TWI264458B - Iridium metal complex compound, and phosphorescence material and organic electroluminescence component using the same - Google Patents

Abstract

Provided is one kind of iridium metal complex compound, and phosphorescence material and organic electroluminescence component using the same, which uses a new type of iridium metal complex compound as a red light doped guest of a phosphorescence material. The said phosphorescence material is applied on the luminescence layer of an organic electroluminescence component, which can provide red light closer to pure red. And the conjugated number of this iridium metal complex compound structure is high, which can improve the heat stability of the organic electroluminescence component.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to a ruthenium metal compound, and more particularly to a ruthenium metal compound, a phosphorescent material using a ruthenium metal compound, and an organic electroluminescent device. [Prior Art] 〇rganie Electroluminesence (^EL) has a new generation of technologies that are not easily realized by other flat panel display technologies. A clearer and clearer full-color image and a more agile reaction speed. In addition, the organic electroluminescence display element itself has self-luminous, no viewing angle limitation, fast reaction speed, visible animation image, high photoelectric efficiency, low brittle power consumption, no need for backlight structure and color filter, and the like. 'Thus is considered one of the most likely flat panel display technology to replace liquid crystal displays. The application of organic electroluminescent elements to displays, full color is the market's success. Therefore, the red, blue and green colors that meet commercial needs are the key to moving towards commodities. At present, the effect of green light is the best, and the red organic electroluminescent element required for full color still has many shortcomings in terms of material stability, 兀^ efficiency and excited color purity. Where. Among the results of the exhibition, one of the common methods, as described in the US Patent No. 1, is to infer the red fluorescent compound as a guest in the original gamma of the county (hQst). ) to adjust the light color of the luminescent material and the luminous efficiency. Accordingly, the development of a bulk material filled with an organic heavy metal-missing compound into the host luminescent material further overcomes the limitation of the 25% internal luminescence efficiency of the luminescent material. As disclosed in the "Efficient phosphorescent emission from organic ^leCtr〇luminescent devices" published in the journal NATURE in 1998, the organic phosphorescent material platinum octaethlyp0rphyrin (Pt0EP) is used as a host to immerse in the main luminescent material. - (8-record +19g (Alq3) towel, because the disc light ^ can make the single-excited state and the three-excited state branch participate in the energy transfer, thereby improving the internal energy transfer efficiency of 1264458. Excitation element 2 ίί_ is an important research direction of organic Wei luminescent materials. For example, Universal Display C〇rporation UDC is applied by PATENT COOPERATION TREATY / η / 〇) A new spheroidal material, ΐ 弁 弁 弁 塞 塞 弁 — — — — — — — — — — N N N N N N N N N N N N N N N N N N N N N N 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- 2- Benzothienyl)-pyridinato-N,C3)(acetylacetonate),Ir(btp)2acac), apply 1 to organic electroluminescent elements, the light color is near the wavelength of pure red 617 too ': hot refining temperature up to Celsius 351. 8 degrees. According to this, further development Phosphorescent materials with better thermal stability, light efficiency and light color purity are beneficial to the thermal stability of organic electroluminescent devices in high temperature environments and extend the life of components, and contribute to organic electroluminescent components in full color displays. SUMMARY OF THE INVENTION In view of the above, it is a primary object of the present invention to provide a bismuth metal-missing compound, one of which is a red light doping client required for an organic electroluminescent device. ', for the purpose of the tenth, the present invention discloses the ruthenium metal bis(2-(9'-phenanthryl acridine-N, C3') (2-(9>-phenathyl) -pyridinato-N, C10') (acetylacetona te), Ir(pyp>acac), which has the structure shown by the following formula (!):

R3

2

Rv_ 7 (i) 1264458 wherein Ri, R2 and R3 are selected from a hydrogen atom, an alkyl group containing ruthenium to 3 carbon atoms or an aryl group having 6 to 1 carbon atoms. The ruthenium metal complex compound of the present invention has a high number of conjugated structures and excellent thermal stability. Another object of the present invention is to provide a phosphorescent material comprising a base metal compound comprising a host compound and a dopant guest, the dopant system being a base metal compound having a structure as shown in the aforementioned chemical formula (1) . Wherein, the membrane, oxime and R3 are selected from the group consisting of a hydrogen atom, an alkyl group containing ruthenium to 3 carbon atoms or an aromatic group having 6 to 1 carbon atoms (an electron group). The object is to provide an organic electroluminescent device using a ruthenium metal-missing compound, comprising a pair of electrodes and a layer of an organic electroluminescent material, the two electrodes being respectively disposed on two sides of the layer of the organic electroluminescent material to excite the light. The organic electroluminescent material layer comprises a light-emitting layer formed of a phosphorescent material comprising a host compound and a dopant guest, and the doped guest system is a base metal-defective compound having a structure as shown in the aforementioned chemical formula (I) . Wherein, the two electrodes comprise an anode and a cathode. When the organic electroluminescent element is supplied with direct current, electrons are injected from the cathode and holes are injected from the anode. In order to further understand the objects, structures, features, and functions of the present invention, the embodiments are described in detail below. [Embodiment] The present invention discloses a silver metal compound, a nucleus material using a silver metal compound, and an organic electroluminescence device. A silver metal-doped compound is used as a red light doping guest for the phosphorescent material, and is applied to an organic electroluminescent device. The ruthenium metal compound of the present invention may be blended with different ionic groups, and the structure of the silver metal compound of the present invention is as shown in the above formula (I); wherein Ri, R, and R3 are selected from hydrogen An atom, an alkyl group having 3 to carbon atoms or an aromatic group having 6 to 10 carbon atoms (5) p). In order to explain the ruthenium metal-defective compound of the present invention, compounds 1A to (E) according to the present invention are enumerated: (A) R1 is a hydrogen atom, R2 is a hydrogen atom, and R3 is a hydrogen atom.

〇

(B) h is a decyl group (-CH3), R2 is a decyl group (-CH3), and R3 is a decyl group (-CHs).

^Ir

H3C h3c (8) 0 = 1264458 (C) Ri is an ethyl group (-C2H5) ’ R2 is a phenyl group (-C2H5) ^ R3 is an alkyl group (-GH5).

(D) Ri is a propyl group (-C3H7) ' R2 is a propyl group (-C3H7) ' R3 is a propyl group (-GHO 〇

\

2

C3h7 _J (D) (E) Ri is phenyl (-Cl), R2 is phenyl (-«), and R3 is phenyl (-d).

C6H5 2 ◦6^5 - (E) 10 1264458 Further explaining the synthesis procedure of the examples of the present invention, firstly synthesizing the intermediate (Ir(pyp)2C1)2, taking 3.51 g (Ir(pyp)2C1)2 5. 25 g of acetylacetone and 250 ml of dioxane jdichloromethane were mixed in a three-necked flask. On the one hand, it was stirred at room temperature, and on the other hand, 30% sodium citrate (sodiummeth〇xide) was added dropwise to about 9 41 J. After the dropwise addition was completed, the mixture was stirred at room temperature for 5 hours. Further, 25 ml of water was added to extract, the organic layer was taken out, and the second extraction procedure was repeated. Of course

The Lit water sulphur Wei was dehydrated, filtered with a filter paper, and placed in a rotary concentrating to obtain a crude product of 3.59 g. Finally, the crude product was dissolved in methylene chloride and decolorized by Shi Xi = (sU1Cagel), followed by sublimation purification to obtain the base metal complex Ir(pyp) 2acac. The loyal-batch re-invention of the silver metal-defective compound of the invention is tested by the organic electric excitation as a red-light doping object. Please refer to Fig. 1, which is an organic light structure of the present invention. The surface of the flat substrate 10 is sequentially plated with t, a plurality of electroluminescent material layers 30 and a cathode 40, an organic electroluminescence material f hole transmission layer 31, a light-emitting layer 32, a hole barrier layer 33, and electricity The illusion 2 2 4 'special 疋 light-emitting layer 32 is made of the material (4) using the aforementioned ruthenium metal-missing compound. In the structure of the organic electroluminescent device, the anode and the anode need to transmit light to penetrate the excitation light. And ίίίί, a material with a higher work function, such as indium tin oxide, magnesium or magnesium silver alloy. 7 Further details on the method of fabricating the organic electroluminescent device, firstly, the clear and floc-carrying tray is placed on the 'glass substrate, which is transparent to the indium oxide i-side, and then the niobium is fine, and the glass-based indole aniline (10)) As a hole transport layer, re-steaming 3〇|(^ layer' contains a host compound and a 25% doped guest consisting of a scale material ^ 1264458 hetero-host is a ruthenium metal complex Ir(pyp) 2acac, the main compound is 4, 4'-Ν, Ν'-bisoxazolyldiphenyl (CBP), plus 1 〇N 2,9-dimethyl~4,7-diphenyl-1,10-morphine 2, 9-dimethyl-4, 7-diphenyl-1, ~phenanthroline, BCP) as a hole barrier layer, and 3 〇 nano 3 said 啥 啥 )) | g (Alq3) as an electron transport layer, to have Electromechanical excitation material layer. A 155 nm magnesium-silver alloy was further vapor-deposited as a cathode. The luminescent property of the organic electroluminescent device was measured. As a result, as shown in Fig. 2, it is the wavelength of the electroluminescence of the organic electroluminescent device of the present invention. Pots

Light intensity 'horizontal (four) wavelength. It is known that its maximum luminous intensity ==8 nm' is red light closer to pure red, and (5) compared with the prior art, Ben, has a CIE & degree coordinate closer to red (chr〇maticity o^ Nates) ^ 68, y=〇. 32) ^ CIE ^:^:1〇n ernatl〇nale ^ Γ ECla^e) Qualification 3 ί 施 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭 揭The ___ boundary is the standard. Schematic diagram of the structure; and [Signature description of main components] 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 [The wavelength of the electro-excitation light of the main component. 1264458 40 cathode 13

Claims (1)

1264458: You H \ X. Patent scope: L A bismuth metal compound with a structure of formula (1): Wherein Ri, R2 are selected from a hydrogen atom, having 1 to 3 carbon atoms: an alkyl group and an aryl group having 6 to 10 carbon atoms. 2. The ruthenium metal-defective compound as described in claim 1, wherein the memory is a hydrogen atom, Rs is a hydrogen atom, and R3 is a hydrogen atom. 3. The ruthenium metal-defective compound according to claim 1, wherein the oxime is a decyl group (-CH0, 吣 is a decyl group (-CH3), and R3 is a methyl group (-CiL·). For example, the ruthenium metal compound described in claim 1 wherein R! is a phenyl group (-C2H5), ^ is an ethane group (-C2H0, and R3 is a phenyl group (-C2H0. 5. The ruthenium metal compound according to Item 1, wherein R! is a propyl group (-C3H7), and R2 is a propyl group (-C3H7) 'Rs is a propyl group (-C3H7). The ruthenium metal compound according to Item 1, wherein Ri is a strepyl group (-CeHs), R2 is a phenyl group (-CeHs), and Rs is a phenyl group (-CsEb). A filling material for a compound comprising: 1264458 a host compound; and a structure having a chemical formula (1)-(iv) a guest's silver metal compound: Wherein IU, R2 and R3 are selected from the group consisting of a hydrogen atom, an alkyl group containing ruthenium to 3 carbon atoms, and an aromatic group (_g_p) having 6 to 10 carbon atoms. 8. A phosphorescent material using a ruthenium metal-missing compound according to claim 7, wherein R! is a hydrogen atom, R2 is a hydrogen atom, and is a hydrogen atom. 9. A phosphorescent material using a ruthenium metal-missing compound as described in claim 7, wherein the private is a methyl group (-CH3), R2 is a methyl group (-CHs), and the group is a methyl group (-03⁄4). 10. A spheroidal material using a silver metal-missing compound as described in claim 7, wherein R! is an ethane group (-GH5), R2 is an ethane group (-(3⁄4), and Rs is B. Alkyl (-Μ3) ^ 11. A phosphorescent material using a ruthenium metal-missing compound as described in claim 7, wherein the R1 is a propane group (_C3H7), and the propane group (_C3H7) is a 15 1264458 Propane group (>C3H7:) The use of a ruthenium metal compound as described in claim 7 wherein R1 is a stupid group (-C6H5), R2 is a phenyl group (-C6H5), and R3 is | (-C6H5). 3. An organic electroluminescent device using a ruthenium metal-missing compound, comprising: an organic electroluminescent material layer having a luminescent layer formed of _phosphor material, comprising a host compound and a doping The guest, the doping guest system is a ruthenium metal wrong compound, which has the structure of the chemical formula 1 ... Wherein Rl, R2 and R3 are selected from a hydrogen atom and contain a carbon atom (a%1Sr〇UP)^^6^10^^^^^^ft(a^lgr〇up); They are respectively disposed on the organic electro-optical excitation light layer. "Light_layers on both sides of the number of hairs 14 as described in claim 13 of the scope of the excitation of the light element, which is a hydrogen atom seven metal wrong compound of organic electricity 15. As described in the patent application (4) 13 A wide hydrogen atom, and R3 is a hydrogen atom. Organic electricity of the metal-coated compound 16 1264458 The light-storing light is purely a silk (shed), m Xia (: cm) R3 is methyl OCHS). 3 5 The organic* of the ruthenium metal-missing compound described in the 13th article of the patent application of May, and the luminescent element, wherein R1 is ethane (-C2H5) and R2 is ethane I (-C2H) :)), R3 is ethane group C2H5). 17. The organic Ravine meal light element of the female metal compound as described in claim 13 wherein R1 is a propyl group (_C3H7), R2 is a propyl group (seven 3H7), and R3 is a propane group. (^3Ή7). 18. The organic electroluminescent device using a ruthenium metal-missing compound according to claim 13, wherein the junction R1 is phenyl (-C6H5) and R2 is phenyl (-C6H5) 'R3 is phenyl ( -C6H5). The organic electroluminescent device using a ruthenium metal-missing compound according to claim 13, wherein the organic electroluminescent material layer comprises a hole transport layer, the luminescent layer, and a hole barrier layer. And an electron transport layer. 17