TW200817419A - A kind of iridium based phosphorescent material and organic electroluminescent device thereof - Google Patents

Abstract

A kind of novel iridium based phosphorescent materials and organic electroluminescent elements thereof, and the iridium complexes of the present invention can be used as the red, blue or green-emitting dopants. These phosphorescent materials can be applied in fabrication of the light-emitting layer of organic electroluminescent devices and providing the high efficiently red, blue or green light organic electroluminescent devices of commercial pursuits.

Description

200817419 IX. INSTRUCTIONS OF THE INVENTION 1. Field of the Invention The present invention relates to a ruthenium complex, and more particularly to a ruthenium complex phosphorescent material and an organic electroluminescence device. [Prior Art] Organic light-emitting diodes (OLEDs) have a new generation of technologies that are not easily realized by other flat panel display technologies, a brighter and clearer full-color image and a more agile response speed. In addition, the organic electroluminescent display element itself has self-luminous, no viewing angle limitation, fast reaction speed, display dynamic image, high photoelectric efficiency, low power consumption, no need for backlight structure and color filter structure, etc. It is considered to be one of the flat panel display technologies that can replace the liquid crystal display. Applying organic light-emitting diode components to displays, full color is a necessary condition for market success, so it is one of the key factors for commercial products to obtain red, blue and green light that meets commercial needs. The development of new phosphorescent materials and their doped guest as the light-emitting layer of organic light-emitting diode elements is the research direction of organic electroluminescent materials. The design of high-efficiency inorganic complexes has attracted great attention in the development of organic light-emitting diodes (OLEDs). With the third week, it is a very important material for designing high-efficiency ft poles. Because the central heavy metal ions cause spm-orbit coupling, which promotes the leap between systems, promotes the excited state to the triplet excited state, _ more secretive electrolysis, after the initial charge recombination Excitons that dominate singlet and triplet states. The so-called 200817419 if the material relative to the fluorescent luminescent material, its electroluminescence, can increase the internal reading of the _ on the _ even 1GG%. Directions, new research in organic light-emitting diodes (〇LEDs) materials. In addition, the display of the full-color display can be found in the light area, and the original colors such as “supervised, green, and red” are available. In the text, the emission wavelength of the light emitted by the i-axis is - an important researcher of the Wei. The complete compound meets the above-mentioned requirements for the organic electroluminescent element. The present inventors have been engaged in research and many practical practices, research and design, and special topics. For the purpose of the present invention, a 铱== optical material and an organic electroluminescent device are proposed as the aforementioned expectation-implementation party. In view of the above problems, the present invention has a novel structure, and can be used as a compound, and the optical material has high efficiency. The doping of the desired material in the ox light material, so that the purpose of the phosphorus is to ride the seed, and the (4) μ color element of the test compound is all prepared from the blue to green and then to the saturated red. T color range can be provided for one person, designing the red, blue and green light of the object material of the county. (4) Fiercely meets commercial needs 200817419 The edge is 'for the above purpose, according to the invention, the silver-intercalated material intercepting material and the organic electroluminescence 70 pieces, the bismuth complex includes at least the chemical formula (丨) structure:

According to the above, the erbium complex having the novel structure according to the present invention can be used for the selection of the ring ligand on the silver complex, so that the silver complex of the silver compound is emitted. From blue to green to saturated red, the luminous efficacy of the red, blue / light = electroluminescent elements to meet commercial needs. T-organic is to make the #review committee have a more in-depth understanding and understanding of the technical special effects of the present invention, the following is to provide a more detailed description of the r, and with a detailed description of the text = Ming as 200817419 [ BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the same elements will be described with the same reference numerals as the bismuth complex materials and the organic electroluminescence elements, with reference to the related drawings. Piece, test the compound of the compound (4), electromechanical illuminating element, the doping of the material, the doping object of the Wei material, == in the organic electroluminescent tree, this silver complex, including at least

Where R1, R2

For example, it is selected from the group consisting of a hydrogen atom (H), a fluorine atom (F), a carbon trifluoride group (CF3), a group group, and an aryl group. The above formula (I) is a complex of the formula (I) wherein R1 and P2 are, and Rg, R9, R10, and R11 are the cores of 1^4, 15, 16, 16, and 17, and the chemical formula (1) The structure is the following la structure of [(dfppy)2Ir(fpyro)]: 200817419 la f

F. The above formula (I) is a complex of ruthenium wherein R1 is CF3, R2 is butane (buty C4H9), R3, R8, R9, R10, and R11 are Η, and R4, R5, R6, and R7 are ? The structure of the chemical formula (1) is the following structure of [(_办) 21 noisy 1^〇)]:

F lb The above formula (I) is a complex, wherein when R1 and R2 are CF3, R3, R4, R6, R8, R9, R10 and R11 are Η, and R5 and R7 are decyl (CH3), the chemical formula The structure of (Ϊ) is the following 2a structure of [(tpy)2Ir(fpyro)]· 200817419

2a The above complex of formula (I) wherein R1 is CF3, R2 is butane (butyl, C4H9), R3, R4, R6, R8, R9, R10, R11 are ruthenium, and R5 and R7 are ruthenium In the case of an alkyl group (CH3), the structure of the formula (I) is a 2b structure of the lower 歹W(tpy)2Ir(fpyro)]:

2b The above formula (I) is a complex of ruthenium, wherein R1 and R2 are CF3, R8, 11 200817419 R9 and RIO and R11 are replaced by a benzene ring, and Μ, BA, Μ R6 R are H. The structure of the chemical formula (!) is the following structure of [(9) mouth) by the decoration ^〇)]:

The above formula (I) is a complex of ruthenium, wherein R1 is CF3, R2 is butyl group (buty C4H9), R8, R9 and R1〇, R11 are substituted by benzene ring ^enzene), R3, R4, When R5, R6 and R7 are Η, the structure of the chemical formula (1) is the following 3b structure of [(piq)2lr(fpyro)]:

3b 〇12 200817419 The invention further discloses a disc-lighting material for making an female complex comprising at least a host compound, and a doping guest, which is a ruthenium complex, comprising at least the structure of the above formula (I), Further, other derivatives of this silver complex, such as a silver complex having a structure of ?2a, 2b, 3a, 3b, can also be used as a doping guest of the scale light material of the present invention. The present invention further discloses an organic electroluminescent device which comprises a test compound, comprising at least an organic light-emitting material layer having a light-emitting layer, which is composed of a material of a dish material, including a host compound and a doping guest, which is a ruthenium complex, comprising at least the structure of the above formula (I), and other derivatives of the silver complex, for example, have la, lb, 2a, 2b, 3a, The silver complex of the structure of 3b can also serve as a doping guest for the phosphorescent material of the present invention. The above organic electroluminescent device using a ruthenium complex, wherein the organic electroluminescent material layer comprises a hole transport layer, a light-emitting layer, a hole barrier layer and an electron transport layer. Compared with the prior art, the breakthrough point of the present invention is that it can be successfully prepared and isolated from a so-called heteroleptic Ir(ni) complexes having the following molecular formula: [Ir(CAN) 2(LAX)] wherein CAN is two paracyclic ligands, such as 2,4-difluorophenylpyridine (dfppy), 2-phenylpyridine (ppy), 2_(4-曱Benzene) mouth bite (2_(4_t〇iyi)pyridine, tpy), 7,8-benzoquinoline (bzq) or! - i-phenylisoquinoline (piq) and a third assisted ligand (LAX) that allows the complex to be electrically neutral, thermally stable and sublimable. The color of the light is mainly based on the choice of the ring-based CAN, and the color range can be from the blue light of the county. While the third clamped auxiliary ligand LAX, an oxygen-containing double bud group such as acetoacetate (acac) N decyl salicyl imine (team methyisaii Cyiimine, sal) * ait ^ decanoic acid ( p··咖 ' Pic), or 疋 疋 配 配 例如 例如 例如 例如 例如 坐 坐 坐 坐 坐 坐 y y y y y y y y y y y y y y y y y y y y y y y y y y y y y y y y y Triazolate) and tetrazatelate. In such mixed ligand compounds, they will retain the main emission spectrum characteristics of the Ir(C^N)3 compound, but as the LX ligand changes, the emission wavelength will also be fine-tuned. . For example, as the electron intensity of the ligand LaX on the compound increases (λ < sal~ acac)', the λΐΜχ of the emission spectrum also increases, which is the result of the energy level difference following the decrease. According to this, we can choose the auxiliary ligands by selecting the electron-deficient CF3-substituted pyrazole (frazz) H, triazole (triaz〇le), tz)H, and Electron-deficient CFS-substituted tonpypyridylPyrr〇iide (φγΓ〇) Η ligand, or push-electron butyl substituted. The bpyro H ligand is used to calibrate the light color to the desired red, green and blue color. The invention relates to a bismuth complex phosphorescent material and an organic electroluminescence device. The novel structure of the ruthenium metal complex comprises a third conjugated auxiliary ligand, which is a pyrrole ligand, so that it can be designed with various For the sake of simplicity and simplicity, the following will further illustrate the steps of the synthesis method of the experimental example of the present invention by using a ruthenium complex having a structure of la, lb, 2a, 2b, 3a, 3b. . 14 200817419 Experimental Example 1: Synthesis of compound la [[dfi)py)2lrCl]2 (101 mg, 0·082 mmol), 2-(3, 5-bis(trifluoromethyl) "lH-pyrrol-2-yl Pyridine (fpyroH? 50 mg? 0.17 mmol) and Na2C03 (87 mg, 0.82 mmol) were placed in a 50 ml round bottom flask, and 20 mL of 2-methoxyethanol was added to reflux for 4 hr. After cooling, the precipitate was filtered with water and the solid was washed with hexane. Purification by column chromatography using CH^Cl2 as a solvent and recrystallization from CHfl2 and methanol gave 125 mg of a yellow solid product [[(d§5py)2Ir^yro)] la (0.146 mmol, 89 %) . Experimental Example 2: Synthesis of compound lb [((1φρΥ)2ΙΓα]2 (301 mg, 0.247 mmol), 2-(5-methyl-lH-pyrrol winter yl)pyridine (bpyroH, 125 mg, 〇·465 mmol) And Na2C03 (260 mg, 2.45 mmol), placed in a 50 ml round bottom flask, and added 2 〇' of 2-methoxyethanol to reflux the solvent for 4 hr. After cooling, the precipitate was filtered with water and the solid was washed with hexane. Cl2 was purified by column chromatography on a solvent and recrystallized from <RTI ID=0.0>>>&&&&&&&&&&&&&&&&& 15 200817419 Experimental Example 3: Synthesis of compound 2a [(tpy) 2lrCl] 2 (330 mg, 0.29 mmol), 2-(3 ? 5-bis(trifluoromethyl)-lH- pyrrol-2-yl)pyridine (φγΓ〇 Η, 170 mg9 0.61 mmol) and Na2C03 (310 mg, 2.91 mmol), put into a 50 ml round bottom flask, add 20 mL of 2-methoxyethanol to reflux for 4 hr. After cooling, add water to filter the precipitate and wash with hexane. The solid was purified by column chromatography using CH2C12 as a solvent, and recrystallized from CH2C12 and hexane to obtain 310 mg of a yellow solid product [(tpy)2Ir(fj)yro)] 2a (0.39 mmol 66%). Experimental Example 4: Synthesis of Compound 2b [(tpy)2IrCl]2 (130 mg, 〇.n mmol), 2-(5-methyl-lH-pyrr〇l-2-yl)pyridine (bpyroH, 70 mg, 0·26 mmol) and Na2C03 (100 mg, 0·94 mmol)' were placed in a 50 ml round bottom flask, and 20 mL of 2-methoxyethanol was added to reflux the solvent for 4 hr. After cooling, the precipitate was filtered with water and the solid was washed with hexane. Purification by column chromatography using CHsCl2 as a solvent and recrystallization from CH2Cl2 and hexane gave 80 mg of a yellow solid product [(tpy)2lr(fpyr〇)] 2b (0·10 mmol, 45%) 〇200817419 Experimental Example 5: Synthesis of Compound 3a [(piq) 2lrCl] 2 (400 mg, 0.32 mmol), 2-(5-methyl-lH-pyrrol-2-yl)pyridine (fpyroH, (200 mg, 0·68) Methyl) and Na2C03 (360 mg5 1.76 mmol), placed in a 50 ml round bottom flask, and refluxed with 20 mL of 2-methoxyethanol as solvent for 4 hr. After cooling, filter with water, sink the chamber, and wash the solid with hexane. Purification by column chromatography using CH2C12 as extract, and recrystallization from CH2C12 and hexane' yielded 396 mg of red solid product [(piq)2Ir(fpyro)] 3a (0.45 mmol, 73 %) ° Example 6: Synthesis of compound 3b [(piq)2lrCl]2 (280 mg, 0.22 mmol), 2-(5-methyl-lH-pym)l-2-yl)pyridine (bpyroH, 70 mg, 0.26)

NaAO3 (230 mg, 2.17 mmol) was placed in a 50 ml round bottom flask and 2 mL of 2-methoxyethanol was added to reflux the solvent for 4 hr. After cooling, the precipitate was filtered with water and the solid was washed with hexane. Purification by column chromatography using CH2C12 as a solvent and recrystallization from CH2Cl2 and hexane gave the product of mg red solid [(9) ship (fs)] (0·30 mmol, 53 0/〇). Further, the ruthenium complex of the experimental example of the present invention is finer than the disc material of the organic electroluminescent element. The components are fabricated under a low vacuum of 丨χ 1()·6_ 17 200817419. The evaporation material is on a tin indium tin oxide (ΙΤ0) glass substrate (surface resistance $% ohm). These substrates can be ultrasonically in advance. The towel was cleaned with fine, deionized water, isopropyl alcohol and propylene _ before being pretreated by a photoresist remover (〇2plasma) ten minutes before use. Figure 1 is a schematic view showing the structure of an organic electroluminescent device of the present invention. Referring to the figure, the surface of the flat substrate 10 is sequentially mirrored with an anode 2, an organic electroluminescent material layer 30 and a cathode 40. The organic electroluminescent material layer 3 includes a hole transport layer 31, a light emitting layer 32, and a hole. The barrier layer 33 and the electron transport layer %, particularly the light-emitting layer 32, are formed by using a pre-ship complex as a doping material. The organic electroluminescent element is ejected, and the cathode and the anode are required to transmit light to allow the excitation light to penetrate. It is preferable to use an anode slave. The anode can be selected from materials with a high work function, such as oxidation, 'indium tin or platinum, etc.' cathode can select materials with lower work function, such as Ming, about, magnesium or magnesium-silver alloy. Wait. The second compound is a host compound structure of a phosphorus material which can be used in the present invention, and the host compound of the scale material can be selected, for example, from a material such as TPSi_F, mCp or CBp, and the chemical structure thereof is 200, 202 or 204 in FIG. Shown. Step-by-step details of the electroluminescent element continue to be green, first put the cleaned glass substrate into the _L 'Lang substrate field has a transparent oxidation (rib) anode 'after pretreatment' and then sequentially film In the test, on the surface of the glass substrate, the first shovel hole is passed through 31, and the county Guanyang 32, the phosphorescent material composed of the hull hull compound and the push object is the silver complex of the invention, and then formed. The hole barrier layer 33 and the electron transport layer 34 are further vapor-deposited on the cathode 40 by a layer of the phosphorescent material layer 3, 18 200817419. Experimental Example 7: The light-emitting layer of the device is doped, the compound la is used as a guest, and the device structure is as shown in Fig. 1. In the present experimental example, the substrate 1 is a glass substrate, and the anode 20 The indium tin oxide is a tin-silver alloy having a thickness of 100 nm, which is sequentially present in the organic electroluminescent material layer 30. The hole transport layer 31 is a benzidine (NPB) having a thickness of 30 nm and a mcp having a thickness of 10 nm. a layer (not shown), the light-emitting layer 32 is a phosphorescent material composed of a host compound TPSi-F having a thickness of 30 nm and a 7% doped guest la, and the hole barrier layer 33 is a BCP having a thickness of 10 nm and an electron transport layer 34. It is a TPBI with a thickness of 30 nm. The electroluminescence of this component is blue, the maximum emission wavelength is 464nm, and its corresponding CIE1931 chromaticity coordinate value χ = 〇13, y = 〇23, at low current density (20 mA/cm2), there is Good external quantum efficiency (9·〇3 〇/〇) Monk's shell size (2903 〇(1/1112). At 16 乂, there is a maximum brightness of 25182 〇 (1/1112. Experimental Example 8: The luminescent layer of this element) In the doping method, the compound 2b is used as the guest (gUeSt), and the cultivating structure is as shown in Fig. 1, in the experiment, the substrate H) is a glass substrate, the anode 20 is indium tin oxide, and the cathode 4 is thick. The town silver alloy of m is sequentially present in the organic electroluminescent material layer 3, the hole transport layer 31 is a thickness of 3 〇 nm and the aniline (NPB)% light layer 32 is a host compound having a thickness of 3 〇 nm and 19 200817419 The phosphorescent material composed of the impurity object 2b, the hole barrier layer is the thickness of the 〇 leg BCP and the gate electron transport layer 34 is the thickness of 3Qnm $ qing. The electroluminescence of the component is, the '彔 color' maximum emission The wavelength is at 494 nm 'the corresponding CIE 1931 chromaticity coordinate value X__ai5, y = 0·57 'at a low current density (20 mA/cm2), Quantum efficiency (2.51%) and high brightness (1415 cd/m2). Maximum brightness is 16148 cd/m2 at 13 V. Experimental Example 9: The luminescent layer of this device is doping, using compound 3a as the guest (guest), the element structure is as shown in Fig. 1. In the present experimental example, the substrate 1 is a glass substrate. The anode 20 is indium tin oxide, and the cathode 4 is a magnesium-silver alloy having a thickness of loom. In the organic electroluminescent material. The layer 30 is sequentially arranged, the hole transport layer 31 is a benzidine (NPB) having a thickness of 3 〇 nm, and the luminescent layer 32 is a phosphorescent material composed of a host compound CBP having a thickness of 30 nm and a 7% doped guest 3a, and the hole is blocked. The layer 33 is a BCP having a thickness i 〇 nm and the electron transport layer 34 is Alq3 having a thickness of 3 〇 nm. The electroluminescence of the element is orange-red, and the maximum emission wavelength is 598 nm, and the corresponding CIE 1931 chromaticity coordinate value x = 0.61, y = 0.38, at low current density (20mA/Cm2), good external quantum efficiency (6·14 °/〇) and high brightness (2326 cd/m2). Maximum brightness at 15V 18223 cd/m2 20 200817419 Experimental Example 10: The luminescent layer of the device is doped, using compound 3b The guest has the element structure as shown in Fig. 1. In the experimental example, the substrate 1 is a glass substrate, the anode 20 is indium tin oxide, and the cathode 4 is a magnesium-silver alloy having a thickness of 100 nm. The material layer 30 is sequentially arranged, the hole transport layer 31 is a benzidine (NPB) having a thickness of 30 nm, and the light-emitting layer 32 is a phosphorescent material composed of a host compound CBP having a thickness of 30 nm and a 7% doped guest 3b, and a hole barrier layer. 33 is a BCP having a thickness i 〇 nm and an electron transport layer 34 is Alq 3 having a thickness of 30 nm. The electroluminescence of this element is red, the maximum emission wavelength is 604nm, and its corresponding CIE 1931 chromaticity coordinate value X - 0·64, y-〇.36' at low current density (somA/cm2), Good external quantum efficiency (4·56〇/〇 and high brightness (1618cd/m2). Maximum brightness is 10158 cd/m2 at uv. In summary, a ruthenium complex of the present invention has novel Structure, and a variety of derivatives, can be applied as a doping guest for phosphorescent materials

Multi-color organic light-emitting diodes (OLEDs) 〇 The present invention can be designed to select the ring ligand of the ruthenium complex as a photo-doping containing the green, orange and red The phosphorous material of the guest, the phosphorescent material is turned over to the light-emitting layer of the electroluminescent element to provide a two-efficiency organic electroluminescent element of red, blue and green light in accordance with the prior requirements. The above mentioned only the silk ship, _ is the material. Any uninvented spirit and _, and equivalent modifications or alterations thereto, are included in the scope of the appended patent application. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a schematic view showing the structure of an organic electroluminescence device of the present invention; and Fig. 2 is a view showing the structure of a host compound of a phosphorescent material which can be used in the present invention. [Major component symbol description] 10 : substrate; 20: anode; 30: organic electroluminescent material layer; 31: hole transport layer; 32: light-emitting layer; 33: hole barrier layer; 34: electron transport layer; 40: Cathode; 200: chemical structure of TPSi-F; 202: chemical structure of mCP; and 204: chemical structure of CBP. twenty two

Claims (1)

200817419 X. Patent application scope: Wherein FU, R2, R3, R4, R5, R6, R7, R8, R9, and R11 are selected from the group consisting of a halogen atom (Η), an atom (F), a carbon trifluoride group (CF3), and an alkyl group (alkyl). Group) and aryl gr0Up. 2. The ruthenium complex as described in the first paragraph of the patent application, wherein the formula is CF3, R3, R8, R9, Rio, and R11 are Η, and R4, R5, R6, and R7 are F. (I} is the following |^dfppy)2lr(fpyr〇)] structure: 3. The ruthenium complex as described in claim 1, wherein R1 is 23 200817419 CF3, R2 is butane (buty C4H9), R3, R8, R9, Ri〇, Rll is H, R4 When R5, R6 and Rj are F, the chemical formula (I) is the following structure of [(dfppy)2Ir(bpyro)]: 4. The ruthenium complex as described in claim 1, wherein when the phantom is CF3, R3, R4, R6, R8, R9, R10, and R11 are ruthenium, and R5 and R7 are a methyl group (CH3). , the chemical formula (I) is the following structure: For example, the oxime complex described in the first paragraph of the patent application, wherein the sputum is butyl, (^43⁄4), R3, R4, R6, Rg, sand 3 R11 is Η, R5, R7 are When decylalkyl (CH3), the chemical formula '^1〇, [(tpy)2lr(bpyro)] structure: work for the following 24 200817419 When CF3 'R8, R9, RIO, and R11 are substituted by benzene, R3, R4, R5, R6, and R7 are Η, the chemical formula (I) is the lower [(piq)2Ir(^yro)] structure. : 7. The ruthenium complex as described in claim 1, wherein R1 is CF3, R2 is butane (buty C4H9), R8, R9 and RIO, RU are replaced by benzene. When R3, R4, R5, R6, and R7 are Η, the chemical formula φ is the following structure of [(piq)2Ir(bpyro)]: 25 200817419 8. A phosphorescent material using a ruthenium complex comprising at least: a host compound, and a heterozygous compound, which is a ruthenium complex, comprising at least the structure of the chemical formula (I): Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 blood R11 comprises a hydrogen atom (H), a fluorine atom (f), a carbon trifluoride group (CF3), and a p group (alkyl). Group) and aryl group 〇9. A phosphorescent material using a ruthenium complex as described in claim 8 wherein R1 and R2 are CF3, and R3, R8, R9, R10 and R11 are Η. When R4, R5, R6, and R7 are F, the chemical formula (I) is a structure of [(dfppy)2Ir(fpyro)] 26 200817419 10. A grading material using ruthenium complex as described in claim 8 wherein R1 is CF3' R2 is butyl (C4H9), R3, R8, R9, R10, R11 are Η When R4, R5, R6, and R7 are F, the chemical formula (I) is a structure of [(d^py)2Ir(bpyro)]: 11. The filling material using the ruthenium complex as described in claim 8 wherein IU and R2 are CF3, R3, R4, R6, R8, R9, R10 and R11 are Η, and R5 and R7 are In the case of a methyl group (CH3), the formula (I) is the structure of [(tpy)2lr(fpyro)]: 27 200817419 ^Li~CF3 f3c . 12. A phosphorescent material using a ruthenium complex as described in claim 8 wherein R1 is CF3, R2 is butane (buty C4H9), R3, R4, R6, R8, R9, R10, R11 When R5 and R7 are a methyl group (CH3), the formula (I) is a structure of [(tpy)2lr(bpyro)]: 13. A light-blocking material using a silver complex as described in claim 8 wherein when IU, R2 are CF3, R8, R9 and R10, R11 are replaced by a benzene ring, R3, R4 When R5, R6, and R7 are Η, the chemical formula (I) is the structure of [(piq)2Ir^yro)]· 28 200817419 14 'A phosphorescent material using a ruthenium complex as described in claim 8 wherein R1 is CF3, R2 is butane (buty C4H9), R8, R9 and R1〇, and Rii are derived from benzene ring. Substituted by (benzene), when R3, R4, R5, and R7 are Η, the chemical formula (I) is a structure of [(piq)2Ir(bpyro)]· 15 1 The organic electroluminescent material of the test compound, the electroluminescent material layer, having the light-emitting layer, consisting of - the main compound and the - doped material Object, including at least the structure of chemical formula (1) _· The heterogeneous object is 29 200817419 Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11 comprise a halogen atom selected from the group consisting of a halogen atom, a fluorine atom (F), a carbon trifluoride group (CF3), and an alkyl group (alkyl). Group) and an aryl group; and a pair of electrodes respectively disposed on both sides of the organic electroluminescent material layer to excite the organic electroluminescent material layer. 16. The organic electroluminescent device using a ruthenium complex according to claim 15, wherein when ΓΠ and R2 are CF3, R3, R8, R9, R10, R11 are Η, R4, R5, R6, When R7 is F, the chemical formula (I) is the structure of [(dfi)py)2Ir(fpyro)]: 30 200817419 17. The organic electroluminescent device using ruthenium complex according to claim 15, wherein R1 is CF3, R2 is butane (butyl, C4H9), R3, R8, R9, RIO, R11 When R4, R5, R6 and R7 are F, the chemical formula (I) is the structure of [(d〇>py)2Ir(bpyro)]: 18. The organic electroluminescent device using the ruthenium complex according to claim 15, wherein when R1 and R2 are CF3, R3, R4, R6, R9, RIO and R11 are Η, R5, R7. When it is a methyl group (CH3), the chemical formula (I) is a structure of [(tpy)2Ir(fpyro)]: 31 200817419 a light-emitting element, wherein when R1 is CF3' R2 is butyl 'C4H9' R3, R4, R6, R8, R9, R10, R11 are Η, and R5, R7 are decyl (CH3), The chemical formula (I) is the structure of [(tpy)2Ir(bpyro)]: 20. The organic electroluminescent device using a ruthenium complex according to claim 15, wherein when R1 and R2 are CF3, R8, R9 and R10, R11 are substituted by a benzene ring, R3 When R4, R5, R6 and R7 are sweet, the chemical formula (I) is the structure of [(piq)2Ir(§)yro)]: 32 200817419 21. The organic electroluminescent device using a ruthenium complex according to claim 15, wherein R1 is CF3, R2 is butylene (butyl, C4H9), R8, R9 and R10, R11 are When benzene is substituted, and R3, R4, R5, R6 and R7 are Η, the chemical formula φ is [(piq)2Ir(bpyr〇)]: The organic electroluminescent device using the ruthenium complex according to claim 15, wherein the organic electroluminescent material layer comprises a hole transport layer, the light emitting layer, a hole barrier layer and An electron transport layer. 33