TW200909438A - Transition metal complexes with carbene ligands and their application - Google Patents

Abstract

The present invention discloses a transition metal complex having carbene ligands. The disclosed transition metal complex has a structure of a center transition metal surrounded by two identical carbene ligands and one double-chilating ligand which is a nitrogen-contain heteroaryl group compound with pyridyl group. The disclosed transition metal complex can be represented by the following formula:.

Description

200909438 IX. INSTRUCTIONS OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to a transition metal complexes in particular to a transition metal complex containing a carbene ligand and its use in organic electronic components. .

I [Prior Art] Organic Light Emitting Diodes (〇巧&1^1^汾疋11^咁1^1^0(16,01^0) means that organic semiconductor materials and luminescent materials are driven by current The technology of illuminating and realizing display. The basic principle of illuminating organic light-emitting diodes is to place a luminescent material between the electrodes of the yin and yang and apply a bias voltage so that electrons and holes pass through the electron transport layer respectively. Electron Transport Layer (ETL) and the Hole Transport Layer (HTL) enter an organic substance with luminescent properties. Electrons and holes are recombined in the organic layer to form an exciton and energy. Released back to the ground state, and the energy released from these, due to the different luminescent materials selected, can release part of the energy in the form of light of different colors to achieve the luminous effect. Organic triplet luminescent materials (ie, organic fillers) have recently become an important development direction for OLED materials. Traditional organic luminescent materials belong to the singlet state of fluorescing. Light body, which is different from phosphorescent triplet illuminant; however, in theory, the electroluminescent light efficiency of phosphorescent material is three times that of fluorescent material. Generally, organic compounds are not without phosphorescence, they are very weak and need Observed at low temperatures (such as the temperature of 77 k liquid nitrogen). This limitation can be broken under one condition, that is, adding heavy atoms to the chemical structure of organic compounds. However, not all heavy atoms have this effect; It is found that when the transition metal elements in the sixth cycle, such as ruthenium (Re), ruthenium (〇s), iridium (Ir), platinum (Pt), etc., are used, the effect is best. 200909438 Metal complex has recently been used. Phosphorescent dopants as organic light-emitting diodes. These metal complexes used in the light-emitting layer of organic light-emitting diodes have a strong spin effect due to heavy atomic effects. Spin-orbital coupling, which allows electron transfer through a mixture of metal-ligand charge transfer 3MLCT (Metal to Ligand Charge Transfer) and 3 (7ζ·-τγ*) ligands to cause single and triple excitation Mixed state Therefore, the lifetime of the triplet state is shortened and the phosphorescence efficiency is improved. Among them, the complex containing a ruthenium metal is most widely studied and widely studied. The complex of the ruthenium metal is usually a regular octahedron containing a positive trivalent oxidation state. Structure, its light-emitting mechanism is mainly from the triplet state of the metal to the ligand charge transfer / 3MLCT state or the triplet state of the ligand -3 ( ▲ - ▲ *) state of the light. The cyclone-formed iridium complexes are known as organic phosphorescent diode materials with high efficiency and high brightness.

Iridium(III) bis(4,6-difluorophenylpyridinato)picolate (FIrpic) is the most commonly known triplet blue phosphorescent emitter. Although the components made by FIrpic have a bright performance in terms of efficiency, the biggest problem is the saturation of the color; the 匸圧 coordinates are roughly in (G.16, G.3G), and the high γ coordinate value The color purity is only in the range of blue-green, and it does not reach the deep blue range required for full-color displays. In 2005, Prof. Th〇mpsQn published a new silver metal complex with a carbon material as a ligand; '2' is a dark blue luminescent material from the wavelength of light emission, but the cIE coordinate position of the component However, it has reached (4), G{)6), which does not meet the requirements of (1)·15,0·15) or even (4), 0.09) in terms of color saturation, and the external scorpion efficiency only reaches 5_8 in efficiency performance. %, the brightness is only i7 im/w. On the other hand, in the 2〇〇5, 2_ and Lein years, there is also a place where the ligand of _·· is published. However, there is not much difference in the structure of the professor of Thn I. In the difference, only the substitution of different functional groups on the terpene ligand is carried out. Piece of light organic luminescence - the development of polar materials has not been more than seven or eight years, and the blue scales page 8 200909438 The development of light is only three or four years. The performance of OLED materials is not ideal in many respects, especially the rarer blue phosphorescent organic materials. Phosphorescent organic light-emitting diode materials are an important factor in the rapid development and high expectations of OLEDs in recent years. Whether organic light-emitting diode white light illumination can be practically implemented depends on the blue phosphorescent organic light-emitting diode material. No further leap forward. In summary, the blue-filled organic light-emitting diode material is the key to the new generation of white light illumination applications after enabling OLEDs to follow the semiconductor semiconductor LEDs. Therefore, the development of a blue phosphorescent organic light-emitting diode material having high external quantum efficiency, high purity, high luminance, and high (blue) color saturation is an urgent development technology in the industry. Citations: 1. Sajoto, Tissa; Djurovich, Peter I.; Tamayo, Arnold; Yousufuddin, Muhammed; Bau, Robert; Thompson, Mark E·; Holmes, Russell J·; Forrest, Stephen R· Blue and Near-UV Phosphorescence From Iridium Complexes with Cyclometalated Pyrazolyl or N-Heterocyclic Carbene Ligands. Inorganic Chemistry 2005, 44, 7992-8003. 2. Sajoto, Tissa; Djurovich, Peter I.; Tamayo, Arnold; Yousufuddin, v Muhammed; Bau? Robert; Thompson, Mark E.; Holmes, Russell J.;

Forrest, Stephen R. Saturated deep blue organic electrophosphorescence using a fluorine-free emitter. Applied Physic Letter 2005, 87, 243507. SUMMARY OF THE INVENTION In accordance with the above objects, the present invention discloses a transition containing a fine carbon ligand Metal complexes and their use as primary illuminant materials in organic electroluminescent devices, page 9, 200909438 (host material), electronic transport materials, or hole transport materials. SUMMARY OF THE INVENTION One object of the present invention is to provide a highly thermally stable transition metal complex containing a carbene ligand to enhance the useful life of an organic electronic component. Another object of the present invention is to provide a transition metal complex containing a carbene ligand having a high triplet energy level difference, which can be used to complement the existing main layer material generally applied to blue phosphorescence. The energy level difference, and general-purpose cans of light materials such as silver, platinum (pt), bismuth (Os) and other red, blue, green metal complex materials, and thus developed high external quantum efficiency, A blue-based organic electroluminescence element with high purity, high luminance, and high (blue) color saturation, thereby achieving the effect of fine-tuning the light-emitting range and moving toward a saturated deep blue color.

Transition metal complex. The above transition metal complex containing a carbene ligand has an atomic group having the following chemical structure:

R2 V 2

Page 10 200909438 The complex compound can be combined with a pyridyl polynitrogen compound as a secondary monoanionic chelating ligand. Accordingly, the present invention achieves the effect of causing the luminescent material to shift in the spectrally shifted wavelength toward the red displacement direction by introducing an auxiliary monoanionic double chelating ligand. The invention also discloses the use of the above transition metal complex containing a carbene ligand, in particular, a main light-emitting material for a basic light-emitting material in an organic electroluminescent device and/or a phosphorescent device, and A hole conducting material; or an electron conducting material or a hole conducting material applied to other organic electronic components. [Embodiment] The direction of the present invention as discussed herein is a transition metal δ containing a carbene ligand and its use. In order to thoroughly understand the present invention, the hierarchical structure will be described in the following description. Obviously, the practice of the present invention is not limited to the specific details familiar to those skilled in the art. On the other hand, well-known compositions are not described in detail, and X avoids unnecessary limitations of the invention. The preferred embodiments of the present invention will be described in detail below, but the present invention can be widely applied in other embodiments except for the detailed description, and the scope of the present invention is not limited, and the following patents The scope shall prevail. The first embodiment of the present invention discloses a transition metal 5 containing a carbene ligand. The above transition metal complex containing a carbene ligand has an atomic group, and the chemical structure of the above atomic group can be expressed as follows: 11 pages 200909438

Wherein, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten, rhenium, osmium, iridium, platinum ( Platinum). R1 is selected from one of the group consisting of C1-C20 alkyl, C1-C20 cyclod, aromatic group, heteroaromatic heterocyclic group. R2 to R7 may be the same or different, and R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom (for example, fluorine, gas, bromine, iodine), a C1-C20 alkyl group (alkyl group). ), C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 acyl group, C1- C20 Sester group, C1-C20 amide group, aryl group, halogen-substituted aryl group halogen-substituted aromatic alkyl group, haloalkyl-substituted aryl group, halogen-substituted aromatic group An alkyl group, a cyano group, a nitro group, a conjugated aromatic ring group, and an aromatic heterocyclic group. In a preferred embodiment of the present embodiment, the adjacent R2 and R3, R4 and R5, R5 and R6, R6 and R7, etc. of the transition metal complex containing a carbene ligand may also have at least one The group is any atomic group forming an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocyclic ring group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, page 12, 200909438 aromatic heterocyclic ring, The cycloalkenyl group or the heterocycloalkenyl group or the like may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, chlorine, bromine, hydrazine); an aryl group, a halogen-substituted aryl group, A dentate-substituted arylalkyl group, a dentate-substituted aryl group, a haloalkyl-substituted arylalkyl group, an aryl-substituted C1_C20 alkyl group; an electron donating group such as a C1-C20 alkyl group, C1- C20 cycloalkyl (for example: mercapto, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, Cl-C20 f \ substituted amino group, aromatic having a substituent An amine group [e.g., an aniline] ' or an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, a cyano group (cyano) , -CN) a C1-C20 alkyl group substituted with a halogen (for example, a trifluoromethyl group, CF3); a heterocyclic substituent group. The unsubstituted substituents in the above R2 to R7 may be the same or different, and the unsubstituted substituents in the above R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen 1., a ruthenium atom, a C1_C20 Alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, Cl_C2 (m*(acylgroup) , ci-C20_&(estergr〇up), C1_C20 amide group, aryl, halogen-substituted aryl, halogen-substituted arylalkyl, lS alkyl-substituted aryl, _alkyl-substituted aromatic An alkyl group, a cyano group, a nitro group, a conjugated aromatic ring group (ar〇matic gr〇up), an aromatic heterocyclic group 圑. Page 13 200909438 refers to the following formula, which is expressed as A transition metal complex atomic group of the present example, wherein R2 and R3 form an atomic group of an aromatic ring. It should be noted that this structure is merely illustrative of the present examples and is not intended to limit the scope of the disclosure. The scope of this specification should still be based on the scope of subsequent patents.

In another preferred embodiment according to this embodiment, the structure of the above-mentioned transition metal complex containing a carbene ligand is as follows:

Among them, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten, rhenium, osmium, iridium, Platinum). R1 is selected from one of the following groups: a C1-C20 alkyl group, a C1-C20 cycloalkyl group, a total aromatic group, and a heteroaromatic heterocyclic group. R2 ~ R7 may be the same or different, and R2 ~ R7 are independently selected from one of the following groups: hydrogen atom (H), halogen atom (for example: fluorine, gas, bromine, iodine), C1-C20 Page 14 200909438 Burning Alkyl group, C1-C20 cyclodecyl group, alkoxy group (aik〇Xyi gr0Up), halogen-substituted C1-C20 alkyl group, C1-C20 substituted amine group (arnin〇 group), C1-C20 fluorenyl group (acyl group), C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, dazzle * A radically substituted aryl, cyano, nitro, aromatic aromatic group, aromatic heterocyclic group. In a preferred embodiment of the present example, the adjacent R 2 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 and the like may also form at least one group to form an aromatic ring, an aromatic hetero ring, a ring dilute group or It is an arbitrary atomic group such as a heterocyclic group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or hetero The cycloaliphatic group may further comprise one or more substituents. The unsubstituted substituents in the above R2 to R7 may be the same or different, and the unsubstituted substituents in the above r2 to R7 are independently selected from one of the following groups: a hydrogen atom (Η), a halogen [a atom, a C1-C20). An alkyl group, a C1-C20 cycloalkyl group, an alkoxyl group, an ifi-substituted C1-C20 alkyl group, a C1-C20-substituted amino group, a Cl-C20 fluorenyl group ( Acyl group) 'Cl-C2 ester group, Cl-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aromatic alkyl group, haloalkyl-substituted aryl group, An alkyl group-substituted arylalkyl group, a cyano group, a nitro group, a conjugated aromatic ring group (ar〇matic gr〇up), an aromatic heterocyclic group. Page 15 200909438 According to the present example, z1 in the above structure may be any atomic group for constituting a nitrogen-containing heteroaromatic ring or a nitrogen-containing heterocyclic fluorenyl group. The above nitrogen-containing heteroaromatic ring or nitrogen-containing heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, and the above z1 may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: hydrogenogen f, halogen atom (e.g., fluorine, chlorine, bromine, iodine); aryl, halogen-substituted aryl group , halogen-substituted arylalkyl, haloalkyl-substituted aryl, dentate-substituted arylalkyl, aryl-substituted C1-C20 alkyl; eiectron donating group such as C1-C20 C1-C20 cycloalkyl (for example: methyl, ethyl, butyl 'cyclohexyl), C1-C20 alkoxy group, C1-C20 substituted amino group, aromatic having a substituent An amine group [such as an aniline]; or an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, or a cyano group (Cyano, -CN). a C1-C20 alkyl group substituted with a halogen (for example, a trifluoromethyl group, CF3); a heterocyclic substituent group. In the structure according to the present example, Y may be one selected from the group consisting of nitrogen (N), carbon (C), oxygen (〇), sulfur (S), etc., and Y may further comprise one Substituent. Q is an atomic group containing at least two atoms to constitute a nitrogen-containing heterocyclic ring. The atomic combination contained in Q is selected from the group consisting of nitrogen, carbon, oxygen, and sulfur. And the above nitrogen-containing heterocyclic group may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, mouse, desert '峨); Page 16 200909438 Aromatic group, halogen substitution Aromatic group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, haloalkyl-substituted arylalkyl group, aryl-substituted C1_C20 alkyl group; electron donating group such as C1-C20 alkyl group , C1-C20 cyclodextrin (eg, decyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, C1-C20 substituted amino group, substituted group An aromatic amine group [such as an aniline]; or an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, or a cyano group. , -CN) a C1-C20 alkyl group substituted with a halogen (for example, a trifluoromethyl group, CF3); a heterocyclic substituent group. In another preferred embodiment according to this embodiment, the structure of the above-mentioned transition metal complex containing a charcoal rare ligand is as follows: ~ R6

Where 'the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rh〇dium, tungsten, rhenium, osmium, silver (indlum), Platinum. R1 is selected from one of the following groups: a C1-C20 alkyl group, a C1-C20 cycloalkyl group, a conjugated aromatic ring group (ar〇matic groUp), a heteroaromatic heterocyclic group. R2 to R11 may be the same or different, and R2 to R1 are independently selected from one of the following 200909438 ethnic groups: a hydrogen atom (Η), a halogen atom (for example, fluorine, chlorine, bromine, iodine), C1- C20 alkyl group, C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 awake ( Acyl group), C1-C20 S ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aryl group, haloalkyl-substituted aryl group, A halogen-based aromatic aroma group, a cyano group, a nitro group, a total aromatic group, and an aromatic heterocyclic group. In a preferred embodiment of the present example, the adjacent R2 and R3, R4 and R5, R5 and R6, R6 and R7, R8 and R9, R9 and R1(), R10 and R11, etc. may also have at least one The group forms an arbitrary atomic group such as an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocyclic alkenyl group. The above aromatic ring, aromatic heterocyclic ring, cycloaliphatic group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, aromatic heterocyclic ring or cycloalkenyl group or The heterocyclenyl group or the like may further contain one or more substituents. The substituents contained in the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be the same or different and independently selected from one of the following groups: a hydrogen atom (H), a halogen atom (for example: Fluorine, chlorine, bromine, iodine), C1-C20 alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 danic group, C1-C20 substituted Amino group, C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen substitution Aromatic alkyl, haloalkyl-substituted aryl, haloalkyl-substituted arylalkyl, cyano, nitro, aromatic group, page 18 200909438 aromatic Ring group. The unsubstituted substituents in the above R2 to R7 may be the same or different, and the unsubstituted substituents in the above R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group. (alkyl group), C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group 'Cl-C20 acyl group , Cl-C20 ester group, Cl-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aryl-f-alkyl group, haloalkyl-substituted aryl group, _ alkane A substituted arylalkyl group, a cyano group, a nitro group, a conjugated aromatic ring group (aromatic gr〇up), an aromatic heterocyclic group. In the structure according to the present example, the Y-line is selected from one of the following groups: nitrogen (N), carbon (C) 'oxygen (oxime), sulfur (S), and the like, and Y may further contain a substituent. The Q system is an atomic group containing at least one atom to constitute a nitrogen-containing heterocyclic ring. The atomic combination contained in Q may be an atom selected from the group consisting of nitrogen, carbon, oxygen, sulfur, etc., and the above nitrogen-containing heterocyclic group may further contain one or more substituents. The same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, Dun, Chlorine, Mo, 峨); an aryl group, a halogen-substituted aryl group, a halogen-substituted aromatic group. Aromatic, dentate-substituted aryl, haloalkyl-substituted arylalkyl, aryl-substituted cl_C2 decyl; electron donating group such as C1-C20 alkyl, clC2 〇cycloalkyl (eg: Sulfhydryl, ethyl, butyl, cyclohexyl), C1-C20 alkanoyl (alk〇xy, p. 19, 200909438 group), C1-C20 substituted amino group, substituted aromatic amine group [ For example, an aniline, or an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, a cyano group (CN), and a halogen. C1-C20 alkyl (eg, trifluoromethane, CF3); heterocycle A further example according to this embodiment is a reaction scheme for forming a transition metal complex containing a carbene ligand from a transition metal dimer. The foregoing reaction scheme can be expressed as follows:

2

Wherein, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium 'tungsten, rhenium, osmium, iridium, platinum ( Platinum). R1 is selected from one of the following groups: C1-C20 alkane page 20 200909438 base C1-C20 cycloalkyl, co-light aromatic ring group ((four) fine ship p), heteroaromatic group ° R~R may be the same or Different, and r2 ~ r7 series, independently selected from the following groups: hydrogen atom), _ atom (9) such as: gas, gas, desert d'ci_c2 alkyl group, Cl_C2 〇 cycloalkyl, alkane Oxygen (4) 匕(1)^ gr〇up), halogen-substituted C1-C20 group, Cuc2〇 substituted amino group _in〇, ci c2 acyl group, C1-C20 ester group (estergr〇up) , cl C2 amide group, aryl group, halogen-substituted aryl group, pixel-substituted aromatic alkyl group, dentate-substituted aryl group, i-alkyl-substituted arylalkyl group, cyano group (cyan〇) , nitro (miro), conjugated aromatic %, group (ar 〇 〇), aromatic heterocyclic group. In the preferred embodiment according to the present example, the adjacent r2 and r3, r4 and R, R and R, R 1% r7, etc. may also form at least one group to form an aromatic ring, aroma, and Any group of alkenyl groups or heterocycloalkenyl groups. The above aromatic ring, aromatic heterodish, bad dilute or heterocyclic dilute group may be a five-membered ring 'six-membered ring, or seven 70%', and the above aromatic, aromatic, cycloalkenyl or heterocyclic The cycloalkenyl group or the like may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, gas, bromine, iodine); an aromatic group, a halogen-substituted aromatic group, Halogen-substituted arylalkyl, haloalkyl-substituted aryl, dentate-substituted arylalkyl, aryl-substituted C1-C20 alkyl, electron donating group such as C1-C20 alkyl, C1 -C20 cycloalkyl (eg methyl, ethyl, butyl, cyclohexyl), C1_C20 alkoxy group, C1-C20 substituted amino group, having the 200909438 generation on page 21 An aromatic amine group [such as an aniline], or an electron withdrawing group such as a halogen, a nitriie, a nitro group, a carbonyl group, or a cyano group (cyan〇, _CN) a C1-C20 alkyl group substituted with a halogen (e.g., diterpenoid, CF3), a heterocyclic substituent group. The unsubstituted substituents in the above R2 to R7 may be the same or different, and the unsubstituted substituents in the above r2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group. (aikyl group), Cl-C20 cycloalkyl, alkoxyl group, dentate-substituted C1_C20 alkyl group, cl_C2〇 substituted amino group (amin〇 group), Ci-C20 fluorenyl group (aCyi group), C1_C2〇g基基(ester gr〇up), ci c2 amide group 'aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, _alkyl-substituted aryl group, _alkyl group Substituted aromatic alkyl, cyano 'nitro", conjugated aromatic ring group (ar〇matic 0), aromatic heterocyclic group. According to the present example, the lanthanide atoms in the above structure, such as gas, bromine, and ruthenium atoms. Ζ2 may be any atomic group used to constitute a nitrogen-containing heteroaromatic ring or a nitrogen-containing heterocyclic ring. The above nitrogen-containing heteroaromatic ring or nitrogen-containing heterocycloalkenyl group may be a 5%, /, or a heptacyclic ring, and the above oxime 2 may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from the group consisting of a hydrogen atom and a (iv) atom (for example, fluorine, gas, desert, moth-aromatic, i-substituted aromatic group, "Substituted aryl(tetra)yl'-yl-substituted aryl fluorenyl, aryl-substituted aroma-based, aryl-substituted ci_c2 fluorenyl; for page 22 200909438 electron donating group such as C1-C20 a C1-C20 cycloalkyl group (e.g., methyl, ethyl, butyl, cyclohexyl), a C1-C20 alkoxy group, a C1-C20 substituted amino group, having a substituent Aromatic amine group [eg aniline]; electron withdrawing group such as halogen, nitrile, nitro, carbonyl, cyano, -CN a C1-C20 alkyl group substituted with a halogen (for example, a trifluoromethyl group, CF3); a heterocyclic substituent group. In the structure according to the present example, the Y group is selected from one of the following groups: nitrogen (N), carbon ( C), oxygen (0), sulfur (S) and other atoms. Y may further comprise a substituent. Q is an atomic group containing at least two atoms To form a nitrogen-containing heterocyclic ring, wherein the atomic combination contained in Q is selected from the group consisting of nitrogen, carbon, oxygen, sulfur, and the above nitrogen-containing heterocyclic group may further comprise one or a plurality of substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a halogen atom, a halogen atom (for example, fluorine, chlorine, bromine, iodine); an aromatic group: , a substituted aryl group, a halogen-substituted arylalkyl 'haloalkyl-substituted aryl group, a haloalkyl-substituted arylalkyl' aryl-substituted C1-C20 alkyl group; an electron donating group Such as C1-C20 alkyl, C1-C20 cycloalkyl (eg: decyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group 'C1-C20 substituted amine (amino group) An aromatic amine group having a substituent [e.g., an aniline]; an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, a cyano group ( Cyano, -CN) and halogen on page 23 200909438 substituted C1-C20 alkyl (eg trifluoromethyl) Base, CF3); heterocyclic substituent group. According to this embodiment, the aforementioned aromatic group may be composed of phenyl, naphthyl, diphenyl, anthryl, benzene. And pyrenyl, phenanthryl and fluorenyl or other forms of polyphenyl ring substituents. The aforementioned ring-thin group includes cyclohexene, cyclohexadiene, cyclopentene and cyclopentadiene or other forms of cycloolefin. The aforementioned heterocyclic groups include pyrane, pyrroline, furan, benzofuran, 11 thiophene, benzothiophene. Pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, pyrrole, mouth ratio. Sitting on (pyrazole), mouth rice (imidazole). Introduce 0 (indole), alpha plug. Thiazole, isothiazole, oxazole, isoxazole, benzothiazole, benzoxazole, phenanthroline Phenanthroline) or other forms of heterocyclic ring. The aforementioned (gas-containing heterocyclic group includes: pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, n-pyrrol ( Pyrrole) ' 0 to 0 (pyrazole), 0 m salim (imidazole), ° 引 (indole) ' ° α α (thiazole), 0 0 塞. sitting (isothiazole), σ ox (oxazole), Iso, %^(isoxazole), benzothiazole, benzoxazole and phenanthroline or other forms of heterocyclic rings. In a preferred embodiment according to one example, The above reaction process can be expressed on page 24 200909438

One of the ethnic groups: hydrogen atom (Η), halogen atom (for example: fluorine, chlorine, bromine, iodine), C1-C20 alkyl group, C1-C20 cycloalkyl, alkoxyl group, halogen Substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group , an aryl group, a halogen-substituted aryl group, a halogen-substituted arylalkyl group, a haloalkyl-substituted aryl group, a haloalkyl-substituted arylalkyl group, a cyano group, a nitro group, a co-fortunate fragrance Aromatic group, aromatic heterocyclic group. In a preferred embodiment of the present example, the adjacent R8 and R9, R9 and R1G, R1Q and R11, and the like may also form at least one group to form an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocyclic ring. Any atomic group of an alkenyl group. The above aromatic ring, aromatic heterocyclic ring, cyclodecyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above-mentioned aromatic ring 'aromatic heterocyclic ring and ring number on page 25 200909438 The alkenyl group or the heterocyclic alkenyl group or the like may further contain one or more substituents. The substituents of the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be the same or different and are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom (for example, fluorine, Chlorine, desert, broken), c-C20 alkyl group, C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amine Group) 'C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aryl group a halogen group substituted with a haloalkyl group, an aromatic alkyl group substituted with a halogenoyl group, a cyano group, a nitro group, an aromatic group, and an aromatic heterocyclic group. The unsubstituted substituents in the above r8~r" may be the same or different, and the unsubstituted substituents in the above r8 to R11 are independently selected from one of the following groups: a hydrogen atom (H), a functional atom, and a C1-C20. An alkyl group, a C1-C20 cycloalkyl group, an alkoxy group (alk〇xyl group), a halogen-substituted C1-C20 alkyl group, a CrC20 substituted amine group (amin〇 group, C1-C20 醯) Acyl group, C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aryl group, haloalkyl-substituted aryl group a haloalkyl-substituted arylalkyl group, a cyano group, a nitro group, a conjugated aromatic ring group, an aromatic heterocyclic group. Several kinds of contents according to the present embodiment will be disclosed below. The structure of the transition metal complex of the carbene ligand. However, the scope of this specification should be based on the subsequent patent specification, page 26, 200909438, and should not be limited to the examples disclosed below.

Ir(fpmi)2(tfptz)

Ir(pmi)2(tfpypz)

Ir(fpmi)2(tfpypz)

\=J

Ir(pmi)2(pytz)

Ir(fpmi)2(pytz)

Ir(fpmi)2(pytrz) Page 27 200909438

\=j b*(mpmi)2(mptz)

Ir(mpmi)2(pypz)

Ir(mpmi)2(tfpypz)

Jr(mpmi)2(pytz)

|r(mmpmi)2(mptz)

Ir(mmpmi)2(pypz)

Ir(mmpmi)2(tfpypz)

Page 28 200909438

F

F

F

Lr(mfpmi)2(pytz)

F

Ir(mfpmi)2(tfptz) F

Ir(mfpmi)2(tfpypz)

F

MeO

Ir(mompmi)2(mptz)

MeO

MeO

Ir(mompmi)2(pytz)

MeO

Rr(mompmi)2(pypz)

MeO

Ir(mompmi)2(tfpypz)

MeO

Page 29 200909438

Ir(dmpmi)2(mptz) Ir(dmpmi)2(tfptz) Ir(dmpmi)2(pytz)

Ir(dmpmi)2(pypz) Ir(dmpmi)2(tfpypz)

Ir(dmpmi)2(pytrz) Page 30 200909438

F - F —

Ir(dfpmi)2(mptz) Ir(dfpmi)2(tfptz) Ir(dfpmi)2(pytz)

Ir(dfpmi)2(pypz)

Ir(dfpmi)2(tfpypz)

Ir(dfpmi)2(pytrz)

Page 31 200909438

Lr3 Ir(dfpmi)2(tfptz)

^r3 Ir(dfpmi)2(pytz)

Ir(dfpmi)2(pytrz)

Ir(nmi)2(tfptz)

Page 32 200909438

Page 33 200909438

Page 34 200909438

Ir(bmpi)2(pytz)

Page 35 200909438

Ir(bmopi)2(mptz)

Page 36 200909438

Ir(bmfpi)2(mptz)

Page 37 200909438

MeO MeO MeO

Page 38 200909438 f

Ir(bdfpi)2(pytz)

Ir(bdfpi)2(pytrz)

Page 39 200909438

Page 40 200909438

Ir(mmpmi)2 (you tz)

Ir(mmpmi)2(pytz) Page 41 200909438

Ir(mmpmbi)2(tfpypz)

Ir(mmpmbi)2(pytrz)

Ir(mfpmbi)2(pypz)

F

Ir(mfpmbi)2(pytz)

Ir(mfpmbi)2(tfpypz)

Ir(mfpmbi)2(pytrz)

Ir(pmbi)2(mptz)

,,N〆 0

Ir(pmbi)2(pytz) Page 42 200909438

CF

Ir(pmbi)2(pypz) Q:

/

Ir(pmbi)2(tfpypz) Ir(pmbi)2(pytrz)

Ir(fpmbi)2(tfptz)

Ir (fpmbi) 2 (mp tz)

Ir(ft»mbi)2(pytz)

Ir(fpmbi)2(pytrz)

Ir(fpmbi)2(pypz)

Ir(fpmbi)2(tfpypz)

Ir(dmpmbi)2(pytz) Page 43 200909438 〆

Ir(dfpmbi)2(pypz)

Ir(dmpmbi)2(pytrz)

Ir(dfpmbi)2(pytrz)

Ir(dmopmbi)2(mptz)

Ir(dmopmbi)2(tfptz)

Ir(dmopmbi)2(pytz) Page 44 200909438

Ir(dmopmbi)2(pypz)

Ir(dfpmbi)2(tfptz) Ir(dfpmbi)2(pytz)

Ir(dfpmbi)2(pypz)

Ir(dfpmbi)2(tfpypz) Ir(dfpmbi)2(pytrz)

Ir(nmbi)2(mptz) Ir(nmbi)2(tfptz) Ir(nmbi)2(pytz) Page 45 200909438

Ir(nmbi)2(pypz)

Ir(nmbi)2(pytrz)

Ir(pnmbi)2(mptz)

Ir(pnmbi)2(pytz)

Ir(pnmbi)2(pypz)

Ir(pnmbi)2(pytrz)

Ir(bpbi)2(mptz)

Ir(pnmbi)2(tfpypz)

Ir(bpbi)2(pytz) Page 46 200909438

Ir(pymbi)2(tfptz) Ir(pymbi)2(pytz)

Page 47 200909438

Ir(bmpbi)2(tfptz)

Ir(bmpbi)2(mptz)

Ir(bmpbi)2(pytrz)

Ir(bfpbi)2(pytrz) Page 48 200909438

Ir(bmopbi)2(pypz) Ir(bmopbi)2(tfpypz) Ir(bmopbi)2(pytrz)

Ir(bmmpbi)2(pypz) Ir(bmmpbi)2(tfpypz) Ir(bmmpbi)2(pytrz) Page 49 200909438

Page 50 200909438

Page 51 200909438

Ir(ptmi)2(mptz)

Page 52 200909438

Ir(ptmi)2(pytrz)

Ir(fptmi)2(tfptz)

Ir(fptmi)2(pytz)

Ir(fptmi)2(tfpypz)

Ir(fptmi)2(pytrz)

Ir(mmptmi)2(pytz) Page 53 200909438

F

F

F F

Ir(mfptmi)2(pypz)

F

MeO

MeO

Ir(momptmi)2(pytz) Page 54 200909438

MeO

MeO

MeO

f \ lr(moniptmi)2(pypz)

Ir(momptmi)2(tfpypz)

!r(mtfptmi)2(pytz)

Ir(mfptmi)2(tfpypz) Ir(mfptmi)2(pytrz)

Ir(dmptmi)2(mptz) Ir(dmptmi)2(tfptz) Ir(dmptmi)2(pytz) Page 55 f. 200909438

Ir(dmptmi)2(pytrz)

Ir(dmptmi)2(pypz)

Ir(dfptmi)2(pypz) Ir(dfptmi)2(tfpypz) Ir(dfptmi)2(pytrz) %

Page 56 200909438

/

Lr(dfptmi)2(mptz)

Ir(dmoptmi)2(pytr z)

Ir(ntmi)2(mptz) Ir(ntmi)2(tfptz) Ir(ntmi)2(pytz) Page 57 200909438

Ir(ntmi)2(pytrz)

Ir(pntmi)2(pytz)

Ir(pntmi)2(pytrz)

Ir(pytmi)2(pytz) Page 58 200909438

Ir(bmpdmi)2(tfptz) Ir(bmpdmi)2(mptz) Ir(bmpdmi)2(pytz) Page 59 200909438

Page 60 200909438

Ir(bmmpdmi)2(pypz)

Ir(bmmpdmi)2(tfpypz)

Ir(bmmpdmi)2(pytrz)

Ir(bmfpdmi)2(tfptz)

Page 61 200909438

Ir(bmfpdmi)2(pypz)

ί.

Ir(bmmopdmi)2(mptz) Ir(bimnopdini)^(tiptz) Ir(binmopdn]i)2(pytz) MeO MeO MeO

Ir(bmmopdmi)2(pypz) Ir(bmmopdmi)2(tfpypz) \

Ir(bmtfpdmi)2(mptz) Ir(bmtfpdmi)2(tfptz)

Ir(bmmopdim)2(pytrz)

Page 62 200909438 f3c

Ir(bmtfpdmi)2(pypz)

Page 63 200909438

Page 64 200909438

Page 65 200909438

f

V

Ir(pmdpi)2(pypz)

Λ

Ir(pmdpi)2(tfptz) Ir(pmdpi)2(pytz)

Page 66 200909438

Ir(fpmdpi)2(mptz) Ir(fjpmdpi)2(tfptz)

Ir(fpmdpi)2(pytz)

Ir(fpmdpi)2(pytrz)

Ir(mmpnidpi)2(pytz)

Ir(mmpmdpi)2(pytrz) Page 67 200909438

F

F

Ir(mfpmdpi)2(tfptz)

F

Ir(mfpmdpi)2(pypZ)

F

Ir(mfpmdpi)2(tfpypz)

Ir(mfpoidpi)2(pytrz)

Ir(dmpmdpi)2(pypz)

Ir(dmpmdpi)2(tfpypz) Ir(dmpmdpi)2(pytr2) Page 68 200909438

Ir(dfpmdpi)2(mptz)

Ir(dfpmdpi)2(t^tz)

Ir(dfpmdpi)2(pytz)

Ir(dfpmdpi)2(pypz)

Ir(dfpmdpi)2(tfpypz)

Ir(dfpmdpi)2(pytrz)

Ir(dmoptmi)2(pypz)

Ir(dmoptmi)2(tfpypz) Ir(dmoptmi)2(pytrz) 200909438

Ir(dfptmi)2(mptz)

Ir(dfptmi)2(tfptz) Ir(dfptmi)2(pytz)

Ir(nmdpi)2(mptz)

Ir(ntmdpi)2(tfptz)

200909438

\_

Ir(pymdpi)2(pytz)

Ir(pymdpi)2(mptz) Ir(pymdpi)2(tfptz)

Ir(pymdpi)2(pypz) Ir(pymdpi)2(tfpypz) Ir(pymdpi)2(pytrz) Page 71 200909438

Ir(bpdpi)2(mptz)

Ir(bpdpi)2(tfptz)

Ir(bpdpi)2(pytrz)

Ir(bmpdpi)2(mptz)

Page 72 200909438

f

Page 73 200909438 f

Ir(bmfpdpi)2(mptz)

Ir(bmfpdpi)2(pytz)

Page 74 200909438

\

Ir(bmtfpdpi)2(pypz)

Ir(bmt^»dpi)2(tfptz) f3c

Ir(bmtf^dpi)2(pytz)

Page 75 200909438

f

V

Page 76 200909438

Page 77 200909438

In the present embodiment, the above transition metal complex containing a carbene ligand can be used in an organic electroluminescence element and/or a phosphorescence element, particularly in organic electroluminescence. An illuminant material, an electronic transport material, or a hole transport material in the component and/or the squaring element. Further, the above transition metal complex containing a carbene ligand may also be applied to an eiectronic transport material or a hole transport material of other organic electrons, page 09200909438 (organic electronic devices). ). The organic electronic component described above may be an organic solar cell, an organic thin film transistor, an organic photoconductor, or other organic semiconductor component familiar to those skilled in the art.

Example 1. General procedure for forming a transition metal complex containing a carbene ligand centered on a silver metal. General procedure for synthesizing a ruthenium metal dimer: Refer to the following reaction formula, by reacting compound 4 with ruthenium chloride. A ruthenium metal dimer (compound 5) is formed.

R = H, F, Me The general steps of the above reaction are as follows. First, silver oxide (Ag20) (926 mg, 4 mm〇le) was added to a reactor. Next, the above-mentioned compound 4 (1 22 g, 4 mmole) and hydrazine chloride (353 mg, lmm〇le) were added, respectively, and 4, such as ethylene glycol monoethyl ether, was added as a solvent. Secondly, the faint pigs were coated with the above reactor and placed in a 12 〇 C oil bath steel for reaction hours. Next, add water to the third ruminant-long-year-old scorpion to force the solids out and filter. The filtrate was then removed and the solid was washed with a second field of e + m m & gas, and the soluble product and the insoluble silver oxide were separated accordingly. After that, I will work on the liquid to obtain a solid, and recrystallize it by using ethanol to page 79, 200909438 to obtain the above compound 5, which is a white-gray solid (2〇3 mg) yield of 35%. . (General procedure for synthesizing a transition metal complex containing a olefinic ligand centered on a silver metal: by reacting the compound 6 with a different compound 7, compound 9, and compound 11, respectively, with reference to the following reaction formula, respectively Transition metal complexes (compounds 8, 10, 12) containing different carbene ligands are formed.

+ R3 HN, 々N

Et3N, 85 °C 2-ethoxyethanol

R3 nK u 7a R3 = Me 7b R3 = CF, 8a R1 = Me, R2 = H, R3 = Me 8b R1 = Me, R2 = H, R3 = CF3 8c R1 = Me, R2 = F, R3 = Me 8d R1 = Me, R2 = F, R3 = CF3 8e R1 = Me, R2 = Me, R3 = Me 8f R1 = Me, R2 = Me, R3 = CF3 R2 R2

R2 +

9a R4 = H 9b R4 = CF3 10a R1 = Me, R2 = H, R4 = H 10b R1 = Me, R2 = H, R4 = CF3 10c R1 = Me, R2 = F, R4 = H lOd R1 = Me, R2 = F, R4 = CF3 lOe R1 = Me, R2 = Me, R4 = H lOf R1 = Me, R2 = Me, R4 = CF3 Page 80 200909438 R2

12b R1 = Me, R2 = Η, X = N, Y = N 12c R1 = Me, R2 = F, X = N, Y = C 12d R1 = Me, R2 = F, X = N, Y = N 12e R1 = Me, R2 = Me, X = N, Y = C 12f R1 = Me, R2 = Me, X = N, Y = N

6

The above reaction scheme will be described below by taking the compound 9b as an example. First, the above compound 6 (50 mg, 0.0434 mmole), compound 9b (21 mg, 0.0955 mmole) and triethylamine (14 mg, 0.0955 mmole) were separately added to a fourth reactor. Next, 2 ml of ethylene glycol monoethyl ether was added as a solvent, and the reaction system was placed in a 120 ° C oil bath steel for 1 hour, in which a solid was gradually precipitated during the reaction. After the reaction was completed, the product was directly filtered to remove the solution, and the obtained solid was washed with methanol. Finally, the above compound 10d (notl0b?!) was obtained as a white solid (43 mg) in a yield of about 71%.

Example 2.

Iridium(III) bis(l-phenyl-3-methylimdazolin-2-ylidene-C,C2 ) (2-(5-Methyl-2H-l,2,4-triazol-3-yl)-pyridine) [hereinafter referred to as Ir(pmi)2(mptz)] Page 81 200909438

lH NMR (CD2C12, 400 MHz) 8.04 (d, 1H, CH-N), 7.94 (d, 1H), 7.73 (td, 1H), 7.45 (d, 1H), 7.43 (d, 1H), 7.13-7.11 (m, 2H), 6.96-6.89 (m, 3H), 6.85 (d, 2H), 6.71-6.63 (m, 2H), 6.53 (d, 1H), 6.43 (d, 1H), 3.09 (s, 3H ), 2.99 (s, 3H), 2.33 (s, 3H).

Example 3.

Iridium(III) bis(l-phenyl-3-methylimdazolin-2-ylidene-C,C2 ) (2-(5-Trifloromethyl-2J^-l,2,4-triazol-3-yI)-pyridine) Referred to as Ir(pmi)2(tfptz)]

lU NMR (CD2C12, 400 MHz) 8.19 (d, 1H, CH-N), 7.96 (d, 1H), 7.75 (t, 1H), 7.39 (d, 2H), 7.08-7.02 (m, 2H), 6.91 -6.78 (m, 5H), 6.70-6.61 (m, 2H), 6.48 (d, 1H), 6.39 (d, 1H), 3.08 (s, 3H), 2.95 (s, 3H).

Example 4.

Iridium(III) bis(l-phenyl-3-methylimdazolin-2-ylidene-C,C2 )(2-(2iy-Pyrazol-3-yl)-pyridine) Page 82 200909438 [hereinafter referred to as Ir(pmi) 2 ( Pypz)]

TH NMR (CD2C12, 400 MHz) ^ 7.90-7.92 (m, 1H, CH-N), 7.59-7.68 (m, 2H), 7.46 (d, 1H), 7.42 (dd, 2H), 7.11 (td, 2H ), 6.85-6.93 (m, 2H), 6.83 (d, 1H), 6.82 (d, 1H), 6.76-6.80 (m, 1H), 6.72 (d, 1H), 6.69 (td, 1H), 6.63 ( Td, 1H), 6.48 (d, 1H), 6.56 (dd, 1H), 6.45 (dd, 1H), 3.04 (s, 3H), 2.98 (s, 3H); HRMS Calcd. for C28H24IrN7 651.1722, Found: 651.1725 .

Example 5.

Iridium(III) bis(l-phenyl-3-methylimdazolin-2-yIidene-C,C2 )(2-(5-Trifluoromethyl-2iT-pyrazol-3-yl)-pyridine) [hereinafter referred to as Ir(pmi) 2 ( Tfpypz)]

!H NMR (CD2C12, 400 MHz) ^ 7.95-7.93 (m, 1H, CH-N), 7.72-7.65 (m, 2H), 7.47 (d, 1H), 7.42 (d, 2H), 7.13-7.10 ( m, 2H), 6.98 (s, 1H), 6.82 (d, 1H), 6.94-6.85 (m, 5H), 6.71-6.64 (m, 2H), 6.50 (dd, 1H), 6.42 (dd, 1H) , 3.01 (s, 3H), 3.00 (s, 3H); HRMS Calcd. for Page 83 200909438 C29H23F3IrN7 719.1596, Found: 719.1592.

Example 6.

Iridium(III) bis(l-phenyl-3-methylimdazolin-2-ylidene-C,(72')(5-(pyridine-2-yl)-7£T-triazolate) [hereinafter referred to as Ir(pmi)2 ( Pytz)]

\=J NMR (CD2C12, 400 MHz) 8.15 (s, 1H), 7.95-7.94 (m, 1H), 7.77-7.68 (m, 2H), 7.46 (d, 1H), 7.44 (d, 1H), 7.15 -7.12 (m, 2H), 6.96-6.84 (m, 5H), 6.73-6.65 (m, 2H), 6.55 (dd, 1H), 6.47 (dd, 1H), 3.00 (s, 3H), 2.99 (s , 3H); HRMS Calcd. for C27H23IrN8 652.1675, Found: 652.1677.

Example 7.

Iridium(III) bis(l-phenyl-3-methylimdazolin-2-ylidene-C,C2 )(2-(1H-tetrazol-5-yl)pyridine) [hereinafter referred to as Ir(pmi)2(pytrz)]

NMR (CD2C12, 400 MHz) 8.33 (d, 1H), 8.02 (d, 1H), 7.86 (td, page 84 200909438 1H), 7.46 (d, 1H), 7.44 (d, 1H), 7.16-7.10 ( m, 3H), 6.98-6.90 (m, 2H), 6.87 (d, 1H), 6.84 (d, 1H), 6.74-6.66 (m, 2H), 6.53 (dd, 1H), 6.45 (dd, 1H) , 2.98 (s, 3H), 2.95 (s, 3H); HRMS Calcd. for C26H22IrN9 653.1627, Found: 653.1627.

Example 8. Iridium(III) bis(l-(4-fluorophenyl)-3-methylimdazoIin-2-ylidene-C,C2>) Chloride Dimer [hereinafter referred to as Ir(fpmi)2 dimer]

NMR (CD2C12, 400 MHz) 7.56 (d, 4H), 7.19 (d, 4H), 6.96 (dd, 4H), 6.46 (td, 4H), 5.75 (dd, 4H), 3.87 (s, 12H)

Example 9.

Iridium(III) bis(l-(4-fluorophenyl)-3-raethylimdazolin-2-ylidene-C, C1 2 )(2-(5-Methyl-2H-l,2,4-triazol-3-yl)- Pyridine) [hereinafter referred to as Ir(fpmi) 2 (mptz)]

NyN 1 B. NMR (CD2C12, 400 MHz) ^ 8.05 (d, 1H, CH-N), 7.93 (d, 1H), 2 Page 85 200909438 7.75 (td, 1H), 7.42 (d, 1H), 7.39 (d, 1H), 7.12-7.06 (m, 2H), 6.99-6.96 (m, 1H), 6.86 (d, 2H), 6.66-6.57 (m, 2H), 6.19 (dd, 1H), 6.08 (dd , 1H), 3.08 (s, 3H), 2.98 (s, 3H), 2.33 (s, 3H).

Example 10.

Iridium(III) bis(l-(4-fIuorophenyI)-3-methyIimdazolin-2-ylidene-C, C2 )(2-(5-Trifluoromethyl-2^-l,2,4-triazoI-3-yl)- Pyridine) [hereinafter referred to as Ir(fpmi)2(tfptz)]

Ή ( NMR (CD2C12, 400 MHz) 8.19-8.17 (m, 1H, CH-N), 7.99 (d, 1H), 7.84 (td, 1H), 7.44 (d, 2H), 7.41 (d, 2H), 7.13-7.09 (m, 3H), 6.88 (d, 2H), 6.68-6.56 (m, 2H), 6.17 (dd, 1H), 6.06 (dd, 1H), 3.04 (s, 3H), 2.97 (s, 3H).

Example 11.

Iridium(III) bis(l-(4-f!uorophenyl)-3-methylimdazolin-2-ylidene-C, C2 )(2-(2^-Pyrazol-3-yl)-pyridine) [hereinafter referred to as Ir(fpmi) )2(pypz)]

\=y H NMR (CD2C12, 400 MHz) 7.90 (dd, 1H, CH-N), 7.68-7.61 (m, page 86 200909438 2H), 7.47 (d, 1H), 7.40 (dd, 2H), 7.11 -7.04 (m, 2H), 6.85-6.79 (m, 3H), 6.71 (d, 1H), 6.64-6.54 (m, 2H), 6.23 (dd, 1H), 6.09 (dd, 1H), 3.03 (s , 3H), 2.97 (s, 3H); HRMS Calcd. for C28H24F2IrN7 689.1690, Found: 689.1687.

Example 12.

Iridium(III) bis(l-(4-fluorophenyl)-3-methylimdazolin-2-ylidene-C, C2 )(2-(5-Trifluoromethyl-2^-pyrazol-3-yl)-pyridine) [hereinafter referred to as Ir (fpmi)2(tfpypz)]

lH NMR (CD2C12, 400 MHz) ^ 7.93 (d, 1H, CH-N), 7.71-7.69 (m, 2H), 7.43 (d, 1H), 7.39 (dd, 2H), 7.11-7.07 (m, 2H ), 6.98 (s, 1H), 6.92-6.90 (m, 1H), 6.89-6.85 (m, 2H), 6.63-6.59 (m, 2H), 6.16 (dd, 1H), 6.06 (dd, 1H), 3.00 (s, 3H), 2.99 (s, 3H); HRMS Calcd. for C29H2iF5IrN7 755.1408, Found: 755.1406.

Example 13.

Iridium(III) bis(l-(4-fluorophenyl)-3-methylimdazolin-2-ylidene-C, C2') (5-(pyridine-2-yl)-2^-triazolate) [hereinafter referred to as Ir(fpmi) 2(pytz)] Page 87 200909438

NMR (CD2C12, 400 MHz) 8.15 (s, 1H), 7.94-7.92 (m, 1H), 7.77-7.69 (m, 2H), 7.43 (d, 1H), 7.40 (d, 1H), 7.13-7.07 ( m, 2H), 6.93-6.90 (m, 1H), 6.86 (d, 1H), 6.85 (d, 1H), 6.67-6.58 (m, 2H), 6.22 (dd, 1H), 6.11 (dd, 1H) , 2.99 (s, 3H), 2.98 (s, 3H); HRMS Calcd. for C27H2iF2IrN8 688.1486, Found: 688.1486.

Example 14.

Iridium(III) bis(l-(4-fIuorophenyl)-3-methylimdazolin-2-yIidene-C, C2 ) (2-(2^-tetrazol-5-yl)pyridine) [hereinafter referred to as Ir(fpmi) 2 ( Pytrz)]

\=f lH NMR (CD2C12, 400 MHz) ^ 8.35-8.33 (m, 1H), 8.03-8.01 (m, 1H), 7.89 (td, 1H), 7.43 (d, 1H), 7.42 (d, 1H) , 7.18-7.09 (m, 3H), 6.88 (d, 1H), 6.85 (d, 1H), 6.69-6.60 (m, 2H), 6.20 (dd, 1H), 6.09 (dd, 1H), 2_97 (s ,3H), 2.94 (s,3H); HRMS Calcd. for C26H20F2IrN9 689.1439, Found: 689.1441. Page 88 200909438

Example 15. Iridium(III) bis(l-(4-methylphenyl)-3-methylimdazolin-2-ylidene C,C2) Chloride Dimer [hereinafter referred to as Ir(mpmi)2 dimer]

NMR NMR (CD2C12, 400 MHz) ^ 7.47 (d, 4H), 7.05 (d, 4H), 6.77 (d, 4H), 6.42 (dd, 4H), 5.96 (s, 4H), 3.84 (s, 12H) , 1.95 (s, 12H)

Example 16.

Iridium(III) bis(l-(4-methylphenyl)-3-methylimdazolin-2-yIidene-C,C2,)(2-(5-Methyl-2flr-l,2,4-triazol-3-yl)- Pyridine) [hereinafter referred to as Ir(mpmi)2(mptz)]

!H NMR (CD2C12, 400 MHz) 8.02 (d, 1H, CH-N), 7.96 (d, 1H), 7.72 (td, 1H), 7.42 (d, 1H), 7.39 (d, 1H), 7.02 ( d, 1H), 7.00 (d, 1H), 6.96-6.93 (m, 1H), 6.83 (d, 2H), 6.74-6.69 (m, 2H), 6.30 (d, 1H), 6.20 (d, 1H) , 3.08 (s, 3H), 2.97 (s, 3H), 2.33 (s, 3H), 2.14 (s, 3H), 2.13 (s, 3H). Page 89 200909438

Example 17.

Iridium(III)bis (1-(5-Trifluoromethyl1,2,4-triazol-3-yl)-pyridine) Hereinafter referred to as Ir(mpmi)2(tfptz)]

^ NMR (CD2C12, 400 MHz) 8.16 (d, 1H, CH-N), 8.02 (d, 1H), 7.80 (td, 1H), 7.44 (d, 1H), 7.40 (d, 1H), 7.09-7.02 (m, 3H), 6.86-6.85 (m, 2H), 6.76-6.72 (m, 2H), 6.28 (s, 1H), 6.19 (s, 1H), 3.04 (s, 3H), 2.96 (s, 3H) ), 2.15 (s, 3H), 2.14 (s, 3H).

Example 18.

Iridium(III) bis(l-(4-methylphenyl)-3-methylimdazolin-2-ylidene-C,C2 )(2-(2£T-Pyrazol-3-yl)-pyridine) [hereinafter referred to as Ir(mpmi) 2(pypz)]

'H NMR (CD2C12, 400 MHz) ^ 7.93 (d, 1H, CH-N), 7.67-7.59 (m, 2H), 7.45 (d, 1H), 7.40 (d, 1H), 7.39 (d, 1H) , 7.01 (d, 2H), 7.00 (d, page 90 200909438 2H), 6.82-6.77 (m, 3H), 6.73-6.68 (m, 2H), 6.71 (d, 2H), 6.35 (s, 1H) , 6.22 (s, 1H), 3.01 (s, 3H), 2.97 (s, 3H), 2.15 (s, 3H), 2.13 (s, 3H).

Example 19.

Iridium(III) bis(l-(4-methylphenyI)-3-methylimdazolin-2-ylidene-C,C2 )(2-(5-Trifluoromethyl-2^-pyrazol-3-yl)-pyridine) [hereinafter referred to as Ir (mpmi)2(tfpypz)]

!H NMR (CD2C12, 400 MHz) ^ 7.96 (d, 1H, CH-N), 7.70-7.64 (m, 2H), 7.43 (d, 1H), 7.39 (d, 1H), 7.02 (d, 2H) , 7.00 (d, 2H), 6.96 (s, 1H), 6.90-6.86 (m, 1H), 6.83 (d, 2H), 6.74-6.70 (m, 2H), 6.28 (s, 1H), 6.19 (s , 1H), 2.99 (s, 3H), 2.98 (s, 3H), 2.15 (s, 3H), 2.14 (s, 3H).

Example 20.

Iridium(III) bis(l-(4-methyl phe nyl)-3-me thylimdazolin-2-ylidene- C*,C2 ) (5-(pyridine-2-yl)-/ ugly-triazolate) [hereinafter referred to as Ir (mpmi)2(pytz)]

Page 91 200909438 lH NMR (CD2C12, 400 MHz) ^ 8.14 (s, 1H), 7.95 (d, 1H), 7.75-7.66 (m, 2H), 7.43 (d, 1H), 7.40 (d, 1H), 7.03 (d, 1H), 7.01 (d, 1H), 6.90-6.87 (m, 1H), 6.84-6.82 (m, 2H), 6.74-6.70 (m, 2H), 6.32 (s, 1H), 6.23 ( s, 1H), 2.99 (s, 3H), 2.97 (s, 3H), 2.15 (s, 3H), 2.14 (s, 3H).

Example 21.

Iridium(III) bis(l-(4-methylphenyl)-3-methyIimdazoIin-2-yIidene-C,C2 )(2-(2^-tetrazol-5-yl)pyridine) [hereinafter referred to as Ir(mpmi)2( Pytrz)]

H NMR (CD2C12, 400 MHz) 8.32 (d, 1H), 8.03 (d, 1H), 7.85 (td, 1H), 7.43 (d, 1H), 7.41 (d, 1H), 7.14-7.11 (m, 1H ), 7.05 (d, 1H), 7.03 (d, 1H), 6.84 (d, 1H), 6.82 (d, 1H), 6.77-6.72 (m, 2H), 6.30 (d, 1H),

A second embodiment of the present invention discloses an electric excitation light (A(10).iumi job element

Containing a transition metal complex containing a carbene ligand, the above

As follows: Page 92 200909438

Wherein, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten, rhenium, osmium, iridium, Platinum. R1 is selected from one of the following groups: a C1-C20 alkyl group, a C1-C20 cycloalkyl group, a conjugated aromatic ring group, a heteroaromatic heterocyclic group. R2 ~ R7 may be the same or different, and R2 ~ R7 are independently selected from one of the following groups: hydrogen atom (H), halogen atom (for example: fluorine, gas, bromine, iodine), C1-C20 alkyl group (alkyl group) ) 'C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 acyl group, C1- C20 ester group, C1-C20 amide group 'aryl group, halogen-substituted aromatic group, halogen-substituted aromatic alkyl group, halogen-substituted aromatic group, haloalkyl-substituted aromatic burning a group, a cyan group, a nitro group, a conjugated aromatic ring group, an aromatic heterocyclic group. In a preferred embodiment of the present embodiment, the adjacent R2 and R3, r4 and R5, R5 and R6, R6 and R7, etc. of the transition metal complex containing a carbene ligand may also be Any atomic group forming an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocycloalkenyl group. The substituents which are not % in the above r2 to R may be the same or different, and the unsubstituted substituents in the above R2 to R7 are independently selected from one of the following groups: hydrogenogen, page 93, 200909438, (halogen), halogen atom, C1-C20 alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, C1-C20 醯Acyl group, C1-C20 S ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, substituted aryl group, haloalkyl substituted aromatic a group, an alkyl-substituted arylalkyl group, a cyano group, a nitro group, a total aromatic group, and an aromatic heterocyclic group. r The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring or aromatic heterocyclic ring-alkenyl group Or a heterocycloalkenyl group or the like may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example: hydrazine, chlorine, bromine, broken); an aryl group, a halogen-substituted aryl group, Halogen-substituted arylalkyl, dentate-substituted aryl, haloalkyl-substituted aryl, aryl-substituted C1-C20 alkyl; electron donating group such as C1-C20 alkyl, C1 -C20 cycloalkyl (eg, decyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group 'C1-C20 substituted amino group, aromatic amine with substituent a group [eg, an aniline]; an electron withdrawing group such as a halogen, a nitrile, a nitro group, a carbonyl group, or a cyano group (CNano). a C1-C20 alkyl group substituted with a halogen (e.g., trifluoroalkyl, CF3); a heterocyclic substituent. In another preferred embodiment according to this embodiment, the structure of the above-mentioned carbene-containing ligand, page 94, 200909438, is as follows:

Among them, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten, rhenium, osmium, iridium, platinum ( Platinum). R1 is selected from one of the group consisting of C1-C20 alkyl, C1-C20 cycloalkyl, aromatic aromatic groups, heteroaromatic heterocyclic groups. R2 to R7 may be the same or different, and R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom (for example, fluorine, gas, bromine, iodine) 'CVCm alkyl group, C1-C20 ring-based, alkoxyl group 'halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 vinegar Ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aryl group, haloalkyl-substituted aryl group, haloalkyl-substituted aryl group, Cyano, nitro, aromatic aromatic groups, aromatic heterocyclic groups. According to a preferred embodiment of the present invention, the adjacent R 2 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 and the like may also form an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocyclic ring, respectively. Any atomic group of an alkenyl group. The above aromatic ring, aromatic heterocyclic ring, cyclo-yl group or heterocyclic ring group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above-mentioned aromatic ring, aromatic heterocyclic ring, ring on page 95, 200909438 The dilute or heterocycloalkenyl group may further comprise one or more substituents. The unsubstituted substituents in the above R2 to R7 may be the same or different, and the unsubstituted substituents in the above R2 to r7 are independently selected from one of the following groups: a hydrogen atom (Η), a halogen atom, and a C1-C20 system. (alkyl group), C1-C20 3 alkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group (amino gr〇up), Cl-C20 fluorenyl group ( Acyl group), Cl-C20 ester group, Cl-C20 f amide group, aryl group, halogen-substituted aryl group, halogen-substituted aromatic alkyl group, haloalkyl-substituted aryl group a halogen-substituted aromatic alkyl group, a cyano group, a nitro group conjugated aromatic ring group (ar〇matic group), an aromatic heterocyclic group. According to the present example, Z1 in the above structure may be any atomic group for constituting the nitrogen-containing heteroaromatic ring or the nitrogen-containing heterocycloalkenyl group. The above nitrogen-containing heteroaromatic ring or nitrogen-containing heterocycloalkenyl may be a five-membered ring, a six-membered ring or a seven-membered ring, and the above Z1 may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, Huan, chlorine, bromine, iodine); an aromatic 'halogen-substituted aromatic group, Halogen-substituted arylalkyl, haloalkyl-substituted aryl, ifi-substituted arylalkyl, aryl-substituted C1-C20-based; electron donating group such as C1-C20 alkyl, C1 -C20 cycloalkyl (e.g., thiol, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, C1-C20 substituted amino group, having a page 96 200909438 Aromatic amine group of the base [such as aniline]; electron withdrawing group such as halogen, nitrile, nitro, carbonyl, cyano , -CN) a C1-C20 alkyl group substituted with a halogen (for example, a trifluoroalkyl group, CF3); a heterocyclic substituent group. In the structure according to the present example, Y may be one selected from the group consisting of nitrogen (N), carbon (C), oxygen (oxime), sulfur (S), and the like, and Y may further contain a substituent. Q is an atomic group containing at least two atoms to constitute a nitrogen-containing heterocyclic ring. The atomic combination contained in Q is selected from the group consisting of nitrogen, carbon, oxygen, and sulfur. The above nitrogen-containing heterocyclic group may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, chlorine, bromine 'iodine); an aromatic group, a halogen-substituted aromatic group, Halogen-substituted aroma-based, halogen-substituted aryl, haloalkyl-substituted arylalkyl, aryl-substituted C1-C20 alkyl; electron donating group such as C1-C20 alkyl, C1 -C20 cycloalkyl (for example: methyl, ethyl, butyl, cyclohexyl), C1-C20 alkoxy group, Cl-C20 substituted amino group, substituted aromatic amine group [eg aniline]; electron withdrawing group such as halogen, nitrile, nitro, carbonyl, cyano (-CN) and halogen C1-C20 alkyl (e.g., trifluoromethyl, CF3); heterocyclic substituent. In another preferred embodiment according to this embodiment, the structure of the above-mentioned terminal-olefin-containing ligand on page 97 200909438 is as follows:

Wherein, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten (tungsten), rhenium, osmium, iridium, Platinum). R1 is selected from one of the following groups: C1-C20 leuntyl, C1-C20 cycloalkyl, aroma group aromatic group heteroaromatic heterocyclic group. R2 to R11 may be the same or different, and R2 to R11 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom (for example, fluorine 'chlorine, bromine, an alkyl group, C1-C20 a cycloalkyl group, an alkoxyl group, a halogen-substituted C1-C20 alkyl group, a C1-C20 substituted amino group, a C1-C20 acyl group, a C1-C20 ester group (ester Group), C1-C20 amide group 'aryl group, halogen-substituted aryl group, halogen-substituted aromatic alkyl group, halogen group-substituted aryl group, haloalkyl-substituted aryl group, cyano group ( Cyano), nitro' a total aromatic group, aromatic heterocyclic group. According to this example, the adjacent R2 and R3, R4 and R5, R5 and R6, R6 and R7, R8 and R9, R9 and R1G, R1G and R" and the like may also be any atomic group forming an aromatic ring, an aromatic heterocyclic ring, a cycloaliphatic group or a heterocyclic alkenyl group, respectively. The above aromatic ring, aromatic heterocyclic ring, and ring-shaped ring The base or the heterocyclic group may be a five-membered ring, a six-membered ring, or a seven-membered ring of 200909438, respectively. The above R2 to R7 are not substituted by a ring. The same or different, and the unsubstituted substituents in the above R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group, a C1-C20 naphthenic ring. Alkoxyl group, halogen-substituted C1-C20 yard group, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group , C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, haloalkyl-substituted aryl group (yl, cyano) , a nitro group, an aromatic group, a .3⁄4 aromatic heterocyclic group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may further comprise one or a plurality of substituents. The substituents of the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be the same or different and are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom. (eg, fluorine, chlorine, bromine, iodine), C1-C20 alkyl group, C1-C20 cycloalkyl, alkoxyl group, _ Substituted C1-C20 alkyl, C1-C20 substituted amino group, Cl-C20 acyl group 'Cl-C20 ester group, C1-C20 amide group , an aromatic group, a halogen-substituted aromatic group, a functionally substituted aromatic alkyl group, a haloalkyl-substituted aromatic group, a haloalkyl-substituted aromatic alkyl group, a cyano group, a nitro group, a conjugated aromatic group Aromatic group, aromatic heterocyclic group. In the structure according to the present example, Y is selected from one of the following groups: nitrogen (N), carbon (C), oxygen (oxime), sulfur (S), and the like. Y may further comprise a substituent. Q series is from one to 99. 200909438 A group of atoms containing two atoms is added to form a nitrogen-containing heterocyclic group (heterocyclic

Substituted aryl, 1 different 'and the above substituents are independently selected from one of the following groups of atoms (eg, fluorine, chlorine, bromine, iodine); aryl, halogen halogen substituted arylalkyl, _alkyl substituted Aromatic group, haloalkyl-substituted arylalkyl group, aryl-substituted cl_c2 alkyl group; electron donating group such as Cl-C20 alkyl group, cl_C2 anthracene ring group (for example: methyl group, ethyl group) , butyl 'cyclohexyl), C1-C20 alkoxy group (aik〇Xy group), ci-C20 substituted amino group, substituted aromatic amine group [eg aniline], Electron withdrawing group such as halogen, sub-; nitrile, nitro, carbonyl 'cyano, —CN, and halogen-substituted C1-C20 alkyl (eg Trifluoromethyl, CF3); heterocyclic substituent. According to this embodiment, the aforementioned aromatic group may be composed of phenyi, naphthyl, diphenyl, anthryl, pyrenyi, phenanthryl. And fluorenyl or other forms of polyphenyl ring substituents. The aforementioned cycloalkenyl group comprises cyclohexene, cyclohexadiene, cyclopentene and cyclopentadiene or other forms of cycloolefin. The aforementioned heterocyclic group includes pyrane, pyrroline, furan, benzofuran, thiophene, benzothiophene. Pyridine, 啥琳第100页200909438 (quinoline), isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole ), mouth imwa (imidazole), 0 to 0 (indole), for sale. Thiazole, isothiazole '°ox', oxazole, isoxazole, benzothiazole, benzoxazole, dinitrogen Phenanthroline or other forms of heterocyclic ring. The aforementioned nitrogen-containing heterocyclic group includes D pyridine, quinoline, isoquinoline, "pyazine, pyrimidine, pyrrole, f σ pyrazole, imidazole, indole, thiazole, isothiazole 'oxazole', isoxaz〇ie, stupid and thiazole (benzothiazole), benzopyrene, benzoxazole and phenanthr〇line or other forms of heterocyclic ring. The general flow of forming an electroluminescent device: First, pour the volume ratio into a neutral detergent in the ultrasonic oscillator: go to (Ion water = 1:50 cleaning solution to oscillate and clean the above-mentioned etching to complete the etching 5 minutes. Then, brush the above glass with a soft brush and place it in deionized water and electronic grade (4) for 5 minutes. Then, dry the above-mentioned ιτ〇 glass with nitrogen. The glass is placed in a UV-Ozone machine for 5 minutes, taken out and fixed on a substrate (face down). Next, the substrate is placed in an evaporation machine and evacuated until the vacuum of the chamber When the degree reaches 5xi〇_6 t〇rr, the step of vapor-depositing the film on page 101200909438 is started. When the film is deposited, the rate of organic coating is controlled between 1~2 A/s, and the rate of metal coating is magnesium. 5 A/s and silver 0.5 person/s; wherein the ratio of magnesium/silver alloy is 10:1, and the thickness of the metal film deposited by magnesium-silver is 55 nm. Finally, a layer of 100 nm silver is plated as a protective layer. If the metal system is selected as a lithium fluoride/aluminum system, first 0.1 At a rate of /s, the lithium fluoride is evaporated and the film thickness is controlled to be 1 nm; then, a layer of 100 nm of aluminum is applied as a protective layer. During the above coating, the rotation rate of the element is 20 rpm, and after the end of the evaporation, wait for 20 Minutes to facilitate the cooling of the metal electrode; then, the chamber is backfilled with nitrogen until the normal pressure is restored. On the other hand, after the preparation of the above-mentioned electroluminescent element, the electro-optic fluorescence of the measuring element is measured by the Hitach F-4500 spectra scan spectrometer. The spectrum (EL spectra) and the CIE coordinate diagram (CIEcoordination), in addition, the current (current), voltage (voltage) and brightness (brightness) of the component are measured by the Keithley 2400 programmable voltage-current source. All are operated at room temperature under atmospheric pressure (about 20 ° C).

Example 22. Performance Comparison of Electroluminescent Device The present example will disclose the structure and properties of several preferred embodiments of the electroluminescent device according to the present embodiment. However, the scope of the specification should be based on the scope of the subsequent patent. It should not be limited to the following examples. Sample device structures Each element tested in this example is a layered structure, and its structure is shown on page 102. 200909438 as shown in the figure--. Each of the elements tested in this example employs the above-described rib glass as the substrate 'and contains the above-described face complex containing the chelating ligand as a guest material. On the other hand, the present example performs the performance test of the element by changing other constituent materials such as an electrode material, a host material, and a charge carrier transport layer material in the above elements. Where 'in the selection of the electrode, in addition to the use of Mg: Ag / Ag electrode, also used

The LiF/ΑΙ electrode is tested; in the selection of the host luminescent material, materials with high energy gap and high triplet energy such as mCP (3,5-Bis (N-carbaz〇lyl)benzene), CzSi (9-(4) are selected. -ieri-butylphenyl)-3,6-bis (ίτ; phenylsilyl)-9/f-carbazole) 'BSB (4,4,-bis-triphenylsilanyl-biphenyl) and UGH2 〇?-bis(triphenyl-silyly)benzene) Therefore, the triplet energy is prevented from being reversely transmitted back to the triplet state of the host luminescent material to reduce the element efficiency, wherein when the BSB and the UGH2 are used as the main luminescent material, the body luminescent material is injected to reduce the hole injection. Energy barrier, so join a mCP layer; pass on the charge carder

BCP is used in the selection of the material for the transport layer.

(2,9-Dimethyl-4,7-diphenyl-[l,l〇]phenanthroline) and TPBI (2,9-Dimethyl-4,7-diphenyl-[l,l〇]phenanthroline) can be used as electric resistance The carrier material, or the hole blocking and electron transport layer material, is because the carrier energy transport material BCP, TPBI or mCP with wide energy gap can suppress the diffusion of high energy triplet excitons from the host luminescent material layer to the carrier transport. Floor. The chemical structures of the materials used in the above-mentioned fabrication of the device under test are as shown in the second figure. The detailed structure of each tested component is as follows: Component A: Page 103 200909438 ITO/TCTA (40) / complex: mCP (7 %) (30) / BCP (15) / Alq (30) / Mg: Ag / Ag components B : ITO/NPB (20) / TCTA (10) / complex: CzSi (8 %) (30) / BCP (15) / Alq (30) / Mg: Ag / Ag Component C : ITO / TCTA (30) / mCP (20)/complex: BSB (7 %) (30)/BCP (10)/Alq (30)/ Mg: Ag/Ag Element D: NPB (20)/TCTA (10)/ complex: CzSi (8 % ) (30) / TPBI (30) / LiF / Al ' Component E : ITO / TCTA (40) / mCP (15) / complex: UGH2 (7 %) (30) / BCP (40) / Mg: Ag / Ag Element F: ITO/TPD (20)/mCP (20)/complex: UGH2 (7 %) (30)/BCP (40) / LiF/Al Above is the composition of the component AF', where the cathode of each component is Mg : Ag(55)/Ag(100), or LiF(l)/Al(100). The thickness of each of the above element structures is simply 4 nm.

K sample element luminescence performance comparison The test results of each component luminescence performance are compared as shown in the following table 1:

Maximum brightness (cd/m2) (voltage / volt) /U ΊΤ货夕0 Ί王月 b~仪

Large light length m) Most oscillating (η page 104 200909438 volts) Ir(pmi)2(pypz) A 4.3 8.4 (9.0) 25738 (14.5) 362.4 16.9 (9.0) 6.0 (8.5) (0.14, 0.31) 486 B 4.2 7.9 (10.0) 13955 (16.0) 398.8 13.1 (10.0) 4.2 (9.5) (0.15, 0.32) 486 Ir(pmi)2(tfpypz) A 6.0 5.6 (10.0) 7875 (16.0) 249.8 10.1 (10.0) 3.2 (9.5 (0.14,0.26) 478 B 5.4 5.3 (11.0) 6346 (20.0) 193.2 9.8 (11.0) 3.0 (10.0) (0.14,0.26) 480 C 6.6 3.4 (12.5) 5721 (18.0) 386.3 5.5 (12.5) 1.4 (12.0 (0.14,0.22) 476 Ir(fpmi)2(pypz) B 4.1 8.0 (7.0) 9669 (15.0) 298.7 12.6 (7.0) 5.7 (6.5) (0.14, 0.21) 472 C 4.6 7.5 (8.0) 8428 (13.5) 375.2 10.0 (B.0) 4.0 (7.5) (0.14, 0.16) 466 D 5.2 6.2 (7.5) 6245 (14.5) 321.4 7.9 (7.5) 3.5 (7.0) (0.14, 0.15) 464 E 6.8 8.8 (9.0) 3759 ( 20.0) 68.8 16.8 (9.0) 5.9 (9.0) (0.15, 0.27) 478 Ir(fpmi)2(tfpypz) .1 B 5.3 3.1 (8.5) 2193 (13.0) 236.5 3.0 (8.5) 1.2 (7.5) (0.14, 0.11 ) 458 C 6.2 4.9 (9.5) 3319 (17.0) 342.3 5.7 (9.5) 1.9 (9.5) (0.14, 0.14) 464 D 5.2 2.6 (7.5) 2090 (13.0) 251.7 2.2 (7.5) 0.9 (7.5) (0.15,0 . 10) 452 E 6.2 4.4 (10.0) 3597 (16.0) 222.6 5.4 (10.0) 1.8 (9.0) (0.14, 0.14) 460 F 6.1 4.6 (9.5) 2671 (16.5) 272.4 2.7 (9.5) 0.98 (8.5) (0.14, 0.09) 454 As shown in Table 1, the light-colored Ir(fpmi)2(pypz) complex has an optimum component efficiency of 7%, and in addition, its CIE chromaticity γ coordinate is lower than 〇.2〇 And fall in the pure blue position on page 105 200909438 (0.14, 0.16). On the other hand, the blue-colored Ir(fpmi)2(tfpypz) complex of the light color requires a higher triplet energy for the host luminescent material, so the Ir(fpmi)2(tfpypz) complex is only矽-based main body luminescent materials (BSB, UGH2) can achieve higher component efficiency. As can be seen from the table, under the F structure, the Ir(fpmi)2(tfpypz) complex has a CIE chromaticity coordinate of (0.14, 0.09) and a component efficiency of approximately 5%. - Obviously, the invention may have many modifications and differences in accordance with the description in the above embodiments. Therefore, it is to be understood that the scope of the appended claims are intended to be The above are only the preferred embodiments of the present invention, and are not intended to limit the scope of the claims of the present invention; any equivalent changes or modifications made without departing from the spirit of the invention should be included in the following patents. Within the scope. 'i Page 106 200909438 [Simple description of the diagram] The first diagram is a schematic diagram of the structure of the electroluminescence element; and the second diagram is a schematic diagram of the chemical structure of the material of the electroluminescence element. [Major component symbol description] / \第107页

Claims (1)

200909438 X. Patent Application Range: 1. A transition metal complex containing a carbon ruthenium ligand having a carbonyl group-containing transition metal complex having an atomic group whose chemical structure is as follows: Among them, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten (tungsten), chain (rhenium), iron (osmium), silver (iridium), turning ( Platinum); R1 is selected from one of the following groups: C1-C20 alkyl, C1-C20 cycloalkyl, aromatic aromatic ring group, heteroaromatic heterocyclic group; and R2 ~ R7 They may be the same or different, and R2 to R7 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, an alkoxyl group, Halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group ), an aryl group, a halogen-substituted aryl group, a halogen-substituted arylalkyl group, an i-alkyl-substituted aryl group, a haloalkyl-substituted arylalkyl group, a cyano-cyano group, a nitro group An aromatic group, an aromatic heterocyclic group. The transition metal complex containing a carbon-dilute ligand according to claim 1, wherein the transition metal complex containing a carbene ligand in the structure of the above-mentioned carboxy carbene ligand is as follows: _ R6 Wherein R8 to R11 may be the same or different, and R8 to R11 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, An alkoxyl group, a halogen-substituted C1-C20 alkyl group, a C1-C20 substituted amino group, a C1-C20 acyl group, a C1-C20 ester ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, haloalkyl-substituted arylalkyl group, cyano group, cyano Nitro (nitro), a total aromatic group, aromatic heterocyclic group; Y is selected from one of the following groups: nitrogen (N), carbon (C), oxygen (Ο), sulfur ( S) an atom; and a Q group-containing at least two atomic groups to form a nitrogen-containing heterocyclic ring, wherein the atomic combination of the Q group is selected from the group consisting of nitrogen, carbon, and oxygen. Sulfur, wherein the above nitrogen-containing heterocyclic group may further comprise one or more substituents. The transition metal complex containing a carbene ligand according to claim 2, wherein Y further comprises a substituent selected from one of the following groups: Page 109 200909438 Hydrogen atom (Η), halogen atom, C1-C20 alkyl group, C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 compound, C1-C20 substituted amine Group), C1-C20 acyl group, C1-C20 @ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aromatic group a halogen group-substituted aromatic group, a dentate-substituted aromatic alkyl group, a cyano group, a nitro group, a total aromatic group, and an aromatic heterocyclic group. The transition metal complex containing a carbene ligand according to claim 2, wherein the nitrogen-containing heterocyclic group is one selected from the group consisting of pyridine and quinoline. (quinoline), isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole, imidazole, indole, thiazole , isothiazole, oxazole, isoxazole, benzothiazole, benzoxazole, phenanthroline 〇 5. Claims 2, the transition metal complex containing a carbonium ligand, wherein the substituents constituting the nitrogen-containing heterocyclic group of Q may be the same or different, and the above substituents are independently selected from one of the following groups; : hydrogen atom (H), halogen atom, C1-C20 alkyl group, C1-C20 cycloalkyl group, alkoxy group (aik〇Xyi group), halogen-substituted C1-C20 alkyl group, C1-C20 substitution Amino group, C1-C20 acyl group 'C1-C20 ester group, page 110 20 0909438 C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, alkyl-substituted aromatic alkyl group, cyano group, Nitro (nitro), a total aromatic group, aromatic heterocyclic group. The carbene ligand-containing transition metal complex according to claim 1, wherein the above aromatic group is selected from one of the following groups: phenyl, naphthyl, Diphenyl, anthryl, pyrenyl, phenanthryl, fluorenyl. The transition metal complex containing an anthracene ligand according to claim 1, wherein the cycloalkenyl group is one selected from the group consisting of cyclohexene and cyclohexane. Cyc〇hexadiene, cyclopentene, cyclopentadiene (CyCl〇pentadiene). The carbene ligand-containing transition metal complex according to claim 1, wherein the heterocyclic group is selected from one of the following groups: pyrane, η 〇 〇 琳(pyrroline), furan, benzofuran, thiophene, benzothiophene, 11 pyridine, quinoline, 啥啥琳(iSOqUin〇iine), „pyrazine' pyrimidine, pyrrole, pyrazole, °m. imidazole, alpha indole, congestion Thiazole, isothiazole, oxazole, sputum, isoxaz〇ie, benzophenone, sitting (benz〇thiaz〇le), benzo-mouth σ sitting Benzoxazole), phenanthroline. Page 111 200909438 权! The transition metal containing a carbene ligand as described in the term 2, the formation of a transition metal complex with a rare ligand Compound + as follows: Λ R 11 R8 R9 Rio 10. A transition metal complex comprising a carbene ligand, the transition metal complex containing a carbene ligand having an atomic group, the chemical structure of which is as follows: Among them, the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten, rhhemum, osmium, iridium, and Platinum); Page 112 200909438 R1 is selected from one of the following groups: C1-C20 alkyl, C1-C20 cycloalkyl, conjugated aromatic ring group, heteroaromatic heterocyclic group; R2- At least one of R3, R4-R5, R5-R6, and R6-R7 forms any atomic group of an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocycloalkenyl group, and the above aromatic ring, aromatic heterocyclic ring, ring The alkenyl or heterocycloalkenyl group may further comprise one or more substituents, and the unsubstituted substituents in the above R 2 to R 7 may be the same or different, and the unsubstituted substituents in the above r 2 -R 7 are independently selected from the following groups One of them: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, an alkoxyl group, a halogen-substituted C1-C20 alkyl group, C1- C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group, aromatic , halogen-substituted aryl group, dentate-substituted arylalkyl group, haloalkyl-substituted aryl group, haloalkyl-substituted arylalkyl group, cyano group, nitro group, common aromatic ring group Aromatic group, aromatic heterocyclic group. The transition metal complex containing a carbene ligand according to claim 10, wherein the above aromatic ring, aromatic hetero ring, cycloaliphatic group or heterocycloalkenyl group is a five-membered ring or a six-membered ring. Or a seven-member ring. The transition metal complex containing a carbon-poor ligand according to claim 1 wherein the structure of the above transition metal complex containing a carbene ligand is as follows: page 113 200909438 One of the column groups: a hydrogen atom (Η), a li atom, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, an alkoxyl group, a halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aroma a halogen-substituted arylalkyl group, a haloalkyl-substituted aryl group, a haloalkyl-substituted arylalkyl group, a cyano group, a nitro group, a total aromatic group, an aromatic group a heterocyclic group; Y is selected from one of the following groups: nitrogen (N), carbon (C), oxygen (oxime), sulfur (S), etc.; and .r 1 Q system, at least two atoms. a radical to form a nitrogen-containing heterocyclic ring, wherein the atomic combination of the Q radical is selected from the group consisting of nitrogen, carbon, oxygen, sulfur, wherein the nitrogen-containing heterocyclic group described above may further comprise One or more substituents. The transition metal complex containing a carbene ligand according to claim 12, wherein Y further comprises a substituent, and the substituent is selected from one of the following groups: a hydrogen atom (H), Halogen atom, C1-C20 alkyl group, C1-C20, page 114, 200909438 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amine (amino Gr〇up), C1-C20 acyl groUp, C1-C20 ester group, C1-C20 amide groUp, aryl, halogen-substituted aryl, halogen-substituted aromatic a haloalkyl-substituted aryl group, a haloalkyl-substituted aromatic alkyl group, a cyano group, a nitro group, an aromatic group, and an aromatic heterocyclic group. 14. The carbene ligand-containing transition metal complex according to claim 12, wherein the nitrogen-containing heterogeneous group is selected from one of the following groups: 11 to pyridine, quinine Quinoline, isquinoline, pyrazine, pyrimidine, pyrrole, 11 to 0 pyrazole 'imidazole, 吲哚(indole), thiazole 'isoazole' (isothiazole) '° evil' sitting (oxazole), isoxazole, benzothiazole, benzoxazole The phenanthroline containing transition metal complex according to claim 12, wherein the substituents constituting the nitrogen-containing heterocyclic group of Q may be the same or different, And the above substituents are independently selected from one of the following groups: hydrogen atom (H), halogen atom, C1-C20 alkyl group 'C1-C20 cyclodextrin, alkoxyl group, halogen Substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group (ester gr 〇up), C1-C20 amide group, aryl group, halogen-substituted aryl group 'halogen' Page 115 200909438 Prime-substituted arylalkyl group, haloalkyl-substituted aryl group, haloalkyl-substituted aroma An alkyl group, a cyano group, a nitro group, a conjugated aromatic ring group (ar〇matic group), or an aromatic heterocyclic group. The transition metal complex containing a carbene ligand according to claim 1 , wherein the above aromatic group is selected from one of the following groups: phenyl, naphthyl , diphenyl, anthryl, pyrenyl, phenanthryl 'fiuorenyi. The transition metal complex containing a carbene ligand according to claim 1, wherein the above ring-dense group is selected from one of the following groups: cyclohexene, cyclohexane (CyCi〇hexadiene), cyclopentene, cyci〇pentadiene. The transition metal complex containing a carbene ligand according to claim 1 , wherein the heterocyclic group is selected from one of the following groups: abbreviated. Pyfane, pyrroline, furan, benz0furan, thiophene, benzothiophene, pyridine, quinoline, isoquine iSOquin〇iine, pyrazine, pyrimidine, pyrrole ' „ ratio. sitting (pyraz〇le) 'imidaz〇le, 0 indole, Thiazole, is〇thiazole, oxazole, isoxazole, benzothiazole, benzoxazole And phenanthroline. The transition metal complex containing a ruthenyl ligand according to claim 12, page 116 200909438 wherein the above transition metal complex containing a carbene ligand The formation is as follows: f Wherein X is a halogen atom. 20. A transition metal complex containing a carbene ligand, wherein the structure of the above transition metal complex containing a carbene ligand is as follows: Where 'the lanthanide is a transition metal and is selected from one of the following groups: ruthenium, rhodium, tungsten, rhenium, osmium, iridium, Platinum); R1 is selected from one of the following groups: C1-C20 alkyl, C1-C20 cycloalkyl, page 117 200909438 conjugated aromatic ring group, heteroaromatic heterocyclic group; Q system An atomic group containing at least two atoms to form a nitrogen-containing heterocyclic ring 'wherein the atomic combination contained in the Q atomic group is selected from the group consisting of nitrogen, carbon, oxygen, sulfur, wherein the above nitrogen is contained The heterocyclic group may further comprise one or more substituents; Y is selected from one of the following groups: nitrogen (N), carbon (helium, oxygen (strontium), sulfur (s), etc.; and R8 ~ R11 may The same or different, and R8 to R11 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group, a ci_c2 anthracene group, an alkoxyl group. 'Halogen-substituted cl_C2 decyl group, C1-C20 substituted amino group, C1-C20 acyl group C1-C20 ester group, C1-C20 amide gr0Up, aryl, halogen-substituted aryl, halogen-substituted arylalkyl, haloalkyl-substituted aryl, halo-substituted a fragrant group, a cyailo, a nitro group, a conjugated aromatic ring group, an aromatic heterocyclic group, 21. A carbene-containing ligand according to claim 20. a transition metal complex, wherein the above R2 to R7 may be the same or different, and R2 to R7 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, a C1-C20 alkyl group, a C1-C20 a cycloalkyl group, an alkoxyl group, a halogen-substituted C1-C20 alkyl group, a C1-C20 substituted amino group, a C1-C20 acyl group, a C1-C20S group ( Ester group), C1-C20 amide group, aromatic U8 page 200909438 base, halogen-substituted aromatic group, halogen-substituted aromatic alkyl group, halogen-substituted aromatic group, haloalkyl-substituted aromatic A group, a cyano group, a nitro group, a aromatic group, and an aromatic heterocyclic group. The transition metal complex containing a carbene ligand according to claim 20, wherein at least one of R2-R3, R4-R5, R5-R6, and R6-R7 described above forms an aromatic ring. Any aromatic group of an aromatic heterocyclic ring, a cycloalkenyl group or a heterocycloalkenyl group, wherein the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may further comprise one or more substituents, R2 to R7 above. The unsubstituted substituents may be the same or different, and the unsubstituted substituents in the above R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group. , C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 Ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, i-alkyl-substituted aryl group, halogen-based substituted aromatic alkyl group , cyano, nitro, aromatic group, aromatic heterocyclic group. The transition metal complex containing a carbene ligand according to claim 20, wherein Y further comprises a substituent. The substituent is selected from one of the following groups: a hydrogen atom (H), _ atom, C1-C20 alkyl group, Cl-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1_C20 Acyl group, page 119 200909438 C1-C20 ester group, C1-C20 amide group, aryl, halogen-substituted aryl, halogen-substituted arylalkyl, halothane a substituted aryl group, a halogen group-substituted aromatic alkyl group, a cyano group, a nitro group, a total aromatic group, and an aromatic heterocyclic group. The transition metal complex containing a carbene ligand according to claim 20, wherein the nitrogen-containing heterocyclic group is one selected from the group consisting of: pyridine, B-quinone Quinoline, isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole 'imidazole, ° bow Ind (indole), thiazole, isothiazole, oxazole, isoxazole, benzothiazole, benzoxazole, bis A phenanthroline containing transition metal complex according to claim 20, wherein the substituents constituting the nitrogen-containing heterocyclic group of Q may be the same or different, and The substituents are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, an alkoxyl group, a halogen-substituted one. C1-C20 Hyun: base, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group Ester group), C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, dentate-substituted aromatic group-cyano group (cyano), nitro, a total of aromatic ring groups (aromatic page 120 200909438 group), aromatic heterocyclic groups. The carbene ligand-containing transition metal complex according to claim 20, wherein the above aromatic group is selected from one of the following groups: phenyl, naphthyl, Diphenyl, anthryl, pyrenyl, phenanthryl, flllorenyi. 27. The carbene ligand-containing transition metal complex according to claim 20, wherein the cycloalkenyl group is selected from one of the group consisting of cyclohexene and hexadiene. (CyCi〇hexadiene), cyclopentene, cyclopentadiene. The transition metal complex containing a carbene ligand according to claim 20, wherein the above-mentioned heterogeneous group is selected from the group consisting of: Pyrane, and 〇辰口(pyrroline), alpha furan, benzo beta. Benzofuran, thiophene, benzothiophene, "pyridine, quinoline, isoquinoline, pyrazine, Pyrimidine, pyrrole, pyraz〇ie, imidazole, indole, and lane. Sitting (thiazole), different α plug. Isothiazole, oxazole, is〇xazole, benzothiazole, benzoxazole, phenanthroline. 29. The transition metal complex containing a carbene ligand according to claim 20, wherein the transition metal complex containing a carbene ligand is formed as follows: Page 121 200909438 An eiectroluminescence element comprising a pair of electrodes and at least one organic layer between the pair of electrodes, the at least one organic layer comprising a light-emitting layer, and the at least one organic layer comprising A Transition Metal Complex Containing a Carbon Association Site The transition metal complex containing a carbene ligand has the following chemical structure: Among them, the lanthanide is a transition metal and is selected from the following groups: ruthenium, rhodium, tungsten (tungSten), 铢 (rheniUm), 锇 p. 122, 200909438 (osmium), silver (iridium) ); R1 is selected from one of the following groups: C1-C20 alkyl, Cl_C2 anthracycline A, conjugated aromatic ring group (aromatic group), heteroaromatic heterocyclic group; Q system one An atomic group containing at least two atoms to constitute a nitrogen-containing heterocyclic ring, wherein the atomic combination contained in the Q atomic group is selected from the group consisting of nitrogen, carbon, oxygen, sulfur, and the above-mentioned nitrogen-containing impurities The ring group may further comprise one or more substituents; r Y is selected from one of the following groups: nitrogen (N), carbon (C), oxygen (0), sulfur (8), etc.; and R8 ~ R11 may be the same Or different, and R8 ~ R11 are independently selected from one of the following groups: hydrogen atom (H), halogen atom, C1-C20 ^* (alkyl group), Cl-C20 ring-based group, alkoxyl group , halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, C1-C20 acid group (acyl group), Cl -C20 ester group, C1-C20 amide group 'aromatic, yl, iS substituted aryl, halogen substituted aryl, haloalkyl substituted aryl, haloalkyl Substituted aromatic alkyl, cyano, nitro, aromatic group, aromatic heterocyclic group. The electroluminescent device according to claim 30, wherein said R2 to R7 are the same or different, and R2 to R7 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, and a C1-C20 burn. Alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted page 123 200909438 amino group, C1-C20 &acyl group, C1-C20 @为S(ester group), C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, i-alkyl group Aromatic group, _alkyl substituted arylalkyl group, cyano group, nitro group, aromatic aromatic group, aromatic heterocyclic group. The electroluminescent device according to claim 30, wherein at least one of the above-mentioned r2_r3, R4-R5, R5-R6, and R6-R7 forms an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or Any of the heterocyclic alkenyl groups, the above aromatic ring, aromatic heterocyclic ring, cycloaliphatic group or heterocycloalkenyl group may further contain one or more substituents, and the unsubstituted substituents in the above R2 to R7 may be the same or different. And the unsubstituted substituents in the above R2 to R7 are independently selected from one of the following groups: a hydrogen atom (H), a halogen atom, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, an alkoxy group. Alkoxyl group, S-substituted C1-C20 alkyl group, C1-C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group, C1- C20 amide group, aryl group, dentate-substituted aromatic group, halogen-substituted aromatic alkyl group, halogen-substituted aromatic group, halogen-substituted aromatic group, cyano-cyano Nitro, aromatic aromatic groups, aromatic heterocyclic groups. 33. The electroluminescent device of claim 30, wherein Y further comprises a substituent selected from one of the group consisting of a hydrogen atom (H), a halogen atom, and a C1-C20 alkyl group. (alkyl group), C1-C20 cyclodextrin, methoxy (aikoxy1, p. 124, 200909438 group), halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 fluorenyl (acyl group), C1-C20 ester group (ester grouP), C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, haloalkyl-substituted aryl group, A haloalkyl-substituted aromatic alkyl group, a cyano group, a nitro group, a total aromatic group, and an aromatic heterocyclic group. 34. The electroluminescent device of claim 30, wherein the nitrogen-containing heterocyclic group is selected from one of the group consisting of: pyridine, quinoline, and iso-quinone Lin (isoquinoline), 0 than rhino (pyrazine), pyrimidine (pyrimidine), 0 ratio (pyrrole), ° ratio. Pyrazole, sigma, imidazole, π, thiazole, isothiazole, "evil. Oxazole, isoxazole, benzopyrene. Benzothiazole, benzoxazole, phenanthroline. The electroluminescent device according to claim 30, wherein the substituents constituting the nitrogen-containing heterocyclic group of Q may be the same or different, and the substituents described above are independently selected from one of the following groups: Hydrogen atom (H), halogen atom, C1-C20 alkyl group, C1-C20 ring-based group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted amine group (amino group), C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aromatic burning Aromatic group, halogenated group-substituted aromatic group, halogenated group-substituted aromatic alkyl group, cyano, cyano, page 125, 200909438 nitro, co-rolling aromatic ring group, aromatic heterocyclic ring Group. 36. The electroluminescent device of claim 30, wherein the aromatic group is selected from one of the group consisting of phenyl, naphthyl, diphenyl, hydrazine. Anthryl, pyrenyl, phenanthryl, fluorenyl. 37. The electroluminescent device of claim 30, wherein the cycloalkenene group is selected from one of the group consisting of cyclohexene, cyclohexadiene, cyclopentene (cyclohexadiene) The electroluminescent device of claim 30, wherein the heterocyclic group is selected from one of the following groups: pyrane, α bottom 0 pyroline, furan, benzopyrene. Benzofuran, thiophene, benzothiophene ' σ σ, quinoline, isoquinoline, pyrazine, pain Pyrimidine, 11 pyrrole 'pyrazole, imidazole, indole, thiazole, isothiazole, oxazole, dysentery Isozolium (iSOXazole), benzothiazole, benzoxazole, phenanthroline, 39. The electroluminescent device according to claim 30, wherein the above carbene is contained The transition metal complex of the ligand is formed as follows: Page 126 200909438 Among them, the lanthanide is an atom. The electroluminescent device according to claim 30, wherein said transition metal complex containing a carbene ligand has a chemical structure such as one of the following groups: Ir(pmi)2(mptz) Ir(pmi)2(pytrz) Page 127 200909438 Ir(pmi)2(tfpypz) Ir(fpmi)2(tfpypz) Ir(fpmi)2(pytz) Ir(mpmi)2(tfptz) Ir(fpmi)2(pytrz) Ir(mpmi)2(tfpypz) Ir(mpmi)2(pytrz) Ir(mpmi)2(pytz) Page 128 200909438 XI. Illustration Ag or Al Mg : Ag or LiF ETL HBL Guest: Host EBL HTL ITO Glass First diagram of the structure of the electro-excited light element Page 129 200909438 Fig. 2 Schematic diagram of the chemical structure of the material for electroluminescent device fabrication Page 130 200909438 VII. Designated representative map: (1) The representative representative of the case is: ( ). (2) A brief description of the symbol of the representative figure: 8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: Among them, the lanthanide is a transition metal, and the R1 to R7 groups respectively represent the same or different substituents. Page 6 200909438 (3) Sexual bacteria Name: Lu Minyi 讥 Nationality: Republic of China Μ k.