 is a cross-sectional view schematically showing a light emitting diode to which a phosphorescent compound according to an exemplary embodiment of the present invention is applied to an organic light emitting layer.
2 is a cross-sectional view schematically showing an organic light emitting diode display device in which a phosphorescent compound according to an exemplary embodiment of the present invention is applied to a light emitting diode.
Figs. 3 to 7 are graphs showing NMR measurement results of the phosphorescent compound synthesized in the exemplary embodiment of the present invention, respectively.
FIGS. 8 to 12 are graphs showing PL spectral measurement results for the phosphorescent compound synthesized in the exemplary embodiment of the present invention, respectively.

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

[Phosphor compound]

Conventional green phosphorescent dopants of the Ir (ppy) ₃ series have molecular vibration and rotation modes. When vibration and rotation are enabled, the excitons generated broaden the spectrum when they emit light, which adversely affects the color purity. In addition, the material consumes energy not only by light emission but also by vibration and rotation, resulting in poor material life. Accordingly, the present invention proposes a novel phosphorescent compound which can improve the lifetime and luminous efficiency of the iridium complex by suppressing the vibration and rotation mode of the ligand connected to the iridium main chain.

According to this approach, a phosphorescent compound in the form of an iridium complex in which the vibration and rotation mode of the ligand is suppressed can be represented by the following formula (1).

[Chemical Formula 1]

(Wherein R ₁ to R ₂₀ each independently represent hydrogen, deuterium, tritium, halogen atom, CF ₃ , cyano group, C 1 to C 20 alkyl group, C 1 to C 20 alkoxy group, unsubstituted or substituted C 5 to C 20 aryl group , Unsubstituted or substituted C5-C20heteroaryl group, unsubstituted or substituted C1-C20 amine group or unsubstituted or substituted silyl group, X is O, S or -NR, and R is hydrogen, deuterium, hydrogen, halogen, CF _3, cyano group, C1 ~ C20 alkyl group, C1 ~ C20 alkoxy group, an unsubstituted or substituted C5 ~ C20 aryl group, an unsubstituted or substituted C5 ~ C20 heteroaryl group, unsubstituted or substituted A C1-C20 amine group or an unsubstituted or substituted silyl group, and n is an integer of 1 to 3, preferably 1 or 2. [

As used herein, "unsubstituted" or "unsubstituted" means that a hydrogen atom is substituted, in which case the hydrogen atom includes hydrogen, deuterium, and tritium.

As used herein, the substituent in the term "substituted" includes, for example, an alkyl group which is unsubstituted or substituted by halogen, an alkoxy group which is unsubstituted or substituted by halogen, halogen, cyano group, carboxyl group, carbonyl group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a hydrazyl group, a sulfonic acid group, an alkylsilyl group, an alkoxysilyl group, a cycloalkylsilyl group, But is not limited thereto.

The terms "heteroaromatic ring", "heterocycloalkylene group", "heteroarylene group", "heteroarylalkylene group", "heteroaryloxylene group", "heterocycloalkyl group", "heteroaryl group", " The term "hetero" as used in heteroarylalkyl group, heteroaryloxyl group, heteroarylamine group and the like means one or more carbon atoms constituting these aromatic or alicyclic rings, for example, Means that five carbon atoms are replaced by one or more heteroatoms selected from the group consisting of N, O, S, and combinations thereof.

For example, the aryl group in the present specification is an unsubstituted or substituted phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, an anthracenyl group, an indenyl group, a phenalenyl group, a phenanthrenyl group, an azulenyl group, Non-condensed or fused homoaromatic rings such as, for example, fluorenyl, fluorenyl, tetranenyl, indacenyl or spirobifluorenyl groups. In the present specification, the heteroaryl group is an unsubstituted or substituted pyrrolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, tetrazinyl group, imidazolyl group, pyrazolyl group, indolyl group , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, an indenocarbazolyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, A quinazolinyl group, a quinazolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, an acridinyl group, a phenanthrolinyl group, a phenanthrolinyl group, An oxazolyl group, an oxadiazolyl group, a triazolyl group, a dioxinyl group, a benzofuranyl group, a dibenzofuranyl group, a thiopyranyl group, a thiazinyl group, a thiophenyl group or a N Substituted spirobifluorenyl group and < RTI ID = 0.0 > It may be unsubstituted or have condensation condensed heteroaromatic ring.

In one exemplary embodiment, the phosphorescent compound according to the present invention can be represented by the following formula (2).

(2)

Wherein R ₂₁ to R ₂₅ each independently represents a halogen atom, CF ₃ , cyano group, C 1 to C 20 alkyl group, C 1 to C 20 alkoxy group, unsubstituted or substituted C 5 to C 20 aryl group, unsubstituted or substituted C 5 C20 heteroaryl group, an unsubstituted or substituted C1-C20 amine group or an unsubstituted or substituted silyl group, and X and n are each the same as defined in formula (1)

The phosphorescent compound in the form of iridium complex represented by the formula (1) or (2) has a bulky fused ring structure in which the ligand connected to the main chain of iridium has a fused ring structure, so that the oscillation and rotation mode of the ligand are suppressed. By suppressing the oscillation and rotation of the ligand, the luminescence spectrum of the iridium complex due to the exciton emission can be limited to a specific range, so that the color purity can be improved and energy consumption due to vibration and rotation can be prevented, , The luminous efficiency can be improved. For example, the phosphorescent compound of Formula 1 may be applied to a light emitting material layer of a light emitting diode to increase the green light emitting efficiency and improve the lifetime of the device.

More specifically, the phosphorescent compound of the present invention may be any compound represented by the following general formula (3).

(3)

As described above, the phosphorescent complexes of formulas (1) to (3) do not have molecular vibration and rotation mode. When the iridium complexes of the formulas (1) to (3) in which molecular vibration and rotation mode are not present are applied to the organic light emitting layer of the light emitting diode, the luminescence spectrum of the iridium complex by the light emission of the excitons injected from the anode and the cathode, respectively, So that color purity can be improved. In particular, when the iridium complex of the present invention emits light, it does not consume energy by molecular vibration and rotation. Since energy is not consumed by the molecular vibration and rotation, the lifetime of the material can be improved and the luminous efficiency can be improved. For example, phosphorescent compounds represented by Chemical Formulas 1 to 3 may be applied to a light emitting material layer of a light emitting diode to increase the green light emitting efficiency and improve the lifetime of the device.

[Light Emitting Diodes and Display Devices]

The phosphorescent compound represented by Chemical Formulas 1 to 3 may be applied to an organic light emitting layer of a light emitting diode and used as an organic light emitting diode display device. A light emitting diode and a light emitting diode display device using the phosphorescent compound according to the present invention will be described.

1 is a cross-sectional view schematically illustrating a light emitting diode to which a phosphorescent compound is applied according to an exemplary embodiment of the present invention. 1, the light emitting diode E according to the present invention includes a first electrode 110 and a second electrode 130 facing each other, and a first electrode 110 and a second electrode 130 located between the first and second electrodes 110 and 130, The organic light emitting layer 120 is formed. In the exemplary embodiment, the organic light emitting layer 120 includes a hole injection layer (HIL) 121, a hole transport layer (HTL) 122, a light emitting material layer (EML) 123, A transport layer (ETL) 124 and an electron injection layer (EIL) 125.

The first electrode 110 may be an anode for supplying holes to the light emitting material layer 123. The first electrode 110 is preferably formed of a conductive material having a relatively large work function value, for example, a transparent conductive oxide (TCO). For example, the first electrode 110 may be formed of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), zinc- Tin-oxide. ≪ / RTI >

The second electrode 130 may be a cathode for supplying electrons to the light emitting material layer 123. The second electrode 130 may be formed of a conductive material having a relatively low work function value such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag) ≪ / RTI >

The hole injection layer 121 is located between the first electrode 110 and the hole transport layer 122 and improves the interface characteristics between the inorganic first electrode 110 and the organic hole transport layer 122. In one exemplary embodiment, the hole-injecting layer 121 is formed of a mixture of 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine (4,4' MTDATA), copper phthalocyanine (CuPc), tris (4-carbazoyl-9-yl-phenyl) amine, TCTA), N, N'- N'-diphenyl-N, N'-bis (1-naphthyl) - 1,1'-biphenyl- (NPB), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (1, 4, 5, 8, 9, HATCN), 1,3,5-tris [4- (diphenylamino) phenyl] benzene, 1,3,5-tris [4- (diphenylamino) (4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), N- (biphenyl-4-yl) -9,9-dimethyl- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene- -9H- carbazol-3-yl) phenyl) -9H-fluoren-2-amine and / or any one of the compounds represented by the following formula (4).

[Chemical Formula 4]

The hole transport layer 122 is positioned adjacent to the light emitting material layer 123 between the first electrode 110 and the light emitting material layer 123. [ In one exemplary embodiment, the hole transport layer 122 is formed from N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine TPD), NPD, 4,4'-bis (N-carbazolyl) - N'-diphenyl- (4,4'-bis (N-carbazolyl) -1,1'-biphenyl; CBP), N- (biphenyl- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene- 9-phenyl-9H-fluoren-2-amine and / or N- (biphenyl-4-yl) -N- Yl) phenyl) biphenyl-4-yl) -N- (4- (9-phenyl-9H-carbazol- amine, and the like.

The light emitting material layer 123 may be doped with a phosphorescent compound represented by the general formulas (1) to (3) to improve the luminous efficiency and the like of the host and the device. For example, the light emitting material layer 123 may add about 1 to 30% by weight of the phosphorescent compound of the present invention to the host material and emit green light.

In one exemplary embodiment, a p-type host with good hole mobility characteristics and a dual host system with n-type host with excellent electron mobility can be used as the host of the light emitting material layer 123. When the dual host system is used, the light emitting material layer 123 can further improve the transfer characteristics of charges such as holes and electrons, thereby realizing the light emitting efficiency and the long life. Considering that the phosphorescent compound of the formulas (1) to (3) synthesized according to the present invention emits green light, the light emitting material layer 123 is formed of a host material composed of a carbazole compound, a thiophene compound and / Can be used. For example, the host material of the light emitting material layer 123 may be a metal complex such as dp ₂ Ir (acac), op ₂ Ir (acac), 4- (3-triphenylene- b, d] thiophene and / or 3- (4,6-diphenyl-1,3,5-triazine 2-yl) -1-phenyl-1,3-dihydroindolo [2,3-b] 1-phenyl-1,3-dihydroindolo [2,3-b] carbazole).

An electron transport layer 124 and an electron injection layer 125 may be sequentially stacked between the light emitting material layer 123 and the second electrode 130. The material of the electron transport layer 124 requires high electron mobility and stably supplies electrons to the light emitting material layer 123 through smooth electron transport.

In one exemplary embodiment, the electron transporting layer 124 may comprise at least one of oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, benzimidazole, , Triazine, and the like. For example, the electron transport layer 124 may be formed of tris (8-hydroxyquinoline aluminum; Alq ₃ ), 2-biphenyl-4-yl-5- (4- Phenyl) -1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate 2-anthracenyl) phenyl] -1-phenyl-1H-benzimidazole ((2- [4- ( Phenyl-1-phenyl-1H-benzimidazole, 3- (biphenyl-4-yl) -5- (4- tert- butylphenyl) -4-phenyl -4H-1,2,4-triazole (TAZ), 4,7 < RTI ID = 0.0 > (4,7-diphenyl-1,10-phenanthroline (Bphen), tris (phenylquinoxaline) (TPQ), 1,3,5-tris N-phenylbenzimidazole-2-yl) benzene (TPBI) and / or any one of the following chemical formula (5) The invention is not limited to this.

[Chemical Formula 5]

The electron injection layer 125 is located between the second electrode 130 and the electron transport layer 124 and may improve the lifetime of the device by improving the characteristics of the second electrode 130. In one exemplary embodiment, the material of the electron injection layer 125 is an alkali halide-based material such as LiF, CsF, NaF, BaF ₂ , and / or lithium quinolate (Liq), lithium benzoate, An organic metal-based material such as sodium stearate may be used, but the present invention is not limited thereto.

If necessary, the lifetime and efficiency of the device may be reduced when the hole moves the light emitting material layer 123 to the second electrode 130 or when the electrons pass through the light emitting material layer 123 to the first electrode 110 Can be imported. In order to prevent this, the light emitting diode E according to the exemplary embodiment of the present invention may include an exciton blocking layer in at least one of the upper and lower portions of the light emitting material layer 123.

For example, the light emitting diode E according to the exemplary embodiment of the present invention includes an electron blocking layer (not shown) capable of controlling the movement of electrons between the hole transporting layer 122 and the light emitting material layer 123, ; EBL, not shown) may be located. In one exemplary embodiment, an electron blocking layer (not shown) is formed of 4,4 ', 4 "-tris (carbazol-9-yl) -triphenylamine (4,4', 4" (9,9-dimethyl-9H-fluoren-2-yl) -9,9'-spiro (9,9-dimethyl-9H-fluoren-2-yl) -9,9'-spirobi [fluorene] -2- amine, but the present invention is not limited thereto.

In addition, a hole blocking layer (HBL) (not shown) is disposed as another exciton blocking layer between the light emitting material layer 123 and the electron transporting layer 124 to form the light emitting material layer 123 and the electron transporting layer 124, Thereby preventing the movement of holes. In one exemplary embodiment, oxadiazole, triazole, phenanthroline, benzoxazole, benzoquinone, and the like, which can be used for the electron transport layer 124 as the material of the hole blocking layer, Benzothiazole, benzimidazole, triazine and the like can be used. For example, the hole blocking layer may be formed by using 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline having a low HOMO level (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline; BCP), bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-biphenyl- ) - (1,1'-Biphenyl-4-olato) aluminum BAlq), Alq3, (2-biphenyl- (4-t-butylphenyl) -1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate (Liq) and / The present invention is not limited thereto.

The light emitting diode E according to the exemplary embodiment of the present invention includes a phosphorescent compound represented by Chemical Formula 1 to Chemical Formula 3 in the light emitting material layer 123 constituting the organic light emitting layer 120. The vibrations and rotations of the ligands are controlled in the compounds of formulas (1) to (3), so that energy due to the vibration and rotation of the ligand is not consumed. When the iridium complexes of the formulas (1) to (3) in which no molecular vibration and rotation mode are present are applied to the organic light emitting layer of the light emitting diode, the spectrum is not widened when the excitons injected from the positive electrode and the negative electrode respectively emit light, great. In addition, the iridium complex of the present invention does not consume energy by molecular vibration and rotation when emitting light, so that the lifetime of the material is particularly excellent. Therefore, by using the phosphorescent compounds of formulas (1) to (3), it is possible to obtain a light emitting diode (E) having excellent device lifetime and good light emitting efficiency.

Next, a display device to which the light emitting diode of the present invention is applied will be described. 2 is a schematic cross-sectional view of an organic light emitting diode display device according to an exemplary embodiment of the present invention.

2, the organic light emitting diode display 100 includes a driving thin film transistor Td, a planarization layer 160 covering the driving thin film transistor Td, And a light emitting diode E connected to the thin film transistor Td. The driving thin film transistor Td includes a semiconductor layer 140, a gate electrode 144, a source electrode 156 and a drain electrode 158. In FIG. 2, a thin film transistor Td having a coplanar structure is formed. .

The first substrate 101 constituting the array substrate and the second substrate 102 facing the first substrate 101 are adhered to each other to form a display panel. The first substrate 101 and the second substrate 102 may be a glass substrate, a thin flexible substrate, or a polymer plastic substrate. The first substrate 101 on which the driving thin film transistor Td and the light emitting diode E on which the organic light emitting layer 120 is formed is formed as an array substrate. The first substrate 101 is encapsulated by a second substrate 102, which is referred to as an in-cap substrate. For example, the first substrate 101 and the second substrate 102 are provided with an adhesive 180 made of a sealant or a frit along the edge thereof. The first substrate 101 and the second substrate 102 are bonded together by the adhesive 180, The second substrate 102 is adhered to maintain the panel state.

A semiconductor layer 140 is formed on the first substrate 101. For example, the semiconductor layer 140 may be made of an oxide semiconductor material. In this case, a light shielding pattern (not shown) and a buffer layer (not shown) may be formed under the semiconductor layer 140. The light shielding pattern prevents light from being incident on the semiconductor layer 140, To be deteriorated by the light. Alternatively, the semiconductor layer 140 may be made of polycrystalline silicon. In this case, impurities may be doped on both edges of the semiconductor layer 140.

A gate insulating layer 142 made of an insulating material is formed on the entire surface of the first substrate 101 on the semiconductor layer 140. A gate insulating film 142 may be formed of an inorganic insulating material such as silicon oxide (SiO ₂₎ or silicon nitride (SiNx).

A gate electrode 144 made of a conductive material such as metal is formed on the gate insulating layer 142 to correspond to the center of the semiconductor layer 140. A gate line (not shown) and a first capacitor electrode (not shown) may be formed on the gate insulating layer 142. The gate wiring may extend along the first direction, and the first capacitor electrode may be connected to the gate electrode 144. [ The gate insulating layer 142 is formed on the entire surface of the first substrate 101. The gate insulating layer 142 may be patterned to have the same shape as the gate electrode 144. [

An interlayer insulating layer 150 made of an insulating material is formed on the entire surface of the first substrate 101 on the gate electrode 144. The interlayer insulating film 150 may be formed of an inorganic insulating material such as silicon oxide (SiO ₂ ) or silicon nitride (SiN x), or formed of an organic insulating material such as benzocyclobutene or photo-acryl .

The interlayer insulating film 150 has first and second semiconductor layer contact holes 152 and 154 exposing upper surfaces on both sides of the semiconductor layer 140. The first and second semiconductor layer contact holes 152 and 154 are spaced apart from the gate electrode 144 on both sides of the gate electrode 144. Here, the first and second semiconductor layer contact holes 152 and 154 are also formed in the gate insulating film 142. Alternatively, when the gate insulating film 142 is patterned in the same shape as the gate electrode 144, the first and second semiconductor layer contact holes 152 and 154 are formed only in the interlayer insulating film 150.

A source electrode 156 and a drain electrode 158 made of a conductive material such as metal are formed on the interlayer insulating layer 150. A data line (not shown), a power line (not shown), and a second capacitor electrode (not shown) may be formed on the interlayer insulating layer 150 in the second direction.

The source electrode 156 and the drain electrode 158 are spaced apart from each other around the gate electrode 144 and are electrically connected to both sides of the semiconductor layer 140 through the first and second semiconductor layer contact holes 152 and 154, Contact. Although not shown, the data wiring extends along the second direction and intersects the gate wiring to define the pixel region, and the power wiring for supplying the high potential voltage is located apart from the data wiring. The second capacitor electrode is connected to the drain electrode 158 and overlaps the first capacitor electrode to form a storage capacitor with the interlayer insulating film 150 between the first and second capacitor electrodes as a dielectric layer.

The semiconductor layer 140, the gate electrode 144, the source electrode 156, and the drain electrode 158 constitute a driving thin film transistor Td. The driving thin film transistor Td illustrated in FIG. 2 has a coplanar structure in which a gate electrode 144, a source electrode 156, and a drain electrode 158 are disposed on a semiconductor layer 140. Alternatively, the driving thin film transistor Td may have an inverted staggered structure in which a gate electrode is located below the semiconductor layer and a source electrode and a drain electrode are located above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

Further, a switching thin film transistor (not shown) having substantially the same structure as the driving thin film transistor Td is further formed on the first substrate 101. The gate electrode 144 of the driving thin film transistor Td is connected to a drain electrode (not shown) of a switching thin film transistor (not shown) and the source electrode 156 of the driving thin film transistor Td is connected to a power supply wiring Not shown). A gate electrode (not shown) and a source electrode (not shown) of a switching thin film transistor (not shown) are connected to the gate wiring and the data wiring, respectively.

A planarization layer 160 is formed on the entire surface of the first substrate 101 above the source electrode 156 and the drain electrode 158. The planarization layer 160 has a flat upper surface and a drain contact hole 162 exposing the drain electrode 158 of the driving thin film transistor Td. Here, the drain contact hole 162 is formed directly on the second semiconductor layer contact hole 154, but may be formed apart from the second semiconductor layer contact hole 154.

The light emitting diode E includes a first electrode 110 located on the planarization layer 160 and connected to the drain electrode 158 of the driving TFT Td, A light emitting layer 120 and a second electrode 130. As described above, the first electrode 110 is made of a relatively large work function material and functions as an anode, and the second electrode 130 is made of a material having a relatively low work function value, thereby acting as a cathode.

The second substrate 102, which is an encapsulation substrate covering the light emitting diode E, is bonded to the first substrate 101 through the adhesive 180. Although not shown, a barrier layer may be formed between the second substrate 102 and the light emitting diode E to prevent moisture and oxygen from penetrating into the light emitting diode E by attaching the substrates to each other.

The organic luminescent layer 120 includes a luminescent material layer 123 (see Fig. 1) in which a phosphorescent compound represented by Chemical Formulas 1 to 3 is doped into a host material, as described with reference to the embodiment of Fig. In addition, the organic light emitting layer 120 includes a hole injection layer 121 (see FIG. 1), a hole transport layer 122 (see FIG. 1), and an electron transport layer 124 (See FIG. 1), an electron injection layer 125 (see FIG. 1), an optional hole blocking layer (not shown) and an electron blocking layer (not shown).

The light emitting diode E according to the exemplary embodiment of the present invention includes a phosphorescent compound represented by Chemical Formulas 1 to 3 in a light emitting material layer constituting the organic light emitting layer 120. The compounds of the formulas (1) to (3) control the oscillation and rotation of the ligand, and do not consume energy due to vibration and rotation. When the iridium complexes of the formulas (1) to (3) in which no molecular vibration and rotation mode are present are applied to the organic light emitting layer of the light emitting diode, the spectrum is not widened when the excitons injected from the positive electrode and the negative electrode respectively emit light, great. In addition, the iridium complex of the present invention does not consume energy by molecular vibration and rotation when emitting light, so that the lifetime of the material is particularly excellent. By using the phosphorescent compounds represented by the formulas (1) to (3), a light emitting diode (E) having excellent device lifetime and good luminous efficiency can be obtained. As described above, in the organic light emitting diode display device 100 to which the phosphorescent compound of the present invention is applied, lifetime of the device can be improved, good luminous efficiency and power consumption can be realized.

Hereinafter, the present invention will be described in more detail with reference to exemplary embodiments.

Synthesis Example 1: Synthesis of GD1 compound

1) Compound 1A Synthesis

[Reaction Scheme 1-1]

2-Hydroxyphenylboronic acid (19.2 g, 139.2 mmol), K ₂ CO ₃ (35.0 g, 253.2 mmol) and Triphenyl phosphine (3.3 g, 12.7 mmol) were added to a 500 mL round bottom flask, , And Pd (OAc) ₂ (1.4 g, 6.3 mmol) were added to a mixed solvent (Toluene: Ethanol: H ₂ O = 150 mL: 75 mL: 75 mL) and stirred at 90 ° C for 16 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. Crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 18.0 g (yield: 83.1%) of Compound 1A.

2) Synthesis of compound 1B

[Reaction Scheme 1-2]

To a 250 mL round bottom flask was added 1A (10.0 g, 58.4 mmol), 2-Chlorobenzyl bromide (13.2 g, 64.3 mmol) and K ₂ CO ₃ (16.1 g, 116.8 mmol) in 150 mL of Acetone, Lt; / RTI > After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. Crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 13.6 g (yield 78.7%) of Compound 1B.

3) Synthesis of Compound 1C

[Reaction 1 - 3]

1B 250 mL round bottom flask (10.0 g, 33.8 mmol), K 2 CO 3 (14.0 g, 101.4 mmol), PCy 3 -HBF 4 (7.5 g, 20.3 mmol), Pd (OAc) 2 (2.3 g, 10.1 mmol) were added to DMA (150 mL), and the mixture was stirred at 130 DEG C for 16 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 3.9 g (Yield: 44.5%) of Compound 1C.

4) Synthesis of compound 1D

[Reaction Scheme 1-4]

Add Iridium chloride hydrate (8.00 g, 26.8 mmol), 2-phenylpyridine (10.4 g, 67.0 mmol) and a mixed solvent (2-ethoxyethanol: H ₂ O = 90 mL: 30 mL) into a 250 mL round- Lt; / RTI > for 24 hours. After the reaction is completed, the temperature is lowered to room temperature, and methanol is added thereto, and the resulting solid is filtered under reduced pressure. To obtain 9.9 g of a solid compound 1D (yield: 68.9%).

5) Compound 1E Synthesis

[Reaction Scheme 1-5]

1D (9.00 g, 8.4 mmol), AgOTf (6.5 g, 25.2 mmol) and dichloromethane were added to a 1000 mL round bottom flask, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solid is removed by filtering with celite. The solvent was distilled off under reduced pressure to obtain 9.0 g of the resulting solid compound 1E (yield: 75.1%).

6) Compound GD1 synthesis

[Reaction Scheme 1-6]

1C (2.3 g, 8.8 mmol) and 1E (2.5 g, 3.5 mmol) were added to a 100 mL round bottom flask in a mixed solvent (2-Ethoxyethanol: DMF = 75 mL: 75 mL) and stirred at 130 ° C for 24 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography with toluene: hexane to obtain 1.3 g (yield: 48.9%) of compound GD1. Figure 3 shows NMR analysis results of the synthesized GD1 compound.

Synthesis Example 2: Synthesis of GD2 compound

1) Compound 2A Synthesis

[Reaction Scheme 2-1]

2-Bromo-5-methylpyridine (25.0 g, 145.3 mmol), Phenylboronic acid (21.3 g, 174.4 mmol), K ₂ CO ₃ (40.2 g, 290.7 mmol), Triphenyl phosphine (7.6 g, 29.1 mmol) mmol) and Pd (OAc) ₂ (3.3 g, 14.5 mmol) were mixed in a mixed solvent (THF: MeOH = 300 mL: 150 mL) and refluxed for 16 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 20.0 g (yield: 81.3%) of Compound 2A.

2) Synthesis of compound 2B

[Reaction Scheme 2-2]

Add Iridium chloride hydrate (8.00 g, 26.8 mmol), 2A (11.3 g, 67.0 mmol) and a mixed solvent (2-ethoxyethanol: H ₂ O = 90 mL: 30 mL) into a 250 mL round bottom flask, Lt; / RTI > After the reaction is completed, the temperature is lowered to room temperature, and methanol is added thereto, and the resulting solid is filtered under reduced pressure. To obtain 9.8 g (yield: 64.8%) of solid compound 2B.

3) Synthesis of Compound 2C

[Reaction Scheme 2-3]

2B (9.0 g, 8.0 mmol), AgOTf (6.1 g, 23.9 mmol) and dichloromethane were added to a 1000 mL round bottom flask, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solid is removed by filtering with celite. The solvent was distilled off under reduced pressure to obtain 9.2 g (yield: 77.7%) of the resulting solid compound 2C.

4) Compound GD-2 synthesis

[Reaction Scheme 2-4]

1C (2.2 g, 8.4 mmol) and 2C (2.5 g, 3.4 mmol) were added to a 100 mL round bottom flask in a mixed solvent (2-Ethoxyethanol: DMF = 75 mL: 75 mL) and stirred at 130 ° C for 24 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. Crude product was subjected to column chromatography with toluene: hexane to obtain 1.3 g (yield: 49.0%) of compound GD2. Fig. 4 shows NMR analysis results of the synthesized GD2 compound.

Synthesis Example 3: Synthesis of GD3 Compound

1) Compound 3A Synthesis

[Reaction Scheme 3-1]

Phenylboronic acid (26.7 g, 219.2 mmol), K ₂ CO ₃ (55.1 g, 398.5 mmol), Triphenyl phosphine (10.5 g, 39.9 mmol) were added to a 1000 mL round bottom 2,5-Dibromo-4-methylpyridine mmol) and Pd (OAc) ₂ (4.5 g, 19.9 mmol) were mixed in a mixed solvent (THF: MeOH = 300 mL: 150 mL) and refluxed for 16 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. Crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 19.2 g (yield: 78.6%) of Compound 3A.

2) Synthesis of Compound 3B

[Reaction Scheme 3-2]

Add Iridium chloride hydrate (8.00 g, 26.8 mmol), 3A (16.4 g, 67.0 mmol) and a mixed solvent (2-ethoxyethanol: H ₂ O = 90 mL: 30 mL) into a 250 mL round bottom flask, Lt; / RTI > After the reaction is completed, the temperature is lowered to room temperature, and methanol is added thereto, and the resulting solid is filtered under reduced pressure. 12.1 g of solid compound 3B (yield: 63.0%) was obtained.

3) Compound 3C Synthesis

[Reaction Scheme 3-3]

3B (9.0 g, 6.3 mmol), AgOTf (4.8 g, 18.8 mmol) and dichloromethane were added to a 1000 mL round bottom flask, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solid is removed by filtering with celite. The solvent was distilled off under reduced pressure to obtain 8.6 g (yield: 76.6%) of the resulting solid compound 3C.

4) Compound GD3 synthesis

[Reaction Scheme 3-4]

1C (1.8 g, 7.0 mmol) and 3C (2.5 g, 2.8 mmol) were added to a 100 mL round bottom flask in a mixed solvent (2-Ethoxyethanol: DMF = 75 mL: 75 mL) and stirred at 130 ° C for 24 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. Crude product was subjected to column chromatography with toluene: hexane to obtain 1.2 g (yield: 45.7%) of compound GD3. 5 shows NMR analysis results of the synthesized GD3 compound.

Synthesis Example 4 Synthesis of GD4 Compound

1) Synthesis of Compound 4A

[Reaction Scheme 4-1]

2-Bromopyridine (20.0 g, 126.6 mmol), 4-hydroxyphenylboronic acid (19.2 g, 139.2 mmol), K ₂ CO ₃ (35.0 g, 253.2 mmol) and Triphenyl phosphine (3.3 g, 12.7 mmol) were added to a 500 mL round- , And Pd (OAc) ₂ (1.4 g, 6.3 mmol) were added to a mixed solvent (Toluene: Ethanol: H ₂ O = 150 mL: 75 mL: 75 mL) and stirred at 90 ° C for 16 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 15.6 g (Yield: 72.0%) of Compound 4A.

2) Synthesis of compound 4B

[Reaction Scheme 4-2]

To a 250 mL round bottom flask was added 4A (10.0 g, 58.4 mmol), 2-Chlorobenzyl bromide (13.2 g, 64.3 mmol) and K ₂ CO ₃ (16.1 g, 116.8 mmol) in 150 mL of Acetone, Lt; / RTI > After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography using Hexane: ethylacetate to obtain 13.5 g (yield: 78.1%) of Compound 4B.

3) Compound 4C Synthesis

[Reaction Scheme 4-3]

4B 250 mL round bottom flask (10.0 g, 33.8 mmol), K 2 CO 3 (14.0 g, 101.4 mmol), PCy 3 -HBF 4 (7.5 g, 20.3 mmol), Pd (OAc) 2 (2.3 g, 10.1 mmol) were added to DMA (150 mL), and the mixture was stirred at 130 DEG C for 16 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography with hexane: ethylacetate to obtain 3.8 g (yield: 43.3%) of compound 4C.

4) Compound GD4 synthesis

[Reaction Scheme 4-4]

4-C (2.2 g, 8.4 mmol) and 2C (2.5 g, 3.4 mmol) were added to a 100 mL round-bottomed flask in a mixed solvent (2-Ethoxyethanol: DMF = 75 mL: 75 mL) and stirred at 130 ° C for 24 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. Crude product was subjected to column chromatography with toluene: hexane to obtain 1.3 g (yield: 49.0%) of compound GD5. 6 shows NMR analysis results of the synthesized GD4 compound.

Synthesis Example 5: Synthesis of GD5 compound

[Reaction Scheme 5]

4C (1.8 g, 7.0 mmol) and 3C (2.5 g, 2.8 mmol) were added to a 100 mL round bottom flask in a mixed solvent (2-Ethoxyethanol: DMF = 75 mL: 75 mL) and stirred at 130 占 폚 for 24 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and distilled water, and the solvent was removed by distillation under reduced pressure. The crude product was subjected to column chromatography with toluene: hexane to obtain 1.3 g (yield: 49.5%) of compound GD6. Fig. 7 shows the NMR analysis results of the synthesized GD5 compound.

Experimental Example 1: PL measurement of synthesized compounds

Photoluminescence (PL) of the compounds GD1, GD2, GD3, GD4, GD5 and GD6 synthesized in Synthesis Examples 1 to 6 was measured. The measurement was carried out at room temperature, and methylene chloride (MC) was used as a solvent. The PL measurement results for each compound are shown in FIGS. 8 to 12, and Table 1 below shows the maximum emission peak and half width for each compound. The compounds synthesized in Synthesis Examples 1 to 5 respectively emitted light in the green wavelength band, and showed a good half width.

PL measurement results of compounds compound Maximum emission wavelength (nm) Half width (FWHM, nm) GD1 514 60 GD2 513 59 GD3 520 62 GD4 504 63 GD5 521 66

Example  1: Fabrication of light emitting device (GD1 compound applied)

An organic electroluminescent device in which ITO (reflector) / HIL / HTL1 / HTL2 / EBL / EML / ETL / EIL / Cathode / CPL were stacked in this order was fabricated. First, the glass substrate with 40 mm x 40 mm x 0.5 mm thick ITO (with reflector) electrodes was ultrasonically cleaned with isopropyl alcohol, acetone, DI water for 5 minutes, and then dried in an oven at 100 ° C. After the substrate was cleaned, it was subjected to an O ₂ plasma treatment in a vacuum for 2 minutes and transferred to a deposition chamber for deposition of other layers on the top. Layers were deposited in the following order by evaporation from a heated boat under a vacuum of about 10 ^-7 Torr.

(a) Hole injection layer: 100 Å, HIL (3%) / N-biphynyl-4-yl-9,9- phenyl) -9H-fluoren-2-amine; 97%)

(b) First hole transporting layer: 1200 Å, HTL1

(c) Second hole transporting layer: 250 Å, HTL2 (N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) biphenyl-

(d) Electron barrier layer: 150 Å, EBL (biphenyl-2-yl) -N- (9,9-dimethyl-9H-fluoren-2-yl) -9,9'-spirobi [ 2-amine)

(e) luminescent material layer: 400 ANGSTROM, a first host (Host1; 4- (3- (triphenylen-2-yl) phenyl) dibenzo [b, d] thiophene, 1,3-dihydroindolo [2,3-b] carbazole (1: 1) / GD1 (5%)

(f) Electron transport layer: 300 Å, ETL / Liq (2: 1)

(g) Electron injection layer: 30 Å, Mg / LiF (3: 1)

(h) Cathode: 140 Å, Ag / Mg (4: 1)

(i) a capping layer (CPL)

After the CPL was formed, it was encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a dry box for subsequent film formation and subsequently encapsulated using a UV cured epoxy and a getter. This organic electroluminescent device has an emission area of 9 mm 2. The structures of HIL, HTL1, HTL2, EBL, ETL, Liq, Host1 and Host2 used in the lamination of the respective organic layers in this embodiment are shown below.

Examples 2 to 5: Fabrication of light emitting device

Except that GD2 (Example 2), GD3 (Example 3), GD4 (Example 4), and GD5 (Example 5) were used instead of GD1 used in Example 1 as a dopant of the light emitting material layer. Was repeated to fabricate a light emitting device.

Comparative Examples 1 and 2: Fabrication of light emitting device

(Tris [2,5-diphenyl-4-methylpyridinato-C ² , N] iridium (III), Comparative Example 1) and D2 (Bis The procedure of Example 1 was repeated except that [2-phenylpyridinato-C ² , N] (2- (dibenzofuran-4-yl) pyridinato) iridium (III) was used.

Experimental Example  2: Measurement of physical properties of light emitting device

The properties of the light-emitting devices fabricated in Examples 1 to 5 and Comparative Examples 1 and 2 were measured. Each of the organic electroluminescent devices having an emission area of 9 mm 2 was connected to an external power source and device characteristics were evaluated at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The results of the power luminous efficiency (power efficiency), the current efficiency, the lifetime time (T ₉₅ ) falling from 100% to 95% at the CIE color coordinate and the constant current of 20,000 nit luminance of the manufactured organic electroluminescent device based on 8,000 nit Are shown in Table 2 below.

As shown in Table 2, when the compound synthesized according to the present invention is used as a dopant of the light emitting material layer, the power efficiency, current efficiency and / or lifetime of the device is improved compared to the case of using the material of the comparative example as a dopant . In particular, as compared with the light emitting device to which the dopant used in Comparative Example 2 was applied, the power efficiency and the current efficiency were improved in the light emitting device in which the phosphorescent compound according to the present invention was applied as a dopant of the light emitting material layer, . Particularly, when the compound according to the present invention was used as a dopant for the light emitting material layer, lifetime of the device was improved by 95.8% in comparison with Comparative Example 1, and the lifetime of the device was the highest 48.1%. Accordingly, it has been confirmed that the phosphorescent compound synthesized in the present invention can be applied to an organic light emitting layer of a light emitting diode to improve luminous efficiency, improve device life, and reduce power consumption.

Characteristics of light emitting device device Power efficiency
(lm / W) Current efficiency
(cd / A) CIE (X) CIE (Y) life span
(T ₉₅ , hrs) Example 1 79.95 118.4 0.231 0.723 172 Example 2 82.40 122.3 0.234 0.721 201 Example 3 85.36 128.7 0.256 0.710 231 Example 4 75.66 112.1 0.226 0.723 186 Example 5 81.41 122.8 0.239 0.720 212 Comparative Example 1 74.91 111.0 0.201 0.721 118 Comparative Example 2 74.78 113.6 0.227 0.727 156

Although the present invention has been described based on the exemplary embodiments and examples of the present invention, the scope of the present invention is not limited to the technical ideas described in the embodiments and the examples. It will be apparent to those skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope of the present invention. It is evident, however, that the appended claims are intended to cover all such modifications and changes as fall within the true scope of the invention.

100: organic light emitting diode display device 110: first electrode
120: organic light emitting layer 121: hole injection layer
122: hole transport layer 123: light emitting material layer
124: electron transport layer 125: electron injection layer
130: second electrode E: light emitting diode

Claims (6)

A phosphorescent compound represented by the following formula (1).
[Chemical Formula 1]

(Wherein R ₁ to R ₂₀ each independently represent hydrogen, deuterium, tritium, halogen atom, CF ₃ , cyano group, C 1 to C 20 alkyl group, C 1 to C 20 alkoxy group, unsubstituted or substituted C 5 to C 20 aryl group , Unsubstituted or substituted C5-C20heteroaryl group, unsubstituted or substituted C1-C20 amine group or unsubstituted or substituted silyl group, X is O, S or -NR, and R is hydrogen, deuterium, hydrogen, halogen, CF _3, cyano group, C1 ~ C20 alkyl group, C1 ~ C20 alkoxy group, an unsubstituted or substituted C5 ~ C20 aryl group, an unsubstituted or substituted C5 ~ C20 heteroaryl group, unsubstituted or substituted A C1-C20 amine group or an unsubstituted or substituted silyl group, and n is an integer of 1 to 3)
The method according to claim 1,
Wherein the phosphorescent compound is a compound represented by the following formula (2).
(2)

Wherein R ₂₁ to R ₂₅ each independently represents a halogen atom, CF ₃ , cyano group, C 1 to C 20 alkyl group, C 1 to C 20 alkoxy group, unsubstituted or substituted C 5 to C 20 aryl group, unsubstituted or substituted C 5 C20 heteroaryl group, an unsubstituted or substituted C1-C20 amine group or an unsubstituted or substituted silyl group, and X and n are each the same as defined in formula (1)
The method according to claim 1,
Wherein the phosphorescent compound is any one of compounds represented by the following formula (3).
(3)

A first electrode;
A second electrode facing the first electrode;
An organic light-emitting layer which is located between the first and second electrodes and contains a phosphorescent compound according to any one of claims 1 to 3,
.
5. The method of claim 4,
Wherein the phosphorescent compound is used as a dopant of a light emitting material layer constituting the organic light emitting layer.
A first substrate;
A driving thin film transistor located on the first substrate;
The light emitting diode according to claim 4, wherein the light emitting diode is disposed on the first substrate and connected to the driving thin film transistor. And
A second substrate covering the light emitting diode and being attached to the first substrate,
And an organic light emitting diode (OLED) display device.

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