TW584661B - Light emitting material and organic light-emitting device - Google Patents

Abstract

This invention provides a polymer light emitting material, in which the material has a light emitting mechanism based on transition from an excited triplet state to a ground state or transition through an excited triplet state to a ground state of an electron energy level, and the material comprises a nonionic light emitting part which constitutes a part of the polymer or is bound to the polymer. The polymer light emitting material exhibits high light emission efficiency above 35%, which is the limit of external quantum efficiency of fluorescence and can be designed so as to have a large area and hence are suitable for mass production of organic light emitting devices.

Description

584661 B7 V. Description of the Invention (1) [Technical Field of the Invention] The present invention relates to a flat display panel or an organic light-emitting element (OLED) used for a backlight and a light-emitting material used therefor. [Prior technology] Organic light-emitting devices have been developed rapidly since CW Tang of Kodak Co., Ltd. in 1987 revealed high-brightness light emission (Appl. Phys. Lett., Vol. 51, p. 913, 1987). , And has been put into practical use from recent car audio or mobile phone displays. In order to further expand the application of this organic EL (electroluminescence) element, many materials development and full-color display development for improving luminous efficiency and durability are being vigorously performed. In particular, in the case of a medium-sized panel or a large-sized panel, or higher luminance required to improve luminous efficiency for lighting applications. The aforementioned conventional use of metal complexes such as aluminum quinoline phosphonium salt (Alq3) as a light-emitting material has been widely used because of its high light-emitting efficiency and high light-emitting intensity. However, the method for forming the light-emitting layer of the organic light-emitting device using the aforementioned low-molecular-based material can be a method such as vacuum evaporation, which is a benefit of the device production process. In Nature, 397 (1 999) 1 2 1 there are light-emitting materials derived from 7Γ atom conjugated polymers such as polyparaphenylene vinylene (PPV) or its derivatives (MEH-PPV), and some of them have already begun. Used as a backlight for watches. Since the aforementioned polymer materials can be formed into films by a casting method, they not only have the advantages of productivity, but also have the advantage of lower luminous efficiency than the low-molecular-based luminescent materials. The method used in the aforementioned luminescent materials is based on the application of the Chinese National Standard (CNS) A4 specification (210 X 297 male f) ~~ -4-¾-- (Please read the notes on the back before filling (This page)

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, 1T 584661 A7 ______B7 V. Description of the invention (2) The luminescence produced by the state is the so-called fluorescence. In the display monthly, October 1998 issue of "Organic EL Display", the content recorded on page 58 contains the excitons produced by the singlet and triplet excitons generated by electrical stimuli at a ratio of 1: 3. Therefore, the internal quantum efficiency of the organic EL element is limited to 25%. In contrast, when M. A. Baldo et al. Used phosphorescence-emitting iridium complex produced by excited triplet state, the external luminous efficiency was 7.5% (When the external extraction efficiency was set to 20%, the internal quantum efficiency was 37.5% ) In this way, a higher external quantum efficiency of 5%, which is the upper limit, can be obtained in this way (Appl. Phys. Lett., Vol. 75, p. 4, 1999, W00 / 70655). However, generally, as the iridium complex used before, there are very few materials that can stably emit phosphorescence at normal temperature, so the freedom of material selection is extremely low, and it must be doped under specific host materials when used. Waiting for '-----------------------------—— — —, so it fails to fully meet the display style, resulting in extremely difficult to choose materials Disadvantages. In contrast, with MA Baldo et al., Using an iridium complex as a sensitizer, moves the energy from the excited triplet state to the excited singlet state of the fluorescent pigment, so that it eventually generates fluorescent light from the excited singlet state of the fluorescent pigment. Get better luminous efficiency (Nature, Vol. 403, 750 pages, 2000). The luminescent material obtained by this method has the advantage of being able to select most fluorescent and pigments according to the purpose. However, in this method, moving from the excited triplet state of the sensitizer to the excited singlet state of the fluorescein involves a process of prohibiting rotation, so theoretically, it is easy to cause a great disadvantage of a decrease in the quantum efficiency of light emission. Subsequently, for the mass production method of the panel, vacuum evaporation is currently used (please read the precautions on the back before filling this page)

、 1T The printed paper size of the consumer cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs is printed in accordance with the Chinese National Standard (CNS) A4 specifications (210X 297 mm) ^ 584661 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs A7 B7 5. Description of the invention ( 3) Method. However, this method has the disadvantages of requiring vacuum equipment and not being able to uniformly form a large area of organic thin films, so it is not completely suitable for mass production of large area panels. In contrast, a manufacturing method for a polymer-based light-emitting material, which is easy to form a large area, has been developed, that is, an inkjet method or a printing method. In particular, the printing method can continuously form long-size films, and is very suitable for large-scale production and mass production. In the above description, in order to obtain an organic light-emitting device having a high luminous efficiency and a large area, a phosphorescent polymer material must be used. The aforementioned phosphorescent light-emitting polymer material, for example, a ruthenium complex is connected to the main chain or branched chain of the polymer (Ng, PK et al ·, Polymer Prep 1 · in its ·, 40 (2), 1 2 1 2 (1 999)). It is an ionic compound, so when a voltage is applied, a redox reaction occurs on the electrode and electrochemical light emission occurs. The response speed of this electroluminescence will be extremely slow if it is partial response, so it is generally not suitable for general display panels. In addition, because it is not a strictly defined polymer material, it is a europium complex compound in which poly (N-vinylcarbazole) is mixed and dispersed with a phosphorescent light-emitting low molecular compound (P. J. Djurovich et al. , Ploymei Preprine, 41 (1), 770 (2000)). However, when compared with a homogeneous polymer material, its thermal stability is inferior and it is easy to cause phase separation or deviation. Japanese Unexamined Patent Publication No. 200 1-1 8 1 6 16, Japanese Unexamined Patent Publication No. 2001-1 8 1 6 1 7 and Japanese Unexamined Patent Publication No. 200 1-247859 respectively disclose phosphorescent luminescence orthometalated palladium complexes, The organic light-emitting element materials composed of ortho-metalized platinum complex and ortho-metalized iridium complex are both mentioned. The paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm). (Please read the notes on the back before filling this page)

-6- 584661 A7 B7 V. Description of the Invention (4) High molecular compound structured as a repeating unit. However, in these bulletins, it is necessary to form a polymer by combining the complex structure of repeating units in the bulletin (please read the precautions on the back before filling this page). There are specific disclosures, so it has not been said that the purpose of revealing practical phosphorescent light-emitting polymer compounds has been achieved. There are also compounds that consider phosphorescent light-emitting metal complexes that are conjugated to polymer branches (side chain type). Polymer complex). At this time, since the degree of freedom of the phosphorescent luminescent complex in the polymer matrix during film formation is large, in terms of the thermal stability, life, brightness, and luminous efficiency of the light-emitting element, etc. More disadvantaged J. [Contents of the Invention] As described in the previous edition, it is used for ^^ $ 1 pieces of n-light materials, and has not been found to exceed 5% of the critical threshold of the external quantum efficiency of conventional fluorescent light emission. In addition, materials produced by the Intellectual Property Bureau of the Ministry of Economic Affairs (industrial and consumer cooperatives) and materials with high luminous efficiency have a small energy loss and can suppress the heating of the element, so they are extremely needed from the viewpoint of improving the durability of the element. That is, to solve the problems of the prior art, and to provide an organic light-emitting element that can be used for high brightness and durability, and the light-emitting material obtained by using it is an object of the invention. The present inventors, in order to solve the aforementioned problems, Through various in-depth research results, it is known that the high-efficiency light emission of excited triplet state can be obtained through the combination of a luminescent substance and a polymer, and thus the present invention has been completed. Some kind of effect forms the meaning of immobilization. The method of immobilization, such as covalent bond -7- This paper standard is applicable. National National Standard (CNS) A4 specification (210 X 297 mm) 584661 Employees of Intellectual Property Bureau, Ministry of Economic Affairs Printed by the Consumer Cooperative A7 ___ B7_ V. Description of the Invention (5) ^ Junction, Coordination Bonding, Charge Movement Complexation, Ion Binding, Van der Waals Force Chemical bonding, physical bonding, etc., such as host-guest bonding, such as intercalation, are not limited to this. In addition, the structure of the light-emitting substance of the present invention may be a part that is combined with the light-emitting substance to form a part of a polymer. Or, a part of the ligand of the complex of the luminescent substance may be mismatched with the polymer. In addition, the present inventors found that the polymerizable composition containing at least one luminescent compound was processed into a film and then applied. The polymer-based light-emitting material obtained by polymerization has good durability and processability. In addition, after the light-emitting substance (light-emitting part) of this method is immobilized by the polymer, it can emit light with high efficiency to generate an excited triplet or pass through. The excited triplet state obtains high-efficiency light emission, thus completing the present invention. That is, the present invention relates to the following inventions of light-emitting materials and light-emitting elements. [1] A polymer-based light-emitting material whose light-emitting mechanism is an electron energy level Migration from excited triplet state to ground state or migratory state from excited triplet state to ground state [2] A luminescent material such as [1], in which the luminescent part described above is formed by a metal atom bonded to more than one part of the polymer. [2] 3] The luminescent material as in [2], wherein the binding in the luminous part of the preamble is a covalent bond and / or coordination bond. [4] The luminescent material as in [1], wherein the luminous part on the preface The composition is a metal complex structure or an organometallic structure with a metal atom at the center. (Please read the precautions on the back before filling this page) _Package-Order d This paper size applies to China National Standard (CNS) A4 specifications (210X297 (Mm) -8-584661 A7 B7 V. Description of the invention (6) [5] A luminescent material such as [2] or [4], in which the foregoing metal atom is a transition metal atom. [6] The luminescent material as described in [5], wherein the transition metal atom mentioned above is a transition metal atom in the sixth period of the periodic table. [7] The light-emitting material according to [6], wherein the transition metal atom is iridium. [8] The light-emitting material according to [6], wherein the transition metal atom is platinum. [9] The luminescent material according to [2] or [4], wherein the foregoing metal atom is a rare earth metal atom. [10] The light-emitting material according to any one of [1] to [9], wherein the light-emitting part of the foregoing is formed by a combination of a metal atom and a nitrogen atom of a polymer including a coordination bond. [11] The light-emitting element according to [10], wherein the coordination bond between the metal atom and the nitrogen atom of the polymer described above is formed by a pyridine skeleton and / or a pyrimidine skeleton and / or a quinoline skeleton on the polymer side. . [12] The luminescent material according to [11], in which the coordination bond between the metal atom and the high molecular nitrogen atom described above is formed by the phenylpyridine skeleton on the polymer side. [13] A luminescent material such as Π 1], in which the coordination bond between the metal atom of the preface and the nitrogen atom of the polymer is formed by the benzodiazepine pyridine skeleton on the polymer side. [14] The luminescent material as in [1], wherein the luminescent part includes the phosphorescent luminescent part and the fluorescent luminescent part, and the paper size of the phosphorescent luminescent part is applicable to the Chinese National Standard (CNS) Α4 size (21〇 × 297mm) ^^ clothing-(Please read the precautions on the back before filling this page)

Printed by 8T Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs -9- 584661 A7 _B7_ V. Invention Description (7) (Please read the precautions on the back before filling this page} Excited triplet state Excite the triplet state, so that at least one of the 'phosphorescent part' and the fluorescent part in the light-emitting material where the fluorescent light-emitting part causes the fluorescent light to form a part of the polymer, or Molecular bonding. The polymer-based luminescent material as in [1] is obtained by polymerizing a polymerizable composition containing at least one kind of luminescent compound. [16] The polymer-based luminescent material as in [15], wherein The light-emitting compound is a polymerizable light-emitting compound. [17] The polymer-based light-emitting material according to [15], wherein the polymerized polymer is a non-crosslinked polymer. [18] The polymer-based light-emitting device according to [16] Materials, in which at least one of the polymerizable light-emitting compounds is a cross-linked polymerizable light-emitting compound having two or more polymerizable functional groups, and the polymer system after polymerization is a cross-linked polymer. [19] Such as [15] Polymer light-emitting materials to [18], in which The polymerizable composition contains polymerizable compounds other than at least one luminescent compound. The polymer-based luminescent materials printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [20], such as [19], are polymer-based luminescent materials, among which At least one of the polymerizable compounds is a polymerizable electron-transporting compound. [21] The polymer-based light-emitting material according to [15], wherein the polymerizable composition contains at least one polymerizable compound other than the light-emitting compound ' And at least one of the polymerizable compounds is a cross-linkable polymerizable compound having two or more polymerizable functional groups. This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) -10- 584661 A7 _B7___ V. Description of the invention (8) [22] The polymer-based light-emitting material as in [15], in which the part formed by the metal structure (please read the precautions on the back before filling this page) or the organic metal structure is Metal complex structure [23] A polymer light-emitting material such as [22], in which the metal atom is a transition metal atom. [24] A polymer light-emitting material such as [22], in which, The metal atom is a rare earth metal atom. [25] The polymer light-emitting material according to any one of [22] to [24], in which the light-emitting part is formed by a metal complex structure or an organic metal structure [26] A polymer light emitting material such as [25], in which the complex structure forming part of the light emitting part includes a pyridine skeleton, a pyrimidine skeleton, and a quinoline skeleton. [27] ] The polymer light-emitting material according to [16], wherein the polymerizable light-emitting compound is a polymerizable compound not represented by the formula (C-1),

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs [wherein at least one of Ac, Bc, and Cc is a substituent having a polymerizable functional group ', and the remaining residues in Ae, Bc, and Ce are independent hydrogens. The original paper size is applicable to the Chinese National Standard (CMS) A4 specification (210X 297 mm) -11-584661 A7 ____ B7 V. Description of the invention (9) Product, halogen atom, nitro, amine, sulfonate, sulfonate Or an organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R21 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic group, a sulfonate group, or a carbon which may have a hetero atom Organic groups of 1 to 20]. [28] The polymer light-emitting material according to [16], wherein the polymerizable light-emitting compound is a polymerizable compound represented by the formula (D-1); y

ID

rlD

rlD

P

0 O

(Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where, at least one of X1D, Y1D, Z1D is a substituent with a polymerizable functional group, X1D, Y1D, Other residues in Z1D are independent gas atoms or organic groups having 1 to 20 carbon atoms which may have a hetero atom; to R16 are each independent hydrogen atom, halogen atom, nitro group, amine group, sulfonic group, A sulfonate group or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [2 9] The local molecular light-emitting material according to [1 6], wherein the polymerizable light-emitting compound is a polymerizable compound represented by the formula (E -1); This paper size applies the Chinese National Standard (CNS) A4 specification ( 210X 297 mm) -12- 584661 A7 B7

[In the formula, XE is a substituent having a polymerizable functional group, R1E to R3E are each independently a hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms that may have a hetero atom; R4 to R19 are each independent hydrogen An atom, a halogen atom, a nitro group, an amine group, a sulfonic group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [3 0] As in [16] ^ polymer light-emitting materials, wherein the polymerizable light-emitting compound is a polymerizable compound represented by formula (F-1); clothing-(Please read the precautions on the back before filling in this Page) Ordered by the Intellectual Property Bureau of the Ministry of Economy

[In the formula, at least one of X1F, Y1F, and Z1F is a substituent having a polymerizable functional group, and the remaining ones in X1F, Y1F, and z1F are each independently a hydrogen atom, a halogen atom, or a carbon that may have a hetero atom. Organic basic paper sizes from 1 to 20 apply Chinese National Standard (CNS) A4 specifications (210X297 mm) -13- 584661 A7 __ B7 V. Description of invention (11) (Please read the precautions on the back before filling this page) R1 to R16 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]; [31] The polymer light-emitting material according to [16], wherein the polymerizable light-emitting compound is a polymerizable compound represented by the formula (G-1); R3 L R3

[In the formula, L is a monovalent anionic two-segment coordination group, X ° is a polymerizable functional group, and JH to R7 are each independent hydrogen atom, halogen atom, nitro group, amine group, and sulfonic acid group. , A sulfonate group or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [32] A light-emitting composition characterized in that it comprises the light-emitting material of any one of [1] to [31] and a carrier polymer compound. Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [33] Luminous compositions such as [32], where the carrier-transporting high molecular compound is a hole-transporting high molecular compound. [34] The luminescent composition according to [32], wherein the carrier-transporting high molecular compound is an electron-transporting high molecular compound. [35] A luminous composition comprising the light-emitting material of any one of [1] to [31], and a carrier-transporting low-molecular compound. [36] Luminous composition such as [35], in which the carrier is low in transportability and the paper size is applicable to China National Standard (CNS) A4 specification (210 × 297 mm) -14-584661 Printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs A7 _ B7 V. Description of the invention (12) The molecular compound is a hole-transporting low-molecular compound. [37] The luminescent composition according to [35], wherein the carrier-transporting low-molecular compound is an electron-transporting low-molecular compound. [3 8] A light-emitting material layer containing an organic light-emitting element, which is a polymer light-emitting material containing [1]. [39] The light-emitting material layer for an organic light-emitting element as described in [38], which is obtained by forming the polymer light-emitting material of [1] through film formation. [40] The light-emitting material layer for an organic light-emitting element according to [39], wherein the polymer-based light-emitting material is a non-crosslinked polymer. [41] The light-emitting material layer for an organic light-emitting element according to [39], wherein the polymer-based light-emitting material is obtained by polymerizing a polymerizable composition containing at least one kind of light-emitting compound after being formed into a film. [42] The light-emitting material layer containing an organic light-emitting element according to [41], wherein the polymer light-emitting material is a non-crosslinked polymer ^ [43] The light-emitting material layer containing an organic light-emitting element according to [41], wherein The polymer-based light emitting material is a crosslinked polymer. [44] An organic light-emitting device characterized by using the polymer light-emitting material of any one of [1] to [31]. [45] The organic light-emitting element according to [44], characterized in that both sides and / or one side of the light-emitting layer obtained from the polymer-based light-emitting material in any of [1] to [31] are coated with a film-type electron transport layer And / or coated with a film-type hole transport layer and then obtained by film formation. The present invention relates to the novelty shown in the following [C1] to [C60], [D1] to [D3 8], [E1] to [E34], [F1] to [F38], and [G1] to [G26] Polymerization (please read the precautions on the back before filling this page), 1T This paper size applies Chinese National Standard (CNS) specifications (210X 297 mm) -15- 584661 A7 B7 V. Description of the invention (13) Production method and invention of polymer obtained by polymerizing polymerizable compound. (Please read the notes on the back before filling this page) [C1] A polymerizable compound represented by formula (C-1);

[In the formula, at least one of Ae, Be, and Ce is a substituent having a polymerizable functional group, and the remaining ones in Ae, Be, and Ce are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, Acid group, mineral acid group or organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R21 are names An organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C2] A polymerizable compound printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs as described in [C1] above, in which at least one of Ae, Be, and Ce shown in the above formula (C-1) has an acrylate group or Substituents for methacrylate groups. [C3] The polymerizable compound according to the aforementioned [C2], wherein at least one of Ae, Be, and Ce represented by the aforementioned formula (C-1) is a substituent having an acrylate group or a methacrylate group. [C4] Polymerizable compound as shown in the foregoing formula (C-2); This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 584661 A7 B7 V. Description of the invention (14) ch3

(Please read the notes on the back before filling this page) [In the formula, R1 and R2 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group or may have a hetero atom. Organic groups having 1 to 20 carbons]. [C5] The polymerizable compound as described in [C4] above, wherein R1 and R2 in the formula (C-1) are hydrogen atoms. [C6] a polymerizable compound represented by the aforementioned formula (C-3);

R2 Printed by Xiao Gong Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs [where Ri, R2 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group, or carbon which may have hetero atom Numbers 1 to 20]. [C7] The polymerizable compound as described in [C6] above, in which the formula (C-3) is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -17- 584661 A7 B7 V. Description of the invention (15 R1 and R2 are hydrogen atoms. [C8] The polymerizable compound according to the aforementioned [C2], wherein at least one of Ae, Be, and Ce represented by the aforementioned formula (C-1) is a substituent having an acrylate group or a methacrylate group. [C9] Polymerizable compound represented by the above formula (C-4); I ·-· (Please read the precautions on the back before filling this page)

[In the formula, R1 is a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C10] The polymerizable compound as described in [C9] above, wherein R1 in the formula (C-4) is a hydrogen atom. [C11] Polymerizable compound as shown in the formula (C-5) above; d Printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economy

O-C-NH- (CH2) 2-0-C-C = CH2 〇 & CH,

(C-5) This paper size applies to Chinese National Standard (CNS) A4 specification (210 × 297 mm) -18- 584661 A7 ____ B7 V. Description of the invention (16) [where V is an argon atom, halogen atom, nitro , An amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C12] The polymerizable compound as described in [C11] above, wherein R1 in the formula (C-5) is a hydrogen atom. [C1 3] The polymerizable compound as shown in the aforementioned [C2], wherein all of Ac, Bc, and Cc in the aforementioned formula (C-1) are substituents having an acrylate group or a methacrylate group. [C14] A polymerizable compound represented by the aforementioned formula (C-6);

CH. I 3 OCC = CH. II 〇 (Please read the precautions on the back before filling in this page) (C-6) [C15] Polymerizable compounds as shown in the previous formula (C-7); CH. Ministry of Economic Affairs Printed by the Intellectual Property Bureau Staff Consumer Cooperative

oc ~ nh- (ch2) 2-〇.Cc = ch2 〇 | 丨 " CH, 〇 (C-7) [C16] A polymer, which is a polymerizable compound represented by formula (C-1) Paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -19- 584661 A7 B7 V. Description of the invention (17) The compound obtained by polymerization;

Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where, at least one of Ae, Be, and Ce is a substitution-generation group with a polymerizable functional group, and the remaining ones in Ae, Be, and Ce are independent of each other. Hydrogen atom, halogen atom, nitro group, amine group, sulfonate group, sulfonate group or organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R21 are each independently hydrogen atom, halogen atom, nitro group , An amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C17] The polymerizable compound according to the aforementioned [C16], wherein at least one of Ae, Be, and Ce represented by the aforementioned formula (C-1) is a substituent having an acrylate group or a methacrylate group. [C 18] The polymerizable compound according to the aforementioned [C 17], wherein at least one of Ae, Be, and Ce represented by the aforementioned formula (C-1) is a substituent having an acrylate group or a methacrylate group . [C19] A polymer obtained by polymerizing a polymerizable compound represented by the formula (C-2); (Please read the precautions on the back before filling out this page). China National Standard (CNS) Α4 Specification (210 × 297 mm) -20- 584661 CH. I 3

A7 B7 V. Description of the invention (18)

H2C (C-2) [wherein R1 and R2 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom base]. [C20] The polymerizable compound as described in [C19] above, wherein R1 and R2 in the formula (C-2) are hydrogen atoms. [C21] A polymer obtained by polymerizing a polymerizable compound represented by formula (C-3); CH. I 3 H2C = CC-0 (CH2) 2-NH-C-0 ο ο clothing -(Please read the notes on the back before filling this page)

Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs®

R-based acid, —_ sulfo ’, organic

R

3-c Proton hydrogen stand alone as the base element of the basic nitrite element halal carbon element ^ 2 with cocoa or sulfonyl ester acid ο 2 to the paper size applicable Chinese National Standard (CNS) A4 specifications (210X 297 mm ) -21-584661 A7 B7 V. Description of the invention (19) [C22] The polymerizable compound as described in the above [C21], wherein R1 and R2 in formula (c-3) are hydrogen atoms. [C23] The polymerizable compound according to the above-mentioned [C17], wherein two of Ac, Bc, and Cc shown in the above-mentioned formula (C-i) are a substituent having an acrylate group or a methacrylate group. [C24] A polymerizable compound represented by the aforementioned formula (C-4); CH.

CH? I 3 OCC = CH. II 〇Rx-(Please read the notes on the back before filling in this page) (C-4) [where R1 is hydrogen atom, halogen atom, nitro, amine, An acid group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C25] The polymerizable compound as described in [C24] above, wherein R1 in the formula (C-4) is a hydrogen atom. Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [C26] — a polymer obtained by polymerizing a polymerizable compound represented by formula (C-5); this paper size applies to China National Standard (CNS) A4 specifications (210X297 mm) 584661 A7 B7 V. Description of the invention (20 CH ^ I 3 H2C = CC-0 (CH2) 2-NH-C-0 ο

ch3 OC-NH- (CH2) 2-0-CC = CH. 0 0 RJ (C-5) [wherein R1 is a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C27] The polymerizable compound according to the above-mentioned [C26], wherein R1 in the formula (C-5) is a hydrogen atom. [C28] The polymerizable compound as shown in the above-mentioned [C17], wherein all the substituents of the Ae-based acrylate group in the above-mentioned formula (C-1) [C29]-a polymer

Be and Ce both have acrylate group or methyl formaldehyde which is not polymerizable by the formula (C-6) (Please read the notes on the back before filling out this page) Printed by P Bayong Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs Compound obtained by polymerization; ch3 H2C == CC0

CH, I 3 occ = ch9 II 2 〇 (C-6) This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -23- 584661 A7 B7 V. Description of the invention (21) [C30] — A polymer obtained by polymerizing a polymerizable compound represented by formula (C-7);

[C31] A copolymer containing at least one monomer unit derived from a polymerizable compound represented by the formula (CM) to formula (c-7). [C32] A species containing a mononuclear iridium A method for producing a polymerizable compound of the complex part, which is characterized by reacting an iridium dinuclear complex represented by the formula (C-8) with a phenylpyridine derivative represented by the formula (C-9) Then, the method of reacting the reactive substituent in the reaction product with the compound having a polymerizable functional group; ^^-(Please read the precautions on the back before filling this page) Order d Intellectual Property Bureau of the Ministry of Economic Affairs Printed by Employee Consumer Cooperative

This paper size applies Chinese National Standard (CNS) A4 specification (210X: 297 mm) -24 584661 A 7 B7 V. Description of the invention (22) [where xe and γα are reactive substituents, or hydrogen atoms, Halogen atom, nitro group, amine group, sulfonate group, sulfonate group or organic group having 1 to 20 carbon atoms which may have a hetero atom; V to R28 are each independently hydrogen atom, halogen atom, nitro group, amine group , Sulfonic acid group, sulfonic acid ester group or organic group having 1 to 20 carbon atoms which may have a hetero atom]

Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where Ze is a reactive substituent, or a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or a carbon having a hetero atom Organic groups of 1 to 20; R1 to R7 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom —But in the formula f 乇 4), at least one of Zee ¥ y ′ in Ze is a reactive substituent]. [C33] A method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C32], wherein Xe and Ye in the formula (C-8) are independent hydrogen atoms, halogen atoms, and nitro groups , An amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom; Ze in the formula (C-9) is a reactive substituent. [C34] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C33], wherein the system in the formula (C-9) is a hydroxyl group. [C35] A method for producing a polymerizable compound containing a mononuclear complex complex as in [C34], wherein the compound containing a polymerizable functional group is an acid halide. Clothing-(Please read the precautions on the back before filling this page) This paper size applies Chinese National Standard (CNS) A4 specification (2 丨 〇 > < 297 mm) -25- 584661 A7 __ B7 Five 'invention (23) [C36] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C34], wherein the compound containing a polymerizable functional group is an isocyanate compound. [C37] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C32], wherein Xc and Yc in the formula (C-8) are reactive substituents' formula (C-9) Ze in the above is an arbitrary hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom. [C38] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C37], wherein Zc in the formula (C-9) is a hydroxyl group. [C39] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C38], wherein the compound containing a polymerizable functional group is an acid halide. -_________________________________________________________________________ [C40] A method for producing a polymerizable compound containing a mononuclear iridium complex part as in [C37], wherein the compound containing a polymerizable functional group is an isocyanate compound. [C 4 1] A method for producing a polymerizable compound containing a silver complex portion, which is characterized by combining a dinuclear complex represented by the formula (C -1 0) with a polymerizable functional group. The compound reacts according to a certain molar ratio. If unreacted reactive substituents remain, the method of reacting them with the reactive substituents in the resulting product and the non-polymerizable compounds; China National Standard (CNS) A4 Specification (210X297 mm)-(Please read the precautions on the back before filling out this page) -Order-Printed by the Employees' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs -26- 584661 A7 ΒΊ One --- --- ----------- ---- V. Description of the invention (24)

[Wherein, is a reactive substituent; R1 to R21 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom; base]. [C42] A method for producing a polymerizable compound containing an iridium complex part as in [C4 1], wherein the iridium complex represented by the formula (C-10) and a polymerizable functional group—a customary benefit -Tomb! The above 1- [C43] A method for producing a polymerizable compound containing an iridium complex part such as [C4 2], wherein the reactive substituent of the formula (C-10) is a hydroxyl group. [C44] The method for producing a polymerizable compound containing an iridium complex part as in [C43], wherein the compound containing a polymerizable functional group is an acid halide. [C45] The method for producing a polymerizable compound containing an iridium complex part as in [C43], wherein the compound containing a polymerizable functional group is an isocyanate compound. [C4 6] The method for producing a polymerizable compound containing an iridium complex part as in [C41], wherein the iridium complex represented by the formula (C-10) and the compound having a polymerizable functional group are moles. The ratio is 1: (1.5 ~ 2.5). Clothing-(Please read the precautions on the back before filling this page)

、 1T Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs I- 1 1 --- --- This paper size is applicable to the Chinese National Standard (CNS) Λ4 specification (210X297 mm) -27- 584661 A7 B7 V. Description of the invention ( 25) [C47] A method for producing a polymerizable compound containing a silver complex part as in [C46], wherein the reactive substituent of the formula (C_ 1 0) is a hydroxyl group. [C 4 8] A method for producing a polymerizable compound containing an iridium complex part as in [C 4 7], wherein the compound containing a polymerizable functional group is an acid halide. [C49] The method for producing a polymerizable compound containing an iridium complex part as in [C47], wherein the compound containing a polymerizable functional group is an isocyanate compound. [C50] The method for producing a polymerizable compound containing an iridium complex part as in [C41], wherein the molar ratio of the iridium complex represented by the formula (C-10) to the compound having a polymerizable functional group For 1: (above 2.5). [C51] The method for producing a polymerizable compound containing an iridium complex part as in [C50], wherein the reactive substituent of the formula (CMO) is a hydroxyl group. [C5 2] The method for producing a polymerizable compound containing an iridium complex part as in [C51], wherein the compound containing a polymerizable functional group is an acid halide. [C53] The method for producing a polymerizable compound containing an iridium complex part as in [C5 1], wherein the compound containing a polymerizable palace energy group is an isocyanate compound. [C54] The compound represented by formula (C-11); This paper size applies the Chinese National Standard (CNS) A4 specification (210 > < 297 mm)-(Please read the precautions on the back before filling this page) Printed by W-Industrial Cooperative Cooperative of the Intellectual Property Bureau of the Ministry of Economy -28-584661 A7 B7 V. Description of Invention (26) iR3 Xc R4 R5,

10 衣 — (Please read the precautions on the back before filling in this page) (C-ll) [In the formula, at least one of Xc, Yc, zc is a hydroxyl group, and the remaining ones are independent hydrogen atoms and halogen atoms. , Nitro, amine, sulfonate, sulfonate, or organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R21 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group An acid group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [C 5 5} tG [C 44 ^ ^ ^ ^ Xc '

One of Yc and Zc is a hydroxyl group. [C56] Compound represented by formula (C-12); printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs

(C-12) [C57] A compound such as [C54], wherein one of X 'Ye and Ze of formula (C-11) is a hydroxyl group. [C58] Compounds represented by formula (C-13); This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 29-584661 A7 B7 V. Description of the invention (27

0H (013) [C59] A compound such as [C54], wherein χ (Ye and Ze are both hydroxyl groups in formula (c-n). [C60] Compound represented by formula (C-14);

0H 0H (C-14)

[D Π A kind of faint (^ -1 winter repeated beams of 1 and together) 1 ^ Xia rlD Intellectual Property Bureau of the Ministry of Economic Affairs (printed by the Industrial and Consumer Cooperative)

(Dl) [In the formula, at least one of XID, YID, and Z1D is a substituent having a polymerizable functional group, and the remaining ones in X1D, Y1D, and z1D are each an independent hydrogen atom or a carbon that may have a hetero atom. Organic groups of the number 1 to 2 (3; R1 to R are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic group, a sulfonate group, or an organic group having a carbon number of 1 to 20 [] (Please read the notes on the back before filling out this page)

This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) -30- 584661 A7 B7 V. Description of invention (28) (Please read the precautions on the back before filling this page) [D2] as [D1 ] A polymerizable compound shown in which either X1D or Z1D in the formula (D-1) is a substituent having a polymerizable functional group. [D3] — a polymerizable compound represented by the formula (D-2);

Q1D

x1 ° yVq2D

0, P

[In the formula, X1D is a substituent having a polymerizable functional group, and Q1D and Q2D are each independently a hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [D4] The polymerizable compound according to any one of [D1] to [D3], wherein the polymerizable functional group is a photo-shy ________________________________________—— [D5] — a polymerizable compound represented by the formula (D-3) ; Rr ^ Bureau of Intellectual Property, Ministry of Economic Affairs

[D6] The polymerizable compound according to any one of [D1] to [D3], wherein the polymerizable functional group is a styryl group. [D 7] —Polymerizable compound represented by the formula (D-4); This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) -31-584661 A7 B7 V. Description of the invention (29)

[D8] The polymerizable compound according to any one of [D1] to [D3], wherein the polymerizable functional group is an acrylate group or a methacrylate group. [D 9] A polymerizable compound not represented by formula (D-5), (Please read the precautions on the back before filling in this page). 〇

1T Intellectual Property Bureau of the Ministry of Economic Affairs 2 (printed by Industrial and Consumer Cooperatives [where R is a hydrogen atom or a methyl group]. [D 1 0] A polymerizable compound not included in formula (D-6),

[Wherein R is a hydrogen atom or a methyl group]. The size of this paper applies the Chinese National Standard (CNS) A4 specification (210 × 297 mm) -32- 584661 A7 B7 V. Description of the invention (30) [D11] — polymerizable compound represented by formula (D-7);

[Wherein R is a hydrogen atom or a methyl group]. [D 1 2] A kind of polymerizable compound not represented by formula (D-8),

0 R

[Wherein R is a hydrogen atom or a methyl group]. [D13] — Polymerizable compound represented by formula (D-9); (Please read the precautions on the back before filling this page) Printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs 〇

[Wherein R is a hydrogen atom or a methyl group]. -33- This paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) 584661 A7 B7 V. Description of the invention (31) [D 14] — polymerizable compound shown by formula (D-10)

〇 R

Ο

Η (D-10) [wherein R is an argon atom or a methyl group]. [D 1 5] —Polymerizable compound represented by formula (D -11)

0 0 R

(Please read the precautions on the back before filling out this page) (D-11) [wherein R is a hydrogen atom or a methyl group]. [D 16] — Polymerizable compound shown by formula (D-12) Printed by the Industrial and Commercial Bureau of the Ministry of Economic Affairs and Industrial Cooperatives R .0

〇 0 0 people

(D-12) [In the formula, R is a hydrogen atom or a methyl group] 584661 A7 B7 V. Description of the invention (32) [D17]-a polymerizable compound represented by the formula (D-13)

(D-13) [D18] The polymerizable compound according to [D1], wherein Y1D in the foregoing formula (D) is a substituent having a functional group. [D19] —Polymerizable compound represented by formula (D-14); (Please read the precautions on the back before filling this page)-clothing.

γ 1D

(D-14), 11 Intellectual Property Bureau of the Ministry of Economic Affairs (industrial and consumer cooperation, Du Yinzhihe [wherein, Y1D is a substituent having a polymerizable functional group, Q2d and each independent hydrogen atom or a carbon that may have a heteroatom] Numbered from 1 to 20. [D20] A polymerizable compound such as [D18] or [D19], wherein the polymerizable functional group is a carbon-carbon double bond. [D21] such as [D18] or [D19] [D22] A polymerizable compound such as [D18] or [D19], in which the size of the paper is in accordance with Chinese National Standard (CNS) A4 (210X 297) (Mm) -35 584661 A7 B7 V. Description of the invention (33) The functional group is acrylate or methacrylate. [D23]-polymerizable compound represented by formula (D-15); 〇

(D-15) (please read the precautions on # ^? Face first, then ^^), [D24] — polymerizable compound represented by formula (D-16) 〇

Η

R

, 1T

Printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs (D-16) [where R is a hydrogen atom or a methyl group]. [D25] A method for producing a polymerizable compound containing a mononuclear iridium complex, characterized in that an iridium dinuclear complex represented by the formula (D-17) is combined with the formula (D-18) Method for reacting compounds with polymerizable functional groups as shown; This paper size applies to Chinese National Standard (CNS) 8-4 (210 X 297 mm) -36- 584661 A7 B7 V. Description of the invention (34 t > 3 P, 31 R 30

(D-17) (Please read the notes on the back before filling this page)

Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where R1 to R32 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group or may have heterogeneous Organic group having 1 to 20 carbon atoms] Ί (D-18) [wherein at least one of X1D, Y1D, Z1D is a substituent having a polymerizable functional group, and other residues in X1D, Y1D, z1D Are each independently a hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [D26] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [D25], wherein the parent group or Z1D in the formula (D-18) is a substituent having a polymerizable functional group. [D27] The method for producing a polymerizable compound containing a mononuclear iridium complex part as described in [D25], wherein Y1D in the formula (D-18) is a substituent having a polymerizable functional group. This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) -37-584661 A7 B7 V. Description of the invention (35) [D 2 8]-a kind of polymerization containing a mononuclear silver complex The method for producing a basic compound is characterized in that the iridium dinuclear complex represented by the formula (D-17) is reacted with a compound having a polymerizable functional group represented by osmium (D-19), and then the obtained A method for reacting a reactive substituent of a mononuclear iridium complex with a compound having a polymerizable functional group;

(D-17) [In the formula, R1 to R32 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom. ] (Please read the notes on the back before filling out this page) Printed by R Industrial Consumer Cooperative of Intellectual Property Bureau, Ministry of Economic Affairs

〇 〇 (D-19) [In the formula, at least one of X2D, Z2D is a reactive substituent, and the remaining ones in X2D, Y2D, and Z2D are independent hydrogen atoms or carbon numbers that may have heteroatoms. 1 to 20 organic groups]. [D29] Polymerization of mononuclear iridium complexes such as [D28] This paper is sized according to the Chinese National Standard (CNS) A4 (210X 297 mm) -38 584661 M ___B7 V. Description of the invention (36 ) A method for producing a compound, wherein X2D or z2D in the formula (D-19) is a substituent containing a hydroxyl group. [D30] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [D28], wherein Y2D in the formula (D-19) is a substituent containing a hydroxyl group. [D31] a compound represented by formula (D-20);

(D-20) Clothing — (Please read the notes on the back before filling this page) Order printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [in the formula, X2D, —Z—2D—A, Y2D, Z2D Other residues are each independent hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom; V to R16 are each independent hydrogen atom, halogen atom, nitro group, amine group, sulfonic group, sulfonic acid An ester group or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [D32] The compound according to [D31], wherein X2D or 22 ° in the formula (D-20) is a substituent containing a hydroxyl group. [D 3 3] —The compound represented by the formula (D-2 1); This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -39- 584661 A7 B7 V. Description of the invention (37)

(D-21) [In the formula, 11 is an integer of 0 to 20, Q1. And Q2D are each independently a hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [D34] a compound represented by formula (D-22);

Q 1D

(D-22) (Please read the precautions on the back before filling out this page) Printed by K Industrial Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs [where η is an integer from 0 to 20, and Q1D and Q2D are independent hydrogen atoms Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [D35] The compound according to [D31], wherein Y2D in the formula (D-20) is a substituent containing a hydroxyl group. [D36] —The compound represented by the formula (D-23); This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -40- 584661 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs A7 ______ B7 V. Description of Invention (38)

[In the formula, η is an integer of 0 to 20, and 02 and Q3D are each independently a hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [D37] A polymer which is a polymer of any one of the polymerizable compounds in [D1] to [D24]. [D38] A polymer obtained by polymerizing a composition of any polymerizable compound of [D1] to [D24]. [E -1] a polymerizable compound represented by formula (E -1);

[Where χε is a substituent having a polymerizable functional group, R1E to R3E are each independently hydrogen atom, halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom; R4 to R19 are each independent hydrogen Atom 'halogen atom, (Please read the notes on the back before filling out this page)

This paper size is applicable to China National Standard (CNS) A4 (210X 297mm) -41-584661 χΕ

A7 B7 5. Description of the invention (39) Nitro, amine, sulfonic, sulfonate or organic group having 1 to 20 carbon atoms which may have a hetero atom]. [E2] The polymerizable compound according to [E1], wherein the polymerizable functional group of XE in the aforementioned formula (E-1) is a carbon-carbon double bond. [E3] a polymerizable compound represented by the formula (E-2); (E-2) [wherein, XE is a substituent having a polymerizable functional group]. [ε 4 ^^ m m v & φ energy group is acryloxy or methacryloxy. [E5] A polymerizable compound such as [E1] or [E3], wherein in the formula (E-2), XE is a methacryloxy group. [Ε6] — Polymerizable official formula of polymerizable compound represented by the formula (E-3) (E-1 (please read the precautions on the back before filling this page) system

Ο CH. ^ // ▲ C—C

(Ε-3) This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -42- 584661 A7 B7 V. Description of the invention (4〇) [E7] Such as [El] or [E3] polymerization A sex compound, wherein in the formula (E-1) or (E-2), 乂 is methacryloxymethyl. [E 8] — a polymerizable compound not represented by the formula (E-4),

CH, I, (E-4) [E9] A polymerizable compound such as [E1] or [E3], wherein in formula (E-1) or (E-2), XE is methacrylic acid Methylaminomethyloxymethyl. [E10] — polymerizable compound represented by formula (E-5); (Please read the precautions on the back before filling out this page), ^ 1 Intellectual Property Bureau of the Ministry of Economic Affairs (printed by the Industrial and Consumer Cooperative)

[E11] A polymerizable compound such as [E1] or [E3], wherein in the formula (E-1 or (E-2), XE is a methacryloxyethyloxycarbonyl group. [E12]-a formula (E-6) polymerizable compounds; this paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) -43- 584661 Μ B7 V. Description of the invention (41

(E-6) (Please read the precautions on the back before filling in this page) [E13] Polymerizable compounds such as [El] or [E3], where the polymerizable functional group is a styryl group. [E14] The polymerizable compound according to [E1] or [E3], wherein in the formula (E-1) or (E-2), XE is a vinyl benzyloxy group. [E15] a polymerizable compound represented by formula (E-7);

(E-7) Bureau of Intellectual Property, Ministry of Economic Affairs (printed by the Industrial and Consumer Cooperatives [E16]-polymerizable compound shown by the formula (E-8). The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297) %) -44- M4661

V. Description of the invention (42 ° v / H2

(E-8) [E 17] A method for producing a polymerizable compound containing a mononuclear iridium complex, characterized in that an iridium dinuclear complex represented by the formula (E-9) is combined with After the picolinic acid derivative represented by the formula (E-10) is reacted, the reaction product is reacted with a polymerizable functional group and a reactive substituent Ye produced by the formula (E-10). Method for reaction of basic compounds; (Please read the notes on the back before filling out this page) Order printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, Consumer Consumption Cooperative

R R

R

[In the formula, R4 to R19 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms that may have a hetero atom] — · This paper Standards are applicable to Chinese National Standard (CNS) A4 specifications (210X 297 mm) -45- 584661 Α7 Β7 5. Description of the invention (43)

[Wherein, 'E' is a reactive substituent, and r1e, r2E, and r3E are each independently a hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [E 18] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [E 17], wherein YE in the formula (E — 1 0) is a base having an active gas. [E 19] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [E 17], wherein YE in the formula (E-10) is a hydroxyl group or a methylol group. [E20] The manufacturing method of polymerizable compounds containing a mononuclear iridium complex part as in [E 19], where the beautiful shoulder 1 poly straight__Straight_ 能 _Sha Yushengji YE reaction combined with The functional group compound is an acid chloride having a polymerizable functional group. [E21] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [E 19], wherein the compound having a functional group is obtained by combining a polymerizable functional group with a reactive substituent ^ It is an alkyl chloride having a polymerizable functional group. [E22] A method for producing a polymerizable compound containing a mononuclear iridium complex, such as [E 18] or [E1 9], wherein the polymerizable functional group has a functional group obtained by combining a reactive functional group with a reactive substituent Υε The compound of the group is an isocyanate compound having a polymerizable functional group. [Ε23] If [EI 17] contains the polymerized part of the mononuclear iridium complex, the paper size applies the Chinese National Standard (CNS) A4 specification (210 × 297 mm) (Please read the precautions on the back before filling in this Page), 1T. Printed by the Consumer Cooperatives of the Intellectual Property Office of the Ministry of Economy -46- 584661

Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs and the Industrial Cooperative Cooperative Association ΑΊ B7 V. Description of the invention (44) A method for producing a compound, wherein YE of formula (E-10) is a carboxyl group. [E24] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [E23], wherein the compound having a functional group obtained by combining a polymerizable functional group with a reactive substituent YE is A compound having a hydroxyl group of a polymerizable functional group. [E25] A method for producing a polymerizable compound containing a mononuclear iridium complex, characterized in that an iridium dinuclear complex represented by the formula (E-9) is combined with the formula (E-11) A method for reacting the picolinic acid derivative shown;

[Wherein R4 to R19 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]

[In the formula, XE is a substituent of a polymerizable functional group, and R1E, R2E, and R3E are each an independent hydrogen atom or an organic carbon number of 1 to 20 which may have a halogen atom. The paper size applies to Chinese national standards (0 ~ 5) Eight &4; (210 '/ 297 mm) (Please read the notes on the back before filling out this page)

-47- 584661 A7 ______ B7___ V. Description of Invention (45) Base]. [E26] A method for producing a polymerizable compound containing a mononuclear iridium complex part as in [E25], wherein XE in the formula (E-11) is methacrylic acid, methacrylic acid Any one of methyl, methacryloxyethylaminomethyloxymethyl, methacryloxyethyloxycarbonyl, and vinylbenzyloxy. [E27] a compound represented by formula (E-12);

(Please read the notes on the back before filling out this page} Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where YE is a reactive substituent, and R1E ~ R3E are independent hydrogen atoms, halogen atoms or may An organic group having 1 to 20 carbon atoms; R4 to R19 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or a carbon atom having 1 to 2 0 [E28] A compound such as [E27], wherein Ye in the formula (E-12) is a hydroxyl group. [E29]-a compound represented by the formula (E-13); __ This paper size applies China National Standard (CNS) A4 specification (210X 297 mm) _ 48 _ 584661 kl B7

V. Description of the invention (46 HO

F (E-13) [E30] — a compound represented by formula (E-14);

(E-14) [E31]-a compound represented by the formula (E-15)

COOH F

〇 C 〇 N

F (E-15) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [E32] — A composition containing a polymerizable compound of any of [E1] to [E16]. [E33] A polymer comprising a polymerizable compound shown in any one of [E1] to [E16]. [E34] A polymer characterized by being polymerized from a polymerizable component of [E32]. [Polymerizable compound represented by FU formula (F-1); (Please read the precautions on the back before filling in this page)

This paper size applies to Chinese National Standard (CNS) A4 specification (210XM7 mm) -49- 584661 kl B7 V. Description of the invention (47

Y IF

R 11 (Please read the precautions on the back before filling this page) (Fl) [In the formula, at least one of X1F, Y1F, Z1F is a substituent with a polymerizable functional group, and other residues in X1F, Y1F, z1F Which are each independently hydrogen atom, halogen atom or organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R16 are each independent hydrogen atom, halogen atom, nitro'amine group, sulfonic acid group, sulfonic acid group An acid group or an organic group having 1 to 20 carbon atoms which may have a hetero atom] 〇 [F2] A polymerizable compound represented by [F1], wherein any one of formula (F-1) or Z] F is A substituent having a polymerizable functional group. [F3] a polymerizable compound represented by formula (F-2);

〇 〇 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

(F-2) [In the formula, x1F is a substituent having a polymerizable functional group, and Q1F and Q2F are each independently a hydrogen atom, a halogen atom, or a carbon number that may have a hetero atom. 1 to this paper standard applies Chinese national standards ( CNS) A4 specification (210X 297 mm) -50- 584661 A7 B7 V. Description of invention (48) 20 organic group]. Poly [F4] The polymerizable compound according to any one of [F1] to [F3], wherein the synthetic functional group is a carbon-carbon double bond [F5] polymerizable compounds represented by formula (F-3);

(F-3) (wherein N is an integer of 0 to 20). [F6] The polymerizable compound according to any one of [F1] to [F3], wherein the synthetic functional group is a styryl group. [F7] — polymerizable compound represented by formula (F-4); poly (please read the precautions on the back before filling out this page).. Clothing. 11 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs.

(F-4) (wherein N is an integer from 0 to 20). [F8] —Polymerizable compound represented by formula (F-5) The paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -51-584661 A7 B7 V. Description of the invention (49

0 0

(F-5) [F9] The polymerizable compound according to any one of [F1] to [F3], wherein the polymerizable functional group is an alkoxyloxy group. [F10] a polymerizable compound represented by formula (F-6);

(Please read the notes on the back before filling out this page) (F-6) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where η is an integer from 0 to 20, and A is an acrylic or methacrylic group An fluorenyl or propylene fluorenyloxy or methacryl fluorenyloxy group having 3 to 20 carbons]. [F 1 1] — * Polymerizable compound not in the formula (F-7); This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -52-584661 A7 B7

V. Description of the invention (50

0 0 (F-7) [wherein R is a hydrogen atom or a methyl group]. [F12] —Polymerizable compound represented by formula (F-8) (Please read the precautions on the back before filling this page)

R 0 (F-8)

, 1T Printed by R Industrial Consumer Cooperatives, Intellectual Property Bureau, Ministry of Economic Affairs 0 0

[Wherein R is a hydrogen atom or a methyl group]. [F13] — polymerizable compound represented by formula (F-9)

• A (F-9) This paper size is applicable to China National Standard (CNS) A4 (210X297 mm) -53- 584661 A7 B7 V. Description of the invention (51) [where η is an integer from 0 to 20, A is an organic group having a carbon number of 3 to 20 having a propylene fluorenyl group, a methacryl fluorenyl group, a propylene fluorenyl group, or a methacryl methoxy group]. [F 14] a polymerizable compound represented by the formula (F-10);

0 0 R

(F-10) [wherein R is a hydrogen atom or a methyl group]. [F15] —Polymerizable compound represented by formula (F-11) 〇 R Ο 〇 (Please read the precautions on the back before filling this page) Order ---- Printed by the 8th Industrial Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs Ο 0

(F-11) [wherein R is a hydrogen atom or a methyl group]. [F16] The polymerizable compound according to [F1], wherein Y1 F in the formula (F-1 is a substituent having a polymerizable functional group. [F17] — a polymerizable compound represented by the formula (F-12) ; This paper size applies Chinese National Standard (CNS) A4 specification (2 丨 〇 < 297 mm)-54- 584661 A7 B7 V. Description of the invention (magic)

Y1F

[In the formula, Y1F is a substituent having a polymerizable functional group, and q2F and q3F are each an independent hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [F18] The polymerizable compound according to [F16] or [F17], wherein the polymerizable functional group is a carbon-carbon double bond. [F19] The polymerizable compound according to [F16] or [F17], wherein the polymerizable functional group is a styryl group. [F20] The polymerizable compound according to [F16] or [F17], wherein the polymerizable functional group is an alkoxyloxy group. [F21] — Polymerizable compound represented by formula (F-13); (Please read the precautions on the back before filling this page), 11 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 0

[Wherein R is a hydrogen atom or a methyl group]. This paper size applies to China National Standard (CNS) A4 (210X297 mm) -55- 584661 A7 B7 V. Description of the invention (53) [F22] — polymerizable compound represented by formula (F-14)

R H l (F-14) [wherein R is a hydrogen atom or a methyl group]. [F23] A method for producing a polymerizable compound containing a mononuclear iridium complex, characterized in that the iridium dinuclear complex represented by the formula (F_15) is represented by the formula (F-16) Method for reaction of compounds with polymerizable functional groups; (Please read the precautions on the back before filling this page)

Printed by 1T Consumer Cooperatives, Intellectual Property Bureau, Ministry of Economic Affairs

RJ

(F-15) RXA R

[Wherein R1 to R16 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having a carbon number of 1 to 20 which may have a hetero atom] The paper size is applicable China National Standard (CNS) A4 Specification (210 × 297 mm) -56- 584661 A7 _____B7 V. Description of Invention (54)

Y1F

Ο ο Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where, at least one of X1F, Y1F, Z1F is a substituent with a polymerizable functional group, and the other residues in X1F, Y1F, z1F are independent of A hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom] [F24] A method for producing a polymerizable compound containing a mononuclear iridium complex part such as [F23], wherein, the formula ( F ^ or 2 ^ in F-16) is a substituent having a polymerizable functional group. [F25] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [F23], wherein Y1F in the formula (F-16) is a substituent having a polymerizable functional group. [F26] A method for producing a polymerizable compound containing a mononuclear iridium complex, which is characterized by combining an iridium dinuclear complex represented by the formula (F-15) with the formula; (F-1 7) After the compound having a polymerizable functional group shown in the figure is reacted, the reactive substituent of the obtained mononuclear iridium complex is replaced with, and the polymerizable functional group is substituted with a reactive substituent produced by the formula (F-17). Method (at least one of X2F, Y2F, Z2F) reaction combined with the functional group of the compound; (Please read the precautions on the back before filling this page).

、 1T This paper size applies to Chinese National Standard (CNS) A4 specification (210 X 297 mm) -57- 584661 A7 B7 V. Description of the invention (55 ΙΓ R-

(F-15) R R

[Wherein Ru is a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom] independently of each other] y2F I «2F ( F-17)

• 2 F-ϊ HI —111 In 1-I- I-I-I (Please read the notes on the back before filling this page)

, 1T, Duong-Chung Consumer Cooperation, Intellectual Property Bureau, Ministry of Economic Affairs [where, at least one of x2F, Y2F, z2F is a reactive substituent, and the remaining residues in X: Y2F, Z2F are independent hydrogens. Atom, halogen atom or organic group having 1 to 20 carbon atoms which may have a hetero atom]. [F27] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [F26], wherein X2F or Y2F or Z2F in the formula (F-17) is a substituent containing an active hydrogen. [F28] The method for producing a polymerizable compound containing a mononuclear iridium complex part as in [F26], wherein 乂 2 !? or 22 !? in the formula (F-17) is a substituent containing a hydroxyl group. [F29] A method for producing a polymerizable compound containing a mononuclear iridium complex part as in [F26], wherein γ2P in the formula (F-17) is a paper containing hydroxyl groups, and the Chinese paper standard (CNS) A4 is applied. Specification (210 × 297 mm) -58- 584661 A7 B7 V. Substituent of invention description (56). [F30] a compound represented by formula (F-18);

γ 2F

R 11 (F-18) (Please read the precautions on the back before filling this page). [In the formula, Y2f, X2F, Y2F, Z2F must contain at least i substituents containing hydroxyl groups, and other residues in X2F Z2F. Are each independently a hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms that may have a hetero atom; R1 to R16 are each independently a hydrogen atom + a subdihalogen atom, a nitro group, an amine group, and a sulfonic acid Group, sulfonate group or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [F31] The compound according to [F3 0], wherein f or ^ in the formula (F-18) is a substituent containing a hydroxyl group. [F32] — Compounds of the formula (F-19); printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

n〇H

(F-19) [where η is an integer from 0 to 20, and 0 ^ and Q2F are independent hydrogens. The original paper size applies the Chinese National Standard (CNS) A4 specification (2 丨 0X297 mm) _ie 584661

Q 1F

OH A7 B7 V. Description of the invention (57) A daughter element atom or an organic group which may have a carbon number of from 20 to 20] [F33]-a compound represented by formula (F-20); (F-20) [ In the formula, 'η is an integer of 0 to 20, and ^ and Q2F are each independently a hydrogen atom, a halogen atom, or an organic group having a carbon number of from 1 to 2]. [F34] The compound according to [F3 0], wherein Y2F in the formula (F-18) is a substituent containing a hydroxyl group. [F35] — Compounds represented by formula (F-21); (Please read the precautions on the back before filling this page), 11

Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs

(F-21) [In the formula, 11 is an integer of 0 to 20, (^ and Q3F are each independently a hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [F 3 6 ] —A kind of polymer, which is a polymer of any of the polymerizable compounds in [F1] ~ [F 2 2]. This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -60-584661 A7 ____B7___ V. Description of the invention (58) [F3 7]-A polymer, which is a polymerized composition containing at least one polymerizable compound of [F1] to [F22]. [F3 8] A composition, which is a composition containing at least one polymerizable compound of [F1] to [F22]. [G1]-a polymerizable compound represented by formula (G-1);

[In the formula, L is a monovalent anionic two-segment ligand, XQ is a substituent having a polymerizable functional group; R1 to R7 are each independently a hydrogen atom, a halogen atom, a nitrate, a amine group, and an amine group. An ammonium bisulfate or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. (Please read the notes on the back before filling out this page) Printed by Xiao Gong, Consumer Cooperation, Intellectual Property Bureau, Ministry of Economic Affairs

[G2] Polymerizable compound represented by formula (G-2); a2G

[Wherein A1 c to A3C are each independently hydrogen atom, halogen atom, or organic group having 1 to 20 carbon atoms which may have a hetero atom; Xσ is a substituent having a polymerizable functional group, and R1 to R7 are each independently Hydrogen atom, halogen atom, this paper size applies to China National Standard (CNS) A4 specification (21〇 × 297 mm) -61-584661

3 1 GI Printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs A7 B7 V. Description of the invention (59) Nitro, amine, sulfonic, sulfonate or organic with 1 to 20 carbon atoms which may have heteroatoms base]. [G3] The polymerizable compound represented by [G1] or [G2], wherein the polymerizable functional group of Xσ in the formula (G-1) or (G-2) is a group having a carbon-carbon double bond. [G4] The polymerizable compound as shown in [G1] or [G2], wherein Xα in the formula (G-1) or (G-2) is methacryl ethoxy group, methacryl ethoxy group Any of aminomethylamino and vinylbenzyloxy. [G5] —Polymerizable compound other than that of formula (G-3); c——c

13 II

He 2

H

2 Η

3 C c ι c——c cmmo [G6] — polymerizable compound represented by formula (G-4);

This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) (Please read the precautions on the back before filling this page)

-62- 584661 A7 B7 V. Description of the invention (60 h2c = hc -o- wCH3

HX

CH = CH〇 (G-5) [G8] —A method for producing a polymerizable compound containing a mononuclear iridium complex, characterized in that the iridium dinuclear complex represented by formula (G-6) After the compound is reacted with the monovalent anionic two-segment ligand L, the reaction product is combined with a functional group obtained by reacting a polymerizable functional group with a substituent Yc having a reactive functional group of the formula (G_6). Method for reaction of basic compounds; (Please read the notes on the back before filling out this page)

[In the formula, Y0 is a substituent having a reactive functional group, and R1 to R7 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or a carbon number which may have a hetero atom. Organic groups from 1 to 20] [G9] Polymeric compounds containing mononuclear iridium complexes such as [G8] This paper is sized to the Chinese National Standard (CNS) A4 (210X297 mm) 63-584661 A 7 B7 V. The method for producing a substance according to the invention (61), wherein Yc in the formula (G-6) is a group having active hydrogen. [G 1 0] A method for producing a polymerizable compound containing a mononuclear iridium complex part as in [G 8], wherein YQ in the formula (G-6) is a hydroxyl group. [G 11] A method for producing a polymerizable compound containing a mononuclear iridium complex part as in [G 1 〇], wherein the polymerizable functional group and a substituent having a reactive functional group of the formula (G-6) The functional group compound obtained by the Yc reaction is an acid chloride having a polymerizable functional group or an alkyl halide compound having a polymerizable functional group. [G 12] A method for producing a polymerizable compound containing a mononuclear iridium complex part such as [G9] or [G 10], wherein the polymerizable functional group and a reactive functional group having the formula (G-6) The functional group compound obtained by the reaction of the substituent groups is an isocyanate compound having a polymerizable functional group. [G 13] A method for producing a polymerizable compound containing a mononuclear iridium complex, characterized in that an iridium dinuclear complex represented by the formula (G_7) is coordinated with a monovalent anionic dibasic complex Method for reaction of the base L; Yi-(Please read the precautions on the back before filling this page)

1T Intellectual Property Bureau, Ministry of Economic Affairs

This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -64- 584661 A7 B7 V. Description of the invention (62) [wherein 'Xc is a substituent with a polymerizable functional group, R1 to R7 are A hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom, each independently]. (Please read the precautions on the back before filling in this page) [G14] A method for producing a polymerizable compound containing a mononuclear iridium complex, such as [G 13], where χ〇 in formula (G_7) is Any of methacrylfluorenyloxy, methacryloxyethylaminomethylmethyl, and vinylbenzyloxy. [G15] — an iridium dinuclear complex represented by the formula (G-6);

Printed by the Intellectual Property Workers' Cooperatives of the Ministry of Economics [where YQ is a substituent with a reactive functional group; to R7 are each independently hydrogen, halogen, nitro, amine, sulfonate, sulfonate Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [G16] The compound according to [G15], wherein Yc in the formula (G-6) is a hydroxyl group. [G 1 7] —Iridium dinuclear complex of different type (G-8); This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -65- 584661 A7 B7 [G18] — A compound represented by formula (G_9); R3 T. R3

R3 V. Description of the invention (63

(G-8) (G-9) [wherein 'L is a monovalent anionic two-segment ligand, γ. Is a substituent having a reactive functional group; R1 to R7 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonate group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom base]. (Please read the precautions on the back before filling out this page), -5 mouths Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

[G 1 9] —a compound represented by the formula (G -1 0); t, 2G

(G-10) [In the formula, A1C) ~ A3C are each independent hydrogen atom, halogen atom or may have -66-This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) 584661 A7 B7 __ 5 Explanation of the invention (64) Organic groups having 1 to 20 carbon atoms having hetero atoms, Υσ is a substituent having a reactive functional group, and R1 to R7 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, and a sulfonic acid group. An acid group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. [G20] The compound according to [G18] or [G19], wherein YQ in the formula (g-6) or (G-10) is a hydroxyl group. [G21] — Compound represented by formula (G-11); (Please read the precautions on the back before filling this page)

, 1T

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

R R

R 'IT

[G22] — an iridium dinuclear complex represented by formula (G-7); (G-7) [wherein, R is a substituent having a reactive functional group, and R1 to r7 are each independently hydrogen atoms, A halogen atom, a nitro group, an amine group, a sulfonic group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -67 584661 A7 ______ B7 V. Description of the invention (65) [G23] As the iridium dinuclear complex of [G22], where, the formula ( Xc in G, 7) is any of methacryloxy, methacryloxyethylaminomethyl, and ethoxybenzyloxy. [G24] A composition containing an arbitrary compound in [G1] to [G7]. [G25] A polymer, which is a polymer of any of [G1] to [G7] to polymerize individual compounds. [G26] A polymer obtained by polymerizing a composition containing at least one polymerizable compound of [Gl] to [C} 7]. [Brief description of the diagram] FIG. 1 is a cross-sectional view of an example of an organic light emitting device according to the present invention. '... S ------------

[Description of symbols of main elements in the figure] S 1 glass substrate 2 anode 3 hole transport layer 4 light emitting layer 5 electron transport layer 6 cathode [Embodiments of the invention] Hereinafter, embodiments of the present invention will be described with reference to the drawings as follows. Figure 1 is a cross-sectional view of an example of the organic light-emitting element composition of the present invention, which is based on the Chinese paper standard (CNS) A4 specification (210X297 mm) _ 68 (Please read the precautions on the back before filling this page}- Ordered by the Intellectual Property Bureau of the Ministry of Economic Affairs and printed by the 8th Industrial Cooperative Cooperative 584661 A7 __ _____B7 V. Description of the invention (66) Between the anode 2 and the cathode 6 on the transparent substrate 1, the hole transport layer 3, the light emitting layer 4, The electron transport layer 5. The organic light-emitting element of the present invention is not limited to the example shown in FIG. 1, and a hole transport layer / light emitting layer may be sequentially disposed between the anode and the cathode, (2 Either the light-emitting layer or the electron-transporting layer is acceptable, and then a layer (3) containing a hole-transporting material, a light-emitting material, and an electron-transporting layer is provided, and (4) a layer containing a hole-transporting material and a light-emitting material, (5) a layer containing a luminescent material and an electron transporting material, (6) any one of a layer containing a luminescent material alone, and the luminescent layer shown in FIG. 1 is a single layer, which can also be obtained by laminating more than two layers In the present invention The part having a molecular structure with excited triplet state to emit light, that is, a part having phosphorescence luminescence, or a part having a molecular structure that emits light through the excited triplet state (hereinafter, also referred to as a light emitting part through excited triplet state) Part), the aforementioned luminescent part may be formed by a part of the polymer or formed by combining with the polymer. For example, as disclosed in Japanese Patent Application Laid-Open No. 2002-050483, it is equivalent to the first organic compound of phosphorescence. It is composed of an excited triplet state that moves the energy to an excited triplet portion corresponding to the portion of the second organic compound that is fluorescently luminescent, and causes the second organic compound to generate fluorescent light. In addition, if the organic light-emitting element of the present invention includes a portion that emits light through the excited triplet state described above, at least a part of the light-emitting portion is a phosphorescent light-emitting portion and a fluorescent light-emitting portion, and the polymer Binding is preferred. Also, in this case, a polymer composed of a part of the polymer or a phosphorescent part or / and a fluorescent part that is combined with the polymer to form a high This paper size applies to China National Standard (CNS) A4 (210X297 mm) (Please read the precautions on the back before filling this page)

Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs-69- 584661 A7 B7 V. Description of the invention (67) The main chain of the child can also be formed, or the branch of the polymer can be formed (referring to the function based on the side chain group in the main chain It is also possible to form long chain branches). The quantum efficiency of the excited triplet state of the phosphorescence-emitting part described above is preferably 0.1 or more, more preferably 0.3 or more, and most preferably 0.5 or more. A compound having a higher quantum efficiency such as a metal complex is suitable for the excited triplet state of the phosphorescent part. Specific examples of the above metal complexes include transition metal complexes such as iridium complexes and platinum complexes, and transition metal complexes thereof. It has the advantage of forming a more stable excited triplet at high temperatures. In addition, as will be described later, a polymer having a functional group having a coordination function and a transition metal atom is more likely to generate a complex when the fluorene is coordinated to the transition metal atom. In addition, other compounds with high quantum efficiency in the excited state to which the aforementioned phosphorescent light-emitting portion is applied can be selected, for example, from "Handbook of Photochemistry, Second Edition" (Steven L. Murov et al., Marcel Dekker Inc., 1993) . It can be used for the transition metals used in the above-mentioned transition metal complexes, such as Zn in atom number 2 1 to Zn in atom number 30 in the first transition metal element series of the periodic table, and Y in atom number 39 in the second transition metal element series. Cd to atomic number 48, Hf of atomic number 72 to Hg of atomic number 80 in the third transition metal element series, and the like. In addition, other specific examples of the metal complex that emits light through an excited triplet state include a rare earth metal complex and the like. The rare earth metals which can be used for the aforementioned rare earth metal complexes include, for example, La of atom number 57 to Lu of atom number 71 in the periodic table. In the present invention, a luminescent material generally refers to a luminescent substance itself. The paper size of this invention is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) (please read the precautions on the back before filling this page), printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economy -70- 584661 A7 B7 Fifth, the luminous part of the invention description (68) is a metal complex, which can be combined with a polymer. That is, the luminescent substance of the present invention may be a high molecule itself having a luminescent portion, and it may be a luminescent material. However, for the convenience of description, the light-emitting portion bound to a polymer is often described as a light-emitting substance. In addition, in a broad sense, a substance composed of a light-emitting layer containing a light-emitting substance, an adhesive, a hole transporting material, or an electron-transporting material is referred to as a light-emitting material. The luminescent part of the present invention is a non-ionic part. It is because when the light-emitting part is ionic, the light-emitting layer containing the light-emitting part is liable to cause electrochemical light emission when a voltage is applied. The response speed of this light emission is, for example, a very slow speed of partial response, so it is generally not suitable as a general Display panel. In the present invention, "the light-emitting part forms a part of a polymer" means that the structure of the light-emitting part is intended to constitute at least one kind of repeating unit of a polymer. When the polymer is copolymerized, at least one of the constituent monomers is a structure having a light-emitting portion. The light-emitting portion may be a main chain of a polymer or a branched chain (such as a side chain group). "Bonding the light-emitting part with the polymer" means that the light-emitting part of the polymer compound is bound to a certain degree and is bound regardless of the form. Specific methods, such as a method of combining a light-emitting portion into a polymer main chain, or a method of combining side chains (including branched groups), are not limited to these methods. In addition, in the case of the transition metal complex compound and the rare earth metal complex compound described above, for example, a method of combining at least one kind of ligand among the ligands formed by the complex as the main chain of the polymer , Or combining in a branched manner. In addition, the paper size used for the above-mentioned transition metal complexes and rare earth metal complexes applies the Chinese National Standard (CNS) A4 specification (21 × 297 mm) (Please read the precautions on the back before filling this page) 、 11 Intellectual Property Bureau of the Ministry of Economic Affairs (printed by the Industrial and Consumer Cooperatives-71-584661 A7 ____B7 V. Coordination group of invention description (69), such as acetoacetone, 2, 2, bipyridine, 4, 4, -Dimethyl-2,2, bipyridine, ι, ιο_phenanthroline, 2-phenylpyridine, (I-line, phthalocyanine, pyrimidine, _line, 2-phenylxanthene and / or Derivatives and the like are exemplified, but are not limited thereto. The aforementioned ligands may form one or more kinds of coordinations on one complex. In addition, the above complex compounds may use dinuclear complexes or multinuclear complexes. It may be a complex complex composed of two or more complexes, etc. In the light-emitting part of the present invention, a metal atom serving as the center metal of the metal complex may be bonded to one or more sites of the polymer. The method for achieving the foregoing purpose is not particularly limited, for example, it can be started by the above-mentioned coordination to form a complex, Or use charge transfer to generate complexes, ionic binding, covalent bonding and other methods. Among them, the method of complexing the luminescent substance by the coordination of a ligand and a polymer is to easily change the electronic state of the luminescent substance. It is better to immobilize the polymer. In addition, when the metal atom of the central metal is an ion, a method in which the light-emitting part is neutral for the reason described above can be used. For example, in addition to coordination bonds, it also has sufficient neutralization ions. Covalently bonded organometallic compounds and other methods are not limited thereto. The polymer that can be combined with the metal atom of the present invention is not particularly limited. For example, a pyridyl group having a coordination energy can be used. Or bipyridyl, bipyrimidyl, quinolinyl and other heterocyclic compounds are bonded to the main chain and / or branched chain of the polymer. The aforementioned polymer compound is specifically, for example, polypyridyl, polypyridine Diphenyl, polyDquinoline diyl, etc., polymers and / or derivatives thereof containing ligands in the main chain, polyvinylpyridine, poly (meth) propenylpyridine, polyvinyl Dquinoline, etc., The polymer with a ligand on the chain and / or its paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm)-I-72- Clothing-(Please read the precautions on the back before filling in this page)

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, 1T 584661 A7 _________B7 V. Description of the Invention (70) Derivatives' and / or polymers obtained from the above-mentioned structural combination. ------_ Clothing II (Please read first. Note on the back and then fill out this page) Also 'The polymer used in the present invention, whose luminous part is composed of one part' or by A combination of a monomer unit and a copolymer obtained from a monomer unit having no luminescent part. Among them, monomer units which do not have a light-emitting portion such as alkyl (meth) acrylates such as methyl acrylate and methyl methacrylate, styrene and derivatives thereof, are not limited thereto. When the copolymer formed from the monomer unit having no light-emitting portion described above is used as a light-emitting layer of an organic light-emitting element, it can improve processability and impart flexibility to the film after film formation. This is an extremely advantageous advantage when using a polymer thin-film substrate to make a flexible light-emitting element. The degree of polymerization of the polymer used in the present invention is preferably 5 to 10,000-and 10 to 50 0_00 塁 1_. -------------------------------------------------- -Consumption cooperation by employees of the Intellectual Property Bureau of the Ministry of Economic Affairs Du Yinzhi Because the molecular weight of a polymer is determined by the molecular weight of the constituent monomers and the polymer, the molecular weight of the polymer used in the present invention is not easy to set appropriately. range. In the illustrations, the molecular weight of the polymer used in the present invention is generally based on the above-mentioned degree of polymerization. Generally, the weight average molecular weight is preferably 1,000 to 2,000,000, and more preferably 10 to 5000. Among them, the measurement method of molecular weight includes, for example, the method described in the "Basics of Polymer Chemistry" (Tokyo Chemical Co., 1978), edited by the Polymer Society, that is, the GPC method (sol chromatographic analysis method) and the method using osmotic pressure , Light scattering method, ultracentrifugation and other methods. The light-emitting mechanism of the organic light-emitting element of the present invention is as follows. That is, the lowest excited triplet state generated by electrical agitation is 25%, and the lowest excited triplet paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -73- 584661 A7 B7 5. The invention description (71) state is The proportion of 75%, when the luminescent substance is a transition metal complex or a rare earth metal complex, due to the effect of heavy atoms, it is extremely easy to produce the cross-talk effect between the lowest singlet state and the lowest triplet state, so the lowest excited triplet state The proportion increased to more than 75%. Therefore, when the transition metal complex of phosphorescent emission is generated in the lowest excited triplet state, both the radiation migration and the non-radiation migration of phosphorescent emission exist simultaneously. In the case of a rare earth metal complex, the lowest excited triplet excited energy of the ligand is to move the energy to the central metal ion, so that it emits light from the excited level of the central metal ion. At this time, the luminescence emission migrates. There is no radiation migration at the same time. This non-radiative migration cannot be suppressed below the temperature of liquid nitrogen, and the luminescence of the aforementioned compounds at ordinary temperature is generally very weak. However, the organic light-emitting element of the present invention, because the light-emitting substance is fixed at the molecular level to the molecular level, can suppress the vibration of the molecules, and the excited energy will not form and disappear. In addition, although the excited triplet state is deactivated due to oxygen, the organic light-emitting element of the present invention can block oxygen from entering because the light-emitting substance is enclosed in the polymer. The polymer light-emitting material of the present invention can be obtained by polymerizing a polymerizable composition containing at least one light-emitting compound. The polymerizable composition means a polymerizable compound containing at least one type of polymerizable functional group such as a (meth) acrylic group, a vinyl group, a vinyl group, a styrene group, an isocyanate group, or a thioisocyanate group. When the number of polymerizable functional groups of all polymerizable compounds is one, the polymer system after polymerization is a non-crosslinked structure. If the number of polymerizable Gongneng groups of at least 1 polymerizable compound is 2 or more, the paper size after polymerization is subject to the Chinese National Standard (CNS) A4 (210X297 mm) (please read the precautions on the back first) (Fill in this page) Order Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, Industrial and Commercial Cooperatives 74 584661 A7 One __ B7_ V. Description of the Invention (72) The polymer forms a crosslinked structure. When the polymer has a crosslinked structure, thermal stability can be improved. Therefore, at least one of the polymerizable compounds used is preferably a crosslinkable polymerizable compound having two or more polymerizable functional groups. The base layer refers to an electrode, a charge transporting layer (hole transporting layer, electron transporting layer), and the like, and it differs depending on the constitution and manufacturing method of the organic EL element. The polymerizable compound in the polymerizable composition used in the polymer light-emitting layer of the present invention may be a light-emitting compound having a polymerizable functional group, an electron-transporting compound having a polymerizable functional group, or a polymerizable functional group. Hole transporting compounds may be used, or other polymerizable compounds and mixtures thereof may be used. In the polymerizable composition used in the polymer light-emitting material of the present invention, if the polymerizable compound other than the light-emitting compound having a polymerizable functional group is used, the polymer light-emitting material of the present invention is a copolymer thereof. In light emitting parts such as conjugated structures such as erbium structures, light metal complexes such as aluminum quinoline key complexes, or transition metal complexes, structures such as metal stability are considered in terms of stability and design freedom. The structure is better. The light-emitting layer of the organic light-emitting element of the present invention is a layer containing a light-emitting substance combined with a polymer as a light-emitting material, and may also contain other light-emitting materials, hole transport materials, electron transport materials, and the like. Specifically, in order to improve the carrier transportability of the phosphorescent compound of the present invention, the organic light-emitting device of the present invention can also use a composition obtained by combining the phosphorescent compound of the present invention and a carrier-transporting compound as light emission. Use of materials. The dimensions of this paper are in accordance with Chinese National Standard (CNS) A4 (210X297 mm) (please read the precautions on the back before filling out this page), 1T printed by the Intellectual Property Office Employee Consumer Cooperative of the Ministry of Economic Affairs 584661 A7 73) That is, the hole-transporting compound and the electron-transporting compound may be mixed in the phosphorescent compound of the present invention. When the hole-transporting compound of the present invention is hole-transporting, it is preferably mixed with the electron-transporting compound. The present invention When the phosphorescent compound is electron-transporting, it is preferably mixed with a hole-transporting compound. In this case, the hole-transporting compound and the electron-transporting compound may each be a low-molecular compound or a high-molecular compound. As the low-molecular hole transporting compound added to the phosphorescent compound of the present invention, for example, TPD (N, N, -diphenyl-N, N,-(3-methylphenyl) -1,1 , Biphenyl-4,4, diamine), a-NPD (4,4, -bis [N- (bnaphthyl) -N-phenylamino) biphenyl), m-MTDATA (4,4, , 4 ,,-tris (3-methylphenylphenylamine) triphenylamine) and other triphenylamine derivatives, CBP (4,4, NN, dicarbazole-biphenyl) derivatives From the beginning of the event to the known number of holes in the hole, "Dan is not only" is determined here. Also, the polymer hole-transporting compound added to the phosphorescent compound of the present invention, such as poly (N-vinylcarbazole), such as the above-mentioned low molecules such as TPD, α-NPD, m-MTDATA, and CPB A polymer compound obtained by polymerizing a hole-transporting compound by introducing a polymerizable functional group monomer such as a vinyl group, a styryl group, an acrylate group, or a methacrylate group. Japanese Patent Laid-Open No. 8-1 57 5 75 The disclosed polymer compounds having a triphenylamine skeleton are not limited thereto. In addition, the low-molecular-weight electron-transporting compound added to the phosphorescent compound of the present invention is, for example, a quinolinol derivative metal complex such as Alq3 (trialuminum quinolinol), PBD (2-biphenyl-4- 5- (4-tert-butyl-phenyl) -Π, 3,4] oxadiazole), 0XD-7 (1,3-bis [5- (p-tert-butyl paper) China National Standard (CNS) Α4 specification (210 × 297 mm) — (Please read the precautions on the back and save this page)

Printed by KT Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs, 1T-76-584661 ΑΊ _B7 V. Description of the Invention (74) Phenyl) -1,3,4-oxadiazol-2-yl] benzene), etc. Diazole derivatives, TAZ (3-biphenyl-4-yl-5- (4-tert > butyl-phenyl) -4-phenyl-4H_ [1,2,4] triazole) and other triazoles Derivatives, imidazole derivatives, triazine derivatives, and the like are not limited thereto. In addition, the polymer electron-transporting compound added to the phosphorescent compound of the present invention is, for example, Japanese Patent Application Laid-Open No. 1 (PBD disclosed in M 665 (compound obtained by introducing a PBD into a polymer obtained by introducing a vinyl group), for example, Alq3 described above Polymer compounds obtained by repolymerizing monomers such as vinyl, styryl, acrylate, and methacrylate groups with low-molecular-weight electron-transporting compounds such as OXD-7, TAZ, etc., but The addition of the low-molecular hole-transporting compound and 7 or compound added to the phosphorescent compound of the present invention is preferably 0 to 100% by mass of the phosphorescent compound of the present invention, and more preferably It is 10 to 70% by mass, and most preferably 20 to 50% by mass. The addition ratio of the low-molecular hole-transporting compound and / or the electron-transporting compound added to the phosphorescent compound of the present invention is preferably to the present invention. The phosphorescent compound of the invention is from 0 to 200% by mass, more preferably from 20 to 150% by mass, and most preferably from 40 to 100% by mass. In addition, the purpose is to improve the physical properties of the film obtained by film formation. In this case, a composition obtained by adding a polymer compound having no relation to light emission characteristics to the phosphorescent compound or phosphorescent composition of the present invention may be used as a light emitting material. For example, to impart a film to the obtained film For softness, PMMA (polymethyl methacrylate), polycarbonate, polystyrene, etc. can be added. The paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm). Clothing — (Please read the back first Please fill in this page for the matters needing attention), tr Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, S Industry Consumer Cooperatives -77- 584661 A7 B7 V. Invention Description (75), but it is not limited to this. Please read the notes before you read The proportion of the macromolecular compound that has nothing to do with the luminescence properties of the phosphorescent compound of the present invention added on this page is preferably 0 to 40% by mass, and more preferably 0 to 20% of the phosphorescent compound of the present invention. %, Preferably 0 to 10% by mass. Specific examples of the polymerizable luminescent compound used in the present invention include, for example, the following formulae (Cl), (Dl), (El ), Metal complexes of polymerizable functional groups represented by (F-1) and (G-1), and the like.

(c -1) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [where, at least one of Ae, Be, and Ce is a substituent having a polymerizable functional group, and the remaining ones in Ae, Be, and Ce are: Each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic group, sulfonate group or organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R21 are each independent hydrogen atom, halogen atom , Nitro, amine, sulfonate, sulfonate or organic group having 1 to 20 carbon atoms which may have a hetero atom]. This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -78- 584661 A7 B7

Y 1D

R, κ R3 5. Description of the invention (76 (D-1) [wherein at least one of X1D, Y1D, and Z1D is a substituent having a polymerizable functional group, and the remaining ones of X1D, Y1D, and Z1D are: Each independently hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R1 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group or may have Heteroatoms with 1 to 20 carbons]. -------- · Packing-(Please read the precautions on the back before filling this page)

R

(E-1) Printed by the Consumer Cooperative of Intellectual Property Bureau, Ministry of Economic Affairs [where Xe is a substituent having a polymerizable functional group, and R1E to R3E are each independently a hydrogen atom, a halogen atom, or a heteroatom Organic groups having 1 to 20 carbon atoms; R4 to R19 are each independently hydrogen atom, halogen atom, nitro, amine, sulfonic acid group, sulfonate group or organic group having 1 to 20 carbon atoms which may have a hetero atom ]. This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -79- 584661 A7 B7 V. Description of the invention (77

Y IF

R 11 ru r (Fl) [In the formula, at least one of X1F, Y1F, and Z1F is a substituent having a polymerizable functional group, and the other residues in X1F, Y1F, and Z1F are independent hydrogen atoms and halogen atoms. Or an organic group which may have a carbon number of 1 to 20; y to R10 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic group, a sulfonate group, or a carbon number which may have a hetero atom 1 to 20 organic groups]. RJ T,

Ra (Please read the notes on the back before filling out this page) (Gl) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs [wherein 'L is a valent anionic two-block ligand, which is a polymerizable functional group R1 to R7 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonate group, a sulfonate group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. Hereinafter, the polymerizable compounds of (CM) to (G-1) will be described. This paper size applies to Chinese National Standard (CNS) A4 specification (210 X 297 mm) 80-584661 A7 B7 V. Description of the invention (78) Polymerizable compound (ci) clothing-(Please read the precautions on the back before filling (This page) In the formula (C-1), Ac, Be, and Ce have polymerizable functional substituents, such as urea having vinyl, acrylate, methacryloxyethyl carbamate, and the like. Substituents for alk (meth) acrylate, styryl and its derivatives, vinylamido and its derivatives. Among the polymerizable functional groups, an acrylate group, a methacrylate group, and a urethane (meth) acrylate group are preferably used from the viewpoint of polymerizability. The position to which the substituent is bonded is, for example, the 2nd, 3rd, 4th, or 5th position of the phenyl group of the phenylpyridine ligand. In the compounds represented by the formulae (C-1) to (C-5) and (C-8) to (C-11), the "organic group having 1 to 20 carbon atoms which may have a hetero atom" does not detract from the object of the present invention. There is no particular limitation below, preferably an alkyldi_alk_oxyl group having 1 to 20 carbon atoms "," oxyalkyl, allyl, allyloxy, aralkyl or aralkoxy Or a halogen substitute thereof. In the printed formula (C-1) of the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, Ae, Be, and Ce have no polymerizable functional group substituents, and R1 to R21 may be a hydrogen atom, a halogen atom, a nitro group, Sulfonate groups such as amino groups, sulfonic groups, methyl sulfonates, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl and other alkyl groups, Or an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, an isobutoxy group, a t-butoxy group, or an ester group such as an acetoxy group or a propoxycarbonyl group. The organic group may further include a substituent such as a halogen atom, a nitro group, or an amine group. Next, examples of the method for synthesizing the polymerizable compound represented by the formula (C-1) are shown below. The present invention is not limited to the following methods. This paper size applies the Chinese National Standard (CNS) A4 specification (210x 297 mm) -81-584661 A7 _____B7 V. Description of the invention (79) Among them, in the first synthesis method, for example, the formula (C-8) A mono-iridium complex having a reactive substituent obtained by reacting a di-nuclear complex of iridium with a phenylpyridine derivative represented by formula (C-9) as an intermediate, and a reactive substituent of this intermediate A method of reacting with a compound having a polymerizable substituent to obtain a polymerizable compound containing a mononuclear iridium complex part, and the like.

8 I C

[In the formula, Xc and Yc- are reaction groups of 1stino'nitro, amine, sulfonic acid, sulfonic acid ester, or organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R28 are each independently Hydrogen atom, halogen atom, nitro group, amine group, sulfonate group, sulfonate group or organic group having 1 to 20 carbon atoms which may have a hetero atom] (Please read the precautions on the back before filling this page)

1T Printed by Xiao Gong Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs 〇R3 ZC R4 R5 6

H R7 (C-9) [In the formula, ze is a reactive substituent, or a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or a carbon atom having 1 to 5 hetero atoms. Organic group of 20; R1 to R7 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group or carbon number which may have a hetero atom. 1 Paper size applies Chinese National Standard (CNS) A4 specification (210 × 297 mm) -82- 584661 μ B7 V. Organic group of invention description (80) to 20; However, in formula (C-8), Xe, Ye and Ze of formula (C-9) Wherein at least one is a reactive substituent]. The dinuclear complex of iridium of the formula (C-8) can be synthesized by a known method (3. Lamansky et al., Inorganic Chemistry, 40, 1704 (200 1)). In the formula (C-8), R1 to R28 are a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Alkyl groups such as isobutyl, t-butyl, pentyl, and hexyl, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, and butoxy, or ethoxyl , Organic groups such as ester groups such as propoxycarbonyl. The organic group may further have a substituent such as a halogen atom, a nitro group, or an amine group. At least one of Xe and Ye of the formula (C-8) and Ze of the formula (C-9) is a reactive substituent. For example, a hydroxyl group is exemplified, but it is not limited thereto. The reactive substituent may be protected by a protecting group. At this time, the reaction is performed under the protection of a protecting group to prepare a mononuclear iridium complex, and then a mononuclear iridium complex having a reactive substituent is prepared as an intermediate by deprotection. Then, the reaction will have! A mononuclear iridium complex with a reactive substituent is used as an intermediate, and this intermediate is reacted with a compound having a polymerizable functional group to obtain a polymerizable compound containing a mononuclear iridium complex. When xe and Yc are reactive substituents in the iridium dinuclear complex represented by formula (c_8), and ze is a non-reactive substituent in the phenylpyridine derivative represented by formula (C_9), The reaction can produce a mononuclear iridium complex with 2 reactive substituents as an intermediate. When this intermediate is reacted with a compound having a polymerizable functional group, 2 Functional polymerizable compounds This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) (Please read the notes on the back before filling this page) Order printed by the Intellectual Property Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs -83-584661 A7--B7___ 5. Description of the invention (81) The second synthesis method of the polymerizable compound represented by formula (C-1), for example, using an iridium complex compound represented by formula (C-1 0) as an intermediate, and This intermediate is reacted with a compound having a polymerizable functional group in a certain mole ratio to prepare a polymerizable compound having a specific number of polymerizable functional group-containing iridium complexes.

[Wherein xe is a reactive substituent; R1 to R21 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or a carbon number of 1 to 20 which may have a hetero atom; Organic group] In the iridium complex represented by the above formula (C-1 0), XC as a reactive substituent such as a hydroxyl group, an amine group, and the like is not limited thereto. Moreover, the polymerizable functional group-containing compound 'such as a polymerizable acid halide or a polymerizable isocyanate which can react with an iridium complex of the formula (C-10) is not limited thereto. Subsequently, the case where a polymerizable acid halide and / or a polymerizable isocyanate is used in this second synthesis method will be described in detail. That is, when the molar ratio of the iridium complex of the formula (C-10) to the polymerizable acid halide and / or the polymerizable isocyanate approaches 丨: 丨, for example, when 1: (0.5: 1.5), Obtained mainly monofunctional polymerizable compounds, the paper size will be in accordance with the Chinese National Standard (CNS) A4 specification (210X 297 mm). Clothing — (Please read the precautions on the back before filling this page] Order the Ministry of Economic Affairs Intellectual Property Printed by the Bureau's Consumer Cooperatives -84-A7 ______B7 V. Description of the Invention (82) The monofunctional polymerizable compound can be obtained after the finished product is refined. Also, when the Morrby approaching side is < 1 '2, such as 1: ( 1 · 5 ·· 2 · 5), a difunctional polymerizable compound can be obtained, and the product can be purified to obtain a difunctional polymerizable compound. When the molar ratio approaches 1,3, for example, 1: When (2.5 or more), a trifunctional polymerizable compound can be obtained, and after purification of the product, a trifunctional polymerizable compound can be obtained. In addition, when the molar ratio is 1: (3 or more), the There is no need to go through a refining step to remove monofunctional or difunctional. When forming a monofunctional or difunctional polymerizable compound, after reacting the polymerizable acid halide in a certain mole ratio, it is necessary to perform a reaction to change the remaining reactive substituents of the product to non-reactive. The reactive substituent is In the case of a hydroxyl group, non-polymerizable compounds used for this purpose, such as alkyl halides, carboxylic acids, carboxylic acid halides, sulfonic acid halides, chloro formaldehyde esters, isocyanates, etc., are not limited thereto. The Intellectual Property Bureau P Shelley Consumer Cooperative Co., Ltd. printed polymerizable acid halides such as acrylic acid chloride and fluorenyl acrylic acid chloride used in this second synthesis method, and non-polymerizable acid chlorides such as propionic acid chloride and acetic acid. Polymerizable isocyanates such as chlorides, such as methacryl isocyanate, methacrylic acid, oxyethyl isocyanate, and the like, and non-polymerizable isocyanates, such as hexyl isocyanate, pentyl isocyanate, and the like. Polymerization shown by the formula (C-1) For other synthetic methods, for example, the complex of iridium (III) bis (2-phenylpyridine disodium salt) acetamidine and acetone sodium salt has a reaction with the formula (C-9). Method for preparing a monofunctional polymerizable compound containing an iridium complex part by introducing a polymerizable substituent into a phenylpyridine derivative having a reactive substituent, and the like. Polymers and copolymers of the present invention The degree of polymerization is from 3 to 5000 as the paper standard. It is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -85- 584661 A7 ________B7 5. The invention description (83) is good. Polymerizable compound (D -1) Formula ( In D-1), the substituent having a polymerizable functional group in x1D, Y1D, and Z1D may be, for example, any of radically polymerizable, anionic polymerizable, cationic polymerizable, additional polymerizable, and condensation polymerizable. This polymerizable functional group has, for example, a urethane (meth) acrylate group such as a vinyl group, an allyl group, an alkenyl group, an acrylate group, a methacrylate group, or a methacryloxyethylaminocarbamate group. , Styryl and its derivatives, vinylamido and its derivatives. Among the polymerizable functional groups, an acrylate group, a methacrylate group, and a urethane (meth) acrylate group are preferably used from the viewpoint of polymerizability. Among the compounds represented by the formula 丄 Dvl—), (D-2), 1D, and (D-Π to (D-23), "an organic group which may have a carbon number of 1 to 20 with a hetero atom" is not detrimental to the present invention. There is no particular limitation under the purpose, and preferably it is a radical, a radical, a radical, a radical, a propane, a propane, an aralkyl or an aralkyloxy or a halogen thereof having a carbon number of 1 to 20 Substitutes, etc. In the formulae (Dl), (D-2), (D-14), and (D-18) to (D_23), X1D, Y1D, and Z1D do not have a substituent having a polymerizable functional group, and QiD To q3d may be, for example, a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, or a hexyl group, or a methoxy group or an ethoxy group; , Alkoxy groups such as propoxy, isobutoxy, t-butoxy, or ester groups such as acetoxy, propoxycarbonyl, organic groups such as aryl, etc. Formula (Dl), (D-17 ) And (D-20), R1 to rw and (Please read the notes on the back before filling this page) Order the paper size printed by the R Industrial Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs and apply the Chinese National Standard (CNS) A4 specification (210x297 mm) -86- 584661 A7 ____ B7 Explanation of the invention (84) to R32 may be, for example, a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonate group, a sulfonate group such as a sulfonate group, a methyl group, an ethyl group, a propyl group, an isopropyl group, Alkyl such as butyl, isobutyl, t-butyl, pentyl, and hexyl, or alkoxy such as methoxy, ethoxy, propoxy, isobutoxy, t-butoxy, or Esters such as ethoxyl and propoxycarbonyl, organic groups such as aryl, etc. The organic group may further have a substituent such as a halogen atom, a nitro group, or an amino group. Sub-formula (D -1 An example of a method for synthesizing the polymerizable compound shown in () is shown below, and the present invention is not limited in any way by the following method. Among them, in the first synthesis method, for example, the dinuclear iridium represented by the formula (D -1 7) is used. A method of reacting a complex with a compound having a polymerizable substituent represented by formula (D-1 8) to obtain a polymerizable compound containing a mononuclear iridium complex part, and the like.

[Wherein R1 to R32 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having a carbon number of 1 to 20 which may have a hetero atom] The paper size applies China National Standard (CNS) A4 specification (210X297 mm) (Please read the notes on the back before filling out this page),-Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economy

-87- 584661 A7 B7 V. Description of the invention (85)

ylD

0 〇 [In the formula, at least one of X1D, Y1D, and Z1D is a substituent having a polymerizable functional group, and the other residues in x1D, Y1D, and z1D are each an independent hydrogen atom or a carbon number that may have a hetero atom. 1 to 20 organic groups]. The dinuclear complex of iridium of the formula (D-1 7) can be synthesized by a known method (S. Lamansky et al., Inorgani D Dhemistry, 40, 1704 (2001)). Wherein, R1 to r32 in formula (D- 丨 7) are a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonate group, a sulfonate group such as methyl sulfonate, methyl, ethyl, propyl, iso Alkyl groups such as propyl, butyl, isobutyl, t-butyl, pentyl, and hexyl, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, and t-butoxy Or an organic group such as an ester group such as an ethoxy group and a propoxycarbonyl group. The organic group may further have a substituent such as a halogen atom, a nitro group, and an amino group. At least one of the substituents X1D, YID, and Z1D of the compound represented by the formula (D-18) is a substituent having a polymerizable functional group. Its content is the same as that of the formula (D-1). The substituents x1D, Y1D, and Z1D of the compound represented by formula (D-18) which do not have a polymerizable functional group have the same contents as those described by formula (D-1). The second method for synthesizing a polymerizable compound represented by the formula (D-1) is, for example, combining a dinuclear complex of iridium represented by the formula (D-17) with a compound having a reactive substituent represented by the formula (D-19) In the reaction, a mononuclear iridium complex having a reactive substituent group is used as an intermediate, and then the intermediate and the reactive material are taken to the size of this paper to apply the Chinese National Standard (CNS) A4 specification (210X 297 mm). — (Please read the notes on the back before filling this page)

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs of the 1T -88- 584661 A7 V. Description of the invention (86) Reactive compounds of the gen-based compound. Polymerization with mononuclear iridium complex

(26, 25 I24, 23 (D-17)-(Please read the precautions on the back before filling out this page)

Ο Ο Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs [where R1 to R32 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group, or may have heteroatoms. Organic group having 1 to 20 carbon atoms] (D-19) [wherein at least one of X2D, γ2ϋ, Z2D is a reactive substituent, and the remaining ones in X2D, Y2D, and Z2D are independent hydrogen atoms. Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. At least one of X2D, Y2D, and Z2D in the formula (D-19) is a reactive substituent, which has a functional group such as a hydroxyl group. Functional groups include, but are not limited to, hydroxyl, amine, and carboxyl groups. Reactive substituents having such functional groups are, for example, hydroxy, hydroxyalkyl, hydroxyphenyl and the like. This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -89- 584661 ____B7_ V. Description of the invention (87) Moreover, these reactive substituents can be protected by protective groups. At this time, the reaction is performed under the protection of a protective group to obtain a mononuclear iridium complex, and then a mononuclear iridium complex having a reactive substituent is prepared as an intermediate by deprotection. Subsequently, a reactive substituent of the intermediate is reacted with a compound having a polymerizable functional group to prepare a polymerizable compound containing a mononuclear iridium complex part. The functional group of the reactive substituent does not include the polymerizable functional group. Among the substituents X2D, y2d, and z2D of the compound represented by formula (D-19), which are not reactive substituents, for example, a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Carboxyl such as isobutyl, t-butyl, pentyl, and hexyl, or alkoxy such as methoxy, ethoxy, propoxy, isobutoxy, butoxy, or ethoxy The above-mentioned organic group such as an ester group such as a propoxycarbonyl group and an aryl group may further have a substituent such as a halogen atom. A polymerizable functional group compound obtained by reacting a mononuclear iridium complex with a reactive substituent obtained by reacting an iridium dinuclear complex with a compound represented by the formula (D_ 丨 9) having a reactive substituent, except In addition to the polymerizable group, a functional group having a group capable of reacting with the reactive substituents X2D, Y2D, and Z2D of the formula (D-19) is required. In the second synthetic method of the polymerizable compound of the present invention, R1 to R32 of the formula (D-17) must be selected from groups that do not react with the compound having a polymerizable functional group that can react with the mononuclear iridium complex as described above. The compound having a polymerizable functional group which can react with the mononuclear iridium complex as described above is, for example, a polymerizable acid chloride compound or an isocyanate, but it is not limited thereto. The polymerizable functional group of the aforementioned compound has, for example, radical polymerizability, ionic polymerizability, cationic polymerizability, additional polymerizability, and condensation. This paper is applicable to the size of the paper. National Standard (CNS) A4 Specification (210 X 297 mm) — (Please read the precautions on the back before filling out this page), 1-90- ΚΊ _ Β7 printed by S Industrial Consumer Cooperatives, Intellectual Property Bureau of the Ministry of Economic Affairs, V. 5. Description of the invention (88) Any one of the agglomeration is acceptable A polymerizable functional group is preferred. This polymerizable functional group has, for example, a urethane (methyl) group such as a vinyl group, an allyl group, an alkenyl group, a propionate group, a methacrylic acid group, a methacrylic acid ethoxylate group, and the like. Substituents for acrylate, styryl and its derivatives, ethenylamido and its derivatives. Among the polymerizable functional groups, 3 ′ is preferably a propionate group, a methyl propionate group, or a urea (meth) propionate group in terms of polymerizable properties. Specifically, polymerizable fluorene chlorides such as acrylic acid chloride, methacrylic acid chloride, and the like, and polymerizable isocyanates such as methyl isocyanate, methacrylic acid oxyethyl isocyanate, and the like. Furthermore, the chemical formula such as formula (D-1) of the compound of the present invention is represented by a metal complex structure, and it may also be represented by a resonance structure such as 0-C-C-C-0, or by a structural formula permitted by chemistry. Polymerizable compound (E-1) In the formula (E-1) printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, the substituent having a polymerizable functional group shown by XE, and the polymerizable functional group has, for example, a carbon-carbon double bond Substituents are preferred, for example, urethane (meth) acrylate groups such as vinyl, propylene ethoxy, methacryl ethoxy, methacryl ethyl urethane, and phenylethyl Substituents such as alkyl and its derivatives, vinylamido and its derivatives. Among the aforementioned polymerizable functional groups, in terms of polymerizability, it is preferable to use a propylene radical, a methacrylic acid group, a urethane (meth) acrylic acid group, or a styrene group. The positions to which the substituents are bonded may be, for example, the 3rd, 4th, 5th, and 6th positions of the picolinic acid ligand. This paper size applies to China National Standard (CNS) A4 specification (210 × 297 mm) -91-A7 _____ B7 __ 5. Description of the invention (89) Formulas (E-1) and (E-9) to (E-12) In the above, "organic group having 1 to 20 carbon atoms which may have a hetero atom" is not particularly limited without impairing the purpose of the present invention, and is preferably an alkyl group, alkoxy group, or alkoxy group having 1 to 20 carbon atoms Alkyl, allyl, allyloxy, aralkyl or aralkoxy, or halogen substitutes thereof. In formula (E-1), RH, R2E, and R3E may be, for example, a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, or a pentyl group. Alkyl groups such as hexyl, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, t-butoxy, aryloxy, or esters such as ethoxyl and propoxycarbonyl And other organic groups. The organic group may further have a substituent such as a halogen atom. In the printed formula (E-1) of the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, R4 to R19 may be, for example, hydrogen atom, halogen atom, nitro group, amine group, sulfonate group, sulfonate group such as methyl sulfonate group, Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl and other fluorenyl groups, or methoxy, ethoxy, propoxy, isobutyl Organic groups such as alkoxy groups such as oxy, t-butoxy, aryloxy or ester groups such as acetamido, propoxycarbonyl, and the like. The organic group may further have a substituent such as a halogen atom, a nitro group, or an amine group. Among them, a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms are more preferable. Next, an example of a method for synthesizing the polymerizable compound represented by the formula (E-1) is shown below, and the present invention is not limited to the following methods. In the first synthesis method of the polymerizable compound represented by the formula (E -1), for example, a dinuclear complex of iridium represented by the formula (E-9) and picolinic acid represented by the formula (e -1 〇) are used. Derivatives are reacted to produce a single paper with reactive substituents. The size of the paper is applicable to China National Standard (CNS) A4 (210X 297) -92- 584661 A7 B7 V. Description of the invention (90) A method of preparing a polymerizable compound containing a mononuclear iridium complex part by reacting a reactive substituent of the intermediate with a compound having a polymerizable banning group as an intermediate. R3

13 14 R (E-9) [wherein R4 to R19 are each independently a hydrogen atom, a halogen atom, a nitro group, a sulfonic acid group, a sulfonic acid ester group, or a carbon number i to 'which may have a hetero atom '--------------- 20 organic groups]

HO N-^ \ RJE (E-10) (Please read the notes on the back before filling this page)

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs [where Υε is a reactive substituent, and r1e, r2E, and r3E are independent hydrogen, halogen, or organic carbons with 1 to 20 carbon atoms that may have heteroatoms The dinuclear complex of iridium of formula (E-9) can be synthesized by a known method (S. Lamansky et al., InorganiE Ehemistry, 40, 1 704 (2001)). Among them, R4 to R19 in formula (E-9) are hydrogen atom, halogen atom, nitro group, amine group, sulfonate group, sulfonate group such as methyl sulfonate group, methyl group and ethyl paper. The Chinese paper standard is applicable. (CNS) A4 specifications (210X297 mm) -93- 584661 A7 ______B7 V. Description of the invention (91) Group, propyl, isopropyl, butyl, isobutyl, N-butyl, pentyl, hexyl, etc. Or organic groups such as methoxy, ethoxy, propoxy, isobutoxy, alkoxy such as _-butoxy, aryloxy, or ester groups such as ethoxy, propoxycarbonyl, etc. . The organic group may further have a substituent such as a halogen atom, a nitro group, or an amine group. Among them, a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms are more preferable. YE in the formula (E -10) is a reactive substituent such as a methyl group, a hydroxyl group, a hydrogen thio group, an amine group, an active hydrogen-containing group, or a carboxyl group, but is not limited thereto. These reactive substituents may be protected by a protecting group. At this time, a reaction is performed under the protection of a protecting group to obtain a mononuclear iridium complex, and then a mononuclear iridium complex having a reactive substituent is prepared as an intermediate by deprotection. Subsequently, a reactive substituent of the intermediate is reacted with a compound having a polymerizable functional group to prepare a polymerizable compound containing a mononuclear iridium complex part. The functional group of the reactive substituent does not include the poly-i-functional group. The compounds R1E, R2E, and 1 ^ in the formula (E-10) are a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, Alkyl groups such as hexyl, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, t-butoxy, aryloxy, or ester groups such as ethoxy and propoxycarbonyl Of organic radicals. The organic group may further have a substituent such as a halogen atom. Among them, a hydrogen atom, a halogen atom, and a radical having 1 to 20 carbon atoms are preferred. A mononuclear iridium complex with a reactive substituent obtained by reacting an iridium dinuclear complex of formula (E-9) with a compound represented by formula (E-1 0) having a reactive group (please read the precautions on the back first) (Fill in this page again) • ^ Order the paper size printed by the Employees' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs to apply the Chinese National Standard (CNS) A4 specification (2 丨 〇 > < 297 mm) -94- 584661 A7 B7 V. DESCRIPTION OF THE INVENTION In addition to the polymerizable group, the compound having a polymerizable functional group obtained by the reaction of the (92) compound (intermediate) needs to have a functional group capable of reacting with the reactive substituent YE of the formula (E-1 0) . Among the functional groups, the reactive substituent γE is a methylol group, and an isocyanate group or an acid chloride (R-C0C1) group when the hydroxyl group is a hydroxyl group. In addition, R4 to R19 in the formula (E-9) need to be selected from the group that does not react with the compound having a polymerizable functional group that reacts with the mononuclear iridium complex described above. The polymerizable function that can react with an intermediate is described above. The polymerizable functional group in the compound of the base group is preferably a group having a carbon-carbon double bond, for example, a vinyl group, an acryloxy group, a methacrylic acid group, or a methacrylic acid group. Substituents such as urethane (meth) acrylate, styryl and its derivatives, vinylamido and its derivatives. Among the polymerizable functional groups, from the viewpoint of polymerizability, it is preferable to use propylene fluorenyloxy group, methacryl fluorenyloxy group, urethane (meth) acryl fluorenyloxy group, and styryl group. 1) A second method for synthesizing a non-polymerizable compound, for example, by reacting a dinuclear complex of iridium represented by the formula (E-9) with a picolinic acid derivative represented by the formula (E-1 1), A method for directly producing a polymerizable compound containing a mononuclear iridium complex.

[Wherein, εε is a substituent having a polymerizable functional group, and r1e, r2E, and rh are each independent hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, and the Chinese paper standard (CNS) A4 specification (210X297 mm) (Please read the notes on the back before filling this page), 11 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs-95- 584661 A7 B7 V. Description of the invention (93) Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. In the formula (E-11), it is a substituent having a polymerizable functional group, and the polymerizable functional group is preferably a substituent having a carbon-carbon double bond, for example, having a methylpropyl fluorenyloxy group, a methacrylic acid Oxyethylaminomethylmethyl, methylpropanyloxyethylaminomethyloxymethyl, vinylbenzyloxy, fluorenylpropylene with oxyethyloxycarbonyl, and the like are not limited thereto. [In the compound of formula (E-ι 1), Rib, r2b, and r3E are a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, or a pentyl group. Alkyl groups such as alkyl, hexyl, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, t-butoxy, aryloxy, or ethoxyl'propoxycarbonyl, etc. Organic groups such as ester groups. The organic group may further have a substituent such as a halogen atom. Polymerizable compound (F-1) In the formula (F-1), X1F, Y1F, and the polymerizable functional group in the substituent having a polymerizable functional group, for example, may have radical polymerizable property, anionic polymerizable property, and cationic polymerizable property. Any of polymerizable properties, additional polymerizable properties, and condensation polymerizable properties are possible, and a radical polymerizable functional group is preferred. The polymerizable functional group is preferably a group having a carbon-carbon double bond, for example. For example, urethane (meth) acrylic acid such as vinyl, allyl, alkenyl, propylene alkoxy, and methacryl oxy, methacryl ethoxyethyl carbamate, and the like Substituents for ester groups, styryl groups and derivatives thereof, vinylamido groups and derivatives thereof, and the like. Among the aforementioned polymerizable functional groups, from the viewpoint of polymerizability, acryloxy, methacryloxy, and urethane (meth) acrylic are used in accordance with the Chinese paper standard (CNS) A4 (210X297). (Mm) (Please read the notes on the back before filling out this page) 、 \ Yi Yikou Printed by the K Industry Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs-96- 584661 A7 _____ B7 Preparation of the invention (94) Phenoxy is preferred. In the compounds represented by the formulae (Fl), (F-2), (F-12), and (F-15) to (F-21), "an organic group having 1 to 20 carbon atoms which may have a hetero atom" is used in Without prejudice to the object of the present invention, it is not particularly limited, and it is preferable to contain heteroatoms such as an oxygen atom, a nitrogen atom, a sulfur atom, and a halogen atom. An alkyl group, an alkoxy group, an alkoxyalkyl group, an allyl group, an allyloxy group, an aralkyl group, an aralkyloxy group, or a halogen substituent thereof, etc. are preferred. In the formulae (Fl), (F-2), (F-12), and (F-15) to (F-21), X1F, Y1F, and Z1F do not have a substituent having a polymerizable functional group, and Q1F to Q3F are, for example, It may be an alkyl group such as a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, an aryloxy group, or a methoxy group , Alkoxy groups such as ethoxy, propoxy, isobutoxy, t-butoxy, or ester groups such as ethoxyl, propoxycarbonyl, and organic groups such as aryl. The organic group may further include a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, and the like. In the formulae (Fl), (F-15) to (F-18), R1 to R16 fall into the conditions defined in the foregoing range, and may be, for example, a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic group, Sulfonate groups such as methyl sulfonate, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, alkyl, aryloxy, or methyl An alkoxy group such as an oxy group, an ethoxy group, a propoxy group, an isobutoxy group, a t-butoxy group, an ester group such as an ethoxy group, a propoxycarbonyl group, and an organic group such as an aryl group. The organic group may further have a substituent such as a halogen atom, a nitro group, or an amino group. Among them, a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms are preferred. (Please read the precautions on the back before filling out this page). 11 This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -97- 584661 Α7 ___ Β7 V. Description of the invention (95) Formula (F- 6) In formula (F_9), A is an organic group having 3 to 20 carbon atoms having acrylfluorenyl group or methacrylfluorenyl group or acrylfluorenyl group or methacrylfluorenyl group. The organics are mentioned before not impairing the gist of the present invention, and may further include heteroatoms such as an oxygen atom, a nitrogen atom, a sulfur atom, and a halogen atom. The organic group is preferably an alkyl group, an allyl group, or an aralkyl group. It is more preferable to use an isocyanate bond. Examples of the method for synthesizing the polymerizable compound represented by the formula (F-1) are shown below, but the present invention is not limited to the following methods. The first synthesis method is to react a dinuclear complex of iridium represented by formula (F-1 5) with a compound having a polymerizable substituent represented by formula (F-16) to obtain a mononuclear iridium complex. Method of polymerizable compound in the compound part. (Please read the precautions on the back before filling this page) · Install. 、 \ 一 一口 R3

(F-15) Printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs [where R1 to R16 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonate group, sulfonate group or may have Atoms having 1 to 20 carbons]

γ 1F rlF

, 1F 〇〇 (F-16) This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297mm) -98- 584661 A7 B7 V. Description of the invention (96) [wherein X1F, Y1F, Z1F At least one is a substituent having a polymerizable functional group, and the remaining ones in X1F, Y1F, and z1F are each independently a hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. (F-15) The dinuclear complex of iridium can be obtained by a known method (S.

Lamansky Ft a 1., InorganiF FhFmistry, 40, 1704 (2001)). Wherein, R1 to .Ru in formula (F-15) are a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonate group, a sulfonate group such as methyl sulfonate, methyl, ethyl, propyl, iso Propyl, butyl, isobutyl, t-butyl, alkyl such as pentyl, hexyl, aralkyl such as benzyl, or methoxy, ethoxy, propoxy, isobutoxy, t -An alkoxy group such as a butoxy group, an aryloxy group, or an organic group such as an ester group such as an acetoxy group or a propoxycarbonyl group; The organic group may further have a substituent such as a halogen atom, a nitro group, and an amine group. Among them, a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms are preferred. At least one of the substituents x1F, y1f, and z1F of the compound represented by the formula (F-16) is a substituent having a polymerizable functional group, and has the same meaning as that described in the formula (F-1). In addition, the substituents of the compound represented by formula (F-1 6), Y1F, and Z1F which do not have a polymerizable functional group also have the same meaning as the description of formula (F_ i). The second method for synthesizing a polymerizable compound represented by the formula (F-1) is, for example, reacting a dinuclear complex of iridium represented by the formula (F-15) with a compound having a reactive substituent represented by the formula (F_17) The obtained mononuclear iridium complex with a reactive substituent is used as an intermediate, and then the reactive substituent of this intermediate is reacted with a compound having a polymerizable substituent to prepare a paper containing a mononuclear iridium complex. China National Standard (CNS) Α4 specification (210X 297 mm) (Please read the precautions on the back before filling this page)

1T 丨 Printed by the Consumers' Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs -99-584661 A7 B7 V. Method of polymerizable compounds in the invention (97).

RJ RJ

(F-15) (Please read the notes on the back before filling this page)

Ο Ο Printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs [where R1 to R16 are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group, or carbon which may have hetero atom Organic groups of 1 to 20] (F-17) [wherein at least one of X2F, Y2F, and Z2F is a reactive substituent, and the remaining ones in X2F, Y2F, and z2F are independent hydrogen atoms, A halogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. In the formula (F-17), at least one of X2F, Y2F, and Z2F is a reactive substituent and has a functional group such as a hydroxyl group. The functional group includes, for example, a functional group containing an active hydrogen such as a hydroxyl group, a hydrogenthio group, and an amine group, a carboxyl group, and the like, but is not limited thereto. Examples of the reactive substituent having a functional group include a hydroxyl group, a hydroxyalkyl group, a hydroxyphenyl group, a hydrogenthio group, and an amine group. The reactive substituent may be protected by a protecting group. At this time, in accordance with the Chinese National Standard (CNS) A4 specification (210X297 mm) -100-. 584661 A7 B7, the protected paper size is used to react under the protection of the protective base to produce a mononuclear iridium complex. Then, a mononuclear iridium complex with a reactive substituent is prepared as an intermediate in a deprotected manner. Subsequently, a reactive substituent of the intermediate is reacted with a compound having a polymerizable functional group to prepare a polymerizable compound containing a mononuclear iridium complex part. The functional group of the reactive substituent does not include the polymerizable functional group. Examples of the substituents X2F, Y2F, and Z2F which do not have a reactive substituent among the substituents of the compound represented by the formula (F-19) include a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Alkyl groups such as isobutyl, t-butyl, pentyl, and hexyl, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, t_butoxy, ethoxy, Esters such as propoxycarbonyl and organic groups such as aryl. The organic group may further have a substituent such as a halogen atom. A polymerizable functional group compound obtained by reacting a mononuclear iridium complex having a reactive substituent obtained by reacting an iridium dinuclear complex with a compound represented by formula (F-17) having a reactive substituent, except for polymerization A functional group having a group that can react with the reactive substituents X2F, Y2F, and Z2F of the formula (F-17) is required in addition to the reactive group. Among the functional groups, the reactive substituents X2F, Y2F, and Z2F are isocyanate groups or carboxyl groups when they contain hydroxyl groups such as methylol and hydroxyl groups, and X2F, Y2F, and Z2F are isocyanate when they contain hydrogen sulfur groups and amine groups. The radical or acid chloride (R-C0C1) group, and the hydroxyl group when X2F, Y2F, and Z2F are carboxyl groups. In the second synthetic method of the polymerizable compound represented by the formula (F-1), R1 to R16 in the formula (F-1) must be selected and have polymerizable functional groups that do not react with the mononuclear iridium complex as described above. The base of the compound reaction. The above is a polymerizable functional group that can react with a mononuclear iridium complex. The paper size is applicable to the national standard (CNS) A4 specification (210X297 mm) (Please read the note on the back 3 to write this page). ·

1. Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs of the 1T. -101-A7 Γ _-______ B7 V. Description of the Invention Compounds, such as polymerizable acid chloride compounds or isocyanates, are not limited to this. The polymerizable functional group of the compound may be, for example, any of radical polymerizable, anionic polymerizable, cationic polymerizable, additional polymerizable, and condensable polymerizable functional groups, and a radical polymerizable functional group is preferred. This polymerizable functional group preferably has, for example, a group having a carbon-carbon double bond, and also has an allyloxy group such as a vinyl group, an allyl group, an alkenyl group, an acryloxy group, or a methacryloxy group, and a methyl group. Substituents for urea (meth) acrylic acid, styryl and its derivatives, vinylamine and its derivatives, such as methacryloxyethylcarbamate. Among the polymerizable functional groups, from the viewpoint of polymerizability, it is preferable to use an acryloxy group, a methacrylic acid group, or a urethane (meth) acrylic acid group. Specifically, polymerizable acid chlorides include acrylic acid chloride and methacrylic acid chloride, and polymerizable isocyanates include methyl isocyanate and methacrylic acid oxyethyl isocyanate. Also, the chemical formula such as formula (F-1) of the compound of the present invention is represented by a metal complex structure, and it may be represented by a resonance structure such as 0-C-C-C-0, or may include a structurally acceptable structural formula. The polymerizable compound (G-1) printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs is a monovalent anionic two-block ligand represented by L in the formula (G-1), which has a pyridine ring, carbonyl group, A compound obtained by dissociating one hydrogen ion with a non-ionic ligand such as an imine group and a phenyl group, a hydroxyl group, or a carboxyl group, or a compound obtained by dissociating one hydrogen ion like a Θ-diketone The covalent structure of the covalent structure with 2 ligands has a monovalent anion structure. The paper size is applicable to the Chinese National Standard (CNS) A4 (210X 297 mm) ~ ^ ~ -102-584661 A7 B7 V. Description of the invention ( 100) A compound obtained by removing one hydrogen ion from a monovalent anion. In particular, in the aforementioned compounds, when two ligands are coordinated to one iridium atom, it is preferable to form a 5 圜 ring or 6 圜 ring structure containing an iridium atom. For example, 2-phenylpyridine, cold-diketone, picolinic acid, N-coated salicylimide, 8-hydroxyquinoline and its derivatives dissociate one hydrogen ion to form a monovalent anion. Compounds. From the viewpoint of having luminescent properties in two ligands, Θ-diketone, picoacid or N-alkylsalicylide dissociates one hydrogen ion to form a compound formed by a monovalent anion. Better. In the formula (G-1), the polymerizable functional group among the substituents having a polymerizable functional group represented by Xσ includes, for example, radical polymerizability, anion polymerizability, cation polymerizability, additional polymerizability, and condensation polymerizability. Any of them is possible, and among them, a radical polymerizable functional group is preferred. Please read the notes on the back of this polymerizable functional group, and then fill out this page. It is better to print it with a carbon-carbon double bond based on the consumer cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs. Alkenyloxy groups such as methacrylic acid, methacryloxy and methacryloxy, urethane (meth) acrylates, styryl and derivatives thereof such as methacryloxyethylcarbamate , Vinyl amidino and its derivatives. Among the polymerizable functional groups, from the viewpoint of polymerizability, it is preferable to use an acryloxy group, a methacrylic acid group, a urethane (meth) acrylic acid group, or a styryl group. In addition, the above-mentioned substituted Jaeger methacryl methoxide, methacryl ethoxy ethylaminomethyl methenyloxy, vinylbenzyloxy and the like having a polymerizable functional group are not limited thereto. The positions to which the substituents are bonded include, for example, the 3rd, 4th, 5th, and 6th positions of the phenyl group in the phenylpyridine ligand. m This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -103-. 584661 A7 _________B7 V. Description of the invention (101) Formula (Gl), (G-2), (G-6) In (G-7), (G-9) to (G-10), "the organic group having 1 to 20 carbon atoms which may have a hetero atom" is not particularly limited without impairing the purpose of the present invention. It is preferably an alkyl group, an alkoxy group, an alkoxyalkyl group, an allyl group, an allyloxy group, an aralkyl group, an aralkyloxy group, or a halogen substituent thereof, etc., having 1 to 20 carbon atoms. In the formula (G-1), R1 to R7 may be, for example, a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, or a sulfonic acid ester group such as methyl sulfonate, methyl, ethyl, propyl, or isopropyl. Propyl, butyl, isobutyl, t-butyl, pentyl, hexyl and other alkyl groups, or alkoxy groups such as methoxy, ethoxy, propoxy, isobutoxy, t-butoxy Groups, or ester groups such as ethoxyl and propoxycarbonyl, and organic groups such as aryl. The organic group may further have a substituent such as a halogen atom, a nitro group, or an amine group. Among them, a hydrogen atom, a halogen atom, and an alkyl group having 1 to 20 carbon atoms are more preferable. In formula (G-1), R1 to R7 bonded to two phenylpyridine skeletons may be the same, or two phenylpyridine skeletons may be bonded to different substituents, respectively. Among the compounds represented by formula C G -1), the monovalent anionic two-block ligand represented by L is a compound obtained by dissociating one hydrogen ion from / 3-dione, and is represented by formula (G · 2). (Please read the note on the back first to write this page)-1T Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs Employee Consumer Cooperative

This paper size applies the Chinese National Standard (CNS) A4 specification (21 × 297 mm) -104-584661 A7 B7 V. Description of the invention (102) [wherein A1C ~ A3 ° are each independent hydrogen atom and halogen An atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom; X. It is a substituent with a polymerizable functional group, and R1 to R7 are each independently a hydrogen atom and a peptidyl atom. Please read the notes on the back and fill in the IJ page. Nitro, amine, sulfonate, and sulfonate groups Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. In the formula (G-2), A1C to A3. For example, hydrogen atom, halogen atom, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, Nbutyl, pentyl, and hexyl, or methoxy, ethoxy, and propoxy Organic groups such as alkoxy, aryloxy such as isopropyloxy, t-butoxy, aryloxy, and ester groups such as ethoxyl and propoxycarbonyl. The organic group may further have a substituent such as a halogen atom. In the formula (G-2), the substituent having a polymerizable functional group represented by Xc and R1 to R7 have the same contents as those of the formula (G-1). m. 'Chemical formulas such as the formula (G-1) of the compound of the present invention are represented by a metal complex structure.' It may also be expressed by a resonance structure such as 0-C-C-C-0, or may include a structurally acceptable structural formula. Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs, for example, the method for synthesizing a polymerizable compound represented by the following formula (G -1) is shown below, but the present invention is not limited in any way. The first synthesis method is obtained by reacting a dinuclear complex having a reactive substituent group represented by formula (G-6) with a monovalent anionic two-base compound obtained by dissociating one hydrogen ion. The mononuclear silver complex with a reactive substituent is used as an intermediate, and the reactive substituent of this intermediate is reacted with a compound having a polymerizable substituent to produce a polymerizable compound containing a mononuclear iridium complex . This paper size applies Chinese National Standard (CNS) A4 specification (21 Ox297 mm) -105- · 584661 A7 B7 V. Description of the invention (103)

Equipment-(Please read the precautions on the back before filling this page) [wherein Υ ° is a substituent with a reactive functional group, and R1 to R7 are independent hydrogen, halogen, nitro, and amine groups , A sulfonic acid group, a sulfonic acid ester group, or an organic group which may have a carbon atom number of from 20 to 20] A dinuclear complex of iridium of the formula (G-6) can be a known method (S.

Lam an s ky F t a 1., I ηor ga niF FhFm is try, 40, 1704 (200 1)). In the printed formula (G-6) of the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, ¥ ° is a substituent with a reactive functional group, such as a hydroxyl group, a hydrogen sulfide group, an amine group, and a carboxyl group. Limited to this. The substituent Υα having a reactive functional group may be the functional basic body described above, or a substituent containing a functional group such as a hydroxyl group. The functional group of Υ03 may be protected by a protecting group. At this time, the monovalent anion-containing iridium mononuclear complex having a two-valent ligand L obtained by performing the reaction under the protection of a protective group is further deprotected to obtain a reactive functional group substituent Υσ. Iridium complexes serve as intermediates. Subsequently, a reactive functional group of this intermediate is reacted with a compound having a polymerizable functional group to prepare a polymerizable compound containing a mononuclear iridium complex. In addition, the official paper size of the aforementioned reactive substituents applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -106-. A7 __ B7_ V. Description of the invention (104) The energy base system does not contain the aforementioned polymerizable substitution base. The contents of R1 to R7 in formula (G-6) are the same as those shown in formula (G-1). Also, as in the case of the formula (G-1), R1 to R7 combined with the four phenylpyridine skeletons of the formula (G-6) may be different from the phenylpyridine skeleton system. Compounds derived from a monovalent anionic bivalent ligand obtained by dissociating one hydrogen ion, such as 2-phenylpyridine, 10,000-diketone, picolinic acid, N-alkylsalicylide, 8-acylhydrazone And its derivatives and the like, but are not limited to the aforementioned compounds. A reactive functional group obtained by reacting an iridium dinuclear complex having a substituent having a reactive functional group of formula (G-6) with a compound obtained by dissociating one hydrogen ion with a monovalent anionic two-segment ligand. The compound having a polymerizable functional group obtained by a single-core non-reaction of the substituent YQ, in addition to the polymerizable group, does not need to have a functional group capable of reacting with the substituent Yc having a reactive i functional group of formula (G-6) . In addition, R1 to R7 in the formula (G-6) need to select a group of a compound having a polymerizable functional group that does not react with the mononuclear iridium complex described above. The Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs prints compounds having polymerizable functional groups that can react with the above intermediates, such as polymerizable acid chlorides, polymerizable alkyl halides, polymerizable isocyanates, etc., but the present invention is not limited thereto. Limited. The polymerizable functional group in the foregoing compound may have, for example, any of radical polymerizable property, anionic polymerizable property, cationic polymerizable property, additional polymerizable property and condensation polymerizable property, and a free-radical polymerizable functional group is preferred. The polymerizable functional group is more preferably a group having a carbon-carbon double bond, for example. For example, basic paper sizes of vinyl, allyl, and ene are applicable to Chinese National Standard (CMS) A4 specifications (210X297). 107-584661 A7 __B7____ 5. Description of the invention Urethane (meth) acrylate groups such as alkenyloxy, methacryloxyethylamino carbamate, phenethylzanyl and its derivatives, vinylamido and its derivatives, etc. Substituent. Among the polymerizable functional groups, from the viewpoint of polymerizability, it is preferable to use propylene fluorenyloxy, methacryl fluorenyloxy, urethane (meth) acryl fluorenyl, and styryl. Specifically, In terms of polymerizable acid chlorides such as acrylic acid chloride, methacrylic acid chloride, etc., polymerizable alkyl halides such as vinyl benzyl chloride, etc., and polymerizable isocyanates such as methacrylic acid isocyanate, methacrylic acid, etc. Oxyethyl isocyanate, etc. The second synthetic method of the polymerizable compound represented by the formula (G-1) is, for example, an iridium dinuclear complex having a polymerizable functional group represented by the following formula (G-7) Monovalent anion with dissociation of one hydrogen ion The resulting base ligand group of compounds prepared by direct reaction method of the polymerizable compound having an iridium complexes portion of monocyte.

[Wherein, it is a substituent having a polymerizable functional group, and R7 to R7 are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, or a sulfonic acid ester. A4 specification (210X 297 mm) (Please read the notes on the back to write this page first) • Equipment · Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs-108-. A7 ___ B7 V. Description of Invention (1 06) Basic Or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. The substituent having a reactive functional group represented by XG in the formula (G-7) is the same as that in the formula (G-1). The contents of R1 to R7 are the same as those shown in formula (G-6). Compounds of monovalent anionic ligands obtained by dissociating one hydrogen ion, such as 2-phenylpyridine, /?-Diketone, picolinic acid, N-alkylsalicylide, 8-hydroxyquinoline And its derivatives and the like, but are not limited to the aforementioned compounds. The polymerizable light-emitting compound composition used in the polymer-based light-emitting material of the present invention does not include an electron-transporting compound capable of forming an electron-transporting layer. The electron-transporting compound can be, for example, a known electron-transporting material such as a quinolinol derivative metal complex, an oxadiazole derivative, or a triazole derivative, but is not limited thereto. The aforementioned electron transport materials can be used alone or in combination of different electron transport materials. The electron-transporting compound contained in the polymerizable luminescent compound composition used in the polymer light-emitting material of the present invention printed by the employee consumer cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs may be a polymerizable electron-transporting compound that is polymerizable. can. If the electron-transporting compound has polymerizability, it is more preferable to increase the degree of freedom in selecting the polymerizable light-emitting compound composition used in the polymer-based light-emitting material of the present invention. Polymerizable electron-transporting compounds, such as the aforementioned metal complexes of oxalinol derivatives such as Alq3 (aluminum triquinolinol), known electron-transporting compounds such as oxadiazole derivatives and triazole derivatives, and at least 丨This is a (meth) acrylic, vinyl, acetophenoxy, isocyanate, isothiohydrogen, and other polymerizable radicals. Specifically, for example, the paper size of double D queline is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -109- 584661 ΑΊ _Β7__ V. Description of the invention (107) Alcohol methacrylic acid oxygen quinoline Aluminium alkoxide, quinolinol bismethacryl oxo quinolinol aluminum, methacryl oxo oxadiazole, thiazol oxadiazole, bisstyryl oxadiazole and the like. Among the polymerizable electron-transporting compounds, cross-linkable polymerizable electron-transporting compounds such as quinolinol dimethylmethyloxoquinolinol and bisstyryloxadiazole are preferred. The polymerizable light-emitting compound used in the polymer light-emitting material of the present invention may further contain another polymerizable compound. When the polymerizable luminescent compound composition used in the polymer-based light-emitting material of the present invention further contains other polymerizable compounds, the degree of freedom of selection of the polymerizable luminescent compound composition used in the polymer-based light-emitting material of the present invention can be increased. Therefore, it is preferable. Other polymerizable compounds are not limited when they do not hinder the light emission of the polymer light-emitting material of the present invention, such as methyl methacrylate, ethyl acrylate, and ethylene glycol dimethacrylate. Cross-linking polymerizable compounds such as propylene glycol diacrylate, trimethyl cellulose propane triacrylate, trimethene cellulose propane acrylate, and styrene benzene are preferred. The polymerizable composition used in the polymer light-emitting material of the present invention may contain a polymerization initiator. The polymerization initiator is not particularly limited as long as it can polymerize the polymerizable functional group. As the polymerization mechanism of the polymerizable functional group, for example, a radical polymerization initiator, a cationic polymerization initiator, an anion polymerization initiator, or the like can be used, and a radical initiator is more preferable. In addition, when classified by the activation mechanism of the polymerization initiator, it can be classified into a thermal polymerization initiator, a photopolymerization initiator, and the like. Among them, the photopolymerization initiator refers to the use of active energy rays such as visible light, ultraviolet rays, electron rays, and r rays to polymerize the paper. The paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm). Packing-( (Please read the notes on the back before filling out this page)

1,1T Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs -110- 584661 A7 ___ B7 ___ V. The meaning of the invention description (108). Thermal free radical initiators such as 2 / 2-Azobisisobutyronitrile (AIBN), 2,2'-Azobisisovaleronitrile and azo compounds, methyl ethyl ketone, methyl isobutyl ketone Ketone peroxides such as peroxides and cyclohexanone peroxides, diallyl peroxides such as benzoin peroxide, decyl ketone peroxide, and lauryl peroxide, dicumene Dialkyl peroxides such as t-butyl cumyl peroxide, di-t-butyl peroxide, 1,1-bis (Nhexylperoxy) 3,3 Ketal peroxides such as 1,5-trimethylcyclohexane, 1,1-di-t-butyl cyclohexane peroxide, 2,2-bis (t-butylperoxy) butane, t -Butyl trimethyl acetate, t-butyl peroxy-2-ethylhexanone ester, t-butyl isobutyl peroxide, di-t-butyl hexahydroperhydroxylene Formates, di-t-butyl peroxyacetic acid ester, t-butyl peroxy-3,5,5-trimethyl-hexanoic acid ester, t-butyl peroxyacetate, t-butyl Alkyl peroxides such as benzyl peroxide, dibutylbutyl peroxide methyl adipate, t-butylperoxy 2-ethylhexanone ester, and t-hexylperoxy 2-ethylhexanone ester Of esters, diisopropyl peroxy dicarbonate, di -sec- butyl peroxycarbonate, T-butyl peroxy isopropyl carbonate and the like through the carbonates and the like. Photoradical polymerization initiators, such as acetophenone, 2,2-dimethoxy-2 · phenylacetophenone, diethoxyacetophenone, 1-phenyl-cyclohexyl-benzophenone, 2- Methyl-M4- (methylthio) phenyl] -2-morpholinone-1,2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butanone Acetophenone derivatives such as 1,2,2-hydroxy-2-methyl-1-phenyl-propane-1-one, benzophenone, 4,4 ^ bis (dimethylamino) benzophenone , 4-trimethyl-based alkyl benzophenone, 4-benzopyrene-4 乂 methyl-diphenylsulfone, benzophenone, benzoin National Standard (CNS) Α4 specification (210X297 mm) Please read the precautions before making it ▲ 5 pages printed by the Intellectual Property Bureau of the Ministry of Economic Affairs Employee Cooperatives -111-584661 A7 ___B7 V. Description of Invention (109) B Phenyl ether, benzoin propyl ether, benzoin isobutyl ether, benzoin isopropyl ether, benzoin derivatives, methylphenylglyoxylate, benzoin dimethyl ketone, 2 , 4,6-trimethylbenzine diphenylphosphine oxide and the like. The amount of the aforementioned polymerization initiator is in the range of 0.001% by mass to 5% by mass, and preferably 0.01% by mass to 1% by mass of the polymerizable composition of the present invention. When the polymerizable composition containing at least one light-emitting compound of the present invention is used as a substrate, a film-like material can be formed thereon by a coating method. The base layer may be different from the composition of the organic light-emitting element. As shown in the case of FIG. 1, a hole transporting layer of 3 is formed. In Examples 19 and 22, the ITO anode is the base layer. When the polymerizable composition containing at least one light-emitting compound of the present invention is used as a substrate, the composition may be used as a solvent when coating it on the substrate. _Dilution of the solvent can reduce the viscosity of the composition, so that a thin film can be formed. The solvent used can be removed by polymerization, or after polymerization, such as heating, decompression. The thickness of the light-emitting layer formed by the polymer-based light emitting discretion of the present invention, which is printed by the Consumers' Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, does not have a certain standard. It can be 1nm to 10 / zm, and 5nm to 1 # For the better. The layer containing a light-emitting material for an organic light-emitting device of the present invention may include an organic EL device containing a polymer-based light-emitting material composition as a substrate, and then form a film thereon (for example, by a coating method), or contain at least one kind A polymerizable composition of a light-emitting compound is used as a substrate of an organic EL device, and is first formed into a film, and then polymerized to make it polymerized. Layers containing luminescent materials can be divided into individual layers of luminescent materials, or containing the paper standards applicable to China National Standard (CNS) A4 specifications (210X297 mm) -112- A7 __________ B7 V. Description of the invention (11〇) Hole transport Material, luminescent material, electron transport material layer, luminescent material layer containing luminescent material 'electron transport material layer, and so on. When a polymer light-emitting material has a crosslinked structure, the crosslinked polymer itself is generally formed, and it is difficult to form a film. The melt polymerization method can polymerize the parent polymerizable compound alone, and can cause the crosslinked polymer to precipitate as a polymer. Therefore, generally speaking, the polymerizable luminescent compound is dissolved in a solvent or other monomer such as a liquid, and then the spin-coating method, the die coating method, the jet printing coating method, the screen printing coating method, or After forming into a film by various printing methods such as a micro-coating method, a film-like crosslinked polymer is formed through a polymerization reaction. Furthermore, the cross-linking polymerizable compound can be copolymerized with a large amount of monofunctional other monomers to form a solvent-soluble polymer, so that it can be coated in a liquid state and coated with a light emitting device. However, at this time, the proportion of the monofunctional monomer needs to be excessively used in comparison with the cross-linkable polymerizable compound. In the organic light-emitting element of the present invention, the hole-transporting layer and the electron-transporting layer can be formed on both sides or one side of the light-emitting layer to improve the light-emitting efficiency and / or durability. Hole transporting materials such as TPD (Ν, Ν'-Diphenyl-N, N, (3-methylphenyl) -1, Γ-linked Phenyl-4,4, diamine), α-NPD (4,4, bis [N- (1-naphthyl) -N-phenylamine] biphenyl), MTDATA (4,4 ,,, 4 " -Tri (3-methylphenylphenylamine) triphenylamine) and other known hole transport materials such as triphenylamine derivatives and polyvinylcarbazole, but it is not limited to this. The aforementioned hole transporting materials can be used alone or mixed or laminated with different hole materials. The thickness of the hole transport layer is based on -113- This paper size applies to China National Standards (CNS) A4 specifications (2 丨 0X297 mm) A7 B7 V. Description of the invention (彳 11) The conductivity of the hole transport layer is different It cannot be said, but it is generally 10 nm to 1 0 // m, and more preferably 10 nm to 1 m. The electron-transporting material forming the electron-transporting layer can be a known electron-transporting material such as a metal complex of a quinolinol derivative such as Alq3 (aluminum triquinolate), an oxadiazole derivative, and a triazole derivative. It is not limited to this. The aforementioned electron transporting materials may be used alone or in combination or lamination of different electronic materials. The thickness of the electron-transporting layer cannot be considered in terms of the conductivity of the electron-transporting layer, but generally it is preferably i 〇ηη to i 〇 # 1Ώ, and more preferably 10 n m to 1 // m. In addition to the light-emitting materials used in the foregoing light-emitting layer, in addition to forming the layers separately from the hole-transporting material and the electron-transporting material, a polymer material can also be used as an adhesive to form each layer. The aforementioned polymer materials, such as polymethylmethacrylate, polycarbonate, polyester, polyethylene, and polyphenyl oxide, are not limited thereto. The film forming method of the luminescent material, hole transporting material, and electron transporting material used by the consumer cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs to print the above-mentioned light-emitting layer, for example, pressure heating evaporation method, electron beam evaporation method, and sputtering Method, coating method, solution coating method, printing method, etc., but it is not limited to this. In the case of low molecular compounds, pressure heating evaporation method and electron beam method are mainly used. In the case of high molecular materials, coating is mainly used. Cover method. As the anode material of the organic light-emitting element in the present invention, known transparent electrode conductive materials such as IT0 (indium oxide), tin oxide, zinc oxide, polythiophene, polypyrrole, and polyaniline can be used, but it is not limited thereto. The surface resistance of the electrode of the transparent electrically conductive material is preferably 1 to 50 Ω / □ (ohm / square). The foregoing method for forming the anode material can be, for example, the Chinese national standard (CNS) A4 specification (210X 297 mm) -114- ΑΊ Β7 for this paper size. 5. Description of the invention (112) Electron beam evaporation method, sputtering method, Chemical reaction methods, coating methods, and the like are not limited thereto. The thickness of the anode is preferably 50 to 300 nm. Further, a buffer layer may be injected between the anode and the hole transporting layer or the organic layer laminated adjacent to the anode, for the purpose of reducing the hole injection barrier. It can use known materials such as copper phthalocyanine and polyethylene dioxythiophene, but it is not limited to this. Examples of the cathode material of the organic light-emitting device in the present invention include known cathode materials such as A1, MgAg alloy, and alkaline earth metals such as Ca, and alloys of A1 and alkali metals such as AICa, but the invention is not limited thereto. The aforementioned method for forming the cathode material can be, for example, a pressure heating evaporation method, an electron beam evaporation method, a sputtering method, an ion sputtering method, and the like, but is not limited to this. The thickness of the cathode is preferably 10 to 1 // m, and more preferably 50 to 500 nm. > Further, an insulating layer having a thickness of 0.1 to 1 ◦ n can be injected between the cathode and the electron transporting layer or the organic layer adjacent to the cathode to improve the efficiency of electron injection. The insulating layer may be made of known cathode materials such as lithium sulfide, fluorine * magnesium, magnesium oxide, and aluminum oxide, but is not limited to this. Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, it is adjacent to the cathode side of the light-emitting layer to prevent the holes from passing through the light-emitting layer so that it can effectively recombine with the electrons in the light-emitting layer. Block layer. Known materials such as triazole derivatives and oxadiazole derivatives can be used, but are not limited thereto. As the substrate of the oxy-light-emitting element used in the present invention, an insulating substrate that is transparent to the light-emitting material's emission wavelength can be used. In addition to glass, PET (polyethylene terephthalate) or polycarbonate can also be used. Known materials such as transparent plastics such as esters are not limited thereto. This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -115- 584661 A7 B7 V. Description of the invention (113) The organic light-emitting element of the present invention can be formed using known matrix or block methods It can also be used as a backlight when no pixels are formed. Please read the note of the memorandum, and then the example. The present invention will be described in more detail with a representative example below. It should be noted that the following description is merely for illustrative purposes and does not limit the present invention in any way. (Measuring device, etc.)

(1) H-NMR JNM EX270 270Mz manufactured by JEOL. Solvent: heavy chloroform or heavy dimethyl asus. (2) GPC column: Shodex KF-G + KF804L + KF801. Eluent: tetrahydrofuran ( THF)

Temperature: 40 ° C Printed detector of employee cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs: RI (Shodex RI-71) (3) Wood element analyzer CHCO-932 type manufactured by LECO Corporation (4) ICP elemental analysis manufactured by Shimadzu Corporation ICPS 8000 This paper size is applicable to China National Standard (CNS) A4 specification (21〇χ 297 mm) -116- 584661 A7 _____ B7 5. Description of the invention (114), ^ (reagents) are not particularly limited, generally The unrefined commercially available reagent (special grade) [Example 1] Polymerizable compound (phosphorescent polymer monomer): Ir (3-MA-PPy) (3-PrCO-PPy) 2 is synthesized below The description is organized by moving the NMR data and the like to the examples! The first half. (1) Synthesis of 2 · (3-methoxyphenyl) pyridine (3-Me0-PPy) according to the general method. Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs ___ That is, as shown in the following reaction steps, According to a general method, 22.4 g (120 mmol) of 3-bromoanisole in dehydrated tetrahydrofuran (THF) and 3.4 g of magnesium (Mg) were used to synthesize (3-methoxyoxyphenyl) magnesium bromide under argon. It is slowly added to 15- 8 g (100 mm ο 1) and (1,2-bis (diphenylphosphino) ethane) dichloronickel (II) ( Ni (dppe) Ch) in 1.8 g of dehydrated THF solution, and stirred at 50 ° C. for 1 hour. After adding 250 ml of a 5% hydrochloric acid aqueous solution to the reaction solution, the target substance was extracted with chloroform, and the organic layer was distilled under reduced pressure. 17.4 g (93.9 mmol) of 2- (3-methoxyphenyl) pyridine (3-Me0-PPy) was obtained as a colorless transparent liquid. The measurement was performed by CHN elemental analysis and 1H-NMR. ^ -NMRCCDCla ^ ppm) ^; 8.68 (d, lH), 7.72 (m, 2H) 'This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -117- 584661 kl __B7 V. Description of the invention (115) 7.59 (s, 1H), 7.54 (d, lH) 7. 3 7 (t > 1 Η), 7.22 (d, lH) 6.97 (d, lH), 3.89 (s, 3H)

Elementary analysis C a 1 c d: C 7 7 · 8 1, H 0

, N 7.56 Found: C 7 7 · 4 4, H, N 7.53 °

H ^ CO

H ^ CO

Mg

THF ^} " Μ9ΒΓ

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs (2) Subsequently, 3-Me〇-PPy and tris (acetamidine acetone ligand) iridium (III) (Ii. (Acac) 3) 2.0g (4.1mmol) in In 200 ml of glycerol, a reaction was performed at 250 ° C for 9 hours, and a yellow powder of Ir (3-MeO-PPy) 3 0.400 g (0.54 mmol) was purified by a gel column. The foregoing operation was repeated 8 times, and a total of 3.20 g (4.3 2 mmOl) of Ir (3-MeO-PPy) 3 0 was obtained. The measurement was performed by 1H-NMR, C, Er, N and Ir elemental analysis, IR and the like. The data obtained by elemental analysis such as W-NMR and CHN are shown below. This paper size applies to China National Standard (CNS) A4 (21 × 297 mm) -118- 584661 A7 B7

V. Description of the invention (116) 1 — NMR (CDC13, 7.82 (d, 3H), 7 7.53 (s, 3H), 7 6.84 (t, 3H), 6 6.60 (d, 3H), 3 Elementary analysis C a 1 cd: C ppm) δ; 5 6 (t, 3 H), 2 5 (d, 3 1 H) 6 7 (d, 3 H), 8 0 (s, 9 H) 0 5 8 · 0 5, H 5, N 7.56. Found: C 77. 44, H 6, N 7.53. 9 Read the notes of the memorandum before writing this page

H ^ CO

3-MeO-PPy

Ir (acac)-glycerol

OCH, H3CO Ir (3-MeO-PPy) 3 Printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs (3) This Ir (3-Me〇-PPy) 3 is hydrolyzed in a hydrochloric acid aqueous solution according to a general method OH group is formed to obtain powdery tris [2- (3-hydroxyphenyl) pyridine] iridium (III) (Ir (3-H0-PPy) 3). (The reaction steps are shown below.) This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210 × 297 mm) -119- 584661 A7 B7 V. Description of invention (彳 17)

H ^ CO

OCH, H3CO Ir (3-MeO-PPy) 3 H20 HC1

HO

OH Ir (3-HO-PPy); Printed by the Wisdom Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs (4) The (Ir (3-HO-PPy)) 3 is reacted with methyl propionate chloride according to the following reaction steps. The reaction was carried out at a molar ratio of 1: 1, and a part of the obtained group formed a methacrylated Ir (3-MA-PPy) (3-H0-PPy) 2 as a main component complex. Subsequently, The residual oxalyl group was reacted with propionic acid chloride (PrCOCl) to obtain a complex of Ii · (3-MA-PPy) (3-PrC0-PPy) 2 as the main component. Subsequently, dehydration was added to the reaction vessel. Ding Dian 32111, 11 * (3-11〇-PPy) 3 2.81g (4mmol), 2.40g (23.6mmol) of triethylamine as a deacidifying agent, and 0.4424g (4.04g) 4 mm 01) dehydrated THF 16 m 1 of methacrylic acid chloride, and reacted at 20 ° C for 5 hours. Then, 30 ml of dropwise dehydrated THF 16 ml of 1.48 g (16 mmol) of propionic acid chloride was added dropwise, The reaction was carried out at 20 ° C for 5 hours, and the remaining 0H groups were reacted. Then, the triethylamine hydrochloride was filtered off. The solvent of the filtrate was evaporated to dryness, and the obtained solid component was mixed in a chloroform / methanol solution. Secondary recrystallization The obtained material was Ir (3-MA-PPy) (3-PrCO-PPy) 2 2.305 g (2.60 mmol) of powder. The measurement was performed by 1H-NMR, C, Er, N and Ir elemental analysis, IR and other methods The obtained data of elemental analysis such as iH-NMR, CHN, etc. are as follows (please read the precautions on the back before filling out this page)... 11 Spring paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) 120- 584661 A7 B7 V. Description of the invention (彳 18). JH-NMR (CDC 1 7 7 2 8 2 (m 2 6 (m 6 7 (m 3 5 (s 6 7 (m 4 2 (t 3 H) 3 H) 3 H) 1 H) 3 H) 6 H)

5 5 ppm) δ; 7 · 5 6 (m, 6 H 6. 8 4 (m, 3 H 6. 6 1 (m, 3 H 5 · 7 4 (s, 1 H 2 · 0 8 (s, 3 H

Elementary analysis C a 1 c d: C 5 8 · 4 9, H 4 0, N 4.72. , N 4.76 Found: C 58.13, H 4

OH Ir (3-HO-PPy) 3 HO Printed by the Consumer Cooperatives of the Intellectual Property Office of the Ministry of Economy CH I 3

occh2ch〇II 3 0 CH.CH9C0 J 2 | 丨 0 Ir (3-HA-PPy) (3-PrCO-PPy). This paper size applies to China National Standard (CNS) A4 (21 OX M7 mm) 121 584661 A7 ____ B7 V. Description of the invention (119) [Example 2] Ir (3-MA-PPy) (3 邛 rC〇_ppy) 2 Synthesis of polymer The Ir (3- MA-PPy) (3-PrC0-PPy) 2 complex 2.22 £ (2.51111: 100), 2,2, -azobis (isobutyronitrile) (AIBN) O.OlOg (0.061mmol), 30 ml of butyl acetate was placed in a reactor and reacted at 80 ° C for 10 hours (in accordance with the following reaction formula). After the reaction, this was put into acetone to reprecipitate, and the polymer was recovered by filtration. The refining treatment in which the recovered polymer chloroform solution was re-precipitated in methanol was repeated twice. After the recovery, vacuum drying was performed to obtain the target product.]-MA-PPy) (3-PrC0-PPy) 2 polymerization物 粉 i.85g。 Powder i.85g. In addition, elemental analysis of C, Η, N, and Ir of the obtained polymer supports that the system has the same composition as 11 ′ (3-MA-PPy) (3-PrC0-PPy) 2. The weight average molecular weight of this polymer was 8000 in terms of polystyrene (using HFIP (hexafluoroisopropanol) as the eluent and measuring by GPC). (Please read the notes on the back first to write this page).

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

0 Yan 2 called Ir (3-MA-PPy) (3-PrCO-PPy) 2

〇fH2CH2 [Example 3] Synthesis of polymerizable compound (phosphorescent polymer monomer): 1 r (3 M〇I-PPy) (3-PrC〇-PPy) 2 This paper is applicable to national standards. CNS) A4 specification (21 ×; 297 mm) -122- 584661 A7 B7 V. Description of the invention (12) The monomer intermediate Ir (3-H0-PPy) synthesized in the same manner as in Example 1 will be reacted as follows As shown in the steps, it was reacted with methacrylic acid oxyethyl isocyanate (MOI) (trade name "Karens MOI", manufactured by Showa Denko Corporation) at a ratio of 1: 1, and then The remaining 0H group reacts with PrCOCl to prepare a complex of ir (3_MOI-PPy) (3-PrCO-PPy) 2 as the main component. Subsequently, dehydrated THF 32mhIi. (3-H0-PPy) 3 2.81g (4mmol), 0.61g (4mmol) MoI, and dibutyl dilaurate were added to the reaction vessel at 20 Reaction at ° C for 5 hours. To this reaction solution was added 2.400 g (24.5 mmol) of triethylamine as a deacidifying agent, and then 16 ml of dehydrated THF in which 1.48 g (16 mmol) of propionic acid chloride was dissolved was added dropwise over 30 minutes, at 20 ° C. After reacting for 5 hours, the residual OH group was subsequently filtered off from the hydrochloride salt of triethylamine. The solvent of the filtrate was evaporated to dry it, and the obtained solid component was purified by recrystallization in a chloroform / methanol mixed solution twice to obtain Ii · (3-MOI-PPy) (3-PrCO-PPy ) 2 2.62g (2.70mmol) powder. The measurement is performed by 1H-NMR, C, Er, N, and Ir elemental analysis, IR, and the like. The data obtained by elemental analysis such as j-NMR and CHN are shown below. ! H-NMR (CDC1sj ppm) δ; 7.82 (m, 3H), 7.56 (m, 6H), 7.26 (m, 3H), 6.84 (m, 3H), 6 · 6 7 (m, 3 Η), 6 · 6 1 (m, 3 Η), 6.14 (s, 1H), 5.61 (s, 1H), (please read the precautions on the back before writing this page) Tai, 11 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs The paper size of the paper is applicable to the Chinese National Standard (CNS) A4 specification (2 丨 0X 297 mm) -123- 584661 kl B7 V. Description of the invention (121) 5. 2 3 (br, 1 Η) 3 · 5 8 (m , 2 Η), 1 · 9 5 (s, 3 Η), Elementary analysis C a 1 cd: C 59-95

4 · 2 9 (t, 2 Η) .6 6 (Q, 4 Η), .4 1 (t, 6 Η) 0 5 9 .9 5, Η 4 N

Found: C 6 7 8 5 8 H 4. 7

OH Iτ (3-HO-P Py) 3 Please read the memorandum first. I. Printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs

OCCH2CH3 II ο choch2co II ο Ir (3-MOI-PPy) (3-PrCO-PPy) 2 [Example 4] Ir (3-M〇I-PPy) (3-PrC〇-PPy) 2 polymer The synthesis will be synthesized from Example 1 (3-M〇I-PPy) (3-PrCO- This paper size applies the Chinese National Standard (CNS) A4 specification (21 ×: 297 mm) -124- 584661 A7 _____B7 V. Description of the invention (122) PPy) 2 complex 2.43g (2.5mmol), 2,2M Yu nitrogen bis (isobutylamidine) (AIBN) 0.01 Og (0.061 mmol), butyl acetate 30ml In the reactor, the reaction was carried out at 80 ° C for 10 hours. After the reaction, it was put into acetone to reprecipitate, and the polymer was recovered by filtration. The refining treatment in which the recovered polymer chloroform solution was re-precipitated in methanol was repeated twice. After the recovery, the solution was dried under vacuum to obtain the target product Ir (3-M〇I-PPy) (3-PrC〇-PPy). 2 Polymer powder 2.05g. In addition, the elemental analysis of C, N, N, and h · of the obtained polymer supports that they have almost the same composition as Ir (3-M0I-PPy) (3-PrC0-PPy) 2. The weight average molecular weight of this polymer was 1 8000 in terms of polystyrene (using HFIP (hexafluoroisopropanol) as the eluent and measuring by GPC).

Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs

Ir (3-M0I-PPy) (3-PrCO-PPy):

CH

CH

CHO

occh2ch3 [Example 5] The synthesis of the (HPPy) polymer Ir / PPy complex is shown in the following reaction formula. 5-Bromo-2- (4-bromohexaphenyl) is applied to Chinese paper standards (CNS) ) A4 size (210X 297 mm) 125 584661 A7 _____ B7____ V. Description of the invention (123)) Pyridine (HPPyBrO 1.98g (5.00mmol)) According to the general method, in 10ml of dimethylformamide (DMF), and (Cyclooctadiene) nickel (〇) (Ni (COD) 2) (also known as Ni (〇) (cyclooctadiene: COD) 2), cyclooctadiene (COD), 2,2'-bispyridine Polymerization was performed for the catalyst to obtain a hexaphenylpyridine polymer (HPPy polymer). Subsequently, 0.625 g (4 mmol) of this HPPy polymer and 0.099 g (0.2 mmol) of Ir (acac) 3 were dissolved in methylcresol, The reaction was performed at 250 ° C for 10 hours. Subsequently, 0.062g (0.4mmol) of 2-phenylpyridine (PPy) was added to the solution, and the reaction was performed at 25 ° C for 10 hours. After the reaction, it was put into acetone to make The polymer is reprecipitated, and the polymer is recovered by filtration. The refining treatment of putting the recovered polymer DMF solution into acetone to reprecipitate is performed twice, and the vacuum drying after recovery The obtained (HPPy) polymer cap powder was 0.564g. In addition, the elemental analysis of C, P, N, and Ir of the obtained polymer supported the estimated structure. Moreover, the weight average molecular weight of this polymer was based on polystyrene Converted to 23000 (using HFIP (hexafluoroisopropanol) as the eluent,-measured by GPC). (Please read the notes on the back and write this page first) Paper size is applicable to China National Standard (CNS) A4 (210X M7 mm) -126-. 584661 A7 B7 V. Description of the invention (124)

Ni (COD) 2 COD,

DMF

Ir (acac)

Please read the notes of memo 1¾ first

Example I printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs ___ 6 ~ 8] {Production and evaluation of cattle 3 kinds of phosphorescent polymers prepared in Examples 2, 4, and 5, Ir (3-MA-PPy ) (3-PrC0-PPy) 2 polymer, Ir (3-M〇I-PPy) (3-PrC0-PPy) 2 polymer, (HPPy) polymer Ir / PPy complex hexafluoroiso A 5 mass% solution of propanol (HFIP) was spin-coated with a thickness of 5 mm x 5 mm to an IT0 anode obtained by pre-coating 500 angstroms of polyethylene dioxythiophene (PEDOT, manufactured by Bayer). (Those coated with ITO on glass substrates), followed by heating and vacuum drying at 80 ° C for 10 hours, two phosphorescent polymer layer films each having a thickness of about 1000 angstroms were formed on each PEDOT / IT0 anode. The paper size of the aforementioned three kinds (two each) of the phosphorescent polymer / PED0T / IT0 electrode by vacuum evaporation method to form an electron transport layer with a thickness of about 500 angstroms is applicable to the Chinese National Standard (CNS) A4 (210X297) (Centi) 127 584661 A7 _B7 V. Description of the invention (125) PBD (2-(4-bipheny 1 y 1)-5-(4 -1 ert-buty 1 pheny 1) -1,3,4. Oxadiazol) film. Subsequently, the cathode system formed Ag / Mg at a weight ratio of 9/1 to form a film with a thickness of about 1000 angstroms, and 6 organic light-emitting elements (2 each) were fabricated. The aforementioned elements were placed in an isolated processing chamber under an argon atmosphere, with wires attached thereto, and sealed in a glass container with an argon atmosphere to evaluate their luminous effects. The power of the luminous brightness was applied to an organic light-emitting element using a program DC voltage / current source TR6 143 made by Atlas Co., Ltd. The luminous brightness was measured using a luminance meter BM-8 manufactured by Dekang Corporation. After the direct current power is applied to the luminous element of the head 3, the initial voltage at 10V, the initial brightness at 10V, and the subsequent continuous light emission at a fixed voltage of 10V, the brightness after 240 hours is shown in Table 丨Two averages [Comparative Examples 1 to 2] The Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs printed the HFIP 5 mass% solution of the three phosphorescent polymers used in Examples 6, 7, and 8 and synthesized them in Example 丨. The same intermediate complex ir (3-Me0-PPy) 3 and PMMA (polymethyl methacrylate) obtained were dissolved in chloroform at the ratio shown in Table 2 to prepare a 5% by mass solution, and everything else was in accordance with Example 6. 4, 7 and 8 were used to fabricate 4 organic light-emitting elements (2 each). After applying the DC power to the aforementioned elements in the same manner as in Examples 6, 7, and 8, the light emission starting voltages were measured as 10 and 11 v, respectively. The initial brightness at 12 V and subsequent continuous light emission at a fixed voltage of 12 V are shown in Table 2 (2 averages each) after 240 hours of brightness. This paper size applies Chinese National Standard (CNS) A4 specifications ( 21〇 > < 297 mm) -128- 584661 Α7 Β7 V. Description of the invention 126) Table 1 Examples of phosphorescent polymer light emission at the beginning 10V brightness (Cd / m2) voltage (V) after the initial 240 time 6 Ir (3-MA-PPy) (3-PrCO-PPy) 2 polymer 5 1280 1180 7 Ir (3-M〇I-PPy) (3-PrCOPPy) 2 Polymer 6 1450 1250 8 (HPPy) Polymer Ir / PPy complex 3 730 680 (Please read the precautions on the back first \ 4 ^ Maben (Page) -5 Table 2 Comparative example error JtmMeO-PPv WPMMA (mass ratio) 12V light emission luminance (Cd / m2) voltage (V) voltage 1V after initial 240 time 1 1/5 10 150 70 2 1/2 11 120 50 line economy Production and Evaluation of Organic Light-Emitting Elements Produced by the Employees' Cooperatives of the Ministry of Intellectual Property Bureau [Example 9] Phosphorescent Polymer Compounds and Luminescent Compositions Added with Hole-Transporting Polymer Compounds Phosphorescent polymer: Ir (3-MOL · PPy) (3-PrCO-PPy) 2 polymer and poly (N-vinylcarbazole) 3% by mass chloroform solution. The ratio is Ir (3-M〇 I-PPy) (3-PrC0-PPy) 2 polymer 70 mass% para- (N-vinylcarbazole) 30 mass This paper size applies Chinese National Standard (CNS) A4 specification (210 ×; 297 mm) 129 584661 A7 __ B7 V. invention is described in (127)%. After applying the DC power to the aforementioned components in the same manner as in Examples 6, 7, and 8, the light emission starting voltages were measured to be 5V each, and the initial brightness at 12V was 1 8 60 cd / m2, and then continuously emitted at a fixed voltage of 12V. The brightness after 24 hours was 1 690 cd / m2 (average of 2). [Example 10] Production and evaluation of an organic light-emitting device obtained from a phosphorescent light-emitting polymer compound and a light-emitting composition to which an electron-transporting polymer compound was added. First, a phosphorescent polymer obtained in Example 4 was prepared: 11. 3_ "〇1- PPy) (3-PrCO-PPy) 2 polymer and poly (N-vinylcarbazole) in a 4% by mass chloroform solution. The ratio is Ir (3-MOI-PPy) (3- Pi'C〇-PPy) · 2 polymer 70% by mass to poly (N-vinylcarbazole) 30% by mass. This solution was spin-coated m cloth _5mmxjmm in size and pre-coated with 500 angstroms of PEDOT Two phosphorescent polymer layers with a thickness of about 1,000 angstroms were formed on the PED0T / IT0 anode, respectively, on the anode, followed by heating and drying at 80 ° C for 10 hours. Subsequently, the cathode system was Ag / Mg A film with a thickness of about 1,000 angstroms was formed on the phosphorescent light-emitting polymer composition layer at a weight ratio of 9/1, and a total of two organic light-emitting elements were fabricated. The foregoing elements were added in an isolation processing chamber under an argon atmosphere. The wire was sealed in a glass container with an argon atmosphere to evaluate its luminous effect. The aforementioned elements were according to the examples After applying DC power in the same way as in 6, 7, and 8, the light-emission starting voltages were measured at 6V, and the initial brightness at 12V was 1 80 cd / m2, and subsequent continuous light emission at a fixed 12V, the brightness after 240 hours was 1 340cd / m2 (average of 2). This paper is again applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) (Please read the note on the back first ¾¾¾ this page) Printed by the Consumer Cooperative of the Property Bureau-130- 584661 A7 B7 V. Description of the invention (128) [Example 11] Organic light-emitting device obtained from a phosphorescent polymer compound and a light-emitting composition added with an electron-transporting polymer compound Production and Evaluation First, the phosphorescent polymer obtained in Example 4 was prepared: 1 !; (3-] ^ 〇1-PPy) (3-PrC〇-PPy) 2 polymer and JP-A-10-1665 3% by mass of chloroform solution of poly PBD synthesized by the method. The ratio is 70% by mass of Ir (3-M0I-PPy) (3-PrC0-PPy) 2 polymer and 30% by mass of poly PBD. This solution was used in place of the chloroform solution of the phosphorescent polymer and PBD used in Example 10. Two organic light-emitting elements were produced in the same manner as in Example 10. The aforementioned elements were applied in the same manner as in Embodiments 6, 7, and 8]] After a DC power supply, the light-emission starting voltages and voltages were measured at 11 ”and 12V. When the degree is niOcd / m2, and the subsequent continuous light emission is fixed at 12V, the brightness after 240 hours is 1 580 cd / m2 (average 値 of 2). [Example 12] Synthesis of polymerizable luminescent compound: Ir (3-MA-PPy) 3 was synthesized by the consumer cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, and was synthesized in the same manner as in Example 1 and Ir (3-Me. -PPy) 3 According to a general method, MeO groups are hydrolyzed in an aqueous hydrochloric acid solution to form OH groups, and powdered tris (3-hydroxyphenylpyridine) iridium (III) (

Ir (3-HO-PPy) 3) (the following reaction formula). Subsequently, in the reaction vessel, 321111, 1] * (3-11〇-PPy) 3, 2.81g (4mmol), and triethylamine, a deacidifying agent, were added to the reaction vessel. ) A4 specification (210X 297 mm) 584661 Kl __B7 printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 5. Description of the invention (129) 23.6 mmol), and then 1.293 g (12. 2 mmol) of A dissolved in 90 minutes Dehydrated THF of methacrylic acid chloride at 32m was reacted at 20t for 5 hours, and then the precipitated triethylamine hydrochloride was filtered off. The solvent of the filtrate was evaporated to dryness, and the obtained solid component was purified by recrystallization in a mixed solution of hexafluoroisopropanol / methanol to obtain the trifunctional Ir (3-MA- PPy) 3 2.805 g (3.070 mmol) powder. The measurement system was performed by j-NMR, C, ytterbium, N, and element analysis, and IR. The data obtained by elemental analysis such as W-NMR and CHN are shown below.

'H-NMRCCDCla ^ 7.82 (d, 3H), 7 7.55 (s, 3H), 7 6.86 (t, 3H), 6 6.63 (d, 3H), 6 5.74 (s, 3H), 2 Elementary analysis C a 1 cd: C Found: C ppm) δ; • 5 8 (t, 3 H), • 2 6 (d, 3 H), • 6 7 (d, 3 H), • 3 6 (s, 3 H), • 〇9 (s, 9H). 5 9 · 5 9, H 4. N 4.63. 5 9. 2 1, H 4. 0 0 5 8

ch3 3 H2C = C-C-C1 Δ II o Ir (3-HO-PPy):

Ir (3-MA-PPy) 3 This paper size is applicable to Chinese National Standard (CNS) A4 (210 X 297 mm) -132 584661 A7 B7 V. Description of the invention (13〇) [Example 13] Polymerizable luminescent compound : Synthesis of Ir (3_MOI-PPy) 2 (· 3-PrCO-PPy) The monomer intermediate Ir (3-HO-PPy) 3 will be synthesized in the same manner as in Example 1 according to the following reaction steps. Oxyethyl isocyanate (MOI) (trade name: Karens MOI, manufactured by Showa Denko Corporation) was reacted at a ratio of 1 ·· 2 (mole), and the remaining OH group was then reacted with acrylic acid chloride ( PrCOCl) reaction to obtain lr (3-MoI-PPy) 2 (3-PrCo-PPy) complex. Subsequently, dehydrated THF48mhIr (3-H0-PPy) 3 2.81g (4mmol) and MOI 1.272g (8mmol) were added to the reaction vessel, and then a catalyst amount of dibutyl dilaurate was added at 20 ° Reaction at C for 5 hours. After adding 2.400 g (24_5 mmol) of triethylamine as a deacidifying agent to this reaction solution, drip into a solution of 0.74 g (8.0 nimol) of dehydrated THF in 8 mL of manganese solution, and then add 2 (TC The reaction was carried out for 5 hours to react the remaining 0H group, and then the precipitated triethylamine hydrochloride was filtered off. The solvent of the filtrate was evaporated to dryness, and the obtained solid component was recrystallized in a chloroform_ mixed solution. Refined twice to obtain 2.75 g (2.57 mmol) of 11 '(3-MOI-PPy) 2 (3-PrCO-PPy) as the target. The measurement is based on j-NMR, C, Er, N, and Ir elements. Analysis, IR and other methods. The data obtained for elemental analysis such as j-NMR, CHN and the like are shown below. 〇-NMR (CDC 1 3 ^ PP m): 7.81 (η, 3Η), 7.54 (m, 6H) '7. 2 6 (m > 3 Η), 6.86 (ηι, 3') 'equipment-(Please read the precautions on the back page first) Ding,-0 Intellectual Property Bureau, Ministry of Economic Affairs, Consumer Consumption Cooperative The scale of paper waves is in accordance with Chinese National Standard (CNS) A4 (2IOX297 mm) -133- 584661 A7 B7 V. Description of the invention (131) 6.68 (m, 3H), 6.59 (m, 3H), 6.13 (s, 2H ), 5.60 (s, 2H), 5.22 (br, 2H), 4.27 (t, 4H), 3.57 (m, 4H), 2.67 (q, 2H), 1.95 (s, 6H), 1.41 (t, 3H) Elementary analysis Calcd: C 5 6.17 'H 4. 3 4, N 6 o Found * C 55.86, H 4. 3 7, N, 6 (Read the precautions on the back before locking the page). CH,

HO

OH 2 H2C = C-CO-CH2CH2-NCO HO h0c = c-co-ch9ch9 -nhco 1 II z zo CH, 〇 (MOI)

CH 3 H9C = C-C0-CH :) CH9-NHC0 Z η Δ π

OH Order Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs

Ir (3-HO-PPy) 3

occh2ch3 〇0 〇Ir (3-MOI-PPy) 2 (3-PrCO-PPy) This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm)% A7 _________ B7 V. Description of the invention (132) [ Examples 14 to 19] Production and evaluation of organic light-emitting device using polymerizable composition Four types of polymerizable phosphorescent light-emitting polymers synthesized in Examples 1, 3, 1, 2, and 13: monofunctional Ir (3- MA-PPy) (3-PrCO-PPy) ^, monofunctional Ir (3-M〇I-PPy) (3-PrCO-PPy) 2, 3-functional 11 * (3- MA-PPy) 3, 2-functional Ir (3-M〇I-PPy) 2 (3-PrC〇-PPy) According to the composition shown in Table 3, a 10% by mass chloroform solution was prepared, and AIBN (azobisisobutyronitrile) as a polymerization initiator was used for After adding 0.02 parts by mass to 100 parts by mass of the total body, a size of 5 mm x 5 mm was applied by spin coating on an ITO anode obtained by pre-coating 500 angstroms of PEDOT (polyethylenedioxythiophene, manufactured by Bayer Corporation). Then, after heating at 60 ° C for 2 hours, each monomer was polymerized and hardened. Then, it was decompressed at 80 ° C and dried for 8 hours to form two phosphorescent polymer layers each having a thickness of about 1,000 angstroms on each PEDOT / ITO anode. The Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs printed a TAZ (approximately 500 angstroms) of an electron transport layer having a thickness of about 500 angstroms on the aforementioned six (12) phosphorescent polymers / PEDOT / IT〇 electrodes by vacuum evaporation 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -l, 2,4-triazol) membrane. Subsequently, the cathode system formed Ag / Mg at a weight ratio of 9/1 to form a film with a thickness of about 1,000 angstroms, and a total of 6 organic light-emitting elements (2 each) were produced. The aforementioned components were placed in an isolated processing chamber under an argon atmosphere, with additional wires, and sealed in a glass container with an argon atmosphere to evaluate their luminous effects. The power of luminous brightness is applied to the organic light-emitting element by the program DC voltage / current source TR 6 14 3 made by Atlas Co., Ltd. The luminous brightness is in accordance with the Chinese national standard (CNS) A4 specification (210X 297) (Centi) -135- 584661 A7 _ _B7 _V. Description of the invention (133) Measured using a brightness meter BM-8 manufactured by Dekang Corporation. After applying the DC power, the light-emitting element mentioned above has its initial light emission voltage, initial brightness at 10V, and subsequent continuous light emission at a fixed voltage of 10V. The brightness after 240 hours is shown in Table 3 (two for each polymer system) Table 3 Average Example Example Phosphorescent Polymer Monomer (Molar Ratio) Polymer Luminescence Start Voltage (V) 10V Height (Cd / m2) Scheme 14 Ir (3-MA-PPy) / (3-PrCO -PPy) 2 Uncrosslinked 5 1560 1150 (A) 15 Ir (3-MA-PPy) 3 Crosslinked 6 1430 1350 t6 5 1580 1420 (B) MA-PPyMl / 1) 17 Ir (3-MOI-PPy) (3-PrCO-PPy) 2 Uncrosslinked 6 1600 1280 (C) 18 Ir (3-MOI-PPy) 2 (3-PrCO-PPy) Crosslinked 6 1510 1380 19 Ir (3-MOI-PPy) (3 -PrCO-PPy) 2 / Ir (3- MOI-PPy) 2 (3-PrCO-PPy) (l / l) Cross-linking 6 1600 1450 (D) (Please read the precautions on the back first ^ write this page) Assembling and setting line Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, Consumer Cooperatives This paper is printed in accordance with Chinese National Standard (CNS) A4 (210X297 mm) -136- 584661 A7 B7 V. Description of Invention (134)

Ir (3-MA-PPy) (3-PrCO-PPy) 2

Scheme B

0

I c-c = ch2 II 0 (Please read the precautions on the back before filling out this page) -5 mouth H? C = C-C-0 2 II 〇

Ir (3-MA-PPy) 3 Printed by W Industry Consumer Cooperatives, Intellectual Property Office, Ministry of Economy

Ir (3-MA-PPy) (3-PrCO-PPy) 2

This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -137- 584661 Printed by the W Industry Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs 5. Description of the invention (135)

Scheme C

CH.CH.CO 〇

Ir (3-MOI-PPy) (3-PrCO-PPy) 2

Scheme D CH,

ch3ch2co

Ir (3-MOI-PPy) (3-PrCO-PPy) 2 CH, C = 0 0 CH? CH2 NH I c = o * o

(Please read the notes on the back before filling in this page) CH. CH2 = CH-COCH2CH2NHCO 0 o

Ir (3-MOI-PPy) 2 (3-PrCO-PPy)

This paper size applies the Chinese National Standard (CNS) A4 specification (21 OX 297 mm) -138- 584661 A7 ____B7__ V. Description of the invention (136) [Examples 20 ~ 23, Comparative Example 3] Organic using polymerizable composition Production and evaluation of light-emitting elements According to a general method, phenylpyridine (PPy) was reacted with tris (ethyleneacetone) iridium (III) (h · (acac) 3) at 30 ° C to synthesize the phosphorescent compound tris (phenyl) Pyridine) iridium (III) (Ir (PPy) 3). Two types of polymerizable phosphorescent polymers synthesized from this Ir (PPy) 3 and Examples 1 and 12: monofunctional Ir (3-MA-PPy) (3-PrC0-PPy) 2, trifunctional Ir (3-MA-PPy) 3 and bifunctional polymerizable electron-transporting compound: bisphenethylfluorenyloxydiazole (BSODA), and electron transportability as compared Compound ·· oxadiazole (ODA) A polymerizable luminescent compound composition containing 10% by mass of a chloroform solution and an electron-transporting compound added in accordance with the composition shown in Table 4. AIBN (azobisisobutyl) as a polymerization initiator -Commission) After coating the mass of monomers, apply 5mm x 5mm to 500 Angstroms by the transfer coating method. The ITO anode obtained from PEDOT (made by Bayer) was then heated at 60 ° C for 2 hours, and then the monomers were polymerized and hardened. The pressure was reduced at 80 ° C, and the mixture was dried for 8 hours at each PED. Two phosphorescent polymer films each having a thickness of about 1,000 angstroms were formed on the T / IT0 anode. Ag / Mg was formed on the foregoing five (10) phosphorescent polymer / PEDOT / ITO electrodes at a weight ratio of 9 / A film with a thickness of about 1000 angstroms was formed as a cathode, and a total of 5 organic light-emitting elements (2 each) were fabricated. The foregoing elements were placed in an isolation processing chamber under an argon atmosphere, and a lead was added to the element, and the glass container was used. Sealed in an argon atmosphere, and evaluated its luminosity according to the same method as in Examples 1 to 19. This paper size is applicable to China National Standard (CNS) Λ4 specification (210X 297 mm) ^ p-batch-(please first Read the notes on the back and fill out this page) Order printed by the Consumers' Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs -139- 584661 Μ__Β7 V. Description of the invention (137) Table 4 Phosphorescent polymer monomer (Mole ratio) The polymer emits light Initial voltage 10V Height (Cd / m2) (V) Example 20 Ir after initial 240 hours (PPy) 3 / BSODA (l / l) Crosslinking 6 1660 1210 Example 21 Ir (3-MA-PPy) (3-PrCO-PPy) 2 / BSODA (l / l) Crosslinking 7 1480 1210 Example 22 Ir (3-MA-PPy) 3 / ODA (l / l) Crosslinked 5 1380 1320 Example 23 Ir (3-MA-PPy) (3-PrCO-PPy) 2 / ODA Uncrosslinked 5 1510 1080 Comparative Example 3 Ir (PPy) 3 / ODA unpolymerized 5 1680 880 ^ batch-(Please read the precautions on the back before filling this page) [Example 24] Production and evaluation of organic light-emitting devices using polymerizable composition- ------------------------------ The polyelectron-transporting compound: bisphenethylfluorenyloxydiazole (BSODA) Mix with chloroform at a molar ratio of 1: 1 to make a 15 mass% chloroform solution containing a polymerizable luminescent compound composition with an electron-transporting compound added, and AIBN (azobisisobutyl) as a polymerization initiator. Nitrile) After adding 0.02 parts by mass to 100 parts by mass of the total amount of monomers, a 5 mm x 5 mm size was applied by spin coating on an ITO anode obtained by pre-coating 500 Angstroms of PEDOT (manufactured by Bayer), and then After heating at 60 ° C. for 2 hours, each monomer was polymerized and hardened. After decompressing at 80 ° C for 8 hours, two phosphorescent polymer films each having a thickness of about 1,000 angstroms were formed on each PEDOT / IT0 anode. The luminous properties were evaluated in the same manner as in Examples 20 to 23. This paper size applies the Chinese National Standard (CNS) Λ4 specification (210X 297 mm). Printed by the Consumers ’Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs-140- 584661 A7 B7 Printed by the Ministry of Economics’ Intellectual Property Bureau of W Property and Consumer Cooperatives. Description of the invention (138) After applying the above-mentioned organic light-emitting element with a DC power source, the light-emission starting voltage was measured to be 4V, and the initial brightness at 10V was 980cd / m2. When the subsequent continuous light emission was fixed at 10V, the brightness after 240 hours was 830 cWm2 (average of 2). [Example 25] Synthesis of polymerizable compound Ir (MA-PPy) (PPy) 2 (1) The methoxy group of 3-Me0-PPy synthesized in the same manner as in Example 1 was hydrolyzed by a general method. That is, as shown in the following reaction step, 16.0 g of 3-MeO-PPy (86 · 4 mm m ο 1) was dissolved in concentrated hydrochloric acid, and then stirred at 130 ° C for 4 hours in a closed container. After the reaction, the reaction solution was neutralized with an aqueous sodium hydrogen carbonate solution, and the target substance was extracted with chloroform. The extract was crystallized with a chloroform / hexane solution to obtain colorless crystals of 2- (3-hydroxyphenyl) pyridine (3- HO-PPy) 10.4 g (60.7 mmol). The measurement was performed by CHN elemental analysis and 1H-NMR. 'H-NMRCCDCls ^ ppm) ^; 8.66 (d, 1H), 7.76 (t, 1H), 7.67 (d, 1H), 7.56 (s, 1H), 7.40 (d, 1H), 7.30 (t, 1H) ), 7.26 (t, 1H), 6.88 (d, 1H), 2.08 (br, 1H) ° Elementary analysis Calcd: C 7 7. 1 7, H 5 · 30, N 8.18. (Please read the notes on the back _ 4 items before filling and loading —: Write this page) Order 4 paper sizes applicable to China National Standard (CNS) A4 specifications (210X297 mm) -141-584661 A7 B7 V. Description of the invention (139) hqco

Found: C 7, N H20 / HC1 DMF • 8 Η 7

3-MeO-PPy 3-HO-PPy (2) Subsequently, the hydroxyl group of 3-H〇-PPy is reacted with tert · • butyldimethylsilyl chloride (TBDMS-C1) according to a general method, and the hydroxyl group is subjected to tert -Protected by butyl dimethyl sand institute. That is, as shown in the following reaction steps, 8.6 g (50.2 mmol) of 3-HO-PPy and 0.2 g of imidazole and 11.3 g (75.0 mmol) of tert-butyldimethylchlorosilane were dissolved in 200 ml of N, N. -In dimethylformamide, it wo n’t beat 4 wins at room temperature. ”Compound angle. Clear liquid p _ 2- (3-tert-butyldimethylsilyloxyphenyl) pyridine (3-Si 〇-PPy) 1 3 · 0 g (4 5 · 5 mm ο 1). The measurement was performed by C Η N elemental analysis and 1 η-N M R. 2H-NMR (CDC I3 j ppm) δ-(Please read the precautions on the back before filling this page)

, 1T Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 8 · 6 8 (d, 1 Η) 7 · 6 8 (d, 1 Η) 7 · 4 8 (s, 1 Η) 7. 2 2 (t, 1 )) 1 · 〇1 (s, 9 Η) 7. 7 4 (t 7. 5 8 (d 7.. 3 2 (t 6. 8 9 (d 0. 2 4 (s

Elementary analysis C a 1 cd: C 71 ·, N 4 · H) H) H) H) H) H 8 This paper size applies to China National Standard (CNS) A4 (21 OX 297 mm) 142- 8584661 Α7 Β7 V. Invention Description (140)

Found: C 7 1., N 4 TBDMS-Cl / imidazole --------- ^ DMF Η 8 4

TBDMSO

3-HO-PPy 3-SiO-PPy (3) Synthesis of bis (/ z-chloro) tetrakis (2-phenylpyridine) iridium (ΠΙ) from 3-Si〇-PPy ([Ii_ (PPy) 2-Cl] 2) The reaction was performed in the presence of silver (I) trifluoromethanesulfonate (AgCF3SO3). That is, as described in the following reaction steps, 5.71 g (20.0 mmol) of MSiO-PPy and [Ir (PPy) 2-Cl] 2 5.37 g (5.0 mmol) of dehydrated toluene suspension were added under an argon flow, and added AgCF3S03 2.70 g, and refluxed over 6 hours. After the reaction solution was purified by a gel column, the solvent was removed, and a yellow powder of (2- (3-tert-butyldimethylsilyloxyphenyl) pyridine) bis (2-phenylpyridine) iridium (ΙΠ) was obtained. (Ir (PPy) 2 (3-SiO-PPy) 2.53g (3.2 mmol). The measurement is performed by CHN elemental analysis and 1 H-NMR. IH — NMR (CDC 13, ppm) 3; (Please read the back Please fill in this page again for attention.) Printed by the Consumer Property Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs.

6 (d, 2 Η), 7 4 (d, 2 Η), 7 6 (s, 1 Η), 66.6〇 (d, lH), 6 Elementary analysis Calcd: C 7.7 · 7 · 7 8 (d , 1 H), 5 5 (m »6 H), 8 5 (m, 9 h), 4 5 (d, 1 h). 5 9 · 6 7, H 4 This paper size applies to Chinese National Standard (CNS) A4 specification (210 X mm) -143- 584661 A7 B7 V. Description of invention (141)

Found: C 59. 53, Η 4.89, Ν 5 · 3 4 ο

[Ir (PPy) 2Cl]

(Please read the notes on the back 1 ·. Fill in the items and then install-; write this page)

Order Ir (PPy) 2 (3-SiO-PPy) (4) Hydrolyze the silyl group of lr (PPy) 2 (3-SiO-PPy) according to a general method. That is, according to the following reaction steps, 1 μ of tetra-n-butylammonium fluoride (TBAF) was added to a solution of 2.00 g (2.55 mm) of Ι ·· (PPy) 2 (3-SiO-PPy) in THF. The THF solution was 5.1 m 1 and reacted at room temperature for 30 minutes. After the reaction solution was purified on a silica gel column, the solvent was distilled off to obtain (2- (3-hydroxybenzyl) pyridine) bis (2-phenylpyridine) iridium (π I) (I r (PP y) 2 ( 3-H0-PPy)) U9g (2.52 mmol). The measurement was performed by CHN elemental analysis and 1 Η-N M R. 1 Η-NMR (CDC 1 3 5 ppm) δ; This paper size is applicable to Chinese National Standard (CNS) M specification (210X297 mm) 1 '-144-4 Intellectual Property Bureau of the Ministry of Economic Affairs g (printed by Industry and Consumer Cooperatives 584661 kl ____B7 V. Description of the invention (142) 7.87 (d, 2H), 7.78 7 · 6 (m, 9 H), 6 · 8 5 (6.63 (d, lH), 4.23 Elementary analysis C a 1 cd: C 59, N 6 Found: C 5 8, N 6 d 0 '. 2 1 H) OH) 1 H), H 4, H 7. 7 4

Ir (PPy) 2 (3-SiO-PPy)

TBAF

THF

Ir (PPy) 2 (3-HO-PPy) (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs (5) As described in the reaction steps below, under argon flow To a solution of 1.34 g (2.0 mmol) of Ir (PPy) 2 (3-H0-PPy) and 0.81 g (8.0 mmol) of triethylamine as a deacidifying agent in dehydrated THF, add methacrylic acid chloride 0.2 5 g (2 · 4 mm ο 1) and reacted at 20 ° C for 5 hours. The triethylamine hydrochloride in the reaction solution was filtered off, and the filtrate was purified by a silica gel column, and then the solvent was distilled off to obtain (2- (3-methacryloxyphenyl) pyridine) bis (2-benzene Pyridine) iridium (III) (Ii · (3-MA-PPy) (ppy) 2 1.28 g (1.73 mmol). The measurement was performed by CHN elemental analysis and 1H-NMr. 1 Η-NMR (CDC 1 3, ppm ) δ; This paper size applies the Chinese National Standard (CNS) Λ4 specification (2 丨 〇 × 29 < 7 mm) 145- 584661 A7 B7 V. Description of the invention (143) 7. 8 7 (d > 2 H), 7.78 (d, lH) '7.6 (m, 8H), 7.40 (s, lH), 6.8 (m, 10H), 6.59 (d, lH)' 6.35 (s, 1H), 5.74 (s, 1H) '2 · 0 8 (s, 3 H) 〇

Elementary analysis Calcd: C 6 0 · 1 5, H 3.85, N 5 · 6 9 0

Found: C 59.85, H 3.86, N 5.66. (Please read the notes on the back before filling this page)

Ir (PPy) 2 (3-HO-PPy) Ir (PPy) 2 (3-MA-PPy)

, 1T Xiao Gong Consumer Cooperative, Intellectual Property Bureau of the Ministry of Economic Affairs, Yin Yi ^ [Example 26] Synthesis of polymerizable compounds: Im · (3-M0I-PPy) (PPy) 2 The synthesis is as described in the reaction steps described below, under argon Ir (PPy) 2 (3-H0-PPy) 1.34 g (2.0 mmol), 2,6-di-4010-butyl-4-methylphenylhydrazone synthesized in the same manner as in Example 25 under a stream of air (81111 [) 91111 £, 13 ml of dibutyltin (IV) dilaurate (DBTL) in dehydrated THF solution, methacrylic acid oxyethyl isocyanate (Μ Ο) (trade name: "Karens MoI ", Manufactured by Showa Denko Corporation) 0.37 g (2.38 mmoI) and reacted at 50 ° C for 1 hour. After the reaction solution was refined with a silica gel column, the size of the dissolved paper was adapted to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) -146-, 584661 A7 B7 V. Description of the invention (144) The solvent was distilled off to obtain (2- (3- ((2-Methacryloxyethyl) aminomethylamido) phenyl) pyridine) bis (2-phenylpyridine) iridium (III) (Ir (PPy) 2 (3-M〇I -PPy)) 1.48 g (1.79 mmol). The measurement was performed by CHN elemental analysis and 1H-NMR. 1 — NMR (CDCl3, ppm) 5; 7.87 (d, 2H), 7.80 (d, 1H), 7.6 (m, 8H), 7.42 (s, 1H), 6.8 Cm »1 0 H), 6.59 ( d, lH), 6.14 (s, lH), 5.60 (s, lH), 5.21 (br, lH), 4.28 (t, 2H), 3.57 (m, 2H), 1.96 (s, 3H). Elementary analysis Calcd : C 5 8. 1 7, H 4.03---------------------------------------, N 6. 7 only ____

Found: C 57.78, H 4., N 6.72. 0 2 (Please read the notes on the back first '

Jm-Item refill * Pack —: Write this page) Order Printed by S Industrial Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs

HO

Ir (PPy) 2 (3-HO-PPy)

ch3 0 I II h9c = c-co-ch9ch:)-nhco II 0 CH ^ I 3 H9C = C-C0-CH.CH9-NC0 II 22 (\ Ν-ΊΓ- _O (MOI) > W THF

Ir (PPy) 2 (3-M〇 工 -PPy) [Example 27] Synthesis of polymerizable compound: Ir (4-MA-PPy) 2 (PPy) This paper is sized to the Chinese National Standard (CNS) A4 specification ( 210 × 297 mm) -147- 584661 A7 B7 V. Description of the invention (彳 45) (1) Synthesis of 2- (4-methoxyphenyl) pyridine (4-MeO-PPy) according to the general method ° That is, according to the following As shown in the reaction steps, 22.4 g (120 mmol) of 4-bromoanisole in dehydrated tetrahydrofuran (THF) and 3.4 g of magnesium (Mg) were synthesized in a dehydration tetrahydrofuran (THF) according to a general method. ) Magnesium bromide, slowly add 15.8 g (100 mmol) of 2-bromopyridine and (1,2-bis (diphenylphosphino) ethane) dichloronickel (II) (Ni (dppe) Ch) In 1.8 g of dehydrated THF solution, refluxed over 1 hour. After adding 250 ml of a 5% hydrochloric acid aqueous solution to the reaction solution, it was washed with chloroform. After the aqueous layer was neutralized with sodium bicarbonate, the target was extracted with chloroform, and the organic layer was distilled under reduced pressure. The distillate solidified immediately at room temperature to obtain 15.1 g (81.5 mmol) of 2- (4-methoxyphenyl) pyridine (4-MeO-PPy) as a white solid. The measurement is performed according to the CHN element version and 1 H-NMR. 0__________ — iH — NMR (CDCl3, ppm) 5; 8.65 (d, lH), 7.95 (d, 2H), 7.71 (t, lH), 7.66 (d, lH ), 7.16 (t, lH), 7.00 (d, lH), 3 · 86 (s, 3H).

Elementary analysis Calcd: C 7 7. 8 1, H 5.99, N 7.56.

Found: C 77.52, H 6.10, N 7 · 4 〇 This paper size applies to China National Standard (CNS) A4 specifications (210X 297 mm) — (Please read the precautions on the back before filling this page) Order if Ministry of Economy Printed by the Employees' Cooperative of the Intellectual Property Office -148- 584661 B7 V. Description of Invention (彳 46) / = \ Mg H3CQ \ / Br

Ni (dppe) Cl2

4-MeO-PPy Printed by the M Industrial Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economy (2) The methoxy group of 4-Me0-PPy is hydrolyzed according to a general method. That is, 15.0 g (80.1 mmol) of 4-Me0-PPy was dissolved in concentrated hydrochloric acid, and the mixture was stirred at 130 ° C for 4 hours in a closed container as described below. After the reaction, the reaction solution was neutralized with an aqueous solution of sodium bicarbonate, and the target substance was extracted with chloroform. The extract was crystallized from a chloroform / hexane solution to obtain colorless crystals of h (4 ^ Fei (58.5 mmol). The measurement was based on CHN Elemental analysis and 1 H-NMR were performed. IH — NMR (CDCl3, ppm) 5; 8.63 (d, 1H), 7.82 (d, 2H) '7.74 (t, 1H), 7.65 (d, 1H), 7.20 (t , LH), 6.85 (d, 2H). Elementary analysis Calcd: C 7 7 · 1 7 'H 5 · 3 0, N 8.18. Found: C 76. 91' H 5.39, N 8.02. I ----- --- φ-Handbook-(Please read the notes on the back before filling in this page) The size of the paper used for this edition applies to China National Standard (CNS) A4 (210X 297mm) -149- 584661 A7 _ B7 V. Invention Description (147)

(Please read the precautions on the back before filling this page) (3) The 4-H〇-PPy is reacted with sodium hexachloroiridium η water and compound (NaHrCh · η〇2〇) to synthesize bis (// -Chloro) tetrakis (2- (4-hydroxyphenyl) pyridine) iridium (III) ([Ir (4-H0-PPy) 2-Cl] 2) ο That is, as described in the reaction steps below, N ^ IrCh · ηΗ20.10 g was dissolved in 400 ml of a mixed solvent of 2-ethoxyethanol and water 1: 1, and after blowing argon for 30 minutes, 4-H0-PPy was added under an argon flow. g (50.2 mmol) was dissolved, and refluxed over 5 hours. After the reaction, Lilly medium distillation m — ^ μ ζ mSM. ^ ^ SE®B crystal of fir (4-H0 di PPy) 2-Cl] 2 5.8 8 g (5.18 mmol). The measurement was performed by CHN elemental analysis and 1H-NMR. 'H-NMR (DMS〇-de > ppm) 5; 9.66 (d, 2H), 9.38 (d, 2H), 7.95 (m, 8H), 7.61 (d, 2H), Employees ’Intellectual Property Office, Ministry of Economic Affairs Cooperative prints 7.54 (d, 2H), 7.38 (t, 2H), 7.26 (t, 2H), 6.33 (d, 2H), 6.28 (d, 2H), 5.67 (s, 2H), 5 · 1 2 ( s, 2 H).

Elementary analysis Calcd: C 46 · 52 ′ H 2.84, N 4.93. -150- This paper size applies to China National Standard (CNS) A4 (2 丨 〇 < 297 mm) 584661 A7 ____ B7 V. Description of the invention (148)

Found: C 46.33, Η 2.51, N 4.76.

[Ir (4-HO-PPy) 2Cl] 2 (Please read the precautions on the back before filling this page) (4) Put [lr (4-H〇-PPy) 2-Cl] 2 in trifluoro In the presence of silver (I) methanesulfonate (AgCFrSO;), it reacts with 2-phenylsquimidine (PPy). Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, according to the following reaction steps, [Ir (4-H〇-PPy) 2-Cl] 2 3.9 8 g (3.5 mmol) and PPy 15.5 g (lO Ommol) in a dehydrated toluene suspension, 1.98 g of AgCF3S03 was added, and refluxed over 6 hours. After the reaction solution was purified by a silica gel column, the solvent was distilled off to obtain (2- (4-hydroxyphenyl) pyridine) (2-phenylpyridine) iridium (III) (Ir (4-HO-PPy)) as a yellow powder & gt (PPy)) 2.20 g (3.2 mmol). The measurement was performed by CHN elemental analysis and 1H-NMR. 1 Η — N M R (C D C 1 3, p p m) 5; 7.88 (d, 1H), 7.78 (d, 2H), 7 · 6 (m, 8 H), 6. 6 (d, 2 H). This paper size applies the Chinese National Standard (CNS) Λ4 specification (210X297 mm) -151-584661 A7 B7 V. Description of the invention (149) Elementary analysis Calcd: C 5 7, N 6 Found: C 5 7, N 5 • 7 1, H • 12 ° • 4 6, H • 99 ° .4

[Ir (4-HO-PPy) 2Cl]:

(Please read the notes on the back before filling this page)

AgCF3S03

OH Ir (4-HO-PPy) 2 (PPy), -5ϊ »Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs (5) As described in the following reaction steps, Ii · (4-H 〇-PPy) 2 (PPy) 1.37g (2.0mmol), deethylated triethylamine 0.8 lg (8.0 in mol) in dehydrated THF solution, 0.50g (4.8mmol) of methacrylic acid chloride was added and The reaction was carried out at 20 ° C for 5 hours. The triethylamine hydrochloride in the reaction solution was filtered off, and the solvent was distilled off after the filtrate was purified on a silica gel column to obtain (2- (4-methacryloxyphenyl) pyridine) (2-phenyl Pyridine) iridium (III) (lr (4-M A-PPy) 2 (PPy)

1.55g (1.88 mmol). The measurement is based on CHN elemental analysis and 1H-NMR. The paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X297mm f) -15? -584661 kl ____B7 V. Description of the invention (15). ΑΗ-NMR (CDCl3, ppm) 5; 7. 8 7 (d ^ 1 1), 7.78 (d, 2H), 7 · 6 (m, 9Η), 6.8 (m, 8Η), 6.59 ( s, 2H), 6.35 (s, 2H), 5.74 (s ^ 2Η), 2.08 (s, 6H). Elementary analysis Calcd: C 59.84, H 3.92, N 5.11.

Found: C 59.95, H 3.82, N 5.04. (Please read the notes on the back before filling this page)

o ch3 Ir (4-HO-PPy) 2 (PPy) Ir (4-MA-PPy) 2 (PPy) Printed by the Ministry of Economic Affairs ’Smart Assets-Bureau Consumer Cooperatives [Example 28] Polymerizable compounds: 1m · (4 The synthesis of -MOI-PPy) 2 (PPy) is as described in the following reaction steps. Under an argon flow, Ii · (4-H0-PPy) 2 (PPy) 1.37g ( 2.0mm〇l), 2,6-di-tert-butyl-4-methylphenol (BHT) 18mg, dibutyltin (IV) laurate (DBTL) 26mg in dehydrated THF solution, methacrylic acid was added醯 Ethyl ethyl isocyanate (MOI) (trade name "This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 gong) -153- 584661 ppm) δ; kl B7 V. Description of the invention (151) Karens "MOI", manufactured by Showa Denko Co., Ltd., was 0.75 g (4.83 mmol), and then reacted at 5 (TC for 1 hour. After the reaction solution was purified on a silica gel column, the solvent was distilled off to obtain double (2- (4- (( 2-Methacryloxyethyl) aminomethylamidino) phenyl) pyridine) (2-phenylpyridine) _ (ΙΙΙ) (Ιι · (4-MOI-PPy) 2 (PPy)) 1.68g ( 1.68 mmol). The measurement was performed by CHN elemental analysis and 1H-NMR. 'H-NMR (CDC 1 7.85 (d, 1H), 7.81 (d, 2H), 7 · 6 (m, 9 H), 6.8 (m, 8 H), 6.58 (d, 2H), 6.12 ( s, 2H), 5.60 (s, 2H), 5.21 (br, 2H) 4.28 (t, 4H), 3.58 (m, 4H), 1.96 (s, 6 H).

Elementary analysis C a 1 c d: C 5 6. 6 2, H 4, N 7.02.

Found: C 56.38, H 4, N 6.72. 2 0 2 (Please read the notes on the back before filling out this page) The Intellectual Property Bureau of the Ministry of Economic Affairs g (industrial and consumer cooperation Du printed on this paper is applicable to the Chinese National Standard (CNS) A4 specification (210X297 male I) -154- 584661 A7 B7 V. Description of the invention (彳 52)

Ir (4-HO-PPy) 2 (PPy)

MOI / BHT, DBTL

? h2 Ir (4-MOI-PPy) 2 (PPy) (Please read the precautions on the back before filling out this page) Printed by the 8th Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economy — ^ 2 + Poly''composite synthesis _ _____ The 1- (3-MA-PPy) (PPy) 2 complex synthesized in Example 25 1.11§ (1.51: 1111〇1), 2,2 ' -Azobis (isobutyronitrile) (AIBN) 0 · 0 1 0 g (0 · 0 6 1 mm ο 1), butyl acetate 10 m 1 was placed in the reactor and replaced with nitrogen, at 80 ° The reaction was performed for 10 hours at C (in accordance with the following reaction formula). After the reaction, the reaction solution was dropped into acetone to reprecipitate, and the polymer was recovered by filtration. Repeatedly, the recovered polymer chloroform solution was further dropped into methanol to make The reprecipitation refining treatment, after recovery and vacuum drying, the target material was obtained as Ii · (3-MA-PPy) (PPy) 2 polymer powder 0.92g. In addition, CΗN element analysis of the obtained polymer supported It has the same composition as I r (3 _ MA-PP y) (PPy) 2. In addition, the weight average molecular weight of this polymer is 1 2000 in terms of polystyrene (determined by GPC, applicable to the paper scale) in National Standard (CNS) A4 size (297 mm 21〇X) -155- 584661 A7 _B7 V. invention is described in (153) was ·· THF).

Ir (3-MA-PPy) (PPy) 2 Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, M Industrial Consumer Cooperative, [Example 30] Ιι · (3-MOI-PPy) (PPy) 2 Synthesis of Polymer Example Ir (3-MOI-PPy) (PPy) 2 complex compound synthesized in 26.1.1 g (1.5 mmol), 2,2'-azobis (isobutyronitrile) (AIBN) 0.0 1 〇g (0.06 1 mmol) and 10 ml of butyl acetate were poured into the reactor and replaced with nitrogen, and then reacted at 80 ° C. for 10 hours (according to the following reaction formula). After the reaction, it was dropped into acetone to reprecipitate, and the polymer was recovered in an over-oven manner. The refining treatment of dripping the recovered polymer chloroform solution into methanol to reprecipitate was repeated twice, and after recovery, vacuum drying was performed to obtain the target substance Ii '(3-M〇I-PPy) (PPy) 2 polymer powder. 1.02 g. Moreover, the CHN elemental analysis of the obtained polymers all supports that they have the same composition as Ir (3-MOI-PPy) (PPy) 2. The weight average molecular weight of this polymer was 20,000 in terms of polystyrene (measured by GPC, eluent · THF). Approval: 1T ------ (Please read the precautions on the back before filling this page) This paper size is applicable to China National Standard (CNS) Α4 specifications (2 丨 〇 > < 297 mm) -156- 584661 A7 B7 V. Description of the invention (彳 54)

Ir (PPy) 2 (3-] VlOI-PPy) (Please read the precautions on the back before filling. Install-: Write this page) Printed by the Consumer Cooperatives of the Intellectual Property Office of the Ministry of Economy [Example 31] Ir ( 3-MA-PPy) (3-PrC0-PPy) 2 Polymer Synthesis The Ir (3-MA-PPy) (3-PrCa-PPy) 2 complex 2-22 g (1.5 mmol) synthesized in Example 1 was synthesized. ), 2,2 azobis (isobutyronitrile) (AIBN) 0.01 Og (0.061 mmol), 30 ml of butyl acetate were placed in the reactor and replaced with nitrogen, and the reaction was carried out at 80 ° C for 10 hours (see below) Reaction formula). After the reaction, it was dropped into acetone to reprecipitate, and the polymer was recovered by filtration. The refining treatment of dripping the recovered polymer chloroform solution into methanol to reprecipitate was repeated twice, and after recovery, vacuum drying was performed to obtain the target substance Ii · (3-MA-PPy) (3-PrC0-PPy) 2 Polymer powder 1. 85g. Moreover, the CHN elemental analysis of the obtained polymers all supports that they have the same composition as Ir (3-MA-PPy) (3-PrCO-PPy) 2. The weight average molecular weight of this polymer was 8,000 in terms of polystyrene (measured by GPC, eluent: THF). Sale • Noise This paper size applies to Chinese National Standards (CNS) A4 specifications (2〗 0X 297 mm) -157- 584661 A7 B7 V. Description of the invention (155)

CH ㈣ JO

〇ϊ〒3 Ir (3-MA-PPy) (3-PrCO-PPy);

OCCH2CH3 Intellectual Property Bureau of the Ministry of Economic Affairs (printed by the Industrial and Consumer Cooperatives [Example 32] Synthesis of Ir (3-MA-PPy) 3 polymer Ill · (3-MA-PPy) 3 synthesized in Example 12 The complex was 2.28 g (2.5 mmol), 2, 2, azobis (isobutyronitrile) (AIBN) 0.01 Og (0.061 mmol), and 30 ml of butyl acetate was placed in the reactor and replaced with nitrogen. Reaction at 10 ° C for 10 hours (according to the anti-mouse formula below) "The insoluble polymer was precipitated, and this polymer was recovered by filtration. After washing with 100 ml of chloroform and 100 ml of methanol, vacuum drying was performed to obtain the target product Ii · ( 3-MA-PPy) 3 polymer powder 2.1 Og. Moreover, the CHN elemental analysis of the obtained polymer supports that it has almost the same composition as that of Ι · (3-MA-PPy) 3. The polymer is presumed to have The cross-linked polymer is insoluble in various solvent systems, and its molecular weight cannot be measured by GPC. This paper size is applicable to the Chinese National Standard (CNS) Λ4 specification (210 × 297 mmt) (Please read the note on the back first) Please fill in this page for the items. • Fill in the wood order for the item --T · -158- 584661 A7 B7 Ministry of Economy Zhici 8 Property Office workers consumer cooperatives printed five or description of the invention (I56)

Ir (3-MA-PPy) 3 [Example 33] Synthesis of Ir (3-M0I-PPy) (3-PrCO-PPy) 2 Polymer The ir (3-M0) synthesized in Example 3 I-PPy) (3-PrCO- PPy) 2 complex 2.43 g (2.5 mmol), 2,2, -azobis (isobutyronitrile) (AIBN) O.OlOg (0.061 mmol), butyl acetate 30 ml Put it in the reactor .....----.--. After replacing with nitrogen in the reactor, react at 80 ° C for 10 hours (according to the following reaction formula). After the reaction, it was dropped into acetone to reprecipitate, and the polymer was recovered by filtration. The refining treatment of dripping the recovered polymer chloroform solution into methanol to reprecipitate was repeated twice, and after the recovery, vacuum drying was performed to obtain the target substance Ir (3-MOI-PPy) (3-PrC0-PPy) 2 polymerization.物 粉 2.05g. In addition, the CHN elemental analysis of the obtained polymers all supports that they have almost the same composition as Ir (3-MOI-PPy) (3-PrCO-PPy) 2. The weight average molecular weight of this polymer was 18,000 in terms of polystyrene (measured by GPC, eluent: THF). This paper size applies Chinese National Standard (CNS) A4 specification (21〇X 297 mm) ^ ^ IT (Please read the notes on the back before filling this page) -159- 584661 A7 B7 V. Description of the invention (彳 57) Ch3 -CH 广 C— c = o CH. 〇I 3 II CH9 = CH-C0CH, CH9NHC0, II 0 ch2 I ch2 I Δ NH I c = c CH.

occh2ch3

° ^ ch2ch3 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

Ir (3-M0I-PPy) (3-PrCO-PPy) 2 [Example 34] Synthesis of Ir (3-M〇I-PPy) 2 (3-PrC0-PPy) polymer Synthesis of 1.26 (3-M0I-PPy) 2 (3-PrC0-PPy) complex 2.46g (2.5mniol), 2,2'-azobis-C (AIBN) O.OlOg (0.061 mmol) and 30 ml of butyl acetate were placed in the reactor and replaced with nitrogen, and then reacted at 80 ° C. for 10 hours (according to the following reaction formula) to precipitate an insoluble polymer and recover the polymer by filtration. After washing with 100 m 1 of chloroform and 100 m 1 of methanol, vacuum drying was performed to obtain 2.21 g of the Ir (3-MOI-PPy) 2 (3-PrCO-PPy) polymer powder as a target. Moreover, the CHN elemental analysis of the obtained polymers all supports that it has almost the same composition as Ir (3-MOI-PPy) 2 (3-PrC0_PPy). It is presumed that this polymer is a polymer having a crosslinked structure, and is insoluble in various solvents, and its molecular weight cannot be measured by GPC. ^ ^ 1T ^ (Please read the notes on the back before filling out this page) This paper size applies to Chinese National Standard (CNS) A4 (2l0x 297 mm) -160- 584661 A7 B7 V. Description of the invention (158)

(Please read 4 notes on the back before filling and filling —: write this page) [[例 35] Ir (3-MA-PPy) (3_PrC〇_PPy) 2 / Ir% PP y) 3 Copolymerization Synthesis of the substance: Ir (3-MA-PPy) (3-PrC0-PPy) synthesized in Example 1 ~ 1.1 lg (1.25 mmol) of the complex, Ir (3-MA-PPy) synthesized in Example 12 ) 3 complex 1.14g (125mmol), 2,2, -azobis (isobutyronitrile) (AIBN) O.OlOg (0.061mm〇i), butyl acetate 300ml 1 into the reactor After the neutralization was replaced with nitrogen, the reaction was performed at 80 ° C for 10 hours (in accordance with the following reaction formula) to precipitate an insoluble polymer, and the polymer was recovered by filtration. After washing with 100 ml of chloroform and 100 ml of methanol, vacuum drying was performed to obtain lr (3-MA-PPy) (3-PrC0-PPy) 2 / Ir (3-MA-PPy) 3 polymer as a target. 2.05 g of powder. In addition, the CHN elemental analysis of the obtained polymers all supports Ir (3_MA-PPy) (3-Pi.C0-PPy) 2 and the paper size. The Chinese National Standard (CNS) 8-4 specification (2 丨 0 > < 297 (Mm) Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Health and Economics -161-584661 A7 B7 V. Description of the Invention (159) Ι · (3-MA-PPy) 3 is obtained by co-polymerization with a molar ratio of 1: 1. It is presumed that this polymer is a polymer having a crosslinked structure, and is insoluble in various solvent systems, and its molecular weight cannot be measured by GPC. Printed by Zhengong Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs

1T (Please read the notes on the back before filling this page)

[Example 36] 11- (3 ^ 〇1-?? 7) (3 邛 1. (: 〇 邛? 7) 2/11. (3-! ^ 〇1-PPy) 2 (3-PrC〇- Synthesis of PPy) Copolymer The 11- (3-! 4〇1-?? ¥) (3 邛 1 _ (: 〇-PP y) 2 complex 1.2 1 g (1.2 5 mm ο 1), Ir (3-M〇I-PPy) 2 (3-Pi.Co-PPy) complexes synthesized in Example 1 1.23 g (1.25 mmol), 2, 2, azo Bis (isobutyronitrile) (AIBN) 0.01 Og (0.061 mmol) Applicable to China National Standard (CNS) 8-4 specification (21〇 × 297 mm) 584661 • A7 ____B7 5. Description of the invention (16〇)), butyl acetate 30 ml was placed in the reactor and replaced with nitrogen, and then reacted at 80 ° C. for 10 hours (according to the following reaction formula) to precipitate an insoluble polymer and recover the polymer by filtration. 100 ml of chloroform After washing with 100ml of methanol, vacuum drying was performed to obtain the target substance.

Ir (3-MOI-PPy) (3-PrCO-PPy) 2 / Ir (3-MOI-PPy) 2 (3.

PrCO-PPy) polymer powder 2.18 g. Moreover, the CHN element analysis of the obtained polymers all supports Ir (3-MOI-PPy) (3-PrCO-PPy) 2 and

Ir (3-MoI-PPy) 2 (3-PrCo-PPy) is based on a molar ratio; [...] [Copolymerization obtained. It is speculated that this polymer is a polymer with a cross-linked structure, which is insoluble to various solvent systems, and its molecular weight cannot be measured with G PC. ^ Batch clothing-(Please read the precautions on the back before filling this page)

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Ir (3-M0I-PPy) (3-PrCO-PPy): Ir (3-MOI-PPy) 2 (3-PrCO-PPy) CH, CH, (Please read the notes on the back first '4 • Items .

C = 0 I 0 CH, I L CH2 I 1 NH I OO c = o meaning 0 ch2 0 ch2 I l NH I oo 0

(NH I CH2 I L ch2 I z 0 Pack-: Write this page)

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[Example 37] Polymerizable compound: (8-nonane-2,4-dione ester) bis (2-phenylpyridine) iridium (III) (hereinafter abbreviated as Ii · (PPy) 2 (1-Bu-acac )) The synthesis is shown in the following reaction steps, and bis (//-chloro) tetrakis (2-phenylpyridine) iridium (ΠΙ) (hereinafter referred to as [Ir (PPy) 2C1] 2) and According to well-known methods (Η · Gerlach et al ·,

HeW. Chim. Acta, 60, 638 (1 9 7 7)) synthesized 8-nonane-This paper size applies to China National Standard (CNS) A4 specification (210X29 *? Mm) 164- 584661 A7 B7 V. DESCRIPTION OF THE INVENTION (162) 2,4-dione is reacted to synthesize h · (PPy) 2 (RayBu-acac). (Please read the notes on the back before filling this page) That is, [Ii · (PPy) 2C1] 2 261mg (0.24mmol)) was suspended in 30ml of methanol obtained by degassing with nitrogen, and then 8-nonane- 87 mg (0.5 6 mmol) of 2,4-dione and 76 mg (0.75 mmol) of triethylamine were heated under reflux in an oil bath for 3 hours. The resulting pale yellow reaction liquid was cooled to room temperature, and then concentrated with a rotary condenser. Subsequently, 200 ml of a dilute hydrochloric acid aqueous solution and 50 ml of chloroform were added thereto, followed by vigorous stirring. The chloroform layer was chromatographed and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained yellow residue was dissolved in dichloromethane, and a thin yellow main product was filtered by gel chromatography using dichloromethane as an eluent. After concentrating the solution under reduced pressure, adding a small amount of hexane and cooling to -20 ° C, the target substance was Ir (PPy) 2 (1-Bu-acac) 2 7 0 mg (0.4 1 mm ο 1) as a thin yellow crystal (Yield: 85%) The measurement was performed by CHN elemental analysis and 1H-NMR .: 1 H-NMR (CDC 1 a ^ ppm) 5; 8.49 (d, J = 5.7 Hz, 2H, PPy), 7.83 ( t, J = 7.8Hz, 2H, PPy), 7.70 (m, 2H, PPy), printed by the Consumer Cooperatives of the 1st Bureau of Smart Finance of the Ministry of Economic Affairs 7.54 (t, J = 6.8Hz, 2H, PPy), 7.1〇 ( m, 2H, PPy), 6.80 (t, J = 7.3Hz, 2H, PPy), 6 · 6 8 (m, 2 Η, PP y), 6.35 (d, J = 6.2Hz, 1H, PPy), 6.25 (d, J = 6.2Hz, lH'PPy), 5.6I (m, 1 H, one CH = CH 2), this paper size applies Chinese National Standard (CNS) A4 (210x297 mm) 584661 A7 __B7 V. Description of the invention (163) 5 · 1 9 (s, 1 Η, diktonate-methine), 4.86 (m, 2H, — CH = CH2), 1.99 (t, J = 7.3Hz, 2H, methylene: 1.79 (s, 3H , CH3), 1 · 7 2 (m, 2 H j methylene), 1 · 3 8 (m, 2H, methylene) 0

Elementary analysis Calcd: C 5 6 · 9 5, H 4., N 4.28. (C 3 1 H 2 9 I r N 2 0 2

Found: C 55.84, H 4., N 3.97. 4 7 3 • Batch of clothes-(Please read the precautions on the back before filling this page)

[Ir (PPy) 2Cl] 2 o o Order d Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

3 NEt

MeOH

[Example 38] Polymerizable compound: [6- (Hethyl ethylene_phenyl) _2, 'hexane dione ester] bis (2-phenylpyridine) iridium (ΠΙ) (hereinafter referred to as (ppy

This paper size applies the Chinese National Standard (CNS) Λ4 specification (21 OX 297 mm) -1RR 584661 A7 B7 V. Description of the invention (164)) 2 [1- (St_Me) -acac]) Synthesis (1) according to As shown in the following reaction steps, acetoacetone and 4-vinylacetobenzyl chloride are reacted to synthesize 6- (4-vinylphenyl) -2,4-hexanedione ester. That is, "weigh 1.23 g (60% in oil) (31 mmol) of sodium hydride under nitrogen" and then add 60 ml of dry tetrahydrofuran (hereinafter referred to as THF), and then cool to 0 ° C in an ice bath. In this suspension, a mixed solution of 2.5 g (24 mmol) of acetamidine and 1 ml of hexamethylphosphinetriamine was added dropwise to form a colorless precipitate. After stirring at 0 ° C for 10 minutes, 17.5 ml (28 mmol) of 11-butyronitrile in hexane solution (1.6M) was added dropwise to dissolve the precipitate, and the mixture was stirred at 0 ° C for 20 minutes. To the obtained pale yellow solution, 4.0 g (26 mmol) of 4-vinylbenzyl chloride was added dropwise. The reaction solution was returned to room temperature and stirred for 20 minutes. Dilute hydrochloric acid was added to make the aqueous layer acidic. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and the solvent was distilled off with a rotary condenser. The obtained reaction mixture was charged into a silica gel column, and developed with a mixed solvent of hexane / dichloromethane 1: 1 (volume ratio), and the main product was filtered. The solvent was distilled off from the obtained solution under reduced pressure to obtain 3.0 g (Hmmol) of 6- (4-vinylphenyl) -2,4-hexanedione as a brown product (yield: 56%). The measurement was performed by CHN elemental analysis and 1H-NMR. 'H- NMR (CDCl3, ppm): e η ο 1; δ 7 · 33 (d, J 28 · 1Hz, 2H, aromatic), 7 · 14 (d, J 28 · 4Ηζ, 2H, aromatic), 6. 68 (dd, J 28. 1Hz, lH, vinylic), this paper size applies Chinese National Standard (CNS) Α4 specification (210 × 297 male f) — (Please read the precautions on the back before filling this page)

Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, M Industrial and Consumer Cooperatives 584661 A7 B7 V. Description of the invention (165) 5.70 (d, J 5.4.6 (s,) 5.2.0 (d2. 9 1 ( t 2.58 (1 2 .03 (sk et ο; δ 7.33 (d 7 2 17.00 Hz, 1H, vinylic H, dinkeonate-methine),

J: 11.1Hz J = 5 · 7 H z, J = 7 · 3 H z, 3 H, methyl) <, 1 H, vinylic 2 H, methylene 2 H, methylene (please read the note on the back first 8.1Hz , 8.4Hz, = 8. 1 H z 2 H, aromatic 2 H, aromatic, 1 H, vinylic J ·, fill in the items again. Printed by S Industrial Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs 1 4 (d, J 6 8 (dd, 7 0 (d, J = 1 7. 0 H z J 1 H »vinylic 2〇 (d, J 2 11. IHz'IH, vinylic 53 (s, 2H, C (= 〇) CH2C (= 〇 ) 2 · 89 (m, 4H, ethylene), 1 9 (s, 3 H, methyl) o enol · · keto = 6: 1 0 Elementary analysis Calcd: C 7 7 · 7 5, Η Ί · (C14H9O2) Found : C 77.49, H 7 ·

NaH, n-BuLi Pack-: Write this page) Order ΙΛ 4 6 0 o

THF

〇〇 This paper size applies Chinese National Standard (CMS) A4 specification (210X 297 mm) 584661 A7 B7 V. Description of the invention (166) (2) According to the following reaction steps, 6-(4-vinylbenzene ) -2,4-hexanedione is reacted with [h · (PPy) 2C1] 2 synthesized according to a general method to synthesize Ir (PPy) 2 [1- (St-Me) -acac]. That is, 'I PP. (PPy) 2C1] 2 242 mg (0.32 mmol), sodium carbonate 15 8 mg (1.5 mmol) and 2,6-dibutyl-4-methylphenyl 5 mg (0.023 mmol) were dissolved in n, N-dimethylformamide (hereinafter referred to as DMF) was added to 210 mg (0.97 mmol) of 6- (cardiovinylphenyl) -2,4-hexanedione, followed by 1 hour at 651 Heat and stir. Subsequently, a dilute aqueous hydrochloric acid solution was added to the reaction solution cooled to room temperature, and the pale yellow component was extracted with chloroform. After the solvent was distilled off using a rotary condenser, the residue was dissolved in a small amount of dichloromethane, and the main yellow component was filtered by silica gel column chromatography (developing solution: dichloromethane). The solution was dried under reduced pressure, and then added to dichloride I, and recrystallized at -20 ° C to obtain the target substance Ii (PPy) 2 [1- (St-Me) -acac] 354mg ( 0.49γπmol) pale yellow crystals (yield 78%). The measurement was performed by CHN elemental analysis and j-NMR. I --------- (Please read the notes on the back before filling out this page), 11 'H-NMR (CDC 1 Printed by the Employee Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs 8877 4 7 (d 2 d 9 a 7. 7. 8 9

d, J 0 (md, J j ppm) δ; • 7Hz, lH, PPy), • 7Hz, lH, PPy), 6 Η, PP y), .. 1 H z, 2 H, stylyl-aromatic Η, PP y),; 1 H z, 2 H, stylyl-aromatic The paper size applies to Chinese National Standard (CNS) Λ4 specification (210X 297 mm) -169- 584661 A7 B7 V. Description of the invention (167) 7 5 111 7 '5 Η, PP y and vinylic), ^ -ϊ. ΒΗζ ^ Η ^ ΡΡγ) 67 (d, J = 17.6 Hz, 8 1 H, vinylic), H z, 1 H, vinylic), s' 1 H , Diketonate-methine), (t 'J = 7.3Hz, 2H, ethylene), β (m, 2H, ethylene), 5 (s' 3 H, methyl) 〇 Elementary analysis Calcd: C 60.40, H 4.36, N 3.91 . (C 3 6 H 3 1 I Γ N 2 O 2) Found: C 61.35, H 4.34 ------------------------------ --------- 8 3 ° 22 1 9 (d 17 6 0 3 7 clothing-(Please read the precautions on the back before filling this page)

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[Ir (PPy) 2Cl],

〇 〇 d

Na2C〇3

DMF

Ir (PPy) 2 [1- (St-Me) -acac: This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297g t) 584661 Printed by the 8th Industrial Cooperative of the Intellectual Property Office of the Ministry of Economy ^^ _________ Β7_ V. Description of the Invention (168) [Example 39] Polymerizable compound: (9-propenyloxy-2,4-nonanedione ester) bis (2-phenylpyridine) iridium (III) (hereinafter abbreviated Synthesis of Ir (ppy) 2 [1- (A-Bu) -acac]) (1) According to the following reaction steps, (9_hydroxy_2,4-nonanedione ester) bis ( 2-phenylpyridine) iridium (III) (hereinafter referred to as Ii. (PPy) 2 [1- (OH-Bu) -acac]). That is, 11.167 mg (0.26 mmol) synthesized in the same manner as in Example 37 was dissolved in 10 ml of THF, and then 9-boron-cyclo [3.3.1] Institute (hereinafter referred to as 9-; 681 ^) 0.5 "111 ^ solution 1.0ml (0.5mmol). After heating this solution for 25 minutes under reflux, the resulting reaction solution was Na2H aqueous solution 0.2ml (0.60mmol) And 3 5% H202 solution 0.060ηι1 (0.62 mmol) were added in this order, and stirred at room temperature for 2 hours. Then 20ml of water was added and concentrated with a transcondenser, and then chloroform was added to fully shake, The organic layer was dried under reduced pressure. The obtained yellow solid was dissolved in a small amount of dichloromethane, and then added to a silica gel column. The impurities were first removed by circulating dichloromethane. The dichloromethane / ethyl acetate 1 : 1 (volume ratio) mixed solvent to make the pale yellow complex flow out. After recovering it, it is dried under reduced pressure. The dichloromethane / hexane mixed solution is cooled to -20 ° C, and lr (pPy) 2 is obtained by recrystallization. [Bu (〇H-BU) -acac] 23 mg (0.034 mmol) of a pale yellow solid (yield 13%). The measurement was performed by CHN elemental analysis and 1H-NMR. NM R (CDCl3, ppm) 5; 8.50 (d, J = 5.9Hz, 2H, PPy), 7.82 (t, J 2 7.〇Hz, 2H, PPy), (Please read the precautions on the back before filling this page ) Refilling of J · item ", · 11 4 This paper size is applicable to Chinese National Standard (CNS) A4 (210 X 297 male 1) -171-584661 A7 B7 V. Description of the invention (169) 7 · 7 2 (t , 7. 5 5 (t 7 6 1 2 (t 8 1 (t 6 9 (t 3 1 (d 2 6 (d 1 9 (s 4 4 (t 9 8 (t 7 9 (s 3 4 (m 0 5 (m J = 7.3Hz, 2H, PPy), J = 7.0Hz, 2H, PPy), J = 5.9Hz, 2H, PPy), J = 7.6Hz, 2H, PPy), J = 7.3Hz, 2H, PPy), J = 5.9 Hz, lH, PPy), J = 5.9 Hz, lH, PPy), 1 H, diketonate-methine), J = 7.〇Hz, 2H, CH2OH) J = 7.〇Hz ， 2H, methylene) 3 H, methyl), 4 H ， methylene), 2 H j methylene) 0

Elementary analysis Calcd: C 4 2, H 4. 6, Ν 4 · 1 (C ί Η Η 3 1 Found: C 5 5 · 7, NR 4. 1 r N 2 0 3), H 4.7 --- (Please (Read the notes on the back before filling out this page)

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〇 o

Ir (PPy) 2 (1-Bu-acac) Ir (PPy) 2 (1- (OH-Bu) -acac) (2) Ir (PPy) “1- (〇H · This paper size applies the Chinese National Standard (CNS) A4 specification (210 × 297 mm) -17?-584661 A7 __B7 V. Description of the invention (17〇)

Bu) -acac] is reacted with acrylic acid chloride to synthesize 11 _ (?? 302 [1- (octa-B u)-acac] 〇 That is, Ir (PPy) 2 [1- (〇H-Bu)- acac] 95 mg (0.1 4 mmol) was dissolved in 10 ml of dichloromethane, and then 0.10 ml (0.72 mmol) of triethylamine was added. To this solution was added 0.060 ml (0.74 mmol) of acrylic chloride, and the mixture was stirred at room temperature. 30 minutes. After adding 1 ml of methanol, the solvent was distilled off under reduced pressure, and the residue was passed through a silica gel column (developing solution: dichloromethane). The yellow liquid that was initially dissolved was filtered and dried under reduced pressure. After the mixed solvent of methyl chloride and hexane, it was recrystallized at -20 ° C to obtain Ir (PPy) 2 [1- (A-Bu) -acac] 99 mg (0.14 mmol) as a pale yellow solid (yield 96). %). The measurement was performed by CHN elemental analysis and 1H-NMR. 'H-NMRCCDCla ^ ppm) ^; 8.50 (d, J = 5.9 Hz, 2H, PPy), 7.80 (m, 4H, ppy), 7.51 (t , J = 7.3Hz, 2H, PPy), 7.18 (t, J = 5.9Hz, 2H, PPy), 6.84 (t, J = 7.3Hz, 2H, PPy), 6.70 (t, J = 7.6Hz, 2H , PPy), 6. 2 5 (m, 3H, PPy + vinylic), 6.12 (dd, J = l5.6, 9.3 Hz, lH, vinylic), 5.75 (d, J = 9 · 3Hz, 1H, vinylic) 5. 1 7 (s, 1 H, diketonate-methine), this paper size is applicable to China National Standards (CNS) M specifications (210X 297 mm)-installed -(Please read the notes on the back before filling out this page) Ding printed by the 8th Industrial Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs-173-584661 A7 B7 V. Description of the invention (171) 4.05 (t, J = 7. Hz, 2H, 1c〇CH2-), 1. 84 (t JJ = 7.0 Hz, 2H? Methylene) »1 · 8 0 (s, 3 H, methyl), 1 · 3 4 (m, 4 H, methylene), 1 · 06 (m, 2H 'methylene).

Elementary analysis Calcd: C 5 6.2 6 j H 4.58, N 3.86. (C 3 4 H 3 3 I Γ N 2 0 4) F o u n d: C 56.55, H 4.53 ′ N 3.60. o (Please read the notes on the back before filling this page)

Ir (PPy) 2 [i. (〇H> Bu) -acac] Ir (PPy) 2 [1-. (A.Bu) .acac] Printed by R Industrial Consumer Cooperatives, Intellectual Property Bureau, Ministry of Economic Affairs [Example 4〇 ] Polymerizable compound: 丨 丨 -μ- (2_propenyloxy) aminomethylmethoxyphenyl] _3_phenyl- 丨,% propanedione ester 丨 bis (2-phenylpyridine) iridium ( ΠΙ) (hereinafter referred to as Ir (PPy) 2 (MoI-Ph-acac)) Synthesis (1) According to the following reaction steps, bis (chloro) tetrakis (2-phenylpyridine) iridium was synthesized by a general method. (III) (hereinafter referred to as [11 (PP y) 2 C1] 2 and, in accordance with known methods (M. C ushmaneta 1.,

Tetrahedron Lett., 31, 6497 (1 990)) Synthesized P-hydroxy-diphenyl ether ^-= ----- 584661 Μ '_ ~ " _............ V. Description of the invention (172) A-Yuan reaction to synthesize Π- (4-based group) -phenyl-1,3-propanyl di 1¾ ester] bis (2-phenylsulfonyl β-deuterium) iridium (III) (Hereinafter referred to as "??" 2 (OH-Ph-acac)) 〇 That is, [Ii · (PPy) 2Cl] 2 1 12mg (〇 · 10mm〇i) and sodium carbonate 6 4 mg (0 · 6 0 mm ο 1) and 76 mg (0.3 2 mmol) of p-hydroxy-diphenylbenzoate were dissolved in 10 ml of DMF, and heated and stirred at 60 ° C. for 0.5 hours. The obtained reaction solution was poured into a 1000 m 1 diluted hydrochloric acid aqueous solution, and the iridium complex was extracted with chloroform. After the chloroform was distilled off with a rotary condenser, the residue was dissolved in a small amount of dichloromethane, and then added to a silica gel column. The mixture was then mixed with a 30: 10 (volume ratio) dichloromethane / acetone solvent to develop an orange component. After recovery, it is dried under reduced pressure. The obtained solid is dissolved in a small amount of diethyl ether. After adding hexane, the precipitated complex precipitate is filtered off and dried under reduced pressure to obtain Ir (PPy) 2 (OH-Ph-acac ) 111 mg (0 · 15 mm ο 1) of an orange solid (72% yield). The measurement was performed by CHN elemental analysis and 1H-NMR. 1 Η — NMR (CDC 1 3, ppm) 6; 8.58 (d, 2H, PPy), 7.9-6.7 (111, 21H, PPy + phenyl), 6 · 5 2 (s, 1 H, diktonate-methine ), 6.37 (d, 2H, PPy), 4.91 (s, 1H, 0H).

Elementary analysis Calcd: C 6 0 · 〇 7 ′ H 3.68, N 3.79. (C 3 7 H 2? I r N 2 0 3)

Found: C 6 0. 7 7 ’H 3.75 — (Please read the notes on the back before filling this page)

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V. Description of the Invention (173), N 3.62.

Ir (PPy) 2 (OH-Ph-acac)-(2 ^ yi-, Ill. (PPy) 2 (OH-Ph-acac) and methacrylic acid oxyethyl isocyanate (MOI) (commodity Named "Karens M〇Ι" 'made by Showa Denko Corporation') to synthesize h · (ppy) 2 (〇H-Ph-acac) 〇 (Please read the precautions on the back side first '

-Item refill I: write this page) Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs, M Industrial Consumption Cooperative, that is, "Ir (PPy) 2 (〇H_Ph_acac) ii〇mg (0.1 5mmol) is dissolved in 50ml of toluene, and then added to it 2,6-di-tert-butyl-4-methylphenol (hereinafter referred to as bHT) 5 mg (0.023 mmol), dibutyltin (IV) dilaurate (DBTL) 32 mg (0.051 mmol) and M. I 121 mg (0.78 mmol) was then stirred at 70 ° C. for 6 hours. After the resulting reaction mixture was cooled to room temperature, it was poured into a silica gel column, and then an orange compound was developed with a 20 ·· 1 (volume ratio) mixed solvent of dichloromethane / acetone, and the solution was decompressed in a rotary condenser. The size of this paper is applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) -176- 584661 A7 ____B7 V. Description of the invention (174), the obtained solid is dissolved in a small amount of dichloromethane, and then hexane is added little by little An orange precipitate was precipitated. The filtrate was dried under reduced pressure to obtain the target substance Ir (PPy) 2 (MOI-Ph-acac) 100 mg (0.1 l mmol) as an orange solid (yield 75%). The measurement is based on CHN elemental analysis and 1H-NMR for H-NMR (CDC 13, ppm) 5; 8.60 (d, 2H, PPy), 7 6 6 9-6 · 7 (m 5 6 3 9 18 6 5 sdss Printed by Intellectual Property Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) 2 1 Η, PP y and phenyl (diketonate-methine), PPy),

1 H 2 H 1 H 1 H 1 H 2 H 2 H 3 H olefinic), olefinic), nh), ethylene), ethylene), methyl) ° Elementary analysis C a 1 cd: C 5 9 · 0 5 'H 4 0, N 4.70. (C44H36 I r N 3 0 6) Found: C 59 · 79, H 4.0, N 4.64. 2 9 (s 3 1 (t 3. 5 9 (t 2. 0 0 (s 4 This paper size applies to Chinese National Standard (CNS) A4 specification (210 × 297 mm) 584661 A7 B7 V. Description of the invention (彳 75)

Ir (PPY) 2 (MOI-Ph-acac) (Please read the notes on the back before filling out this page) Printed by Xiao Gong Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs [Example 41] Polymerizable compounds: [6- ( 4-Methacryloxyphenyl) -2,4-hexanedione ester] bis (2-phenylpyridine) iridium (III) (hereinafter abbreviated as Ii. (PPy) 2 [1- (MA-Ph- Me) -acac]) Synthesis (1) As shown in the following reaction steps, acetone and acetone were synthesized according to a known method (C. Cativiela, et al., Org. Chem., 60 3074 (1 995)). [Benzophenoxy iodide reacts to synthesize 6- (4-benzyloxyphenyl) -2,4-hexanedione. That is, sodium hydride (60% in oil) 0.30 g (7.5 mmol) was weighed in a nitrogen atmosphere, and 20 ml of THF was added, and then cooled to 0 ° C in a water bath. A mixed solution of 0.7 5 g (7.5 mmol) of acetamidine and 0.5 ml of hexamethylphosphinetriamine was added dropwise to the suspension, and a colorless precipitate was formed. In the following paper standards, the Chinese National Standard (CNS) Λ4 specification (2 丨 0X 297 mm) -178- 584661 A7 ___B7 V. Description of the invention (176) After stirring for 10 minutes, add η-butyl lithium Hexane solution (1.6M) (Please read the precautions on the back before filling this page) After 4.6mg (7.5mmol '), stir under Ot for 20 minutes. To the obtained pale yellow transparent solution, T H F 1 0 m 1 in which 2.28 g (7.0 m m ο 1) of 4-phenylhydrazone oxyiodide was dissolved was added dropwise. The reaction solution was stirred at room temperature for 1 hour, and after cooling to 0 ° C, it was neutralized by adding dilute hydrochloric acid. After the organic layer was washed with a saturated sodium chloride aqueous solution, the solvent was distilled off with a rotary condenser, and the residue was passed through a silica gel column (developing solution: dichloromethane / hexane 1: 1 (volume ratio) mixed solvent). The main product was filtered and dried under reduced pressure to obtain 1.31 g (4.4 mmol) of 6- (4-benzyloxyphenyl) -2,4-hexanedione as a pale yellow solid (yield: 63%). The measurement was performed by CHN elemental analysis and 1H-NMR. Η—NMR (CDC 13 »ppm) δ; 7.5 β--8-C-JH-l 9 Η, aromatic), _ 5. 4 6 (s , 1 Η, enol-methine), 5.04 (s, 2H, -〇—CH2—), 2. 88 (t, J = 7.6Hz, 2H, enthylen.e), 2 · 55 (t, J = 8 · 4Hz, 2H, ethylene), 2.04 (S, 3H'methyl). Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs δ 7.5 ~ 6.8 (m? 9H 5 aromatic) j 5.〇4 (s, 2H, — 〇_CH2-), 3.53 (s, 2H, C (= 〇) CH2C (= 〇)), 2 · 8 4 (ni '4 H ， enthylene)' 2 · 19 (s ， 3H, methyl) 0 enol: keto = 5: 1 ° This paper standard applies to Chinese national standards (CNS) A4 specifications (210X 297 male f) -179- 584661 A7 ____B7_ V. Description of the invention (彳 77) Elementary analysis C a 1 cd: C 7 7 · 0 0, H (C 1 9 H 2 〇〇3 ) Found: C 7 7 · 4 6, H o 6.8 7 7

TT 1) NaH 2) n-BuLi

° J〇 (Please read the 4 notes on the back before filling and filling —: Write this page) (2) According to the reaction steps below, change 6- (4-caroxyphenyl) · 2,4- The gastrointestinal gasification was carried out to obtain 6- (4- (4-phenyl) phenyl) -2,4-hexamethylene-hydroxide, which was equal to 0. That is, under a nitrogen environment, Pd-activated carbon (10%) 1.5 g was weighed out. 20 ml of dichloromethane and 1.3 1 g (4.4 mmol) of 6- (4-benzyloxyphenyl) -2,4-hexanedione were further added. The reaction system was replaced with hydrogen at 1 atm and stirred at room temperature for 1 hour. The obtained reaction solution was filtered to remove insoluble matters, and the solvent was removed by reduced pressure treatment. Subsequently, the solution containing the eluted compound was dried under reduced pressure using an acetone / hexane 1: 1: 1 (volume ratio) mixed solvent to obtain 6- (4-hydroxyphenyl) -2, 0.70 g of hexanedione ( 3.4nimol) as a pale yellow solid (yield 77%). The measurement was performed by CHN elemental analysis and j-NMR. ^ -NMRCCDCla ^ pni) ^; e η ο 1; δ table paper rule; trial Chinese National Standard (CNS) A4 specification (210X297 mm) Order printed by the Intellectual Property Bureau of the Ministry of Economic Affairs® Industrial and Consumer Cooperatives 584 661 A7 _ __B7_ V. Description of the invention (178) 7-〇4 (d, j = 8. 4Hz, 2H, aromatic), 6.65 (d, j = 8.4Ηζ, 2Η, aromatic), 5.55 (br, iH, 0H), 5. 4 7 (s, 1 H, enol-methine), 2.86 (t, j = 7.3 Hz, 2H, ethy 1 ene), 2.55 (t, j = 7.3 Hz, 2H, ethylene), 2 · 0 4 (s, 3 H, methy 1). keto; δ 7 · 04 (d, j = 8.4 Hz, 2H, aromatic), 6 · 65 (d, j = 8.4 Hz, 2H, aromatic), 5.55 (br, iH, 0H), 3 · 55 ( s, 2H, C (= 〇) CH 2 C (= 0)), —2— · 8 3——H, ethylene), 2 · 1 9 (s, 3 H, methyl).螓 enol: ket〇 = 5: 1 〇

Elementary analysis Calcd: C 69.88, H 6.84. (Cl2Hl4〇3)

Found: C 69 · 67 ’H 6.79

(3) According to the reaction steps shown below, the 6- (4-hydroxyphenyl)-^. Batch coat-(Please read the precautions on the back before filling this page) The paper size printed by the cooperative applies the Chinese National Standard (CMS) A4 specification (21〇 > < 297 mm) -181-584661 A7

V. Description of the invention (179) 2,4-hexanedione and bis (#-chloro) tetra (2-propyl 1% pyridine) iridium (ΠΙ) ([Ir (PPy) 2 Cl ] 2) Reaction to synthesize [6- (cardiosylphenyl) -2,4-hexanedione] bis (2-phenylpyridine) iridium (ΠΙ) (hereinafter referred to as Ir (PPy) 2 (〇H- Ph-Me) -acac]) That is, a mixture of 71 mg (0.066 mmol) of [Ιι. (PPy) 2Cl] 2 and 47 mg (0.44 mm) of sodium carbonate was added to a solution of 6 · (4 -5 ml of 41 mg (0.20 mmol) of DMF in hydroxyphenyl) -2,4-hexanedione, and stirred at 65 ° C for 1 hour. Dilute hydrochloric acid and chloroform were added to the obtained reaction solution, and the mixture was shaken sufficiently. The separated organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was passed through a silica gel column (developing solution ·· hexane / ethyl acetate 1: 1 (volume ratio) mixed solvent), a light yellow solution was recovered after dissolving a small amount of pale yellow by-products, and then dried under reduced pressure to solidify, and the obtained solid was dissolved. In a small amount of dichloromethane, add hexane and cool to -20 ° C to obtain Ii · (PPy) 2 [1 · (〇H-Ph-Me) -acac] 86 mg (0.12 mmol) as a pale yellow solid. (92% yield). The measurement was performed by CHN elemental analysis and j-NMR. Paper ______ This is printed by W Industrial Consumer Cooperatives, Intellectual Property Office, Ministry of Economic Affairs

8 3 | 3 19

(Please read the note 1 on the back side first • Fill in the items and then install-write this page), \ 一 " 584661 A7 _____B7_ V. Description of the invention (18〇) 6.27 (t, J = 8.1Hz, 2H, PPy ), 5 · 1 8 (s, 1 Η, diktonate-methine), 5.10 (br, 1H, 0H), 2. 54 (t,, 2H, methylene), 2 · 3 1 (m, 2H, methylene) , 1 · 75 (s, 3H, methyl) 〇

Elementary analysis Calcd: C 5 7. 8 6, H 4.14, N 3.97. (C 3 4 H 2 9 I Γ N 2 0 3)

Found: C 58.03, H 4.11, N 3.86. (Please read the notes on the back before filling this page)

[ir (ppy) 2C1] 2 Order Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

Na2C03

DMF

Ir (PPy) 2 [l- (OH-Ph-Me) -acac; ('4) As shown in the following reaction steps, this Ii. (PPy) 2 [1-(This paper wave scale applies Chinese national standards ( CNS) A4 specification (210X29? Mm) -183- 584661 ΑΊ ________ Β7_ V. Description of the invention () OH-Ph-Me) -acac] reacts with methacrylic acid chloride to synthesize Ir (PPy) 2 [1- (MA-Ph-Me) -acac] (Please read the precautions on the back before filling this page) That is, in a nitrogen environment, place Ir (PPy) 2 [1- (OH-Ph-Me) · acac] 169mg (0.24 mmol) was dissolved in 10 ml of dichloromethane, and then 0.30 ml (2.2 mmol) of triethylamine was added. 0.060 ml (0.61 mmol) of methacrylic acid chloride was added to this solution, and a product was formed rapidly. After a small amount of methanol was added, the solvent was distilled off under reduced pressure. The residue was passed through a silica gel column using a mixed solvent of hexane / dichloromethane / acetone (1 0: 1 0 ·· 1 (volume ratio)), and the yellow main product was filtered out. After distilling off the solvent under reduced pressure, it is recrystallized from a mixed solution of methylene chloride-hexane to form the target substance.

Ir (PPy) 2 [1- (MA-Ph-Me) -acac] 141 mg (0.18 mmol) of a yellow solid (yield 76%). The measurement was performed by CHN elemental analysis and 1H_Nmr. 'H — NMR (CDCl3, ppm) 5; 8.48 (d, J = 5.1 Hz, lH, Ppy), printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs 8. 27 (d »1 = 5.9 Hz 5 lH ^ PPy), 7.9- 7.5 (m, 6H, PPy), 7.12 (t, J = 7.0 Hz, 1H, PPy), 7.04 (t, J = 7.0%, 1H, Ppy), 6 · 9 — 6 · 6 (m, 8H, aromatic) '6. 3 3 (S, 1 H, olefinic), 6.27 (d, J = 7.6Hz, 2H, PPy), 5 · 74 (s, 1H, olefinic), 5 · I 7 (s, 1 H, diketonate-methine), 584661 A7 B7 V. Description of the invention (182) 2 · 61 (t, J = 7.〇Hz, 2H, ethy 1 ene), 2. 3 4 (m ， 2 H, ethy 1 ene), 2 · 0 7 (s, 3 H, methacryl-methyl), 1 · 7 6 (s, 3 H, diketonate-methyl).

Elementary analysis Calcd: C 5 8. 9 8, H 4.30, N 3.62. (C38H33 I r N 2 0 4) Found: C 58.69, H 4.17, N 3.81. (Please read the notes on the back before filling this page)

Ir (PPy) 2 [l- (〇H.ph „Me)„ acac] ir (PPy) 2 [i- (MA-Ph-Me) _acac] Ministry of Economic Affairs, Intellectual Property Bureau, S-Site Consumer Cooperation: Printed [Example 42] Polymerizable compound: (1-methylpropenyloxy-2,4-pentanedionate) bis (2-phenylpyridine) iridium (III) (hereinafter referred to as ir (PPy) 2 [ l-MA-acac]) Synthesis (1) 丨 As shown in the reaction steps described below, bis (//-chloro) tetrakis (2-phenylpyridine) iridium (m) ([Ir ( PPy) 2 C1] 2) is synthesized by reaction with (Hydroxy-2,4-pentanedione) synthesized according to a known method (European Patent No. 05 1 42 1 7) to synthesize (1H group-2,4- Pentanedione ester) bis (2-phenylpyridine) iridium (in) (hereinafter referred to as Ir (pPy) 2 [l-〇H-acac]). This paper is applicable to towels; f tablets (CNS) Λ view (2iQx29 ^) 584661 A7 ________B7 _V. Description of the invention (183) βρ, [Ir (PPy) 2 Cl] 2 492mg (0.46mmol) and 139mg (1.31mmol) sodium carbonate were dissolved in 10ml DMF, After adding 1- (tert-butyldimethylsilyloxy) -2,4-pentanedione (l-TBDMS〇-2,4-pentanedione) 321mg (1.39mmol), heat at 70 ° C Stir 1 After the resulting reaction mixture was cooled to room temperature, 100 ml of a saturated ammonium chloride aqueous solution and 50 ml of chloroform were added, and the mixture was shaken sufficiently. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was dichloromethane as the eluent. The solution was passed through a silica gel column to obtain a yellow solution. The yellow solid obtained after drying under reduced pressure was dissolved in 20 ml of THF, and 0.4-ml (0.46 ml) of a 1.0 M THF solution of tetra-n-butylammonium fluoride (hereinafter referred to as Bu \ NF) was dissolved. mmol) was dropped under vigorous stirring. After stirring the reaction solution at room temperature for 0.5 hours, the solvent was removed under reduced pressure. The residue was passed through a silica gel column (eluent ·· hexane / dichloromethane / acetone 1: 3 1 (volume ratio) mixed solvent), the yellow main product was recovered and dried under reduced pressure. The obtained crude product was recrystallized from a dichloromethane / hexane mixed solution to obtain the target product Ir (PPy) 2 (1- OH-acac) (Please read the note 4 on the back first • Fill in the items and refill-write this page) Order d 3 89mg (0.63 mmol) yellow solid (yield 69%). The measurement is based on CHN elemental analysis, 1H-NMR was performed.

Taiji Paper advances from the rule of W φ to the country. () A4 slavery (? 丨 () × 297λM) 584661 kl B7 V. Description of the invention (184) 6.82 (t, J = 7.3Hz, 2H, PPy), 6.69 (m, 2H, PPy), 6.28 (d, J = 6.8 Hz, lH, PPy), 6.23 (d, J = 6.5 Hz, lH, PPy), 5 · 1 7 (s, 1 H, diktonate-methine) , 3.88 (dd, J = 8.1, 5.4 Hz, 1H, — C Η H '-10 —), 3.78 (dd, J = 8.1, 4.3 Hz, 1 H, — CCH' — 0-), 3.10 (t, J 4.6Hz, 1H, 0H), 1. 82 (s, 3H, methyl) o

Elementary analysis Calcd: C 5 2 · 6 7, H 3.77, N 4 · 5 5. (C 2 7 H 2 3 I r N 2 0 3) Found: C 52.45, H 3.68, N 4.790 — (Please read the precautions on the back before filling out this page)-Yikou d Printed by the Industrial and Consumer Cooperatives ^ m vb ran I3fl ^ (r \ IQ 'l Λ (? 1 Π V? Q7y \ ifr' l 584661 A7 ____ B7 V. Description of the invention (185)

(Please read the notes on the back before filling in this hundred <} 1 ·.

Ir (PPy) 2 (1-OH-acac) and -port (2) are shown in the following reaction steps. Ir (PPy) 2 (″ · 〇Η: acac) is reacted with methacrylic acid chloride to synthesize Ir (pPy) 2 (^ MA-acac ·) 〇 namely 'will I r (PP y) 2 (1-〇 Η-acac) 2 0 0 mg (0 · 3 2 mm ο 1 consumption by B worker of Intellectual Property Bureau of Ministry of Economic Affairs Printed by the cooperative) Dissolved in 15 ml of dry dichloromethane, added 0.25 ml of triethylammonium (1.8 mm ο 1) and methacrylic acid chloride 0.20 m 1 (2.0 mm 0) Stir at room temperature for 1 hour. Subsequently, the reaction solution was washed with 20 ml of an aqueous sodium carbonate solution, and the solvent was removed under reduced pressure. The residue was re-dissolved in dichloromethane, added to the upper part of a silica gel column, and developed with a 2: 4: 1 (volume ratio) mixed solvent of hexane / dichloromethane / acetone. The target was Ii. (PPy) _2 (1-MA-acac) 165 mg (0.24 mm) as a yellow solid (yield 74%). The measurement is in CHN yuan. The paper size is in accordance with the Chinese National Standard (CNS) Λ4 specification (210 × 297 mm) -188- 584661 Μ B7. V. Explanation of the invention (鄕) Voxel analysis and 1H-NMR. ! Η — NMR (CDC13, ppm) 5; 8.53 (d, J = 5.7 Hz, lH, PPy), 8.48 (d, J = 5.4 Hz, lH, PPy), 7.84 (d, J = 7.8 Hz, 2H, PPy), 7.73 (t, J = 7.0 Hz, 2H, PPy), 7.53 (t, J = 6.8 Hz, 2H, PPy), 5.14 (m, 2H, PPy), 6.79 (m, 2H, PPy) , 6.69 (m, 2H, PPy), 6.29 (d, J = 7.6Hz, lH, PPy), 6.23 (d, J = 7.6Hz, lH, PPy), 6. 0 4 (s 5 1 H j ο 1 efinic) 5 · 5 1 (s, 1 H, olefinic), 5. 3 1 (sj 1 H 5 diketonate-methine), 4-38 (d, J = 15 · 4 Hz, 1H, — CHH '— 〇C (= 〇) 一), 4.27 (d, J = 14 · 9Ηζ, 1H, —CHH'-〇C (= 〇) 一), 1 · 8 7 (s, 3 H, methacryl-methyl), 1.8 2 (s, 3 H, diktonate-methyl) 0

Elementary analysis Calcd: C 5 4 · 4 5, H 3-98, N 4.10. (C 3 1 H 2 7 I r N 2 0 4) 丨 (Please read the precautions on the back before filling this page)

Printed by 1T Consumer Cooperatives, Intellectual Property Bureau, Ministry of Economic Affairs

This paper size applies to Chinese National Standard (CNS) A4 specification (210 X 297 male f) Λ QO 584661 A7 B7 V. Description of the invention (187)

Found: C 54 ， N 4 Η

Ir (PPy) 2 (l-OH-acac: 〇

Ir (PPy) 2 (l-MA-acac) Printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs [Example 43] Polymerizable compound: [6- (4-vinylphenyl) -2,4-hexane Dione ester] bis [2- (2,4-difluorophenyl) pyridine] iridium (III) (hereinafter referred to as Ii · (2,4-F-PPy) 2 Π- (St-Me) -acac]) Synthesis (1): According to the following reaction steps, 2- (2,4-difluorophenyl) pyridine was synthesized by a general method. That is, 8-69 g (55.0 mmol) of 2-bromopyridine was dissolved in 200 ml of dehydrated tetrahydrofuran under an argon flow, and cooled to -78 ° C. A 1.6 M solution of η-butyllithium in sodium hydroxide 3 8 · 7 m 1 (6 1.9 mm ο 1) was added dropwise over a period of 30 minutes. After the dropwise addition, 7.5 g (55.0 mmol) of zinc chloride was dissolved. 50 ml of a solution of dehydrated tetrahydrofuran was dropped into it over 30 minutes. After the dropwise addition, the temperature was gradually raised to 0 ° C, and then bromo-2,4-difluorobenzene 9.65 g (5 5.0 mm) and tetrakis (triphenylphosphine) palladium (〇) 2.31 g ( After stirring for 2.0 hours under reflux, saturated brine was added to the reaction solution, followed by extraction with diethyl ether. After the extract was dried and concentrated, it was purified by gel chromatography (silica gel; chloroform / hexane (1/1: volume ratio)) to obtain 2- (This paper size is applicable to Chinese National Standard (CNS) A4 specifications ( 210x297 mm) --------- 0 ^ .---- T · f Please read the back of the >! * Issue before filling out this page j-order. 190 584661 A7 _— ___B7 5 2. Description of the invention: (188) 2,4-difluorobenzene) pyridine 6.00 g (31.4 mmol) as a colorless transparent oil (63% yield). The measurement was performed by CHN elemental analysis and 1H-NMR. iH-NMRCCDCls ^ ppm) ^; d Η 8 7 7 • 71 • 00 (td, lH, J = 8 • 8-7 · 7 (m, 2 Η), .3 — 7 · 2 (over wrappe 4.6Hz H z

ith C H C

H 7.1-6. (M, 2 H) (Please read the precautions on the back before filling this page)

Elementary analysis C a 1 c d: C 69, N 7 Found: C 68 1 1, H 3 3 9 8, H -—3— 丄 丄 一 • 8

Br

1) n-BuLi 2) ZnCl2-^ THF

Pd (PPh3) 4

Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs® Industrial and Consumer Cooperatives (2) As shown in the following reaction steps, this 2- (2,4, digas benzyl) pyridine is reacted with sodium hexachloroiridium (III) sodium hydrate In order to synthesize bisfluorene # chloride, tetra [2- (2,4-difluorophenyl) pyridine] iridium (III) (as > ^ ^ ΑΑ abbreviated [Ir (2,4-F-PPy) 2 ci ]2 ). That is, 2-(2,4-difluorophenyl) pyridine 0.96 g (5 and sodium hexachloroiridium (III) sodium eta water 1.00 g dissolved in a 2-B sheet paper scale applicable to Chinese national standards (CNS) A4 specification (210X 297 mm) 584661 A7 B7 V. Description of the invention (189) • • Water = 3: 1 (volume ratio) in a mixed solvent 40ml, after 30 minutes of argon blowing, stir under reflux 5 hours. The generated Shen source was filtered, washed with ethanol and a small amount of acetone, and dried under vacuum for 5 hours. [Ir (2,4-F-PPy) 2 Cl] 2 0.79 g ( 0.065 mmol) as a yellow powder (yield 86%). The measurement was performed by 1H-NMR and CHN elemental analysis. 1H-NMR (CDCl3 ^ ppm) 5; 9.12 (d, 4H, J = 5.7 Hz), 8.31 ( d, 4H, J = 8.6Hz), 7.83 (dd, 4H, 7.6, 7.6Hz), 6.82 (dd, 4H, J = 7.3, 7.3Hz), 6.34 (ddd, 4H, J = 11.6, 10.0.0, 2.4Hz) 〇

Elementary analysis Calcd: C 43.39, H 2,03, N 4.55.

Found: C 43.46, H 1.99, N 4.61. ^ — (Please read the notes on the back before filling this page) D. Intellectual Property Bureau of the Ministry of Economic Affairs a (printed by the Industrial and Consumer Cooperative)

4 F

2Na3IrCl6-nH20 --------------

FF [Ir (2 # 4-F-PPy) 2Cl] 2 This [Ir (2,4-F-PPy))) is shown in the following reaction steps. Paper ruler; Α4 ^ τ (210x-29n -192- 584661 A7 __ B7 __ V. Description of the invention (19〇)

Cl] 2 is reacted with 6- (4-vinylphenyl) -2,4-hexanedione to synthesize 11 '(2,4-F-PPy) 2 [1- (St-Me) -acac]. That is, [Ir (2,4-F-PPy) 2 Cl] 2 243 mg (0.20 mmol), sodium carbonate 212 mg (2.00 mmol), and 2,6-di-tert-butyl-4-methylphenol 1.3 mg 130 mg (0.60 mmol) of 6- (4-vinylphenyl) -2,4-hexadione synthesized in the same manner as in Example 38 was dissolved in 20 ml of DMF under argon flow, and stirred at 80 ° C for 2 hours After that, water was added to the reaction solution, followed by extraction with chloroform. After the extract was dried and concentrated, it was purified by column chromatography (silica gel; chloroform), and then recrystallized from a chloroform / hexane solution. Ii (2,4-F-PPy) 2 [l- (St-Me ) -acac] 261 mg (0.33 mmol) of yellow crystals (yield 83%). The measurement is performed by CHN elemental analysis and 1H-NMR (please read the precautions on the back before filling out this page) 8 9 d Printed by the Consumer Cooperatives of the Intellectual Property Office of the Ministry of Economic Affairs 8 7 7 7 3-8.2 0 4 (d, 8-7.7 19 15 9 7 8 9 d, ddddd,

H m H 111 H • 7 H z .6 7 (d d 6 · 4-6 · • 7 — 5.6

2 H

2 H 7 H z 7.8Hz 1H, J = 1 H, J = H, Bu 7 1 H, J = (m, 2 H m, 3 H) 8 H z 7. E

Hz), Hz), .8 H z (210X 297 mm) This paper size applies the Chinese national standard -193 584661 A7 B7 V. Description of the invention (191) 5 · 2 2 (s, 1 Η), 5.21 (d, lH, J = ll 2 · 6 2 (t, 2 Η, J 2. 3 9 (m, 2 Η), 1 · 7 8 (s, 3 Η). Elementary analysis C a 1 cd: C 54.88, N 3.5 (Found: C 54.82, N 3 · 4 i 1 1. 1 Η z 7.0Hz)

H

H .4 〇 (Please read the notes on the back before filling this page)

[Ir (2,4-F-PPy Printed by Employee Consumer Cooperatives, Intellectual Property Office, Ministry of Economy

Na2C03

DMF

Ir (2,4-F-PPy) 2 [() _ acac] [Example 44] Polymerizable compound: {3- [4- (2-Methacryloxyethyl) aminomethyloxyphenylmethyl Phenyl] -2,4-pentanedione} bis (2-phenylsulfonyl) iridium C III) (hereinafter referred to as Ir (PPy) .2 [3- (MoI-Ph-Me) -acac] Paper size applies Chinese National Standard (CNS) A4 specification (2 丨 OX 297) 嫠 194- 584661 A7 —______ B7 ___ 5. Synthesis of the invention (192)) (1) According to the following reaction steps, according to the general method Synthesis of bis (-chloro) tetra (2-diphenylpyridine) diiridium (III) ([Ir (PPy) 2 Clja) and 3- (4-hydroxyphenylmethyl) -2,4-propanediamine Ketone reaction to synthesize [3- (4-hydroxyphenylmethyl_2,4-propanedione ester) bis (2-phenylpyridine) iridium (III) (hereinafter referred to as h · (PPy) 2 [3- ( 〇H-Ph-Me) -acac]) ο That is, [I r (ppy) 2 C1] 2 5 6 mg (0 · 0 5 2 mm ο 1) and 44 mg of sodium carbonate (0.42m1T1〇i) were dissolved in DMF 5ml. In this solution, 3- (4-hydroxyphenylmethyl)-synthesized by a known method (C. Cativiela, et al., Org. Chem., 60 3074 (1 995)) was dissolved. A solution of 30 mg (0.155 mmol) of 2,4-pentanedione in 5 ml of DMF was heated and stirred at 80 ° C. for 1.5 hours. Subsequently, dilute hydrochloric acid and chloroform were added to the reaction solution cooled to room temperature, and the mixture was shaken sufficiently. The organic layer was filtered off and the solvent was distilled off with a rotary condenser. The residue was 1: 1 in hexane / ethyl acetate ( (Volume ratio) mixed solvent passed through a silica gel column as a developing solution, and the main product was filtered out. The obtained pale yellow solution was distilled off under reduced pressure, and recrystallized from a mixed solution of methylene chloride / hexane to obtain

Ir (PPy) 2 [3- (OH-Ph-Me) -acac] 34 mg (0.048 mmol) of a pale yellow solid (yield 46%). The measurement was performed by CHN elemental analysis and j-NMR. ! H — NMR (CDC I3 »ppm) δ; 8.58 (d, J = 5.9 Hz, 2H, PPy), 7.84 (d, J = 7.8 Hz, 2H, PPy), the paper standard applies to the Chinese National Standard (CNS) A4 specifications (210X2 · "centimeters) (Please read the precautions on the back before filling this page) > Packing. Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs-195- 584661 A7 B7 V. Description of Invention (193) 7.73 ( t, J = 6.5Hz, 2H, PPy), 7.55 (, J = 7.6Hz, 2H, PPy), 7. 1-6 · 6 (γπ, 10Η, aromatic), 6.27 (d, J = 7.6Hz , 2H, PPy), 4.86 (br — s, 1H, 0H), 3. 6 2 (s, 2 H, benzyl), 1. 8 0 (s, 6 H, methyl) o

Elementary analysis Calcd: C 5 7 · 8 6, H 4 · 1 4, N 3.97. (C34H29I ΓΝΟΟ3) Found: C 57.97, H 4.22, N 4.15. (Please read the precautions on the back before filling out this page) _ Install. Order Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs

Ir (PPy) 2 [3-(OH-Ph-Me) -acac] This paper size applies Chinese National Standard (CNS) Λ4 specification (210X297 mm) -196- 584661 A7 _ B7 V. Description of the invention (194) ( (Please read the notes on the back before filling this page) (2) As shown in the following reaction steps, Ill. (PPy) 2 [3- (〇H-Ph-Me) -acac] and methacrylic acid A methyl isocyanate (MOI) (trade name "Karens MOI", manufactured by Showa Denko Corporation) was reacted to synthesize Ir (PPy) 2 [3 · (MOI-Ph-Me) -acac]. That is, 'Ir (PPy) 2 [3- (〇H-Ph-Me) -acac] 71mg (0.10mmol) and 2,6-dibutyl-4-methylphenol 3mg (0.014mmol), dibutyltin (Ιν) 27 mg (0.12 mmol) of dilaurate and 55 mg (0.35 mmol) of MeOH were dissolved in 10 ml of THF and heated and stirred at 7 ° C for 2 hours. The resulting reaction mixture was dried under reduced pressure using a rotary condenser, and the residue was dried. A hexane / ethyl acetate 1: 1 (volume ratio) mixed solvent was used as a developing solution to pass through a silica gel column. The pale yellow solution was recovered after the first dissolution of the pale yellow by-product, and dried under reduced pressure. The obtained solid was dissolved in A small amount of -dichloride, the resulting precipitate was filtered, and the target was Ir (PPy) 2 [3- (MoI-Ph-Me) -acac] 5 9 mg (〇.〇) after drying under reduced pressure. 69mmol) light yellow solid (yield 68%). The measurement was performed by CHN elemental analysis and 1H-NMR. Printed by the 8th Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs ^ I — NMR (CDCl3? Ppm) δ; 8.58 (d , J = 5.9Hz, 2H, PPy), 7.88 (d, Bu 7.8Hz, 2H, PPy), 7.76 (t, j = 6.5Hz, 2H, PPy), 7.57 (d, J = 7.6Hz, 2H, PPy ), 7 · 2 — 6 · 6 (m, 10H, aromatic), 6. 27 (d, j = 7.6Hz, 2H, PPy), 6 · 16 (S ′ 1H, olefinic), this paper size applies Chinese National Standard (CNS) Λ4 specification (210X 297 mm) -197-

Found: C 5 7 · 2 0, Η 4.4, N 4 · 8 8 ο (C 4 1 Η 3 8 I r N 3〇t 3): 5 | 7 · 3 6, H 4. 4, N 4 9 1 0 584661 A7 __ B7 V. Description of the invention (195) 5 · 6 3 (s, 1 Η, olefinic), 5.31 (br- s, lH, NH), 4 · 3 1 (m, 2 H, ethylene ), 3 · 6 9 (s, 2 H, benzyl), 3 · 5 9 (m, 2H, ethylene), 1 · 9 8 (s, 3 H, memethry 1-methy 1) 1 · 8 0 (s, 6 H, diktonate-methyl)

Elementary analysis C a 1 c d: C (Please read the notes on the back before filling this page}

Ir (PPy) 2 [3- (OH-Ph-Me) -acac]

Ir (PPy) 2 [3- (M〇I-Ph-Me) -acac] Printed by the Industrial and Commercial Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs [Example 45] Polymerizable compound: iridium (m) bis (2- ( 2,4-difluorophenyl) imidazole diester) (3-methacryloxyoxypicolinate) (hereinafter referred to as Ir (2,4-F-PPy) 2 (3-MA-Pic) Synthesis of) (1) According to the following reaction steps, the synthesis of iridium (III) bis ((2,4-difluorophenyl) pyridine diester) (3-hydroxypicolinate) (the following simplified paper size applies) China's national standard ((:?) 8 4 specifications (210 > < 297 mm) -198- 584661 B7 V. Description of the invention (196) said h · (2,4-F-PPy) 2 (3-〇 H-Pic)). That is, 2 [Ir (2,4-F-PPy) 2CU2 121.6 mg (0.1 mmol) and 3-hydroxypicolin were synthesized in the same manner as in Example 43 (1) and (2). Acid 4 1. 7 mg (0.3 mmo 1), sodium carbonate 106.0 mg (1.0 mmol) under a smart air flow, add dehydrated N, N-dimethylformamide (DMF) 10 ml, and at 80 ° C Stir for 2 hours. After adding 50 ml of water to the reaction solution, extract with ethyl acetate. This solution was dried over magnesium sulfate and concentrated, and then analyzed by gel column chromatography (silica gel, Methanol: chloroform = 3: 97 (volume ratio)). Recrystallize from hexane / chloroform to obtain Ii · (2,4-F-PPy) 2 (3-OH-Pic) lOl.Omg ( Yield 71%). The measurement was performed by 1H-NMR and CHN elemental analysis. IH-NMR (DMS〇-d6, ppm) 5; 1 3 · 6 (br, 1 Η), 8.50 (d, 1H, J = 5.9Hz), 8.25 (d, 2H, J = ll.lHz), 8.1-8.0 (m, 2H), 7.69 (d, lH, J = 5.7Hz), 7.62 (d, lH, J = 8.1Hz ), 7.53 (d, lH, J = 4.6Hz), 7.50 (d, lH, J = 5.7Hz), 7.36 (t, lH, J = 4.5Hz), 7.24 (d, lH, J = 5.1Hz), 6 · 9-6 · 7 (m, 2 H), 5.66 (dd, 1H, J = 8.6, 2.4Hz), the paper size is suitable for financial ® Team County (CNS) A4 regulations ^ "210X 297 male f) ' — '^' -199--(Please read the notes on the back before filling out this page), 11 • I # Printed by the 8th Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economy 584661 A7 ΒΊ V. Description of the invention (5.48 (dd , LH, J = 8.6, 2.4Hz) 0 Elementary analysis Calcd: C 7 7 · 8 1, Η 5 · 9 9

(Please read the notes on the back before filling out this page) Bureau of Intellectual Property, Ministry of Economic Affairs, B (printed by the Industrial and Consumer Cooperatives (2), as shown in the reaction steps below, to synthesize h. (2,4-F-PPy) 2 ( 3-MA-Pic) 〇 'Ir (2,4-F-PPy) 2 (3-OH-Pic) 71.1mg (0.10mmol) and 2,6-dibutylhydroxytoluene 0.2mg in argon It was dissolved in 10 ml of dehydrated dichloromethane under air flow, 101.2 mg (1.0 mmol) of triethylamine and 52.3 mg (0.50 mmol) of methacrylic acid chloride were added, and the mixture was stirred at room temperature for 2 hours. Add 50ml to the reaction solution. The paper size is applicable to the Chinese National Standard (CNS) A4 (210X29 * 7). -200- 584661 Printed by the Industrial and Commercial Cooperation Bureau of the Ministry of Economic Affairs, W7 Consumer Cooperative. A7, B7. 5. Description of the invention () Water Then, it was extracted with chloroform. The solution was dried over magnesium sulfate and concentrated, and then purified by column chromatography (silica gel, methanol: chloroform = 1: 24 (volume ratio)). Then it was recrystallized from hexane / chloroform to obtain 11_ (2,4-?-PPy) 2 (3-MA-Pic) 63.1 nig (yield 81%) as yellow crystals. The measurement was performed by 1 Η-NMR and CHN elemental analysis. 'H-NMR (DMSO-de j ppm) δ; 8.51 (d, lH, J = 5.4Hz), 8. 3 — 8 · 2 (m, 2 Η), 8. 1 — 7 · 9 (m, 3 Η), 7. 8 — 7 _ 6 (m, 3 Η), 7.52 (dd, lH, J = 6.6, 6.6 Hz), 7.35 (dd, lH, J = 6.6, 6.6 Hz), 6 · 9 — 6.7 (m, 2 H), _______ 6.26 (s, lH), 5.88 (s, lH), 5.68 (dd, lH, J = 8.4, 2.4 Hz), 5.44 (dd, lH, J = 8.4, 2.4 Hz), 2 · 0 〇 (s, 3 H). Elementary analysis Calcd: C 4 9 · 3 6, H 2 · 5 9, N 5. 4 0 0 Found: C 49. 33, H 2.60, N 5.41. (Please read the precautions on the back before filling this page) This paper size applies Chinese national standards ( CNS) A4 specification (210X 297 mm) -201-584661 A7 B7 V. Description of the invention (199)

Ir (2 # 4-F-PPy) 2 (3-OH-pic) Ir (2,4-F-PPy) 2 (3-MA-pic) [Example 46] Polymerizable compound ·· Iridium (III) Bis (2- (2,4-difluorophenyl) pyridine diester) (5-methacryloxymethylpicolinate) (hereinafter referred to as Ir (2,4-F-PPy) 2 (5- CH2MA-Pic)) Synthesis (1) According to the following reaction steps, iridium (III) bis (2- (2,4-difluorophenyl) 1-pyridine diester) (5- (hydroxyl-based)) Skin $ ^^^^^ (hereinafter referred to as Ir (2,4-F-PPy) 2 (5-CH2〇H-Pic)). That is, [Ir (2,4-F-PPy) 2C1] 2 121.6 mg (O.l mmol), 5-methylmethylpicolinic acid 45.9 mg (0.3 mmol), sodium carbonate 10 6.0 mg (1.0 mmol) under argon flow, dehydrated n, N-dimethylformamidine 10 ml of amine was stirred at 80 ° C for 2 hours. After adding 50 ml of water to the reaction solution, it was extracted with ethyl acetate. The solution was dried over magnesium sulfate and concentrated, and then analyzed by column chromatography (silica gel, methanol: Refined with chloroform = 1: 19 (volume ratio). Recrystallized from hexane / chloroform to obtain ^ (2,4-F-PPy) 2 (5-CH2〇H-Pic) 108.7mg (yield) 75%). The measurement is performed by 1H-NMR and CHN elemental analysis. National Standard (CMS) A4 specification (210 X 297 mm) --------- ^ batch clothes-(Please read the precautions on the back before filling this page), -5 Intellectual Property Bureau of the Ministry of Economic Affairs a (Printed by Industrial and Consumer Cooperatives-202-584661

A7 B7 V. Description of the invention (200) " H-NMR (DMS〇-d6, ppm) 5; 8.54 (d, 1H, J 4.6), 8 · 3-8 · 2 (m, 2H) , 8. 1 — 8 · 0 (m, 4 H), 7 · 7 0 (s, 1 H), 7.61 (d, lH, J = 4.9), 7.49 (dd, lH, J = 6.6, 6.6 7.32 ( dd, lH, J = 6.6, 6.6 9-6.7 (m, 2H), 71 (dd, lH, J = 8.9, 2.4 46 (dd, lH, J = 8.5, 2.3 4 2 (t, 1 H, J 4 9 (d, 2 H, J 4

Elementary analysis C a 1 c d: C

4. 6) 4 · 6) 〇 4 8 _ 〇, N 5 · 8: 4 8. 0, N 5. 8 H .5

H • 5 4 Bureau of Intellectual Property, Ministry of Economic Affairs (printed by Industrial and Consumer Cooperatives (please read the precautions on the back before filling this page)

This paper size applies Chinese National Standard (CNS) A4 specification (21〇X 297 mm) -203-584661 A7 B7 V. Description of the invention (2001)

[Ir (2,4-F- PPy) 2ci];

CH.OH

Na0CO〇

DMF

Ir (2,4-F-PPy) 2 (5-CH2OH_pic) ^ Pack-(Please read the precautions on the back before filling this page)

Printed by KT Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, 1T (note the reaction steps and the synthesis of Ιι · (2,4-F-PPy) 2— (5-CH sMA-Pic) 〇 namely 'will Ir (2 , 4-F-PPy) 2 (5-CH2M A-Pic) 72.5mg (0.10mmol) and 0.26-di-tert-4-methylphenol 0.2mg dissolved in dehydrated dichloride under argon flow To methane 10 mi, triethylamine i01.2 mg (1.0 mmol) and methacrylic acid chloride 52.3 mg (0.50 mmol) were added, and the mixture was stirred at room temperature for 2 hours. After adding 50 ml of water to the reaction solution, Extracted with chloroform. The solution was dried over magnesium sulfate and concentrated, and then purified by column chromatography (silica gel, methanol: chloroform = 3: 97 (volume ratio)). Then it was recrystallized from hexane / chloroform to obtain yellow crystals. Of Ir (2,4-F-PPy) 2 (5_

C Η 2 M A-P i c) 7 0.6 mg (yield 89%). The measurement was performed by 1 Η-N M R and CHN elemental analysis. This paper size applies Chinese National Standard (CNS) A4 (210 X 297 mm) -204- 584661 A7 B7 V. Description of the invention (202) 'H-NMR (DMSO-de ^ ppm) 5 8 5 3 (d, 1 Η, J = 5 2 8 (d, 1 H, J = 8 2 2 (d, 1 H, J 2 8 1 — 8 · 0 (m, 4 H) 1 H z) 4 H z) 4. 7 7 4 8 dd

H 5 31 (d d, 1H, J = 6 9 — 6 · 7 (m, 2 H), 8 4 7-.6 f equipment-(Please read the precautions on the back before filling this page)

H 111

2 H .6, 11 Printed by the M Industrial Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs 4 7 (dd, 1 H, J = 8 · 8, 24 (d, 2H, J 2 2.7), _ 7 8 (s, 3 H ). Elementary analysis Calcd: C 5 0 · 0 0, H, N 5 · 3 〇. Found: C 4 9. 9 2 JH, N 5.28. 2. 8 2 7 This paper standard applies to China National Standard (CNS) Α4 Specifications (210X 297mm) -205- 584661 A7 B7 V. Description of the invention (203)

Ir (2,4-F-PPY) 2 (5-CH2OH-pic) CH3 I H2C == CCC1 ο

Et3N CH〇Cl '

Ir (2,4-F-PPy) 2 (5-CH2MA-pic) (Please read the precautions on the back before filling out this page) Printed by Example Consumers' Cooperative of Intellectual Property Bureau, Ministry of Economic Affairs [Example 47] Polymerizable compounds: Iridium (III) bis (2- (2,4-difluorophenyl) pyridine diester) (5-2- (methacryloxy) ethylaminomethoxomethyl) picolinate) (Hereinafter referred to as Ir (2,4_F-PPy) 2 (5- CH2M〇I-Pic)) was synthesized as shown in the following reaction steps to synthesize Ii. (2,4-F-PPy) 2 (5- C Η 2 Μ〇I. Pic) 〇 I, as an intermediate in Example 46. (2,4-F-PPy) 2 (5-CH2〇H-Pic) 7 2.5 mg (0.1 mm ο 1), 2, 6-di-ter-butyl-4-

0.2mg of methylphenol (BHT) and 1.3mg of dibutyltin (IV) dilaurate (DBTL) were dissolved in 10 ml of dehydrated tetrahydrofuran, and then methacryloxyethyl isocyanate (MOI) (trade name: "Kay "Lens M〇ί", manufactured by Showa Denko Corporation) 31.0mg (0.2mmol) at 50 ° C This paper size applies Chinese National Standard (A4) (210X 297mm) -206- 584661 A7 ____B7 V. Description of the invention (204) Loading-(Please read the precautions on the back before filling in this page} and react for 1 hour. After adding 50ml of water to the reaction solution, extract with chloroform. This solution was dried over magnesium sulfate, concentrated, and then packed in a gel column. Chromatographic analysis (silica gel, methanol: chloroform 2: 3: 97 (volume ratio)). Recrystallization from hexane / chloroform to obtain I r (2, 4-F-PP y) 2 (5- C Η 2 MoI-P ic) 76.4mg (yield 87%). The measurement was performed by 1H-NMR and CHN elemental analysis. 'H-NMR (DMSO-de »ppm) 5; 8.53 (d, 1H, J = 5.1Hz), 8.32 (dd, 2H, J = 8.0, 1.8Hz), 8.25 (d, lH, J = 8.9Hz), 8.22 (d, lH, J = 9.2Hz) '8 · 1 — 8.0 ( m, 3H), 7 · 6 〇id, 1H, J = 4.6Hz), __ — 7.51 (dd, lH, J = 6.5, 6.5Hz), 4 7.35 (dd, lH, J = 6.5, 6.5Hz), 6 · 9-6 · 7 (m, 2 H), 6.10 (s, 1H), 5.87 (s, 1H), 5.71 (dd, 1H, J = 8.4, 2.2Hz), printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs 5.4 _6 (dd, 1H, J = 8.8, 2.6Hz), 4 · 9 0 (s, 2 H), 4.23 (t, 2H, J 2 · 1 9Ηζ) '3.47 (m, 2H), 1.9〇 (s' 3H).

Elementary analysis C a 1 cd: C 5 0. 6 2 'H 3.33, N 6.380 This paper size applies to Chinese National Standard (CNS) A4 specification (2 丨 〇297. Mm) -207-584661 A7 B7 V. Description of the invention (205)

Found: C 5 0, N 6 9, Η .3

Ir (2,4-F-PPy) 2 (5-CH2〇H-pic) CH〇 I 3 H2C = CCOCH2CH2NCO 0

MO I

Printed by the Goods and Consumers Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

Ir (2,4-F-PPy) 2 (5-CH2MOI-pic) [Example 48] Polymerizable compound: 钺 (III) bis (2- (2,4-difluorophenyl) 卩 1 ± 卩疋 二 _) (5_ (2-methylpropenyloxy) ethoxycarbonyl) picolin | Purpose 彳 c ίΜ _ ^ ^ Bai Yue) (hereinafter fe is called Ir (2,4-F-PPy) 2 (% COHEM A Pic)) Synthesis (1 > {Synthesis of iridium (ΠΙ) bis (2- (2 A " ^ inch Bu: ~ 4) propidyl diester) (5- Carboxypicolinate (hereinafter referred to as h (2Hppy) 2 (5-C〇〇H-Pic)). That is, ΓΤ / r (254 -F-PPy) 2C1] 2 243.2mg (0.1 mmo 1), 2,5-picodine ~ I < ~ With 100.3mg of acid (0.6mm), sodium carbonate 212.0nig (CMS) Λ4 specification (21 OX 297mm) (Please read the precautions on the back before filling (This page)

• 208-584661 A7 B7 V. Description of the invention (206) (Please read the notes on the back before filling in this page) (2.0mmol) Under argon flow, add dehydrated n, N-dimethylformamide 0 ml, and stirred at 80 ° C for 2 hours. 50 ml of hydrochloric acid was added to the reaction solution to precipitate the product, and the product was collected by filtration. A small amount was dissolved in chloroform and purified by gel column chromatography (sand glue, methanol: chloroform =: 1: 4 (volume ratio)). Then, it was recrystallized with hexane / ethanol to obtain 204.0 mg of Ir (2, F-PPy) 2 (5-COOH-Pic) as a yellow powder (yield 69%). The measurement was performed by 1 H-NMR and CHN elemental analysis. 'H-NMRCCDCla ^ ppm) ^; 1 0 · 7 (s, 1 Η), 8. 5 3 (d, 1 Η, J = 5 · 1 Η ζ), 8.37 (dd, 2H, j = 8.〇 , 1.8Hz) '8.28 (d, lH, j = 8.9Hz), 8.25 (d, lH, j = 9.2Hz), 8. · 1 — 8.0 (m, 3H), 7.59 (d, lH, J = 4.6Hz ), 7.49 (dd, lH, j = 6.5, 6.5Hz), 7.32 (dd, lH, J = 6.5, 6.5Hz), printed by K-Consumer Cooperative of the Intellectual Property Office of the Ministry of Economy 6. 9 — 6 · 7 ( m, 2 H), 5.70 (dd, lH, J = 8.4, 2.2 Hz), 5.48 (dd, lH, J = 8.8, 2.6 Hz). Elementary analysis Calcd: C 4 7 · 1 5, H 2.18, N 5.69.

Found: C 47.1 〇, H 2.28, N 5.66. This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -209- 584661 A7 B7 V. Description of the invention (200

C〇h

/ = \ 〇 Μ j F

(Please read the notes on the back before filling this page)

F r (2,4-F-PPy) 2 (5-COOH_pic) _________________________ (2) According to the iR reaction step, I r (2,4-F-PP y) 2 (5-COHEMA-Pic ). That is, under an argon flow, 1 μ · (2,4-F-PPy) 2 (5-COOH-Pic) 7 3.9 mg (0.1 mm ο 1), triphenyl scale (PP h 3) 5 2.5 mg ( 0.2mmol), 2-hydroxyethyl methacrylate 19 · 5mg (0 · 15mmol printed by the Employees' Cooperative of Intellectual Property Office of the Ministry of Economic Affairs) dissolved in 5ml of dehydrated THF, and added dropwise at -20 ° C. 65.3 mg (0.15 mmol) of a 40% toluene solution of ethyl azodicarboxylate (DEAD). Subsequently, the temperature was gradually raised to room temperature, followed by stirring for 2 hours. After the reaction, the solvent was distilled off, evaporated to dryness, and then dissolved in a small amount of chloroform, and purified by column chromatography (silica gel, methanol: chloroform di 1:19 (volume ratio)). It was then recrystallized from hexane / chloroform to obtain 11 · (2,4-F-P P y) 2 (5-Co Η Μ A -Pic) 61.5 nig (yield 72%) as yellow crystals. The measurement is based on 1H-NMR and CHN yuan. The paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) -210- 584661 A7 B7 V. Description of the invention (208) Elementary analysis. 'H-NMR (DMSO-de ^ ppm) 5; 8 · 5 4 (d, 8. 3 7 (d d 8. 3 1 (d, 8 · 2 7 (d, H, 2 H H,

1 H .1 H z 8 H z 8.9Hz

Hz 8 7 7 7 6 6 1-8.0 m

H 5 7 (d, 1 H, J 46 (dd, 1H, J = 3 2 (d d, 1 H, J = 9-6 · 7 (m, 2 H) 4.6Hz

Hz Hz l〇 (s, lH), 5.87 (3, 1Η), — 7 1 (dd, 1 H, J = 8 · 4, 2.2 Hz) 5.51 (dd, lH, J = 8.8, 2.6Hz) 4.64 (t, 2H, J = 2.0Hz 4.55 (t, 2H, J = 2.0Hz 1 · 9 3 (s, 3 H). Printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Economy

Elementary analysis Calcd: C 4 9.4, N 4. I Found: C 49.3, N 4 · i H 2 8 4 4

H (Please read the notes on the back before filling this page)

This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 211 584661 Α7 Β7 V. Description of invention (209)

Ir (2,4-F-PPy) 2 (5-CH2OH-pic) CH3 I h2c = ccoch2ch2oh ο DEAD, PPh,

THF

丨 — (Please read the notes on the back before filling this page)

Ir (2,4-F-PPy) 2 (5-COHEMA-pic) [Example 49] Polymerizable compound · Iridium (III.) Bis (2- (2i4-difluoroI-yl) pyridine diester) ( The synthesis of 3- (4-ethylphenyl) methoxypicolinate (hereinafter referred to as Ir (2,4-F-PPy) 2 (3-ST-Pic)) is shown in the following reaction steps. Ι · (2,4-F-PPy) 2 (3- ST-Pic). That is, in Example 45, Ii (2,4-F-PPy) 2 (3-OH-Pic) 35.5 mg (0.05 mmol), potassium carbonate 69-1 mg (0.5 mmol), 2,6-bis- To 0.1 mg of 1-butylhydroxytoluene, add 5 ml of N, N-dimethylformamide under argon flow, and then add 30.5 mg (0.2 mm) of 4-vinylbenzyl chloride at 80 ° C. Stir for 4 hours. After adding 50ml of water to the reaction solution, the precipitated product was extracted, and then analyzed by gel column chromatography (silica gel, methanol: chloroform II 3: 97 (volume ratio)) This paper is in accordance with China National Standard (CNS) A4 (210X29? Order 4 Refined by the Intellectual Property Bureau of the Ministry of Economic Affairs (printed by Industrial and Consumer Cooperatives-212- 584661 A7 B7 V. Description of the Invention (21〇)). Recrystallized with hexane / chloroform to obtain Ir (2 , 4-F-PPy) 2 (3-ST-Pic) 24.0 mg (yield 58% was performed by 1H-NMR and CHN elemental analysis. 'H-NMR (DMSO-de ^ ppm) δ; determination 8.8 8 7 7 7 9 d Η mm 1 Η z Η 2 Η 9 (d, lH, J = 8.6Hz) 67 (d, lH, J = 5.1Hz 6 — 7 · 3 (m, 7 Η), 9 — 6 · 7 (m ， 3 Η), 8 5 (d, 1 Η, 6 7 ″ dd, 1 Η 4 5 (dd ， 1 Η 4 H z (Please read the notes on the back _ J # • Items and fill in. Packing -: Write this page), 11 Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs " Bei Gong Consumer Cooperative, printed by J = 8 · 9, 5. 2 9 (s, 2 H), 5.27 (d, lH, J = ll. lH Elementary analysis Calcd: C 5 3 · 7, N 5.0 Found: C 53-7, N 5.0 4 H z H 2 8

H 〇 This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -213- 584661 A7 B7

V. Description of the Invention (211) HO

F Ir (2,4-F-PPy) 2 (5-CH2OH-pic) 2_0 ~ (-CH, K ^ CO,

DMF

CH = CH. 装 — (Please read the notes on the back before filling this page)

Ir (2 / 4-F-PPy) 2 (3 „ST.pic) [Example 50] Polymerizable compound: iridium (III) bis (phenylpyridine diester) (3-methacrylic acid) Synthesis of Picolinate (hereinafter referred to as Ir (PPy) 2 (3-MA-Pic)) (1) The synthesis of iridium (111) bis (2-phenylphenidamine diester) is shown in the following reaction steps. (3-Hydroxypicolinate) (hereinafter referred to as Ir (PP) 2 (3-〇H-Pic)). That is, 'bis (chloro) tetrakis (2-propylsulfuric acid) silver which will be synthesized by a general method (Ιπ) (hereinafter referred to as [h · (ppy) 2C1] 2 107.2 mg (0.1 mmol), 3-hydroxypicolinic acid 4 1.7 mg (0.3 nimol), sodium carbonate 106.0 mg (1.0 mm) i) Under argon flow, 10 ml of dehydrated n, N-dimethylamine amine was added and stirred at 80 ° C for 2 hours. After adding 50 ml of water to the reaction solution, the solution was extracted with chloroform. Magnesium sulfate is dried and concentrated, this paper is suitable for financial purposes_ 家 县 （CNS） 格格 （2 like 297 wonderful）

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, 1T-214- 584661 A7 B7 V. Description of the invention (212) Refined by gel column chromatography (silicone, methanol: chloroform = 1: 9 (volume ratio)) . Then it was recrystallized with hexane / chloroform to obtain 106.0 mg of Ir (PPy) 2 (3-〇H-Pic) as a yellow powder (yield 83%). The measurement was performed by j-NMR and CHN elemental analysis. iH — NMR (DMS〇-d6, ppm) 5; 8 8 8 8 7 7 7 7 7 7 6 6 46 (d, 1H, J = 4.9Hz) 23 (d, 1H, J = 8.1Hz) 20 ( d, lH, J = 8.6 Hz) 0-7.9 (m, 2H), 8 0 (m, 2 H), 60 (dd, lH, J = 5.9, 5 55 (d, lH, J = 1.4Hz 4 7 丄 —di 4 〇 (dd 2 6 (dd 1 6 (dd 9 0 (dd 8 7 dd (Please read the notes on the back before filling in this page))

1 H .4 8 ·

HHHHH 9 4 · 7 · 7 · 7 7 9 H z JH z 9 H z 9 H z 4 H z 6 H z 6 H z Printed by the Industrial and Consumer Cooperatives of the Intellectual Property Office of the Ministry of Economy 6.20 (d, 2H, J II 7.6 6.95 (d, lH, J = 7.6 Elementary analysis C a 1 cd: C 5 2, N i Found: C 5 2

Hz Hz

H

H The paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) -215- 584661 M ______ 5. Description of the invention (213), N 6.57.

Ir (PPy) 2 (3-OH-pic) (Please read the notes on the back-4 items before filling * Pack-: Write this page), 11 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs (2) As shown in the following reaction steps, Ir (PPy) 2 _ (3-MA-Pic) was synthesized. That is, 31.9 mg (0.05 mmol) of Ir (PPy) 2 (3-OH-Pic) and 0.1 mg of 2,6-di + butylhydroxytoluene were dissolved in 5 ml of dehydrated dichloromethane under an argon stream, and then After adding 50.6 mg (0.5 mmol) of triethylamine and 2 6.1 mg (0.2 5 mm ο 1) of methylpropanoic acid chloride, the mixture was stirred at room temperature for 2 hours. After adding 50 ml of water to the reaction solution, it was extracted with chloroform. This solution was dried over magnesium sulfate, concentrated, and purified by column chromatography (silica gel, methanol: chloroform = 1: 19 (volume ratio)). It was then recrystallized from hexane / chloroform to obtain 23.0 mg of Ir (PPy) 2 (3-MA-Pic) as yellow crystals (yield 65%). The measurement was performed by 1H-NMR and CHN elemental analysis. This paper size applies the Chinese National Standard (CNS) Λ4 specification (2 丨 0 × 7mm) -216- 584661 A7 B7 V. Description of the invention (214) 'H-NMR (DMSO-d 8.5〇 (d, lH, J = l 8 · 2 3 (d, 1 Η, J 8 · 2 1 (d, 1 Η, J 8 · 0 — 7.9 (m, 3 H), 81 (t, 2H, J = 8. 7 — 7.5 ( m, 3H),, ppm, 5. 7 H z) 4.9 Hz) 5 · 7 H z) 7 7 7 7 6 6 6 6

Hz (Please read the notes on the back first

4 2 (dd, 1 H 2 5 (dd, 1 H 9 1 (dd, 1 HJ = 6.6, 6.6Hz) J = 7.6, 7.6Hz) J = 7.6, 7.6Hz) J = 7.6,7.6Hz) 8 6 (dd, 1 H 2 5 (s, 1 H), 2 2 (dd, 1 H, J = 7 · 8 H z 7. 3 H z) 6 .〇1 (d 5, 1 Η, J 5. 8 7 (s,, 1 Η), 2 • 〇1 (S 3 • 3 Η.) 0 —0-Refill items, clothes-: Write this page) Order 4 Intellectual Property Bureau of the Ministry of Economic Affairs 3 (Industrial and Consumer Cooperatives) system

Elementary analysis Calcd: C 5 4. 3 8, H, N 5.95. Found: C 54.29, H, N 5.94. 4 2 This paper size is applicable to Chinese National Standard (CNS) A4 specification (210 X 297 mm) -217- 584661 A7 ______B7 V. Description of the invention (215)

HO

Ir (PPy) 2 (3-MA-pic) (Please read the precautions on the back before filling out this page), -5 mouth [Example 5—u—mShizole_Ir (2, 4_F-PPy) 2 ( 3-MA-pic) co-polymer (hereinafter referred to as VCz-co-Ii · (2,4-F-PPy) 2 (3-MA-pic)) will have a unit of light emitting function Ιι · (2,4 -F-PPy) 2 (3-MA-pic), a unit with hole-conveyor function N-vinylcarbazole is synthesized to contain a co-polymer as described above in a luminescent material. N-vinyl D card was added 9 6 mg (5.0 mm ο 1), 11. (2, 4-F-PP y) 2 (3-MA-pic) 38.9 mg (0.05 mmol), AIBN 8.2 mg (0.05 mm 01) was dissolved in 25 ml of dehydrated toluene, and then argon gas was blown for 1 hour. This solution was warmed to 80 ° C, and the polymerization reaction was started, followed by stirring for 8 hours. After cooling, the reaction solution was dropped into 250 m 1 of toluene to precipitate a polymer 'and recovered by filtration. Subsequently, the recovered polymer is dissolved. The paper size is in accordance with the Chinese National Standard (CNS) A4 specification (2) 0X297 mm. D Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs -218- 584661

V. Description of the invention (216) (Please read the precautions on the back before filling in this page) in 25ml of chloroform, and then drop this solution into 250ml of toluene, reprecipitate and refine it, then proceed to 6 (TC 1) Dry in vacuum for 2 hours to obtain VCz-co-Ir (2,4-F-PPy) 2 (3-M A-pic) 67 3 mg of the target. Recovery rate, GPC measurement results, and ICP elemental analysis. The content of the complex is shown in Table 5. [Examples 52 to 56] Polymerizations of Ii · (2,4-F-PPy) 2 (3-MA-pic) prepared in Examples 4 to 60, respectively Copolymers were synthesized in the same manner as in Example 51 except that the compounds were substituted. The recovery rate, GPC measurement results, and Ir complex content obtained by ICP element analysis are shown in Table 5. Table 5 Example Polymer Recovery Rate GPC determination of Ir complex (%) Mη Mw Mw / Mn content (mol%) 51 VCz-co-Ir (2,4-F-PPy) 2 (3-MA-pic) 67 4500 12800 2.84 1.07 52 VCz -co-Ir (2? 4-F-PPy) 2 (5-CH2MA-pic) 79 4300 13600 3.16 1.04 53 VCz-co-Ir (2,4-F-PPy) 2 (5-CH2MOI-pic) 63 5100 14800 2.90 1.02 54 VCz-co-Ir (2,4-F-PPyM5-C〇HEMA-pic) 61 4100 13700 3.34 0.98 55 VCz-co-Ir (2,4- F-PPyM3-ST-pic) 72 4600 11400 2.48 1.04 56 VCz-c〇-Ir (PPy) 2 (3-MA-pic) 74 4400 13000 2.95 1.01 Intellectual Property Office of the Ministry of Economic Affairs g (printed by the Industrial and Consumer Cooperatives) η : Number average molecular weight, Mw: Weight average molecular weight The dimensions of this paper are applicable to Chinese National Standard (CNS) A4 specifications (210X 297 mm) -219- 584661 A7 ____B7 V. Description of the invention (217) [Example 57 ~ 62] Organic light emission The device was fabricated and evaluated on one side of a 25mm square glass substrate, and an ITO (indium tin oxide) substrate with a width of 4mm as an anode was formed from two 1-butt electrodes in a stripe shape (Japan Electric, Nippon Electric Co., Ltd.) ., Ltd.) First, poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (Bayer Co., Ltd.) Co., Ltd., trade name "Bairon P") After coating under the conditions of a spin coating method, a number of revolutions of 3500 rpm and a coating time of 40 seconds, it was dried under reduced pressure in a vacuum dryer at 60 ° C for 2 hours To form an anode buffer layer. The film thickness of the obtained anode buffer layer was about 50 nm. Subsequently, a layer containing a luminescent material and an electron transporting material was prepared to obtain 2- (4-biphenyl) -5- (4-tert-butylphenyl)- 1,3,4-oxa-1 ^ sat (PBD) (manufactured by Tokyo Chemical Industry Co., Ltd.) 9 · 0 mg was dissolved in chloroform (Wako Pure Chemical Industries' 'premium grade') 2 9 70 mg, and the resulting solution was pore size Filtered by a filter of 0 · 2 // m as the coating liquid. Subsequently, the prepared coating was also coated on the anode buffer layer by a spin coating method, a number of revolutions of 3000 rpm, and a coating time of 30 seconds, and then dried at room temperature (25 ° C) for 30 minutes to form a coating containing A layer of luminescent material and electron transport material. The film thickness of the obtained layer containing the light-emitting material and the electron-transporting material was about 1000 nm. Subsequently, the substrate formed with the layer containing the electron transporting material was placed in a vaporizing device, and co-evaporation was carried out at a ratio of silver and magnesium at a weight ratio of 1: 1, and the paper size was applied to a household towel (CNS) ( 2I〇X 297 ^ t ~ ^ Clothes-(Please read the notes on the back before filling this page) Order, 0 Printed by P Bayong Consumer Cooperative, Intellectual Property Bureau, Ministry of Economic Affairs 220- 584661

7 7 A B 5. Description of the invention (218), and two cathodes with a width of 3 mm arranged in a straight stripe arranged at right angles to the anode are formed. The film thickness of the obtained cathode was about 50 nm. Finally, in the argon environment, the anode and the cathode are provided with a lead wire (wiring) to obtain 4 organic light-emitting elements of 4 mm in length and 3 mm in width. A voltage was applied to the aforementioned organic EL element using a program DC voltage / current source TR6 143 manufactured by Atlans Corporation, and the light emission luminance was measured using a Debcom luminance meter BM-8. As a result, the light emission starting voltage and the initial brightness at 20 V are shown in Table 6 (the average of four elements obtained using each light-emitting material). Table 6 — (Please read the precautions on the back before filling out this page) Example of printed guest printing by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economy ----------------__ _Luminescent materials Initial polymer example from 2V Initial voltage (V) Brightness (cd / m2) 57 VCz-co-Ir (2,4-F-PPy) 2 (3-MA-pic) 54 8 790 58 VCz-co-Ir (2,4-F-PPy) 2 (5-CH2MA-pic) 55 8 500 59 ναζ-οο-ΐΓ (2,4-P-PPγ) 2 (5-ΟΗ2ΜΟΙ-ρίο) 56 9 640 60 VCz-co -Ir (2,4-F-PPy) 2 (5-COHEMA-pic) 57 8 740 61 VCz-co-Ir (2,4-F-PPy) 2 (3-ST-pic) 58 9 800 62 VCz -co-Ir (PPy) 2 (3-MA-pic) 59 8 910 [Example 63] Polymerizable compound: [6- (4-vinylphenyl) -2,4-hexanedione ester] bis [2- (2-Pyridyl) benzylthianyl] iridium (III) (4 paper sizes below apply to Chinese National Standard (CNS) A4 specifications (210X 297 mm) -221-584661 Intellectual Property Bureau, Ministry of Economic Affairs Β (Printed by the Industrial and Consumer Cooperative Association Ί ________ B7 V. Description of the invention (219) Abbreviation Ir (btp) 2 [Bu (StMe) -acac] Synthesis according to the following reaction steps, according to the same method of Example 3 8 (1) 6_ (4-vinylphenyl) _2,4-hexyl Dione with two (/-chloro) tetrakis (2- (2-pyridyl)) synthesized by general methods (for example, S. Lam an sky, etal., Inorganic Chemistry, 40, 1704 (2001)) Phenylthiothanyl) iridium (hereinafter referred to as [h · (btp) 2 C1] 2 is reacted to obtain Ir (btP) 2 Π- (StMe) -acac] 0, that is, [I r (bt ρ) 2 C1 ] 2 2 5 3 mg (0 · 20 mm ο 1) Suspended in 10 ml of N, N-dimethylformamide (hereinafter referred to as dMF), and then added 611 (6-vinylphenyl) ) -2,4-hexanedione (0.74111111〇1) and 64 mg of sodium carbonate and i.9 mg of 2,6-di-tert-butyl-4-, methylphenol (hereinafter referred to as BHT) (〇. (0086 mmol), and then heated and stirred at 80 ° C. for 1 hour. After adding 100 ml of water and 5Q ml of chloroform to the obtained inverse mixture, the mixture was shaken sufficiently, and the organic layer was dried over magnesium sulfate, and then dried under reduced pressure with a rotary condenser. Subsequently, dichloromethane was used as an eluent, and the crude product was purified by column chromatography to obtain a red-brown solution. The solution was concentrated under reduced pressure. After adding hexane, it was recrystallized at -20 ° C to obtain the target substance Ir (btp) 2 [1- (StMe) -acac] 1 53mg (0.1 8inmο 1) red. Brown solid (47% yield). The measurement was performed by CHN elemental analysis and j-NMR. 1 Η-NMR (CDC 1 3 ^ ppm) 5; 8.4 (d, J = 5.4 Hz, lH, btp), 7.97 (d, J = 5.4 Hz, lH, btp), 7. 6 5 (m, 6 H, btp), (please read item 1 ♦ on the back side and fill in. ——M write this page), -port 4 This paper size is applicable to China National Standard (CNS) Α4 specification (210 × 297 mm)- 222-584661 A7 B7 V. Description of the invention (220) 7.1-6.7 (ιτι, 10 ，, aromatic), 6.63 (dd, J = 17.8, ll.lHz, lH, vinylic), 4 (d, • 8 丨, 1 Η z, 1 Η, bt P), 6 (d, 1 J = 2 7 • 8 Η z, 1 Η, bt ρ) 5 (d, 1 J = -1 7. 8 ζ ζ, 1 Η vinylic) 2 2 (s, 1 Η, diktonate-methine), 18 (d, J = ll.lHz, lH, vinylic), 2. 5 6 (m, '2 H > ethylene), 2 · 3 7 (m, '2 H ^ ethylene), 1. 7 5 (s, 3 H? Methyl) 0 (Please read the notes on the back first' 1 # • Fill in the items and then make your clothes-: Write this page)

Elementary analysis Calcd: C 5 8. 0 2, H 3 · 77 — ____________________________________________________________ 1 3 ″ 3 8 2 (C 4 0 Η 3 1 I Γ N 2 Ο 2 S 2)

Found: C 57 · 79, H 3.81, N 3.55.

、 1T 4 Printed by the Industrial and Commercial Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs This paper standard applies to the Chinese National Standard (CNS) A4 specification (2) 0 × 297 male f) -223-584661 A7 B7 V. Description of the invention (221)

[Ir (btp) 2Cl]:

Ο ό

Na〇CO〇

DMF

工 r (btp) 2 [(1_ (stMe) (Please read the precautions on the back before filling out this page), iN clothing · -acac)] [consistently Example 6 4] polymerizable compound: [6-(4- Methylpropanyloxyphenyl), 2,4-hexanedione ester] bis [2- (2-pyridyl) phenylsulfanyl] iridium (111) (hereinafter referred to as Ii. (Btp) 2 Π -Synthesis of (MA-Ph-Me) -acac] (1) 6_ (4_hydroxyphenyl) _2,4 was synthesized in the same manner as in Example 4 1 (1) and (2) as shown in the following reaction step. -Hexanedione reacts with [lr (btp) 2 C1] 2 synthesized according to a general method to obtain 6- (4-hydroxyphenyl

), 2,4-dione diketoester] bis [2- (2-pyridyl) phenylsulfanyl] iridium (ΠI) (hereinafter referred to as ir (btp) 2 [1- (StMe) -acac]) . That is, [11 · (btp) 2 C1] 2 2 4 5 mg (〇 · 19 mm ο 1) and 111 mg of sodium carbonate (1.06 mmol) were dissolved in 141 mg of [6 · (4-hydroxyphenyl) ) 9 y, 4-hexanedione] (0.68mm〇l) in 10ml of DMF, at 80t Table _ _ (using Chinese Standards (CMS) A4 specifications (21GX 297 male f) Order Ministry of Economic Affairs Printed by the Intellectual Property Bureau® Industrial and Consumer Cooperatives-224- 584661 A7 ______B7 V. Description of the invention (222) Printed by the Intellectual Property Bureau R Industrial and Consumer Cooperatives of the Ministry of Economic Affairs under heating and stirring for 1.5 hours, and then cooled to room temperature, and then the reaction mixture Chloroform and ammonium chloride water were added to the solution. After the solution was shaken sufficiently, the organic layer was dried over magnesium sulfate and the solvent was distilled off with a rotary condenser. The residue was passed through a silica gel column (eluent; hexane / dichloromethane / acetone = 5 / 10/1 (volume (ratio)) method to filter the red-brown zone containing the main product 5 and dry it under reduced pressure to obtain the target product I r (btp) 2 [1-(OH-Ph-Me ) -acac] 2 1 5 mg (0 :: 2 6 mm 〇1) of]]: brown solid (yield 70%). The measurement is based on the CHN element And 4-] NMR. 1] Η--NMR (CDC 13, ppm) 5 8 • 4 〇 (d, J = 5.4 H z, 1 ，, bt P) > 8 • 〇6 (d, J-5 .4 Η ζ, 1 Η, bt P) 5 7 • 6 3 (m, 6 H, bt ρ), 7 • 〇4 (m, 3 H, bt ρ), 6 • 8 1 (111, 3 H, bt ρ), 6 • 6 6 (d, J = 8 • 4 H z, 2 Η, — C 6 Η 4 — 〇 Η) > 6 • 3 8 (d, J-8 • 4 H z , 2 Η) -C 6 Η 4 〇Η) > 5 • 2 2 (s, 1 H, diketonate-methi ne) 5 5 • 2 〇 (br, 1 H, 〇H), 2 • 4 8 ( m, 2 H, methylene), 2 • 3 1 (m, 2 H, methylene), 1.75 (s, 3H, methyl). Elementary analysis Calcd: C 5 5. 8 〇, Η 3.57-(Please read the precautions on the back before filling out this page), 11 4 This paper size applies the Chinese National Standard (CNS) A4 specification (210 X297 mm)- 225-584661 A7 B7 V. Description of the Invention (223), N 3.42. (Please read the precautions on the back before filling this page) (C38H29 I r N 2 0 3 S 2)

Found: C 56. 19, H 3.57, N 3.31.

Ir (btp) 2 [(1- (〇H-Ph-Me) -acac)] Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs (2) According to the following reaction steps, this ir (btp) 2 [1 -(OH-Ph-Me) -acac] is reacted with methacrylic acid chloride to synthesize Ir (btp) 2 [1- (MA-Ph-Me), acac]. That is, 248 mg (0.3 2 mmol) of I. (btp) 2 [1- (〇H-Ph-Me) -acac] was dissolved in 20 ml of dry dichloromethane, and 0.25 ml (1.8 mm) of triethylamine was added. It was stirred with 0.20 ml of methacrylic acid chloride (2.0 mmol) at room temperature for 1 hour. Subsequently, the reaction solution was applied to the Chinese paper standard (CNS) 8-4 specifications (21〇χ 297 mm) at the carbon paper size. -226- 584661 A7 B7 V. Description of the invention (224) (Please read the notes on the back before filling (This page) Wash 20 ml of an aqueous sodium solution and distill off the solvent under reduced pressure. The residue was purified by a silica gel column chromatography method (eluent: hexane / dichloromethane / acetone == 2: 4: 1 (volume ratio) mixed solvent), and the red-brown solution that was eluted first was filtered. After drying under reduced pressure, lr (btp) 2 Π- (MA-Ph-Me) -acac] 180 mg (0.20 mmol) was obtained as a red-brown solid (yield 64%). The measurement was performed by CHN elemental analysis and 1H-NMR. 1H — NMR (CDC I3 »ppm) δ; 8.42 (d, J = 5.4Hz, lH, btp), 8.10 (d 'J = 5.4Hz, lH, btp), 7.65 (ni, 6H, btp), 7 · 1 — 6 · 7 (m, 10H, aromatic), 6.40 (d, J = 8.1Hz, lH, btp), 6.27 (d, J = 8.1Hz, lH, btp), 6 · 12 (s , LH, olefinic), 5. 7 1 (s, 1 H, 01 e fi nic), 5. 1 9 (s, 1 H, diktonate-methine), 2 · 5 1 (m, 2 H, C 2 H 4), printed by the M Industrial Consumer Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs 2 · 3 9 (m, 2 H, C 2 H 4), 1 · 8 9 (s, 3 H, memethry 1, methy 1), 1. 8 〇 (s, 3 H, diktonate -methyl) 〇

Elemental.y analysis Calcd: C 5 6. 9 3, H 3.75, N 3.16. (C42H33I r N 2 0 2 S 2 The size of this paper applies to Chinese National Standard (CNS) A4 size (210X297 mm) -227-584661 A7

Ir (btp) 2 [(i. (〇H-Ph-Me) -acac)] Ir (btp) 2 [(!. (MA ^ ph.Me) _aca〇)]. System — {Please read the back Note: Please fill in this page again. [贯 例 65] Polymerizable compounds: 丨 6_ μ · (methacryl methoxy) aminomethyl methoxyphenyl] -2,4-hexanedione ester bis [ The synthesis of 2- (2-pyridyl) phenylsulfanyl] ^ ^ [1-(M η T-P h _) -acac] was as shown in the following reaction steps. The Ir (btp) 2 of Example 64 π, (〇H-Ph-Me) -acac] is reacted with methyl propyl thioethyl isocyanate (μ〇ι) (trade name "Karens M ΟI", manufactured by Showa Denko Corporation) to synthesize Ir ( btp) 2 [1- (MoI-Ph-Me) -acac]. That is, 215 mg (0.26 mmol) of Ir (btp) 2 [l_ (〇H-Ph-Me) -acac] was dissolved in 10 ml of THF, and then 4.0 mg of BHT (0-18 mg) and 35 mg of dibutyltin ( IV) After lauric acid ester (hereinafter referred to as DBTL) and 401 mg of MOI (2.5 8 mm ο 1), heat and reflux in a hot water bath for 3 hours. After cooling to room temperature, the reaction solution was dried under reduced pressure, and the residue was passed through a silica gel column (eluent: hexane / dichloromethane / acetone = this paper size is applicable to China National Standard (CNS) A4 size (210X 297mm f)). , = Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economy -228-584661 A7 _____ B7 V. Invention Description (226) (Please read the precautions on the back before filling this page) 5/10/1 (Volume ratio) Mixed solvent). The red-brown zone containing the main product that was eluted at first was filtered and dried under reduced pressure to obtain Ir (btp) 2 [1- (M〇I-Ph-Me) -acac] 223mg ( 0. 23 mmol) as a red-brown solid (87% yield). The measurement was performed by CHN elemental analysis and 1H-NMR. 1 U — NMR (CDC13j ppm) δ; 8.40 (d, J = 5.7 Hz, lH, btp), 8.12 (d, J = 5.1 Hz, lH, btp), 7.65 (m, 6H, btp), 7 · 1 — 6 · 7 (m, 10H, aromamatic), 6.25 (d, J = 8.4Hz, lH, btp), 6.20 (d, J = 8.1Hz, lH, btp), 6 · 1 6 (s , 1 H, olefinic), 5 · 6 3 (s, 1 Η, ο 1 efinic), 5.26 (br — s, lH, NH), 5 · 2 1 (s, 1 H diketonate-methine), 4 · 31 (t, J 5.4Hz, 2H, N-C2H4- 〇), printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs 3. 59 (t, J 5.4, 4H z, 2H, N-C2H4- 〇), 2 · 55 (m, 2H, C-C2H4- C), 2.34 (m, 2H, C-C2H4— C), 1 · 9 8 (s, 3 H, methacryl-methyl), 1. 7 6 (s, 3 H ， diketonate-methyl) 0 This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) -229- 584661 A7 B7 V. Description of the invention (227)

Elementary analysis Calcd: C 55.54, H 3.94, N 4.32. (C45H38 I r N 3 0 6 S 2)

Found: C 55.13, h 3.89, N 4 · 5 8 0

H 0 ° TN 0 -------- | 丨 (Please read the precautions on the back before filling this page)

〇Y

[Example 66] Polymerizable compound: [1- (2-Methacrylfluorenyloxy) aminomethaneoxyphenyl-2,4-pentanedione ester] bis [2- (2-pyridyl) Phenanthrene] silver (III) (hereinafter referred to as Ir (btp) 2 (1-MA -acac) printed by the Consumer Cooperative of the Intellectual Property Office of the Ministry of Synthetic Economy (1) As shown in the following reaction steps, the general [Synthesis of [Ir (btp) 2 Cl] 2 and 1- (ter t-butyldimethylsilyloxy) -2,4-pentane] by a known method (European Patent No. 05 142 1 7) Alkyldione (1-TBDMS〇-2,4-pentanedione) is reacted to synthesize lr (btp) 2 (1-0H- acac) 0 ie 'will [11 · (btp) 2 C1] 2 4 4 9 mg (0 · 3 5 mm ο 1) and 137 mg of sodium carbonate (1.29 mmol) were dissolved in 310 mg of U-TBDMS 0-2,4-pentanedione (15.35 mmol) in a 15 ml DMF solution , At 80 ° C -230- This paper size applies to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) 584661 A7 B7 V. Description of the invention (228) Heat and stir for 1 hour. Subsequently, the obtained reaction solution was cooled to room temperature, and chloroform and dilute hydrochloric acid were added thereto, followed by sufficient shaking. The organic layer was washed with water, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane). The red-brown compound that was eluted at first was filtered and dried under reduced pressure. The obtained solid was dissolved in 10 ml of dry THF. 0.60 ml (0.60 mmol) of a 1.0M THF solution of tetra-η-butylammonium fluoride (n-BiuNF) was dropped into the solution with vigorous stirring. After stirring the solution at room temperature for 0.5 hours, the solvent was distilled off under reduced pressure. except. The residue was purified by silica gel column chromatography (eluent ·· hexane / dichloromethane / acetone = 5 ·· 1 0 ·· 2 (volume ratio) mixed solvent) and the red-brown solution was filtered. After drying under reduced pressure, the target substance was Ir (btp) 2 (1-OH-acac) 360 mg (0.49 mmol) as a red-brown solid (71% yield). The measurement was performed by CHN elemental analysis and 1H-NMR. 'H-NMR (CDC 1 (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 88 7 7 76 4〇 (d 3 5 (d 7 9 (m 6 3 (m 〇4 (m 8 1 (t 2 0 (t 2 4 (s • 8 (dd

J 5.4Hz, J = 5 · 1 H z '2 H »btp), 4 H» btp), 4 H »btp), J = 7 · 3 H z, J = 6 · 8 H z, 1 H, diktonate -: H, b H, b

P P

-C Η H ′-〇 H Z H > b 2 H, be ethine) .1Hz

P P

H This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) -231-584661 • 1 1 z, 1 Η,) Α7 Β7 V. Description of the invention (229) 3.80 (dd, J II 8.1, — C Η Η, —〇Η) ,. 2.92 (t, J = 5.1 Hz, 1H, 0H), 1 · 8 3 (s, 3 Η, diketonate-methyl) 〇

Elementary analysis Calcd: C 5 1 · 1 5, H 3.18, N 3.85. (C 3 1 H 2 3 I r N 2 0 3 S 3)

Found: C 51 · 41, H 3 _ 36, N 3.49. ^ ¾-- (Please read the notes on the back before filling in this page)

+ 2 " Y ^ Y ^ OTBDMS o o [工 r (btp) 2Cl]:

、 1T __ Printed by Xiao Gong Consumer Cooperative, Bureau of Intellectual Property, Ministry of Economic Affairs OH O 0

1) Na2C〇3

2) n-Bu4NF

Ir (btp) 2 (l-〇H-acac) (2) According to the following reaction steps, this Ir (btp) 2 (1- OH ^ cac) and m〇I are subjected to an addition reaction to synthesize Ir (btp ) 2 (The paper size of the paper applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 584661 M_B7 V. Description of the invention (23〇) M〇I-acac) 0 That is, Ir (btp) 2 (1 -OH-acac) 1 77mg and 3.0 mg of BHT (0.086mmol), 20nig of DBTL (0.032mmol) was dissolved in 10mg of THF solution, and then 100mg of MOI (0.64mmol) was added to the oil Heat to reflux on the bath for 2 hours. Subsequently, the obtained reaction solution was cooled to room temperature, and the reaction solution was dried under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: hexane / dichloromethane / acetone = 10: 20 ·· 3 (volume ratio)). Mixed solvent) purification, the second eluted red-brown main product was filtered, dried under reduced pressure, dissolved in a dichloromethane / hexane mixed solvent, and recrystallized at -20 ° C to obtain the target substance. Ir (btp) 2 (1-MOI-acac) 173 mg (0.20 mmol) of a red-brown needle-like solid (81% yield). The measurement was performed by CHN elemental analysis and 1 H-NMR. 1 Η-NMR (C Ό ^) δ 8.49 (d, J = 5.7Hz, lH, btp), 8.40 (d, J = 5.4Hz, lH, btp), 7.74 (m, 2H, btp), 7.61 (m , 4 Η, bt ρ), 7.〇3 (m, 4H, btp), 6.8 (m, 2 H, btp), 6 · 2 1 (m, 2 H, btp), 6 · 〇6 (s, 1H, olefinic), olefinic), diketonate-methine), 1 Η, NH), the Chinese version, shi Zhang, and degree are applicable to the Chinese National Standard (CNS) A4 & grid (210 χ 29ϋ) (Please read the back Note for refilling. .Write this page} Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economy

-233-584661 A7 B7 V. Description of the invention (231) 4.25 3.97 3.16 2H, N-C (= 〇) -101-C2H, N-CH2-CH2-〇) 2H > N-CH2CH2-0), 3H, CH3C (di-CH2)-) 1 · 8 1 (s, 3 H, diktonate-methyl). Elementary analysis Calcd: C 5 1 · 6 9, H 3, N 4. 7 6 0 (C 3 8 H 3 2 I r N 3 0) Found: C 51.88, H 3, N 4.51. s m m s

H S 2 • 65 --------—— (Please read the notes on the back before filling this page) 0 o

Ir (btp) 2 [(1- (OH-Ph-Me) -acac)] Ir (btp) 2 [(1- (MOI-Ph-Me) -acac)] d [Example 67] N-vinylcarbazole seven (btp) 2 [1- (StMe) -acac] copolymer (hereinafter referred to as VC z-co -1 r (btp) 2 [1-(S t M e) -acac]) Synthesis of 11. (btp) 2 Π- (StMe) -acac], which is a unit with a light-emitting function, and vinyl carbazole, which is a unit with a hole transport function, is synthesized. Copolymers are noted on the luminescent materials. N-vinylcarbazole 1.55g (8.0mm〇l), h. (Bpt) 2 [The paper size applies to the Chinese National Standard (CNS) A4 specification (210x 297 mm) 234- 584661 A7 ____ B7 V. Description of the Invention (232) (StMe) -acac] 33 mg (0.04 mmol) > AIBN 13 mg (0.08 mmol) was dissolved in 40 ml of dehydrated toluene, and then argon was blown with fluorine for 1 hour. This solution was warmed to 80 ° C, and the polymerization reaction was started, followed by stirring for 8 hours. After cooling, the reaction solution was dropped into 250 ml of toluene to precipitate a polymer and recovered by filtration. Subsequently, the recovered polymer was dissolved in 25 ml of chloroform, and the solution was dropped into 250 ml of toluene to reprecipitate and refine, and then vacuum-dried at 60 ° C for 12 hours to obtain the target substance. VCz-co-Ii (bpt) 2 [1- (StMe) -acac] l.llg. Table 7 shows the recoveries, GPC measurement results, and Ι · complex content obtained by ICP elemental analysis. [Examples 68 to 70] Ir (bpt) 2 [1- (StMe) -acac] was replaced with the polymerizable compound prepared in Examples 64 to 66, and the others were synthesized by the same method as in Example 67. Thing. Table 5 shows the recoveries, GPC measurement results, and 1m · complex content obtained by ICP elemental analysis. (Please read the Note 4 on the back before filling-Pack-: Write this page) Order Printed by the Employees' Cooperatives of the Intellectual Property Office of the Ministry of Economic Affairs. Table 7 Example Polymer Recovery Rate GPC Determination of Ir Contained Compounds (% ) Μη Mw Mw / Mn (mol%) 67 VCz-co-Ir (btp) 2 [l- (StMe) acac] 71 4500 10800 2.40 0.59 68 VCz-coIr (btp) 2 [l- (MA-Ph- Me) acac] 73 4300 10700 2.52 0.81 69 VCz-co-Ir (btp) 2 [l- (MOI-Ph-Me) acac] 58 4300 10900 2.55 0.89 This paper size applies to the Chinese National Standard (CNS) Λ4 specification (210 × 297 mm) -235-584661 A7 B7 Description of the invention (233)-70 VCz-co-Ir (btp) 2 [l- (lM〇I〇_acac ^ ------ 72 4400 11800 2.66 0.61 Μη: Number average molecular weight 'Mw: Heavy weight average molecular weight [Example 7 1 ~ 74] Production and evaluation of organic light-emitting device Using the light-emitting materials shown in Table 8, the organic light-emitting device was produced in the same manner as in Examples 57-62, and its light emission was measured. Brightness. The results, initial light emission voltage, and initial brightness at 20V are shown in Table 8 (the average of 4 elements using each luminescent material). 袠 8 -------- | 丨 (Please read the back first Notes before filling out this page )

71 VCz-co-Ir (btp) 2 [l- (StMe) acac] 70 420 Order 72 VCz-co-Ir (btp) 2 [l- (MA-Ph-Me) acac] 71 73 VCz-co-Ir (btp) 2 [l- (MOI-Ph-Me) acac] 74 VCz-co-Ir (btpMl-MOI-acac) 73 400 360 390 t [Example 75] Polymerizable compound: Synthesis of iridium (III) bis (2- (4-methacryloxyphenyl) pyridine diester) (acetamidoacetone) (hereinafter referred to as h. (4. MA-PPy) 2 (acac) ( 1) According to the reaction steps shown below, 'Synthesis of 2 iridium complexes to bis (// -chloro) tetra (2- (4-hydroxyphenyl) pyridine) is given by / τττ, (m (III) c Paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -236. 584661 A7 __ B7_ V. Description of the invention (234) hereinafter referred to as [Ir (4-H0-PPy) 2C1] 2. 'HO-PPy 0.86g (5.0mmol) and sodium hexachloroiridium (ΠΙ) sodium hydrate 1.0 · 0 g prepared in the same manner as in Example 27 (1) and (2) were dissolved in 2-ethoxy Ethanol: water = 3: 1 (volume ratio) in a mixed solvent of 40 m 1, after blowing for 30 minutes in an oxygen climate, and stirred under reflux for 6 hours. The solvent was distilled off. Residual The body was washed with distilled water and chloroform, and dried under vacuum for 5 hours to obtain [Ii · (4-H0-PPy) 2C1] 2.63g yellow powder (yield 74%). The measurement was based on 1H -NMR and CHN elemental analysis. 1H — NMR (DMSO- d6j ppm) δ 9 9 8 7 7 7 7 6 6 (d, 2 Η 3 8 (d 0 7 9 Printed by the Consumer Cooperative of Intellectual Property Bureau, Ministry of Economic Affairs 6 1 (d, 5 4 (d, 3 8 (dd 2 6 (dd 3 3 (dd 2 8 (dd 6 7 (d, 1 2 (d,

2 H (m 2 H 2 H 2 H 2 H 2 H 2 H H, H,

J J 8. 8. = 6 2 5 = 8 = 8

Elementary analysis C a 1 c d: C

4 N 9 H 7 H 1 H 4 H .2 .7 .6 .4 2 H 4 H 6 · z 2 H z 7 H z 4 H z 4 H z

H 4

Found: C 4 4 4

H This paper size is applicable to Chinese National Standard (CNS) A4 specification (210 × 297 mm) -237-584661 A7 B7 5 Description of the invention (235)

2Na3IrCl6-nH20 ----- 2-Ethoxyethanol N 4

OHOH (Please read the note on the back first, Bureau of Intellectual Property, Ministry of Economics Β (Printed by Industrial and Consumer Cooperatives [Ir (4-HO-PPy) 2ci] 2 (2) Synthesize iridium (m) double ( 2- (4-Hydroxyphenyl) pyridine diester) (Ethylacetone) (hereinafter referred to as Ιι · (4-Η0-PP y) 2 (acac)). BP 'will be [Ir (4-H〇-PPy ) 2C1] 2 227.2 mg (0.2 mmol), sodium carbonate 2 1 2 · 0 mg (2 · 0 mmo 1) Under degassed M, dehydrated N, N -dimethylformamide (hereinafter referred to as DMF) 2Qinl and After 2,4_pentamidine di-60.0 mg (0.6 mmol), stir at 8 ° C for 2 hours. After adding 100 ml of water to the reaction solution, extract with chloroform, and wash with saturated brine and distilled water. Organic layer After drying and concentrating with magnesium sulfate, it was purified by gel column chromatography (silica gel, methanol: chloroform = 5: 95, volume ratio), and then recrystallized with Kojima / acetone to obtain the Ir (4 · Η〇_ρργ) 2 (acac) 152.0mg yellow crystal (yield 60%). The measurement was performed by 1H_Nmr, CHN elemental analysis. 'H-NMR (CDCl3, ppm) 5; 8.35 (d »2H» j ~ 5-7Hz), 7 · 7-7 · 6 (m, 4 Η), 7 · 41 (d, 2H, j- . L〇.6Hz), J · · reloading equipment items: - written on this page)

， 1T This paper size applies Chinese National Standard (CNS) A4 specification (210 × 297 mm) -238- 584661 A7 B7 V. Description of the invention (236) 7.04 (ddd, 2H, Hz),

6.33 (dd, 2H, J 5.70 (d, 2H, J = 5.24 (s, lH), l Elementary analysis Calcd: C

Found: C

= 8 · 4, 2 · 4Ηζ), 2.7Hz), • 7 8 (s, 6 H) 〇5 1. 3 4, H 3.67 N 4. 4 3 0-(Please read the notes on the back before filling (This page) 5 1 · 3 1, H 3.76

[Ir (4-H〇-PPy) 2Cl] 2 2 0 0

* 1T

Na2C〇3 DMF Intellectual Property Bureau, Ministry of Economic Affairs 0 (Printed by Industrial and Consumer Cooperatives)

Ir (4-HO-PPy) 2 (acac) d (3) is synthesized as shown in the following reaction steps (acac) to synthesize Ir (4-MA-PPy) 2, that is, 'Ii · (4-H〇-PPy) and 2 , 6-A-ten-butyl_4_methylphenol (hereinafter referred to as bhT) O.lmg (acac) 6 3.2 mg (0.1 mmo 1) 21 OX 297 mm) The paper size applies to the Chinese National Standard (CNS) a4 specifications (-239 584661 A7 _B7___ V. Description of the invention (237) Under argon flow, dissolve in 10 ml of dehydrated THF, then add 81.0 mg (0.8 mmol) of triethylammonium and 41.8 mg of methacrylic acid chloride (( Please read the precautions on the back before filling in this page) 0.4mmol), and stir at room temperature for 2 hours. After adding 50ml of water to the reaction solution, extract with chloroform, and wash with saturated brine and distilled water. The organic layer was After drying and concentrating magnesium sulfate, it was purified by gel column chromatography (silica gel, methanol: chloroform = 2 · 98, volume ratio), and then recrystallized from hexane / chloroform to obtain the target substance Ir (4-MA -PPy) 2 (8 (^ (:) 65.31112 yellow crystals (yield 85%). The measurement was performed by 1H-NMR, CHN elemental analysis, 0'H-NMR (DMSO-de ^ ppm) δ; 8.38 (d, 2H, J = 5.7Hz) 8.15 (d, 2H, J = 8.6Hz), 7 · 9 5 (m, 2 Η), one ―... '---------— _______ 7.78 (d, 2H, J = 8.9Hz), 7 _ 3 9 (m, 2 Η), 6.61 (dd, 2H, J = 8.4, 2.4 Hz), 6.0 9 (s > 2 Η), 5.76 (s, 2H), Intellectual Property Office of the Ministry of Economic Affairs Employee Consumer Cooperatives printed 5.71 (d, 2H, J = 2.4Hz), 5.27 (s, 1H), 1.86 (s, 3H), 1 · 7 3 (s, 3 H).

Elementary analysis Calcd: C 5 4 · 7 5, H 4 · 〇 7, N 3. 6 5 0

Found: C 54 · 68, Η 4.13, N 3.61. This paper size is suitable for towels and household materials (CNS) Λ4 specification (· 27 ^ 297 mm) -240- 584661 A7 B7 V. Description of the invention (238)

Ir (4-HO-PPy) 2 (acac: CH ^ I 3 2 H9C = C—C—Cl 2 II ο

Triethylamine-THF

Ir (4-MA-PPy) 2 (acac) (Please read the “Notes on the back” and fill in the 4 items. Packing-: Write this page) Printed by the Employees ’Cooperative of the Intellectual Property Office of the Ministry of Economic Affairs [Example 76] Polymerizable compound: iridium (III) bis (2- (4- (2-methacryloxy) ethyllimyl m-group) benzene cover—) oripidine diester) (acetamidine acetone) (hereinafter abbreviated The synthesis of Ii. (4-MOI-PPy) 2 (acac) was shown in the following reaction steps. Ii. (4-MOI-PPy) 2 (acac) was synthesized. That is, Ir (4-MOI-PPy) 2 (acac) was synthesized as the intermediate of Example 75. H〇-PPy) 2 63.2 mg (0.1 mmol), BHT 0.2 mg, dibutyltin (IV) laurate (hereinafter referred to as DBTL) 1.3 mg was dissolved in 10 ml of dehydrated THF under a nitrogen stream, and then methacrylic acid was added Ethyl isocyanate (MOI) (trade name "Karens MoI", manufactured by Showa Denko Corporation) 6 2 · 0 mg (0 · 4 mm ο 1), and then stirred at 50 ° C for 1 hour. In the reaction solution After adding 50 m 1 of water, it was extracted with chloroform and washed with saturated brine and distilled water. The organic layer was sized with sulfuric acid. This paper is in accordance with the Chinese National Standard (CNS) A4 specification (210X 297 public ^ 7 -241-584661 A7). _______ _B7 _ 15. Description of the invention (239) After drying and concentrating the money, it is purified by gel column chromatography (silica gel, methanol: chloroform 2 5:95, volume ratio), and then recrystallized from hexane / chloroform to obtain the target substance. Ir (4-M0I-PPy) 2 (acac) 73.5 mg of yellow crystals (yield 78%). The measurement was performed by 1H-NMR and CHN elemental analysis. IH-NMR (DMSO-de5 ppm) δ; 8.37 (d, 2H, J = 5.9 Hz), 8.1 (d, 2H, J = 7.8 Hz), 7.93 (dd '2H' 1 = 8. 0'8 · 〇Hz), 7.70 (d, 2H, J = 8.6 Hz), 7 · 6 4 (t, 2 H), 7.4 (dd, 2H, J = 6.3, 6.3 Hz), 6.56 (dd, 2H, J = 8.2, 2.3 Hz), ~ ^ 5.7-5.6 (m, 4H), ~ 5 · 2 6 (s, 1 H), 4.06 (t, 4H, J = 5.4), 3 · 3 (m, 4 H j overwrapped with H 2 0), 1. 8 5 (s, 6 H), 1 · 7 3 (s, 6 H).

Elementary analysis Calcd: C 5 2 · 2 8, H 4.39, N 5.95.

Found: C 52 · 22, Η 4.47, N 5.86. This paper ruler uses the Chinese National Standard Multiplication (CNS) A4 specification (2) 0X 297 cm. (Please read the precautions on the back before filling this page) ----- ^ Approve the clothes.

Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, 1T 584661 A7 B7 V. Description of Invention (24 (D) H3CY < ^ CH3

Ir (4-HO-PPy) 2 (acac) ch3 I h2c = c-c-o ~ (ch2) 2 ~ nco ο

MOI

DBTL, BHT THF

Ir (4-MOI-PPy) 2 (acac) [Example 77] Polymerizable compound: iridium (III) bis (2: (4- (4-vinylbenzyloxy) phenyl) pyridine diester) ( Acetylacetone) (hereinafter referred to as Ii · (4-ST-PPy) 2 (acac) Synthesis (Please read the note on the back 4 • Items and then fill in. Loading — write this page) Synthesis as shown in the following reaction steps Ir (4-ST-PPy) 2 (acac) ° That is, Ii of Example 75 intermediate (4-H0-PPy) 2 63.2 mg (0.1 mmol), BHTO. 2 mg, potassium carbonate 1 38.2nig (1.0 mmol) was dissolved in 10 ml of dehydrated DMF under a nitrogen stream, and then 61.0 mg ((h4 mmol) of 4-vinylbenzyl chloride) was added, followed by stirring at 80 ° C for 6 hours. After adding 50 ml of water to the reaction solution, It was extracted with chloroform and washed with saturated brine and distilled water. The organic layer was dried over magnesium sulfate and concentrated, and then purified by column chromatography (silica gel, methanol: chloroform = 5: 95, volume ratio). Applicable to China National Standard (CRS) Λ4 specification (printed by the Consumers' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs -243- 584661 A7 B7 V. Description of the invention (24 is after recrystallization with hexane / chloroform Ir (4-ST-PPy) 2 (acac) 62.2mg of yellow crystals (yield 72%). The measurement is based on 1H- (Please read the notes on the back before filling this page) NMR and CHN elemental analysis 'H-NMR (DMSO-de ^ ppm) 5; 8.3 7 (d, 2H, J = 5.9 Hz), 8.13 (d, 2H, J = 8.4 Hz), 8.0 — 7_9 (m, 2H), 7.75 (d, 2H, J = 8.9 Hz), 7.5-7. 3 (m, 10H), 6 · 7 3 (m, 2 H), 6.59 (dd, 2H, J = 8.2, 2.4 Hz) , 5.88 (d, 2H, J = 17.8Hz), 5.73 (d, 2H, J = 2.4Hz), _____ 5 · 3 — 5 · 2 (m, 7 H), 1 · 7 8 (s, 3 H) .

Elemental.y analysis Calcd: C 6 2. 5 5, H 4.55, N 3.24. Bureau of Intellectual Property, Ministry of Economic Affairs

Found: C 6 2. 5 8 J H 4.65, N 3.20. This paper size applies Chinese National Standard (CNS) Λ4 specification (210X 297 mm) -244- 584661 A7 B7 V. Description of the invention (242) Η ,,

HO .CH,

Ir (4-HO-PPy) 2 (acac:

OH H2C = CH ~~ ^ y-CH2-Cl K, COq (Please read the notes on the back first

DMF

TrM'qT-PPyl ^ Lacac)

CH = CH, I # Refilling and loading-: Write this page) [Example 78] Polymerizable compound: 1m · (4-MA-PPy) 2 (acac) The second synthesis method (1) As shown in the following reaction steps, 2- (4-methacryloxyphenyl) pyridine (hereinafter, referred to as 4-MA-PPy) was synthesized. That is, 3.42 g (20.0 mmol) of 4-H0-PPy of the intermediate of Example 75 was dissolved in 20 ml of dehydrated dichloromethane under an argon flow, and 6.07 g (60.0 mmol) of triethylamine was added. Acrylic chloride 3.14g (30.0mni0i) was dripped into it over 1 hour, and it stirred at room temperature for 2 hours. After adding 100 ml of water to the reaction solution, it was extracted with chloroform and washed with saturated brine and distilled water. The organic layer was dried and concentrated with magnesium sulfate, and then refined by gel column chromatography (silica gel, chloroform), and then hexane / chloroform was used. This paper is in accordance with the Chinese National Standard (CNS) Λ4 specification (210X 297 mm). Economic Printed by the Ministry of Intellectual Property Bureau, S-Consumer Cooperative, -245- 584661 A7 B7 V. Description of the invention (243) After recrystallization, 4.16 g of 4-MA-PPy of the target substance was obtained as colorless crystals (yield 87%). The measurement was performed by 1H-NMR and CHN elemental analysis. ^ H- NMR (CDCI3, ppm) ό *; 8.63 (d, lH, J = 4.9Hz), 7.98 (d, 2H, J = 8.6Hz), 7 · 5- 7.6 (m, 2H), 7 · 2 -7.1 (m, 3H), 6.0 (s, 1H), 5.53 (s, 1h), 1.83 (s, 3 H).

Elementary analysis Calcd: C 75 · 30, Η 5.48, N 5.85.

Found: C 75.26, H 5.53, N 5 · 7 9.

(2) As shown in the following reaction steps, a bis (#-chloro_) tetra (2- (4-methacryloxyphenyl) pyridine) diiridium (II-nuclear complex) is synthesized. (IIi) (hereinafter, referred to as [Ii. (4-MA-PPy) 2C1] 2). That is, ‘4-MA-PPy 丨 .20g (5.0mmol) and sodium hexachloroiridium (Πι) sodium hydrate! .00g dissolved in 2-ethoxyethanol: water = 3: 丄 (batch of clothing-(Please read the precautions on the back before filling out this page) Order im Printed by the 8th Ministry of Economic Affairs Intellectual Property Bureau Paper scale S 11¾: County (CNsyA4ii5 ^ (210X 297 ^ 1) -246- 584661 A7 B7 V. Description of invention (244) (Please read the precautions on the back before filling this page) Volume ratio) mixed solvent In 40ml, argon was blown for 30 minutes, and then stirred under reflux for 6 hours. The resulting precipitate was filtered, washed with ethanol and a small amount of acetone, and dried under vacuum for 5 hours to obtain the target substance [11 '( 4-MA-PPy) 2C1] 2 0.87 g of yellow powder (82% yield). The measurement was performed by 'H-NMR (DMSO-de »ppm) (5; 9.64 (d, 2H) by j-NMR and CHN elemental analysis , J = 5.7 Hz), 9.37 (d, 2H, J = 5.7 Hz), 8.2 — 8.1 (m, 4H), 7 · 7 5 (m, 4 H), 7.6 — 7.5 (m, 8H), 6. 5 6 (m, 4 H), 5. 8 7 (d ^ 2 E = 2, AH z J i — 5.38 (d, 2H, J = 2.4 Hz), 6.〇9 (s, 2H), 6.03 ( s, 2H), 5.79 (s, 2H), 5.74 (s, 2H), 1. 8 9 (s, 6 H), 1. 8 7 (s, 6 H). Ministry of Economic Affairs Chi Property Office g (consumer cooperatives printed work

Elementary analysis Calcd: C 5 1 · 1 7, H 3-44, N 3.98.

Found: C 51 · 13, H 3.51, N 3.97. This paper size applies to Chinese National Standard (CNS) Λ4 specification (210 X 297 male f) -247-584661 A7 B7 V. Description of the invention (245)

2Na3IrCl6-nH20 2-Ethoxyethanol

[Ir (4-MA-PPy) 2Cl] 2 ^-(Please read the precautions on the back before filling this page)

, 1T (, synthetic Ii ·) 2 (acac) ° namely 'in [Ii. (4-MA-PPy) 2C1] 2 281.7 nig (〇.2minol), sodium carbonate 2 1 2.0 mg (2.0 mmo 1) After adding dehydrated 20ml DMF and 2,4-pentanedione 600.0mg (0.6mmmol) under a clockwise stream, stir at 80 ° C for 2 hours, and add loomi water to the reaction solution. , Extracted with chloroform, and washed with saturated brine and distilled water. The organic layer was dried and concentrated with magnesium sulfate, and then purified by column chromatography (silica gel, methanol: chloroform = 2: 98, volume ratio), and then recrystallized with hexane / chloroform to obtain 11 · of the target substance. (4-MA-PP y) 2 (acac) 2 2 1 · 1 mg yellow crystals (yield 72%). The measurement was performed by 1H-NMR and CHN elemental analysis. It was confirmed that the compound was the same as the compound synthesized in Example 75. This paper size applies to China National Standard (CNS) 8-4 specifications (21 〇χ 297 mm) 4 Printed by Xiao Gong Consumer Cooperative, Intellectual Property Office of the Ministry of Economic Affairs -248, 584661 A7 B7 V. Description of Invention (246)

c 2 H

0 o 1 I 3 CJ " o 3 C-Jno HI Hi CIC CIC

c = o c = o I I o o [Ir (4-MA-PPy) 2Cl] 2

Η 3C 3-Η = Η II CIC CIC

CH 2 + 3 CHη: C 3 Η

Ir (4-MA-PPy) 2 (acac) ---------- (Please read the precautions on the back before filling out this page) Order printed by W Industry Consumer Cooperatives, Intellectual Property Bureau, Ministry of Economic Affairs [Example 79] The synthesis of N-ethoxylated azole-h. (4-MA-PPy) 2 (acac ^ copolymer (hereinafter referred to as VCz-co-Ir (4-MA-PPy) 2 (acac)) will have The unit of light-emitting function Ι · (4-MA-PPy) 2 (acac) ^ The unit with hole-transporting function N_vinylcarbazole is synthesized to contain a copolymer containing a light-emitting material. The N-vinyl fluorene card 11 sits 9 6 6 mg (5.0 mm ο 1), 11 · (4-MA-PP y) 2 (acac) 38.4mg (0.05mmol), AI BN 8.2mg (0.0 5 mmo 1) dissolved in dehydrated toluene 2 5 m 1 Then, blow fluorine for 1 hour in argon. This solution was heated to 80 ° C, the polymerization reaction was started, and stirred for § hours. After cooling, the reaction solution was dropped into 250 ml of toluene to precipitate the polymer, and Recovered by filtration method. Then, the recovered polymer is dissolved in the paper. The size of the paper is applicable to the Chinese National Standard (CNS) A4 specification (21〇X 297). -249- 584661 A7 __ B7 V. Description of the invention (247) in 25ml chloroform Medium This solution was dropped into 250ml of toluene, and it was reprecipitated and refined, and then vacuum dried at 60 ° C for 12 hours to obtain the standard. The VCz-co-Ir (4-MA-PPy) 2 ( acac) 755 mg. The recovery rate, GPC measurement results, and Ir complex content obtained by ICP elemental analysis are shown in Table 9. Ir (4-MA-PPy) 2 (acac) is a difunctional monomer, so it is compatible with N- When compared with vinylcarbazole, its amount is very small, so the degree of crosslinking is low, and insoluble matter cannot be formed. [Example 8 0 to 8 1] Ir (4-MA-PPy) 2 (acac) was separately implemented. Copolymers were synthesized in the same manner as in Example 82 except that the polymerizable compounds prepared in Examples 79 to 90 were replaced with isomolar numbers. The recovery rate and GPC measurement results are shown in Table 9. Table 9 Example polymerization GPC determination of Ir complex (%) Mη Mw Mw / Mn content (mol%) 79 VCz-co-Ir (4-MA- PPy): (acac) 75 7100 29100 4.10 1.09 80 VCz-co-Ir (4-M0I_PPyMacac) 72 6500 28300 4.35 1.07 81 VCz-co-Ir (4-ST-PPy) 2 (acac) 77 6600 30600 4.64 1.06 Mn: number average molecular weight, Mw: weight average molecular weight [Example 82 ~ 84] Organic luminescent element Production and evaluation This paper size applies Chinese National Standard (CNS) Λ4 specification (210X 297 mm) (Please read the precautions on the back before filling out this page) • Packing · Printed by the Intellectual Property Bureau of the Ministry of Economic Affairs and Consumer Cooperatives -250 -584661 A7 B7 V. Description of the invention (248) Using the light-emitting materials shown in Table 10, an organic light-emitting device was manufactured in the same manner as in Examples 57 to 62, and the light-emitting brightness was measured. As a result, when the light emission starting voltage, the initial brightness at 15 V, and the subsequent continuous light emission at a fixed voltage of 15 V, the brightness after 2000 hours was as inconceivable (4 averages of the elements obtained using each light-emitting material) . Comparative Example 4 Poly (N-vinylcarbazole) (manufactured by Tokyo Chemical Industry Co., Ltd.) was used at a hole transporting material of 195 mg, and the light-emitting material was a known method (s. Lamansky et al., Inorganic Chemistry, 40 , 1704 (2〇〇i)) Synthetic formula -------- ^. Zhong Yi-(Please read the precautions on the back before filling in this page) h3c ^^ ch3 ——- 〇——Ό -N /

Order--1 * ---- Printed by 5-M (446-butylphenyl) -1,3,4-oxadiazole (? 80) (Tokyo) 9 · 0 mg of Kasei Kogyo Co., Ltd. was dissolved in 2970 mg of chloroform (manufactured by Wako Pure Chemical Industries, Ltd.), and the resulting solution was filtered through a filter with a pore size of 0.2 // 1Ή. Examples 8 5 to 8 7 An organic light-emitting device was fabricated under the same conditions, and its light emission brightness was measured. As a result, the light emission starting voltage, the initial brightness at 15V, and the subsequent continuous light emission at 15V are shown in Table 10. The brightness after 200 hours is as shown in Table 10. (The national paper standard (CN'S) applies to each paper size.) A4 specification (210X 297 mm) -251-584661 A7 _______ ^ _ B7 V. Description of the invention (249) 4 averages of components obtained from optical materials). Table 10 Example Light emission starting voltage (V) _ 10V Brightness (Cd / m2) 200 hours after initial stage 85 5 370 330 86 6 330 290 87 3 410 350 Comparative example 4 7 360 120 (Please read the precautions on the back first (Fill in this page) Printed by the Ministry of Economic Affairs, Intellectual Property Bureau, M Industrial Consumption Cooperative, and the industry bachelor's property-] --______ Using the polymer light emitting material of the present invention can effectively make the energy of the excited triplet state more efficient Converts light emission, and can provide organic light-emitting elements with high brightness and durability. In addition, when the non-crosslinked and / or crosslinked polymer light-emitting material prepared by using the polymerizable light-emitting compound of the present invention is formed into a film, an organic light-emitting device having good processability can be provided. In particular, the polymerizable compound represented by formula (C-1), formula (D-1), formula (E-1), formula (F-1), or formula (G-1) is a novel one containing an iridium complex part When a polymer is used as a light-emitting material of an organic light-emitting device, it can emit light efficiently from an excited triplet state, and can provide an organic light-emitting device with excellent stability and large area and suitable for mass production. This paper size applies to China National Standard (CNS) A4 (210X 297mm) .252

Claims (1)

584661 A8 B8 C8 D8 々 、 Patent Application No. 9 1 1 1 3 3 9 1 Chinese Patent Application Amendment Amendment December 4, 1992 Amendment 1. A polymer-based luminescent material whose luminous mechanism is It is formed by the migration of the excited triplet state of the electron energy level to the ground state, and the luminous part is a metal complex structure of iridium or lead with a metal atom or an organometal structure, wherein the metal atom is a A pyridine skeleton and / or a pyrimidine skeleton and / or a quinoline skeleton. The coordination bond formed with the polymer is combined with the polymer, or contains at least one selected from polymerizable light-emitting compounds ((Γ-ΐ), (Dl ), (El), (F-1) and (G-1) polymerizable composition of polymerizable light-emitting compound polymerized polymer compound, (C-1 [wherein Ac, Bc, Cc in At least one is a substituent having a polymerizable functional group, and the remaining residues in Ae, Be, and Ce are each independently hydrogen atom, halogen atom, nitro group, amine group, sulfonic acid group, sulfonic acid ester group, or Organic groups having 1 to 20 carbon atoms having a hetero atom; R1 to R21 are Since independence clothes paper scale applicable Chinese National Standard (CNS) A4 size (21〇 X 297 mm) (please read the Notes on the back of the back and then fill the page) 10 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs 584661 A8 B8 C8 D8 ^, patent application scope hydrogen atom, halogen atom, nitro group, amine group, sulfonate group, sulfonate group or carbon number which may have hetero atom Organic group 1 to 20] γ 1D (D-1) -------- 0 ^-(Please read the precautions on the back of the page before filling out this page) [In the formula, at least one of X1D, YID, z1D is a polymerizable functional group Substituents, the other residues in XID, Y] D, Z] D are each independently hydrogen atom or an organic group having 1 to 20 carbon atoms which may have a hetero atom; R] to R are each independent hydrogen atom , Halogen atom, nitro group, amine group, sulfonate group, sulfonate group, or organic group having 1 to 20 carbon atoms which may have a heteroatom], 1T Printed by XE T, ΙΕ Rc (E-1) [In the formula, XE is a substituent having a polymerizable functional group, and RIE to R3E are each paper size. Applicable to China National Standard (dNS) A4 (210 X 297 mm) γ 1F R 11 584661 A8 B8 C8 D8 々, patent applications range from independent hydrogen atoms, halogen atoms or organic groups with 1 to 20 carbon atoms that may have heteroatoms; R4 to R19 are each independent hydrogen atom, halogen atom, nitro , Amine group, sulfonic acid group, sulfonic acid ester group or organic group having 1 to 20 carbon atoms which may have a hetero atom] (F-1)-(Please read the precautions on the back before filling this page) Order.! Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Online Economics [where, at least one of X1F, YIF, Z1F is a substituent with a polymerizable functional group, and the remaining residues in x1F, Y1F, Z1F are independent of each other. A hydrogen atom, a halogen atom, or an organic group having 1 to 20 carbon atoms which may have a hetero atom; R1 to R "are each independently a hydrogen atom, a halogen atom, a nitro group, an amine group, a sulfonic acid group, a sulfonic acid ester group, or May have an organic radical with a carbon number of 1 to 20] This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 584661 ABCD patent application scope RJ RJ RR IT (Gl) [In the formula, L is a monovalent anionic two-segment coordination group, which is a substituent having a polymerizable functional group; R1 to R7 are each independently hydrogen atom, halogen atom, nitro group, An amine group, a sulfonic acid group, a sulfonic acid ester group, or an organic group having 1 to 20 carbon atoms which may have a hetero atom]. 2. For example, the polymer-based light-emitting material in the scope of the patent application, wherein the luminous part described above is formed by metal atoms bonded to more than one part of the polymer. 3. For polymer-based light-emitting materials in the scope of patent application No. 2, ^-(please read the notes on the back of # before filling out this page), 1T printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs, and the preface luminous The bonds in the sex moiety are covalent bonds and / or coordination bonds. 4. For the polymer-based light-emitting material in the scope of the first patent application, wherein the transition metal atom mentioned above is the transition metal atom in the sixth cycle of the periodic table. 5. The polymer-based light-emitting material according to item 1 of the scope of patent application, wherein the foregoing metal atom is a rare earth metal atom. 6. The polymer-based luminescent material according to item 1 of the scope of patent application, wherein the coordination bond between the metal atom and the nitrogen atom of the polymer described above is formed by the phenylpyridine skeleton on the polymer side. 7. For polymer-based light-emitting materials in the scope of the first patent application, the paper scale of the line sheet is applicable to the Chinese National Standard (CNS) A4 (210X297 mm) -4 584661 A8 B8 C8 D8 The coordination bond between the aforementioned metal atom and the nitrogen atom of the polymer is formed by the benzoxanthin pyridine skeleton on the polymer side. 8. If the polymer-based luminescent material in the first item of the patent application scope, (please read the note on the back of # before filling this page) It is obtained by polymerizing a polymerizable composition containing at least one kind of luminescent compound. By. 9. The polymer-based light-emitting material according to item 8 of the patent application scope, wherein the 'light-emitting compound is a polymerizable light-emitting compound. 10. The polymer-based light-emitting material according to item 8 of the scope of patent application, wherein the polymer after the polymerization is a non-crosslinked polymer. 11. For example, a polymer-based light emitting material according to item 9 of the scope of patent application, wherein at least one of the polymerizable light-emitting compounds is a cross-linked polymerizable light-emitting compound having two or more polymerizable functional groups, and the polymer after polymerization It is a crosslinked polymer. 12. The polymer-based luminescent material according to item 8 of the application, wherein the 'polymerizable composition contains a polymerizable compound other than at least one luminescent compound. 13. For example, the polymer-based light-emitting materials in the scope of application for patent No. 12 are printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs, where at least one of the polymerizable compounds other than the luminescent compound is a polymerizable electron-transporting compound. 14. For example, a polymer-based light emitting material according to item 8 of the scope of patent application, wherein the polymerizable composition contains at least one polymerizable compound other than the light-emitting compound, and at least one of the polymerizable compounds has two Crosslinkable polymerizable compound of the above polymerizable functional group. 15. For the polymer-based light-emitting materials in the first patent application scope, the paper size applies to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 584661 A8 B8 C8 D8 6. Among the scope of patent application, the luminescent department The part formed by a metal complex structure or an organometallic structure is one containing a nitrogen atom. 16. For example, the polymer-based light-emitting material of the first patent application scope, wherein the complex-forming structure forming part of the light-emitting part contains a fluorescein D skeleton, a pyrimidine skeleton, and / or a perylene skeleton. 17. A luminescent composition, characterized in that it contains a polymer light-emitting material according to any one of claims 1 to 16 in an application patent range of 10 to 90 wt%, and a carrier of 90 to 10 wt%. Sexual polymer compounds. 18. For example, the luminous composition of item 17 in the scope of patent application, wherein the carrier molecular compound is a hole-transporting polymer compound. 19, for example, the luminous composition of item 17 of the scope of patent application, Among them, the carrier-transporting polymer compound is an electron-transporting polymer compound-(please read the precautions on the back of the page before filling out this page) and order it from the Intellectual Property Bureau of the Ministry of Economic Affairs's Consumer Cooperatives. It is characterized by containing a polymer light-emitting material according to any one of claims 1 to 16 and a carrier-transporting low-molecular compound. 2 1. If the luminous composition of item 20 of the patent application, among which, the carrier-transporting low-molecular compound is a hole-transporting low-molecular compound 022, such as the luminous composition of the 20th application patent scope, Among them, the carrier-transporting low-molecular compound is an electron-transporting low-molecular compound containing 23 kinds of light-emitting material layers for organic light-emitting elements, which are made of thread-bound paper and are applicable to Chinese National Standard (CNS) A4 specifications (210 ×: 297 mm) 6-584661 6. Scope of patent application The polymer-based light-emitting materials in the scope of patent application No. 1 are available. Printed by the Consumers' Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs 24 'If a light-emitting material layer containing organic light-emitting elements is included in the scope of patent application No. 23', its characteristics are obtained by forming a polymer-based light-emitting material under scope of patent application through film formation By. 25 'If the light emitting material layer for an organic light emitting element is contained in the scope of the patent application No. 24, wherein the polymer light emitting material is a non-crosslinked polymer. 26. For example, a light-emitting material layer for an organic light-emitting device containing the light-emitting material layer for organic light-emitting element No. 24, wherein the polymer-based light-emitting material is obtained by polymerizing a polymerizable composition containing at least one kind of light-emitting compound after being formed into a film. 27. For example, the light emitting material layer for an organic light emitting element in the scope of the patent application No. 26, wherein the polymer light emitting material is a non-crosslinked polymer. 28. If the light-emitting material layer for organic light-emitting elements is contained in item 26 of the patent application, wherein the polymer-based light-emitting material is a cross-linked polymer, 29, an organic light-emitting device, which is characterized by using the The polymer light-emitting material according to any one of items 1 to 16. 30. If you apply for organic light-emitting elements in item 29 of the S 靑 patent, you should apply both sides of the light-emitting layer obtained from the polymer-based light-emitting material of any of the items 1 to 16 in the patent application and // Or it is obtained by coating a film-type electron transport layer and / or a film-type hole transport layer on one side and then forming a film. This paper size applies Chinese National Standard (CNS) M specifications (210 × 297 mm) (Please read the precautions on the back of the policy before filling out this page)