TWI618710B - Organic metal compound, and organic light-emitting device employing the same - Google Patents

Abstract

The invention discloses an organometallic compound and an organic light-emitting device comprising the same. The organometallic compound has a structure as shown in the formula (I):

Wherein R ¹ , R ² , R ³ , and R ⁴ are each independently and independently the same or different substituents, and include hydrogen, fluorine, trifluoromethyl, cyano, or nitro, and L is acetamidine. Acetone ligand, pyridine-α-carboxylic acid ligand, 2-phenylcyclo-1,3,4-oxadiazole ligand, 5-(2-pyridine)-3-trifluoromethyl-1, 2,4-triazole ligand, 5-(phenylene)-1,2,3-triazole ligand, N,N'-diisopropylbenzhydrazide ligand, or 5-(2 -pyridine)-1,2,3,4-tetrazole ligand.

Description

Organometallic compound, and organic light-emitting device comprising the same

The present invention relates to an organometallic compound and an organic light-emitting device comprising the same, and more particularly to an organometallic phosphorescent compound and an organic electroluminescent device comprising the same.

An organic electroluminescent device, also known as an organic light-emitting diode (OLED), is a light-emitting diode (LED) having an organic layer as an active layer. Due to the advantages of low voltage operation, high brightness, light weight, wide viewing angle, and high contrast value, organic electroluminescent devices have been gradually used in flat panel displays in recent years. Unlike the liquid crystal display, the organic light-emitting diode array included in the organic electroluminescent display has self-luminous characteristics, so that no backlight is required.

In general, an organic light emitting diode device includes a pair of electrodes, and an organic luminescent dielectric layer between the electrodes. Luminescence is caused by the following phenomenon. When an electric field is applied to the two electrodes, the cathode emits electrons to the organic luminescent medium layer, and the anode emits holes to the organic luminescent medium layer. When electrons and holes are combined in the organic light-emitting medium layer, excitons are generated. Recombination of electrons and holes With the glow.

Depending on the spin state of the hole and the electron, the excitons generated by the recombination of the hole and the electron may have a spin state of a triplet or a singlet (singlet). The luminescence generated by a singlet exciton is fluorescence, and the luminescence produced by a triplet exciton is phosphorescence. The luminous efficiency of phosphorescence is three times that of fluorescent light. Therefore, it is very important to develop a highly efficient phosphorescent material to improve the luminous efficiency of the organic light emitting diode element.

At present, the organic light-emitting diode element light-emitting unit material is mainly composed of small molecular materials, because the small-molecule organic light-emitting diode element has high molecular organic light-emitting diode element (PLED) regardless of efficiency, brightness and lifetime. A lot. Today, small-molecule organic light-emitting diode devices are not processed by spin coating or inkjet printing (Pink), but mainly by vapor deposition. However, the vacuum process equipment used for the evaporation method is costly, and only 5% of the organic light-emitting material is plated on the substrate, and 95% of the organic light-emitting material is wasted on the cavity wall, so that the organic light-emitting diode The manufacturing cost of components is high. Therefore, a wet process (including spin coating, or blade coating) is proposed for the process of small-molecule organic light-emitting diode elements to reduce equipment cost and greatly enhance organic light-emitting materials. Usage rate.

Therefore, the development of soluble phosphorescent materials suitable for wet processes is the most critical material, and is an important issue for organic light-emitting diode technology.

According to an embodiment of the present invention, the present invention provides an organometallic compound which is substituted by strong tensile electron properties such as fluorine (F), trifluoromethyl (CF ₃ ), cyano (CN), and nitro (NO ₂ ). The 4-phenylthieno[3,2-c]pyridine ligand structure is introduced, in addition to making the material have good solubility (we can use wet process) Forming an organic light-emitting diode element) can lower the highest occupied molecular orbital (HOMO) energy level of the material. In addition, the organometallic compound of the present invention is further combined with a wide bandgap ancillary ligand, which can shift the luminescent color of the material from orange light blue to green light range (luminous wavelength At 500-560 nm). Furthermore, the organometallic compound of the present invention can be applied to an organic light-emitting device as a material of a light-emitting unit (for example, a phosphorescent dopant of a light-emitting layer) to enhance the element efficiency of the organic electroluminescent device.

According to an embodiment of the present invention, the present invention discloses an organometallic compound having a structure as shown in formula (I):

Wherein R ¹ , R ² , R ³ , and R ⁴ are each independently and independently the same or different substituents, and include hydrogen, fluorine, trifluoromethyl group, cyano group, or nitrate Nitro group, and L is an acetyl acetone ligand, a pyridine-α-carboxylic acid ligand, 2-phenylcyclo-1,3,4-oxadiazole ( 2-phenyl-1,3,4-oxadiazole) Ligand, 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl)-3- Trifluoromethyl-1,2,4-triazole) ligand, 5-(phenylene)-1,2,3-triazole (5-phenyl-1,2,3-triazole) ligand, N,N' - N,N'-diisopropyl benzamidine ligand, or 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl)-1 , 2,3,4-tetrazole), and when one of R ¹ , R ² , R ³ , and R ⁴ is fluorine and the other three are hydrogen, the L system is 2-benzene ring-1,3 , 4-phenyl-1,3,4-oxadiazole ligand, 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-( 2-pyridyl)-3-trifluoromethyl-1,2,4-triazole) ligand, 5-(phenylene)-1,2,3-triazole (5-phenyl-1,2,3-triazole) N,N'-diisopropylbenzhydrazide (N,N'-diisopropyl b An enzamidine, dipba) ligand, or a 5-(2-pyridyl)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole) ligand.

According to another embodiment of the present invention, there is provided an organic light-emitting device comprising: a pair of electrodes; and a light-emitting unit disposed between the pair of electrodes, wherein the light-emitting unit comprises the organometallic compound described above. In addition, the organic light emitting unit may include a light emitting layer, wherein the light emitting layer comprises a host material and a doping material, and the doping material is the above organometallic compound to cause the light emitting layer to emit green light.

10‧‧‧Organic electroluminescent device

12‧‧‧Base

14‧‧‧ lower electrode

16‧‧‧Lighting unit

18‧‧‧Upper electrode

1 is a cross-sectional structural view of an organic electroluminescent device according to a preferred embodiment of the present invention.

The numbers and symbols corresponding to the different features are generally considered to be corresponding parts unless otherwise noted. The features illustrated are clearly labeled in the relevant embodiments and are not necessarily drawn to scale.

The following is a detailed description of the embodiments and examples accompanying the drawings, which are the basis of the present invention. In the drawings, the shape or thickness of the embodiment may be expanded and simplified or conveniently indicated. Furthermore, the components of the drawings will be described separately, and it is noted that the components not shown or described in the drawings are known to those of ordinary skill in the art and, in addition, The examples are merely illustrative of specific ways of using the invention and are not intended to limit the invention.

Organometallic compound

According to an embodiment of the present invention, the present invention discloses an organometallic compound having a structure as shown in the formula (I):

Wherein R ¹ , R ² , R ³ , and R ⁴ are each independently and independently the same or different substituents, and include hydrogen, fluorine, trifluoromethyl group, cyano group, or nitrate Nitro group, and the group L is an acetyl acetone ligand, a pyridine-α-carboxylic acid ligand, a 2-benzene ring-1,3,4-oxa 2-phenyl-1,3,4-oxadiazole ligand, 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl)- 3-trifluoromethyl-1,2,4-triazole) ligand, 5-(phenylene)-1,2,3-triazole (5-phenyl-1,2,3-triazole) ligand, N, N'-diisopropylcpropyl benzamidine ligand, or 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl) a -1,2,3,4-tetrazole) ligand, and when one of R ¹ , R ² , R ³ , and R ⁴ is fluorine and the other three are hydrogen, the L system is 2-benzene ring-1 , 3,4-oxadiazole (2-phenyl-1,3,4-oxadiazole) ligand, 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5 -(2-pyridyl)-3-trifluoromethyl-1,2,4-triazole) Ligand, 5-(phenylene)-1,2,3-triazole (5-phenyl-1,2,3-triazole ) ligand, N, N'-diisopropyl benzamidine (N, N'-diisopr Opyl benzamidine, dipba) ligand, or 5-(2-pyridyl)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole) ligand . Here, the group L refers to a pair of bidentate ligands which are derived from acetyl acetone, pyridine-α-carboxylic acid, 2-benzene ring-1,3. , 4-phenyl-1,3,4-oxadiazole, 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl) )-3-trifluoromethyl-1,2,4-triazole), 5-(phenylene)-1,2,3-triazole (5-phenyl-1,2,3-triazole), N,N'-di N,N'-diisopropyl benzamidine, or 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3, 4-tetrazole) derived from.

According to another embodiment of the present invention, the present invention has the organometallic compound of the formula (I), wherein when one of R ¹ , R ² , R ³ , and R ⁴ is fluorine and the other three are hydrogen, the organometallic compound Can be , ,or Wherein L ¹ is a 2-phenyl-1,3,4-oxadiazole ligand, 5-(2-pyridine)-3-trifluoromethyl 5-(2-pyridyl)-3-trifluoromethyl-1,2,4-triazole ligand, 5-(phenylene)-1,2,3-triazole (5-phenyl-1,2,3-triazole) ligand, N,N'-diisopropyl benzamidine ligand, or 5-(2-pyridine) -1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole) ligand.

According to some embodiments of the present invention, the organometallic compound of the present invention may be ,or , where the definition of L is the same as above.

The organometallic compound of the present invention is synthesized by reacting a ruthenium chloride compound having a different electron-withdrawing substituent (for example, F, CF ₃ , CN, or NO ₂ ) with _2- thiphenethylamine under basic conditions. A guanamine compound having different electron withdrawing substituents. The intramolecular cyclization reaction is then carried out using POCl ₃ . Further, by dehydrogenation with activated carbon (Pd/C) containing palladium metal, a thienopyridine compound having a functionalized benzene ring can be obtained. This compound is then subjected to a complexation reaction with hydrated ruthenium chloride (IrCl ₃ ‧xH ₂ O(x≧1)) to obtain a dimeric complex. Finally, the dimeric complex compound is further subjected to a substitution reaction with a compound capable of forming a bidentate ligand to obtain an organometallic compound according to the present invention.

According to an embodiment of the invention, the organometallic compound may have A structure wherein R ¹ , R ² , R ³ , and R ^{4 have} the same meanings as defined above. The synthetic route of the organometallic compound is as follows:

According to an embodiment of the invention, the organometallic compound may have A structure wherein R ¹ , R ² , R ³ , and R ^{4 have} the same meanings as defined above. The synthetic route of the organometallic compound is as follows:

According to an embodiment of the invention, the organometallic compound may have A structure wherein R ¹ , R ² , R ³ , and R ^{4 have} the same meanings as defined above. The synthetic route of the organometallic compound is as follows:

According to an embodiment of the invention, the organometallic compound may have A structure wherein R ¹ , R ² , R ³ , and R ^{4 have} the same meanings as defined above. The synthetic route of the organometallic compound is as follows:

According to an embodiment of the invention, the organometallic compound may have A structure wherein R ¹ , R ² , R ³ , and R ^{4 have} the same meanings as defined above. The synthetic route of the organometallic compound is as follows:

According to an embodiment of the invention, the organometallic compound may have a structure wherein R ⁵ , R ⁶ , R ⁷ , and R ⁸ are each independently and independently the same or different substituents, and include hydrogen, fluorine, trifluoromethyl group, cyano group, or a nitro group, and when any of R ⁵ , R ⁶ , R ⁷ , and R ⁸ is hydrogen, the other is a trifluoromethyl group, a cyano group, or a nitrate Nitro group. The synthetic route of the organometallic compound is as follows:

According to an embodiment of the invention, the organometallic compound may have a structure wherein R ⁵ , R ⁶ , R ⁷ , and R ⁸ are each independently and independently the same or different substituents, and include hydrogen, fluorine, trifluoromethyl group, cyano group, or a nitro group, and when any of R ⁵ , R ⁶ , R ⁷ , and R ⁸ is hydrogen, the other is a trifluoromethyl group, a cyano group, or a nitrate Nitro group. The synthetic route of the organometallic compound is as follows:

The synthesis of the organometallic compound of the present invention will be described below by way of the following examples to further clarify the technical features of the present invention.

Example 1: Preparation of organometallic compound (I)

Compound 1 (2-(2-aminoethyl)thiophene, 1 equivalent) was placed in a 500 mL single-necked flask, 200 mL of water was added and the addition funnel was attached. Next, Compound 2 (1 equivalent) was added to the addition funnel, and the mixture was dropped into a reaction flask in an ice water bath (0 ° C) to gradually give a white solid. After the completion of the dropwise addition, stirring was continued for one hour, and then a 20% aqueous NaOH solution (1 equivalent) was added and stirred overnight. After filtration, a white solid product (compound 3) was obtained with a yield of 74%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze compound 3, and the obtained spectral information was as follows: ¹ H NMR (CDCl ₃ , 200 MHz) δ 8.13 (q, J = 6.6 Hz, 1H), 7.22 (dd, J = 7.4, 1.0 Hz, 1H) , 6.80~7.00 (m, 4H), 3.76 (q, J = 6.8 Hz, 2H), 3.15 (t, J = 6.8 Hz, 2H).

Next, Compound 3 (1 equivalent) was placed in a 250 mL round bottom flask, and toluene (toluene, 80 mL) was added. POCl ₃ (3 equivalents) was dropped into the reaction vial via an addition funnel in an ice water bath. After the completion of the dropwise addition, the ice water bath was removed and heated to an oil bath to reflux with toluene. After reacting for 2 hours, the reaction was neutralized with a saturated aqueous solution of sodium hydrogen carbonate (NaHCO ₃ ), and then extracted with ethyl acetate. After removal of water and concentration, compound 4 was obtained in a yield of 58%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze compound 4, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 7.51 (q, J = 6.6 Hz, 1H), 6.78 to 7.06 (m, 4H), 4.00 (t, J = 7.8 Hz, 2H), 2.96 (t, J = 8.6 Hz, 2H).

Next, compound 4 (1 equivalent) and Pd/C (weight ratio of Pd to C of 1:1, 10 wt% (based on the weight of compound 4)) were placed in a 250 mL reaction flask, and xylene was added. Heat to reflux. After 18 hours of reaction, the Pd/C was filtered off. The obtained filtrate was concentrated to give Compound 5 in a yield of 74%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze compound 5, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.57 (d, J = 5.6 Hz, 1H), 7.83 (d, J = 0.6 Hz, 1H), 7.63 (q, J = 6.6 Hz, 1H), 7.51 (d, J = 5.6 Hz, 1H), 7.26 to 7.32 (m, 1H), 7.01 to 7.11 (m, 2H).

Next, Compound 5 (2.2 equivalents) and hydrated ruthenium chloride compound (IrCl ₃ ‧ x H ₂ O (x ≧ 1), 1 equivalent) were placed in a 100 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 15) was added. (mL) and water (5 mL), heated to 140 °C. After 24 hours of reaction, a large amount of water was added and filtered to give a yellow solid product (Compound 6). The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze compound 6, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.95 (d, J = 6.2 Hz, 4H), 8.11 (m, 4H), 7.69 (d, J = 5.8 Hz, 4H), 7.08 (d, J = 6.6 Hz, 4H), 6.32~6.44 (m, 4H), 5.22 (dd, J = 8.8, 2.6 Hz, 4H).

Finally, compound 6 (1 equivalent), acetone acetone (acetyl, aac, 4 equivalents), and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL), heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give the organic metal compound (I) in a yield of 65%. The reaction formula of the above reaction is as follows:

The organometallic compound (I) was analyzed by nuclear magnetic resonance spectroscopy and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.34 (d, J = 6.4 Hz, 2H), 8.14 (dd, J = 5.8, 2.2 Hz, 2H), 7.74 (d, J = 6.6 Hz, 2H), 7.60 (d, J = 6.0 Hz, 2H), 6.33~6.45 (m, 2H), 5.67 (dd, J = 8.4, 2.2 Hz, 2H ), 5.24 (s, 1H), 1.78 (s, 6H).

Example 2: Preparation of organometallic compound (II)

Compound 1 (2-(2-aminoethyl)thiophene, 1 equivalent) was placed in a 500 mL single-necked flask, 200 mL of water was added and the addition funnel was attached. Next, Compound 7 (1 equivalent) was added to the addition funnel, and the mixture was dropped into a reaction flask in an ice water bath (0 ° C) to gradually give a white solid. After the completion of the dropwise addition, stirring was continued for one hour, and then a 20% aqueous NaOH solution (1 equivalent) was added and stirred overnight. After filtration, a white solid product (compound 8) was obtained in a yield of 90%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze compound 8, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 7.67 to 7.71 (m, 1H), 7.45 to 7.58 (m, 3H), 7.17 (dd, J = 5.2) , 1.2 Hz, 1H), 6.93~6.97 (m, 1H), 6.88 (d, J = 3.4 Hz, 1H), 5.90 (br, 1H), 3.75 (q, J = 6.6 Hz, 2H), 3.16 (t , J = 6.6 Hz, 2H).

Next, Compound 8 (1 equivalent) was placed in a 250 mL round bottom flask, and toluene (toluene, 80 mL) was added. POCl ₃ (3 equivalents) was dropped into the reaction vial via an addition funnel in an ice water bath. After the completion of the dropwise addition, the ice water bath was removed and heated to an oil bath to reflux with toluene. After reacting for 2 hours, the reaction was neutralized with a saturated aqueous solution of sodium hydrogen carbonate (NaHCO ₃ ), and then extracted with ethyl acetate. After removal of water and concentration, compound 9 was obtained in a yield of 52%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze compound 9, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 7.74 (d, J = 7.0 Hz, 1H), 7.48 to 7.63 (m, 2H), 7.39 (d, J = 6.6 Hz, 1H), 6.99 (d, J = 5.0 Hz, 1H), 6.54 (d, J = 5.2 Hz, 1H), 4.01 (t, J = 6.0 Hz, 2H), 2.98 (t, J = 8.4 Hz, 2H).

Next, compound 9 (1 equivalent) and Pd/C (weight ratio of Pd to C of 1:1, 10 wt% (based on the weight of compound 4)) were placed in a 250 mL reaction flask, and xylene was added. Heat to reflux. After 18 hours of reaction, the Pd/C was filtered off. The obtained filtrate was concentrated to give Compound 10 in a yield of 70%. The reaction formula of the above reaction is as follows:

The compound 10 was analyzed by NMR spectroscopy and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.58 (d, J = 5.4 Hz, 1H), 7.94 (d, J = 8.1 Hz, 2H), 7.67 ~7.82 (m, 3H), 7.42~7.54 (m, 2H).

Next, Compound 10 (2.2 equivalents) and cesium chloride hydrate compound (IrCl ₃ ‧ x H ₂ O (x ≧ 1), 1 equivalent) were placed in a 100 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 15) was added. (mL) and water (5 mL), heated to 140 °C. After 24 hours of reaction, a large amount of water was added and filtered to give a yellow solid product (Compound 11). The reaction formula of the above reaction is as follows:

Finally, compound 11 (1 equivalent), acetone acetone (acetyl, aac, 4 equivalents), and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL), heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (II). The reaction formula of the above reaction is as follows:

Example 3: Preparation of organometallic compound (III)

Compound 1 (2-(2-aminoethyl)thiophene, 1 equivalent) was placed in a 500 mL single-necked flask, 200 mL of water was added and the addition funnel was attached. Next, Compound 12 (1 equivalent) was added to the addition funnel, and the mixture was dropped into a reaction flask in an ice water bath (0 ° C) to gradually yield a white solid. After the completion of the dropwise addition, stirring was continued for one hour, and then a 20% aqueous NaOH solution (1 equivalent) was added and stirred overnight. After filtration, the product was obtained as a white solid (comp. 13). The reaction formula of the above reaction is as follows:

The compound spectrum was analyzed by NMR spectroscopy, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.16 (s, 2H), 8.00 (s, 1H), 7.21. (dd, J = 5.0, 1.0 Hz, 1H), 6.99 (t, J = 5.2 Hz, 1H), 6.88 (s, 1H), 6.30 (br, 1H), 3.77 (q, J = 6.2 Hz, 2H), 3.20 (t, J = 6.6 Hz, 2H).

Next, Compound 13 (1 equivalent) was placed in a 250 mL round bottom flask, and toluene (toluene, 80 mL) was added. POCl ₃ (3 equivalents) was dropped into the reaction vial via an addition funnel in an ice water bath. After the completion of the dropwise addition, the ice water bath was removed and heated to an oil bath to reflux with toluene. After reacting for 2 hours, the reaction was neutralized with a saturated aqueous solution of sodium hydrogen carbonate (NaHCO ₃ ), and then extracted with ethyl acetate. After removal of water and concentration, compound 14 was obtained. The reaction formula of the above reaction is as follows:

Next, compound 14 (1 equivalent) and Pd/C (weight ratio of Pd to C of 1:1, 10 wt% (based on the weight of compound 4)) were placed in a 250 mL reaction flask, and xylene was added. Heat to reflux. After 18 hours of reaction, the Pd/C was filtered off. The obtained filtrate was concentrated to give Compound 15 in a yield of 65%. The reaction formula of the above reaction is as follows:

The NMR spectrum of the compound 15 was used to obtain the spectral information as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.60 (d, J = 5.4 Hz, 1H), 8.35 (s, 2H), 8.00 (s, 1H) , 7.89 (d, J = 5.6 Hz, 1H), 7.63 (d, J = 5.8 Hz, 1H), 7.54 (d, J = 5.4 Hz, 1H).

Next, Compound 15 (2.2 equivalents) and hydrated ruthenium chloride compound (IrCl ₃ ‧ x H ₂ O (x ≧ 1), 1 equivalent) were placed in a 100 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 15) was added. (mL) and water (5 mL), heated to 140 °C. After 24 hours of reaction, a large amount of water was added and filtered to give a yellow solid product (Comp. 16). The reaction formula of the above reaction is as follows:

Finally, compound 16 (1 equivalent), acetone acetone (acetyl, aac, 4 equivalents), and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL), heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was isolated and purified by column chromatography to give an organic metal compound (III). The reaction formula of the above reaction is as follows:

Example 4: Preparation of organometallic compound (IV)

Compound 6 (1 equivalent), pyridine-α-carboxylic acid (picolinic acid) 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (IV) in a yield of 70%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze the organometallic compound (IV). The spectral information obtained was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.62 (d, J = 6.6 Hz, 1H), 8.36 (d, J = 6.4 Hz, 1H), 8.07~8.18 (m, 2H), 7.98 (d, J = 5.8 Hz, 1H), 7.76 (d, J = 6.6 Hz, 1H), 7.65 (t, J = 6.0 Hz, 1H), 7.56 ( d, J = 6.8 Hz, 1H), 7.42 (t, J = 6.2 Hz, 1H), 7.32 (d, J = 6.6 Hz, 1H), 6.38~6.60 (m, 2H), 5.82 (dd, J = 8.4 , 2.2 Hz, 1H), 5.42 (dd, J = 6.6, 2.2 Hz, 1H).

Example 5: Preparation of organometallic compound (V)

Compound 11 (1 equivalent), pyridine-α-carboxylic acid (picolinic acid) 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (V). The reaction formula of the above reaction is as follows:

Example 6: Preparation of organometallic compound (VI)

Compound 16 (1 equivalent), pyridine-α-carboxylic acid (picolinic acid) 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was isolated and purified by column chromatography to give an organic metal compound (VI). The reaction formula of the above reaction is as follows:

Example 7: Preparation of organometallic compound (VII)

Compound 1 (2-(2-aminoethyl)thiophene, 1 equivalent) was placed in a 500 mL single-necked flask, 200 mL of water was added and the addition funnel was attached. Next, Compound 17 (1 equivalent) was added to the addition funnel, and the mixture was dropped into a reaction flask in an ice water bath (0 ° C) to gradually give a white solid. After the completion of the dropwise addition, stirring was continued for one hour, and then a 20% aqueous NaOH solution (1 equivalent) was added and stirred overnight. After filtration, the product was obtained as a white solid (Comp. 18). The reaction formula of the above reaction is as follows:

The compound spectrum was analyzed by NMR spectroscopy, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 7.69~7.77 (m, 1H), 7.20 (d, J = 1.2 Hz, 1H), 7.17 (t, J = 7.4 Hz, 2H), 7.06 (dd, J = 8.8, 2.2 Hz, 2H), 6.95 (m, 1H), 6.20 (br, 1H), 3.74 (q, J = 6.4 Hz, 2H), 3.16 ( t, J = 6.6 Hz, 2H).

Next, Compound 18 (1 equivalent) was placed in a 250 mL round bottom flask, and toluene (toluene, 80 mL) was added. POCl ₃ (3 equivalents) was dropped into the reaction vial via an addition funnel in an ice water bath. After the completion of the dropwise addition, the ice water bath was removed and heated to an oil bath to reflux with toluene. After reacting for 2 hours, the reaction was neutralized with a saturated aqueous solution of sodium hydrogen carbonate (NaHCO ₃ ), and then extracted with ethyl acetate. After removal of water and concentration, compound 19 was obtained in a 50% yield. The reaction formula of the above reaction is as follows:

The compound spectrum was analyzed by NMR spectroscopy, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 7.64 to 7.71 (m, 2H), 7.07 to 7.16 (m, 4H), 6.98 (d, J = 5.2) Hz, 1H), 3.94 (t, J = 7.8 Hz, 2H), 2.93 (t, J = 8.6 Hz, 2H).

Next, compound 19 (1 equivalent) and Pd/C (weight ratio of Pd to C of 1:1, 10 wt% (based on the weight of compound 4)) were placed in a 250 mL reaction flask, and xylene was added. Heat to reflux. After 18 hours of reaction, the Pd/C was filtered off. The obtained filtrate was concentrated to give Compound 20 in a yield of 66%. The reaction formula of the above reaction is as follows:

The compound 20 was analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.54 (d, J = 5.4 Hz, 1H), 7.78 to 7.87 (m, 4H), 7.50 to 7.60 ( m, 2H), 7.22 (t, J = 8.8 Hz, 2H).

Next, the compound 20 (2.2 equivalents) and the ruthenium chloride compound (IrCl ₃ ‧ x H ₂ O (x ≧ 1), 1 equivalent) were placed in a 100 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 15) was added. (mL) and water (5 mL), heated to 140 °C. After 24 hours of reaction, a large amount of water was added and filtered to give a yellow solid product (Comp. 21). The reaction formula of the above reaction is as follows:

Finally, compound 21 (1 equivalent), 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl)-3-trifluoromethyl-1, 2, 4-triazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was isolated and purified by column chromatography to give an organic metal compound (VII). The reaction formula of the above reaction is as follows:

Example 8: Preparation of organometallic compound (VIII)

Compound 6 (1 equivalent), 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl)-3-trifluoromethyl-1,2,4- Triazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (VIII), yield 56%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze the organometallic compound (VIII). The spectral information obtained was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.28 (d, J = 6.8 Hz, 1H), 8.03 to 8.12 (m, 2H), 7.93 (t, J = 6.2 Hz, 1H), 7.54 to 7.64 (m, 4H), 7.43 (d, J = 6.2 Hz, 1H), 7.21 to 7.32 (m, 3H), 6.41 to 6.64 (m, 2H) , 5.82 (dd, J = 8.4, 2.2 Hz, 1H), 5.46 (dd, J = 6.2, 2.2 Hz, 1H).

Example 9: Preparation of organometallic compound (IX)

Compound 11 (1 equivalent), 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl)-3-trifluoromethyl-1,2,4- Triazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (IX). The reaction formula of the above reaction is as follows:

Example 10: Preparation of organometallic compound (X)

Compound 16 (1 equivalent), 5-(2-pyridine)-3-trifluoromethyl-1,2,4-triazole (5-(2-pyridyl)-3-trifluoromethyl-1,2,4- Triazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (X) with a yield of 70%. The reaction formula of the above reaction is as follows:

The organometallic compound (X) was analyzed by NMR spectroscopy and the obtained spectral information was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.61 (s, 1H), 8.50 (s, 1H), 8.11 (d, J = 5.8 Hz, 2H), 8.00 (d, J = 7.8 Hz, 1H), 7.66 to 7.76 (m, 4H), 7.58 (d, J = 6.2 Hz, 1H), 7.55 (s, 1H), 7.16 (s, 1H) ), 7.06~7.13 (m, 2H), 6.93 (d, J = 6.2 Hz, 1H).

Example 11: Preparation of organometallic compound (XI)

Compound 21 (1 equivalent), 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (XI). The reaction formula of the above reaction is as follows:

Example 12: Preparation of organometallic compound (XII)

Compound 6 (1 equivalent), 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (XII) in a yield of 56%. The reaction formula of the above reaction is as follows:

The NMR spectrum analysis of the organometallic compound (XII) gave the following spectral information: ¹ H NMR (CDCl _3, 200 MHz) δ 8.28 (d, J = 6.8 Hz, 1H), 8.03 to 8.12 (m, 2H), 7.93 (t, J = 6.2 Hz, 1H), 7.54 to 7.64 (m, 4H), 7.43 (d, J = 6.2 Hz, 1H), 7.21 to 7.32 (m, 3H), 6.41 to 6.64 (m, 2H) , 5.82 (dd, J = 8.4, 2.2 Hz, 1H), 5.46 (dd, J = 6.2, 2.2 Hz, 1H).

Example 13: Preparation of organometallic compound (XIII)

Compound 11 (1 equivalent), 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (XIII). The reaction formula of the above reaction is as follows:

Example 14: Preparation of organometallic compound (XIV)

Compound 16 (1 equivalent), 5-(2-pyridine)-1,2,3,4-tetrazole (5-(2-pyridyl)-1,2,3,4-tetrazole ( 4 equivalents, and sodium carbonate (4 equivalents) were placed in a 150 mL reaction flask, and ethylene glycol methyl ether (2-methoxy ethanol, 30 mL) was added and heated to reflux. After reacting for 24 hours, it was warmed to room temperature, and 40 mL of water was added and stirred for 30 minutes. After filtration and concentration, the product was separated and purified by column chromatography to give an organic metal compound (XIV), yield 50%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze the organometallic compound (XIV). The spectral information obtained was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 8.69 (d, J = 8.8 Hz, 2H), 8.19 to 8.29 (m, 3H), 7.94 (t, J = 8.0 Hz, 1H), 7.69 to 7.82 (m, 4H), 7.16 to 7.26 (m, 4H), 7.04 (d, J = 6.4 Hz, 2H).

Example 15: Preparation of organometallic compound (XV)

A 250 mL reaction flask was taken and distilled to remove tetrahydrofuran (THF) and bromobenzene, respectively, and the temperature was lowered to -78 °C. n-Butyllithium (Bu-Li) was added dropwise at -78 ° C, and the mixture was stirred for 30 minutes after the completion of the dropwise addition. Next, N,N-diisopropylcarbodiimide was also added dropwise at -78 ° C, and the mixture was rapidly stirred for 30 minutes after the completion of the dropwise addition. Next, the above reactant was dropped into a tetrahydrofuran (THF) solution containing the compound 21, and after heating, it was heated to reflux. After the reaction overnight, the solvent was drained and filtered, and the solid was washed with ethanol several times to give an organic metal compound (XV). The reaction formula of the above reaction is as follows:

Example 16: Preparation of organometallic compound (XVI)

A 250 mL reaction flask was taken and distilled to remove tetrahydrofuran (THF) and bromobenzene, respectively, and the temperature was lowered to -78 °C. n-Butyllithium (Bu-Li) was added dropwise at -78 ° C, and the mixture was stirred for 30 minutes after the completion of the dropwise addition. Next, N,N-diisopropylcarbodiimide was also added dropwise at -78 ° C, and the mixture was rapidly stirred for 30 minutes after the completion of the dropwise addition. Next, the above reactant was dropped into a tetrahydrofuran (THF) solution containing the compound 6, and after heating, it was heated to reflux. After the reaction overnight, the solvent was drained and filtered, and the solid was washed with ethanol several times to obtain an organic metal compound (XVI) in a yield of 62%. The reaction formula of the above reaction is as follows:

The NMR spectrum was used to analyze the organometallic compound (XVI). The spectral information obtained was as follows: ¹ H NMR (CDCl _3, 200 MHz) δ 9.32 (d, J = 6.2 Hz, 2H), 8.57 (d, J = 5.4 Hz, 1H), 8.09 (t, J = 2.2 Hz, 2H), 7.87 (d, J = 3.2 Hz, 2H), 7.60 (d, J = 5.8 Hz, 2H), 7.42 (s, 2H), 6.96 to 7.16 ( m, 2H), 6.36 (t, J = 6.6 Hz, 2H), 5.58 (dd, J = 6.2, 2.2 Hz, 2H), 3.27 (m, 2H), 0.66 (d, J = 6.2 Hz, 6H), -0.10 (d, J = 6.4 Hz, 6H).

Example 17: Preparation of organometallic compound (XVII)

A 250 mL reaction flask was taken and distilled to remove tetrahydrofuran (THF) and bromobenzene, respectively, and the temperature was lowered to -78 °C. n-Butyllithium (Bu-Li) was added dropwise at -78 ° C, and the mixture was stirred for 30 minutes after the completion of the dropwise addition. Next, N,N-diisopropylcarbodiimide was also added dropwise at -78 ° C, and the mixture was rapidly stirred for 30 minutes after the completion of the dropwise addition. Next, the above reaction product was dropped into a tetrahydrofuran (THF) solution containing the compound 11, and after completion of the dropwise addition, it was heated to reflux. After the reaction overnight, the solvent was drained and filtered, and the solid was washed with ethanol several times to give an organic metal compound (XVII). The reaction formula of the above reaction is as follows:

Example 18: Preparation of organometallic compound (XVIII)

A 250 mL reaction flask was taken and distilled to remove tetrahydrofuran (THF) and bromobenzene, respectively, and the temperature was lowered to -78 °C. n-Butyllithium (Bu-Li) was added dropwise at -78 ° C, and the mixture was stirred for 30 minutes after the completion of the dropwise addition. Next, N,N-diisopropylcarbodiimide was also added dropwise at -78 ° C, and the mixture was rapidly stirred for 30 minutes after the completion of the dropwise addition. Next, the above reactant was dropped into a tetrahydrofuran (THF) solution containing the compound 16, and after completion of the dropwise addition, it was heated to reflux. After the reaction overnight, the solvent was drained and filtered, and the solid was washed with ethanol several times to give an organic metal compound (XVIII). The reaction formula of the above reaction is as follows:

Organic light emitting device

Referring to FIG. 1, a schematic cross-sectional view of an organic electroluminescent device 10 according to the present invention is shown. The organic light-emitting device 10 includes a substrate 12, a lower electrode 14, a light-emitting unit 16, and an upper electrode 18. The organic light-emitting device 10 can be an upper illumination, a lower illumination, or a double-sided illumination organic light-emitting device. The substrate can be, for example, a glass, a plastic substrate, or a semiconductor substrate. The material of the lower electrode 14 and the upper electrode 18 can be, for example, lithium, magnesium, calcium, aluminum, silver, indium, gold, tungsten, nickel, platinum, copper, indium tin oxide (ITO), indium zinc oxide (IZO). , zinc aluminum oxide (AZO), zinc oxide (ZnO) or a combination thereof, which may be formed by thermal evaporation, sputtering or plasma enhanced chemical vapor deposition. In addition, at least one of the lower electrode 14 and the upper electrode 18 needs to have a light transmitting property.

The light emitting unit 16 includes at least one light emitting layer, and further includes a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer or other film layers. It is noted that, in accordance with a preferred embodiment of the present invention, the illumination unit 16 must comprise an organometallic compound of the formula (I) of the present invention. In other words, in the light-emitting unit 16, at least one film layer contains the organometallic compound.

According to another preferred embodiment of the present invention, the organic light-emitting device can be a phosphorescent organic light-emitting device, and the light-emitting unit 16 of the phosphorescent organic light-emitting device has a light-emitting layer, and the light-emitting layer comprises a host material and a phosphorescent light. a doping material, and the phosphorescent dopant material comprises the formula (I) according to the invention The organometallic compound of the structure is shown, and the luminescent layer emits green light. The organometallic compound of the present invention is doped with the desired phosphorescent dopant material and the doping amount of the dopant to be matched is changed by the organic light-emitting material and the required component characteristics which can be used by those skilled in the art. . Therefore, the amount of dopant doping is not a feature of the present invention and is not intended to limit the scope of the present invention. For example, when the organometallic compound of the formula (I) of the present invention is used as a light-emitting layer dopant, the doping amount of the organometallic compound having the formula (I) may be between 0.1-15%, The weight of the host material is based on the weight.

In order to further illustrate the organic light-emitting device of the present invention, the following examples provide an example of a plurality of organic light-emitting devices by using the organometallic compound obtained in the above embodiment as a doping material (by evaporation (dry process) or coating (wet respectively). Process (formed)), with a conventional phosphorescent dopant material (Ir (ppy) ₃ , The organic light-emitting devices were compared to verify that the organometallic compound of the present invention has a relatively high photoelectric property with conventional materials.

Dry process

Example 19: Organic light-emitting device (1)

The patterned indium tin oxide (ITO, 150 nm thick) glass substrate was washed with a neutral detergent, acetone, and ethanol by ultrasonic vibration. The substrate was blown dry with nitrogen and then placed under UV-OZONE for 30 minutes, followed by spinning Transfer coating method (two-stage coating method, the first stage speed is set at 500 rpm (for 5 seconds), the second stage is 2000 rpm (for 30 seconds), and finally heated at 130 °C. Dry) forms PEDOT:PSS (poly(3,4-ethylenedioxythiophene): poly-(styrenesulfonate)) on the indium tin oxide layer.

Next, TAPC (1,1-bis[4-[N,N'-bis(p-tolyl)amine]phenyl]cyclohexane (1,1-bis) was sequentially deposited under a pressure of 10 ^-6 torr. [4-[N,N'-di(p-tolyl)amino]phenyl]cyclobexane)), thickness 35nm), TCTA(4,4',4'-tris(N-carbazolyl)triphenylamine (4,4',4'-tri(N-carbazolyl)triphenylamine)) is doped with the organometallic compound (I) obtained in Example 1 ( (weight ratio of TCTA to organometallic compound (I) is 100:6, thickness is 10 nm), TmPyPB (1,3,5-tris[(3-pyridyl)-3-phenyl]benzene (1,3) , 5-tri[(3-pyridyl)-phen-3-yl]benzene, the structure is .), thickness 42 nm), LiF (thickness 0.5 nm), and Al (thickness 120 nm), resulting in an organic light-emitting device (1) after packaging. The structure of the organic light-emitting device (1) can be expressed as: ITO/PEDOT: PSS/TAPC/TCTA: organometallic compound (I) (6%) / TmPyPB / LiF / Al.

Then, using a luminance meter (LS110) and a colorimeter (PR650) for organic hair The optical device (1) performs brightness, efficiency test, and color coordinate measurement. Refer to Table 1 for the results.

Example 20: Organic light-emitting device (2)

The same procedure as in Example 19 was carried out, except that the dopant used in Example 19 was changed to the organometallic compound (IV) obtained in Example 4 ( ), an organic light-emitting device (2) is obtained. The structure of the organic light-emitting device (2) can be expressed as: ITO/PEDOT: PSS/TAPC/TCTA: organometallic compound (IV) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (2) were measured by a luminance meter (LS110) and a colorimeter (PR650). Refer to Table 1 for the results.

Example 21: Organic light-emitting device (3)

The same procedure as in Example 19 was carried out, except that the dopant used in Example 19 was changed to the organometallic compound (VIII) obtained in Example 8 ( ), an organic light-emitting device (3) is obtained. The structure of the organic light-emitting device (3) can be expressed as: ITO/PEDOT: PSS/TAPC/TCTA: organometallic compound (VIII) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (3) are measured by a luminance meter (LS110) and a colorimeter (PR650). Table 1.

Example 22: Organic light-emitting device (4)

The same procedure as in Example 19 was carried out, except that the dopant used in Example 19 was changed to the organometallic compound (XVI) obtained in Example 8 ( ), an organic light-emitting device (4) is obtained. The structure of the organic light-emitting device (4) can be expressed as: ITO/PEDOT: PSS/TAPC/TCTA: organometallic compound (XVI) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (4) were measured by a luminance meter (LS110) and a colorimeter (PR650). The results are shown in Table 1.

Comparative Example 1: Organic Light Emitting Device (5)

The same procedure as in Example 19 was carried out, but the dopant used in Example 19 was changed to a conventional phosphorescent dopant material (Ir(ppy) ₃ , ), an organic light-emitting device (5) is obtained. The structure of the organic light-emitting device (5) can be expressed as: ITO/PEDOT: PSS/TAPC/TCTA: Ir(ppy) ₃ (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (5) are measured by a luminance meter (LS110) and a colorimeter (PR650). Table 1.

It can be seen from Table 1 that the green organic phosphorescent light-emitting device obtained by using the organometallic compound of the formula (1) as the phosphorescent dopant of the light-emitting layer of the present invention has a lower driving voltage under 1000 cd/m ² operation. And the power efficiency can reach 32 lm / W.

Wet process

Example 23: Organic light-emitting device (6)

The patterned indium tin oxide (ITO, 150 nm thick) glass substrate was washed with a neutral detergent, acetone, and ethanol by ultrasonic vibration. The substrate was blown dry with nitrogen, and then placed under UV-OZONE for 30 minutes, followed by spin coating (rotation setting 2000 rpm, and finally baking at 130 ° C for 10 minutes) to form PEDOT:PSS (poly A (3,4-ethylenedioxythiophene)/poly(3,4-ethylenedioxy-thiophene):poly(styrene sulfonate) layer is deposited on the indium tin oxide layer.

Next, TCTA (4,4',4'-tris(N-carbazolyl)triphenylamine) and the organic metal obtained in Example 1 Compound (I) is dissolved in chlorobenzene solution (weight ratio of TCTA to organometallic compound (I) is 100:6), and TCTA is formed by spin coating (rotation setting 1000 rpm) (4, 4) ',4'-Tris(N-carbazolyl)triphenylamine) is doped with the organometallic compound (I) obtained in Example 1 ( The film layer is on the PEDOT:PSS layer. Next, TmPyPB (1,3,5-tris[(3-pyridyl)-3-phenyl]benzene (1,3,5-tri[(3-pyridyl)) was sequentially deposited under a pressure of 10 ^-6 torr. -phen-3-yl]benzene, the structure is ), a thickness of 50 nm), LiF (thickness: 1 nm), and Al (thickness: 100 nm) are coated on the film layer of the TCTA-doped organometallic compound (I), and the organic light-emitting device (6) is obtained after encapsulation. The structure of the organic light-emitting device (6) can be expressed as: ITO/PEDOT: PSS/TCTA: organometallic compound (I) (6%) / TmPyPB / LiF / Al.

Next, the organic light-emitting device (6) was measured for luminance, efficiency, and color coordinates by a luminance meter (LS110) and a colorimeter (PR650). For the results, refer to Table 2.

Example 24: Organic light-emitting device (7)

The same procedure as in Example 23 was carried out, except that the dopant used in Example 23 was changed to the organometallic compound (IV) obtained in Example 4 ( ), an organic light-emitting device (7) is obtained. The structure of the organic light-emitting device (7) can be expressed as: ITO/PEDOT: PSS/TCTA: organometallic compound (IV) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (7) were measured by a luminance meter (LS110) and a colorimeter (PR650). Refer to Table 2 for the results.

Example 25: Organic light-emitting device (8)

The same procedure as in Example 23 was carried out, except that the dopant used in Example 23 was changed to the organometallic compound (VIII) obtained in Example 8 ( ), an organic light-emitting device (8) is obtained. The structure of the organic light-emitting device (8) can be expressed as: ITO/PEDOT: PSS/TCTA: organometallic compound (VIII) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (8) were measured by a luminance meter (LS110) and a colorimeter (PR650). Refer to Table 2 for the results.

Example 26: Organic light-emitting device (9)

The same procedure as in Example 23 was carried out, except that the dopant used in Example 23 was changed to the organometallic compound (XIII) obtained in Example 13 ( ), an organic light-emitting device (9) is obtained. The structure of the organic light-emitting device (9) can be expressed as: ITO/PEDOT: PSS/TCTA: organometallic compound (XIII) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (9) were measured by a luminance meter (LS110) and a colorimeter (PR650). Refer to Table 2 for the results.

Example 26: Organic Light Emitting Device (10)

The same procedure as in Example 23 was carried out, except that the dopant used in Example 23 was changed to the organometallic compound (XIV) obtained in Example 14 ( ), an organic light-emitting device (10) is obtained. The structure of the organic light-emitting device (10) can be expressed as: ITO/PEDOT: PSS/TCTA: organometallic compound (XIV) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (10) were measured by a luminance meter (LS110) and a colorimeter (PR650). Refer to Table 2 for the results.

Example 27: Organic light-emitting device (11)

The same procedure as in Example 23 was carried out, except that the dopant used in Example 23 was changed to the organometallic compound obtained in Example 16 ((XVI) ( ), an organic light-emitting device (11) is obtained. The structure of the organic light-emitting device (11) can be expressed as: ITO/PEDOT: PSS/TCTA: organometallic compound (XVI) (6%) / TmPyPB / LiF / Al.

Next, the luminance, efficiency test, and color coordinates of the electroluminescent device (11) were measured by a luminance meter (LS110) and a colorimeter (PR650). Refer to Table 2 for the results.

As can be seen from Table 2, the organometallic compound of the formula (1) of the present invention can be used as a dopant for the hair layer and has high solubility, and the light-emitting layer can be formed by a wet process. Further, the organometallic compound having the formula (1) according to the present invention The organic phosphorescent light-emitting device obtained as a phosphorescent dopant of the light-emitting layer has a main peak of an emission wavelength of between 500 and 560 nm and a driving voltage of less than 4.4V.

The foregoing has been described in terms of the embodiments of the invention It will be apparent to those skilled in the art that the present invention can be understood and utilized in the <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; </ RTI> <RTIgt; A person skilled in the art should be able to understand the corresponding description without departing from the spirit and scope of the invention, and various changes, substitutions and modifications can be made without departing from the spirit and scope of the invention.

Claims (6)

An organometallic compound Wherein, the L system is an acetonitrile ketone ligand, a pyridine-α-carboxylic acid ligand, a 2-benzene ring-1,3,4-oxadiazole ligand, 5-(2-pyridine)-3- Trifluoromethyl-1,2,4-triazole ligand, 5-(phenylcyclo)-1,2,3-triazole ligand, N,N'-diisopropylbenzhydrazide coordination a 5- or 2-(2-pyridyl)-1,2,3,4-tetrazole ligand; and, the L ¹ is a 2-phenylcyclo-1,3,4-oxadiazole ligand, 5 -(2-pyridine)-3-trifluoromethyl-1,2,4-triazole ligand, 5-(phenylcyclo)-1,2,3-triazole ligand, N,N'- a diisopropyl benzamidine ligand or a 5-(2-pyridine)-1,2,3,4-tetrazole ligand. An organic light emitting device comprising: a pair of electrodes; An organic light emitting unit disposed between the pair of electrodes, wherein the organic light emitting unit comprises the organometallic compound described in claim 1 of the patent application. The organic light-emitting device of claim 2, wherein the organic light-emitting unit comprises a light-emitting layer, the light-emitting layer comprises a host material and a doping material, and the doping material is the first item of the patent application scope. The organometallic compound. The organic electroluminescent device of claim 3, wherein the luminescent layer emits green light. The organic electroluminescent device of claim 3, wherein the luminescent layer is prepared by evaporation. The organic electroluminescent device of claim 3, wherein the luminescent layer is prepared by a wet process.