CN111560023A - Phosphorescent compound and organic light emitting diode device using the same - Google Patents
Phosphorescent compound and organic light emitting diode device using the same Download PDFInfo
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Abstract
The present invention relates to a phosphorescent compound and an organic light emitting diode device using the same, and more particularly, to a soluble phosphorescent host compound having excellent color purity and high luminance and light emitting efficiency and an OLED device using the same. A phosphorescent compound characterized by: the structural formula is shown as formula 1 and formula 2,
in the above structural formulae 1 and 2, Z is independently selected from the following structures:
x1 to X6 are independently selected from N atoms or C atoms, wherein at least one of X1 to X6 is N wherein Y is selected from O, S and Se. Wherein Ar is independently selected from a C6-C30 aryl group and a C2-C30 heteroaryl group, the C6-C30 aryl group is selected from one of phenyl, naphthyl, biphenyl, terphenyl and phenanthryl, and the C2-C30 heteroaryl group is selected from one of pyridyl, bipyridyl, quinolyl, isoquinolyl, phenanthrolinyl and triazinyl. The present invention uses the chemical formulas shown in structural formulas 1 and 2 as the light emitting layer of the organic light emitting diode device, and has excellent color purity and brightness and a prolonged durability effect.
Description
Technical Field
The present invention relates to a phosphorescent compound and an organic light emitting diode device using the same, and more particularly, to a soluble phosphorescent host compound having excellent color purity and high luminance and light emitting efficiency and an OLED device using the same.
Background
Recently, the demand for flat panel displays (e.g., liquid crystal displays and plasma display panels) is increasing. However, these flat panel displays have a lower response time and a narrower viewing angle than Cathode Ray Tubes (CRTs).
An Organic Light Emitting Diode (OLED) device is one of the next-generation flat panel displays that can solve the above problems and have a small footprint.
The elements of the OLED device may be formed on a flexible substrate, such as a plastic substrate. In addition, OLED devices have advantages in view angle, driving voltage, power consumption, and color purity. Outside, the OLED device is sufficient to produce full color images.
In general, a light emitting diode of an OLED device includes an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Emitting Material Layer (EML), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode.
The OLED device emits light by: electrons and holes are injected into the light emitting compound layer from the cathode as an electron injection electrode and from the anode as a hole injection electrode, respectively, so that the electrons and the holes are recombined to generate excitons, and the excitons are made to transition from an excited state to a ground state.
The principle of luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
When the light emitting material layer emits light corresponding to the energy band gap, singlet excitons having 0 spin and triplet excitons having 1 spin are generated in a ratio of 1: 3. The ground state of the organic material is a singlet state, which allows singlet excitons to transition to the ground state with accompanying light emission. However, since the triplet excitons cannot undergo transition accompanied by light emission, the internal quantum efficiency of the OLED device using the fluorescent material is limited to within 25%.
On the other hand, if the spin orbit coupling momentum is high, the singlet state and the triplet state are mixed so that an intersystem crossing occurs between the singlet state and the triplet state, and the triplet exciton may also transition to the ground state with accompanying light emission. The phosphorescent material may use triplet excitons and singlet excitons, so that an OLED device using the phosphorescent material may have an internal quantum efficiency of 100%.
Recently, iridium complexes, such as bis (2-phenylquinoline) (acetylacetonate) iridium (iii) (Ir (2-phq)2(acac)), bis (2-benzo [ b ] thiophen-2-ylpyridine) (acetylacetonate) iridium (iii) (Ir (btp)2(acac)), and tris (2-phenylquinoline) iridium (iii) Ir (2-phq)3 dopants have been introduced.
In order to obtain high current luminous efficiency (Cd/a) using a phosphorescent material, excellent internal quantum efficiency, high color purity, and long lifetime are required. In particular, referring to fig. 1, the higher the color purity, i.e., the higher cie (x), the worse the color sensitivity. As a result, it is very difficult to obtain light emission efficiency at high internal quantum efficiency. Therefore, there is a need for novel red phosphorescent compounds having excellent color purity (CIE (X) ≧ 0.65) and high luminous efficiency.
On the other hand, in addition to the iridium complex described above, for example, 4,4-N, N-Carbazole Biphenyl (CBP) or other metal complexes are used as the red phosphorescent compound. However, these compounds do not have ideal solubility in a solvent, and thus cannot form a light emitting layer by a solution process. The light emitting layer should be formed through a deposition process, and thus, the manufacturing process is very complicated and the process efficiency is very low. In addition, the amount of waste material in the deposition process is very large, resulting in increased production costs.
Disclosure of Invention
The present invention is directed to provide a phosphorescent compound and an organic light emitting diode device using the same to solve the disadvantages of the related art.
The technical scheme adopted by the invention for solving the technical problem is as follows:
a phosphorescent compound characterized by: the structural formula is shown as formula 1 and formula 2,
in the above structural formulae 1 and 2, Z is independently selected from the following structures:
x1 to X6 are independently selected from N atoms or C atoms, wherein at least one of X1 to X6 is N
Wherein Y is selected from O, S and Se.
Wherein Ar is independently selected from C6-C30 aryl, C2-C30 heteroaryl.
Further, the C6-C30 aryl is selected from one of phenyl, naphthyl, biphenyl, terphenyl and phenanthryl.
Further, the C2-C30 heteroaryl is selected from one of pyridyl, bipyridyl, quinolyl, isoquinolyl, phenanthrolinyl and triazinyl.
Further, Ar is independently selected from one of the following groups: (any of the following groups may be substituted for a position originally having an active hydrogen atom)
Further, the phosphorescent compound is independently selected from the following compounds:
further, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode which are deposited in sequence, and the phosphorescent compound is used as a main material of the light emitting layer.
The invention has the advantages that: the present invention uses the chemical formulas shown in structural formulas 1 and 2 as the light emitting layer of the organic light emitting diode device, and has excellent color purity and brightness and a prolonged durability effect.
Drawings
FIG. 1 is a graph of chromaticity and visibility of light emitted from an organic electroluminescent diode.
Detailed Description
In order to make the technical means, the original characteristics, the achieved purposes and the effects of the invention easy to understand, the invention is further described with reference to the figures and the specific embodiments.
As the red phosphorescent compounds with the structural formulas shown as formula 1 and formula 2 have excellent pure chromaticity, high brightness and excellent luminous efficiency, the technical scheme and the achieved technical effect provided by the invention are proved by taking RH-001, RH-007, RH-073 and RH-079 preparation methods and test results as examples.
In the following embodiments, NPB is 4,4 ' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl, CBP is 4,4 ' -N, N ' -dicarbakisbiphenyl, CuPc is copper phthalocyanine, LiF lithium fluoride, ITO is indium tin oxide, and Alq3 is tris (8-hydroxyquinoline) aluminum.
LC-MS, liquid chromatography-mass spectrometer, M/Z: ratio of number of protons/number of charges.
The following formulae are structural formulae for the compounds copper (II) phthalocyanine (CuPc), NPB, (btp)2Ir (acac), Alq3 and CBP used in embodiments of the present invention.
Examples of formation
1.1. Synthesis of intermediate Sub-1:
in a 2000mL reaction flask was charged M-bromoiodobenzene (50.0g,176.7mmol), 2-amino-1-bromonaphthalene (43.2g,194.4mmol in dry and degassed toluene (1000mL) as solvent, then sodium tert-butoxide (51.0g,530.2mmol), palladium acetate (2 mol%) and 1,1 '-binaphthyl-2, 2' -bis-diphenylphosphine (4 mol%). after the end of the addition, the temperature was raised to 110 ℃ for reaction 16H, the reaction was terminated and cooled to room temperature, filtered after adsorption on activated carbon, the solvent was removed, recrystallized using toluene and ethanol to give intermediate Sub-1(56.6g, yield 85%). LC-MS: M/Z378.1 (M + H)+。
2. Synthesis of intermediate Sub-2:
intermediate Sub-1(50.0g,132.6mmol) was added to a 2000mL reaction flask, followed by the use of dried and degassed DMF (1000mL) as solvent. After 15 minutes of nitrogen substitution, the catalysts palladium acetate (2 mol%) and potassium acetate (89.3g,397.8mmol) were added. After the addition was complete, the temperature was raised to 160 ℃ and the reaction was carried out for 14 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and water was added thereto and stirred for 1 hour to form a solid. The mixture is pumped, filtered, washed with a little ethanol and dried. Recrystallization from toluene and ethanol gave intermediate Sub-2(34.6g, yield 88%). LC-MS: M/Z297.2 (M + H)+。
3. Synthesis of intermediate Sub-3:
a1000 mL reaction flask was charged with intermediate Sub-2(30.0g,101.3mmol), phenylboronic acid (14.8g,121.6mmol), tetrakis (triphenylphosphine) palladium (5 mol%), 2M-K2CO3(150mL), toluene (300mL) and ethanol (150 mL). The reaction system is heated to 120 ℃, and the reaction is carried out under the protection of nitrogenShould be 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain intermediate Sub-3(23.2g, yield 78%). LC-MS: M/Z294.4 (M + H)+。
4. Synthesis of intermediate Sub-4:
intermediate Sub-3(25.0g,85.2mmol), NaCl (74.7g,1278.3mmol) and AlCl3(340.9g,2556.6mmol) were added to a 1000ml reaction flask and dissolved in benzene, washed after hydrolysis with water and aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The concentrate was then column-filtered by dissolving in a small amount of hot p-xylene and the residue was recrystallized from methylcyclohexane to give intermediate 4. intermediate Sub-4(7.4g, yield 30%). LC-MS: M/Z292.4 (M + H)+。
5. Synthesis of intermediate Sub-5:
2, 4-Dichlorobenzofuran [3,2-D ] was added to a 500ml reaction flask]Pyrimidine (10.0g,41.8mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (12.0g,41.8mmol), potassium carbonate (14.5g,104.6mmol), palladium tetrakistriphenylphosphine (2.4g,2.1mmol),1, 4-dioxane (140mL) and water (70 mL). The reaction system is heated to 60 ℃ and reacts for ten hours under the protection of nitrogen. The reaction solution was poured into 450mL of methanol, and the precipitated solid was filtered. The precipitated solid was dissolved in chlorobenzene and filtered through a funnel containing celite and silica gel powder. The orange liquid obtained by filtration was concentrated to dryness and recrystallized from methanol to yield intermediate Sub-5(12.1g, yield 65%). LC-MS: M/Z446.9 (M + H)+。
Synthesis of RH-001:
the intermediate Su was added to a 250ml three-necked flaskb-5(5g, 11.2mmol), intermediate Sub-4(3.6g,12.3mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude RH-001(6.4g, yield 82%). LC-MS: M/Z701.8 (M + H)+。
7. Synthesis of intermediate Sub-6:
2, 4-Dichlorobenzofuran [3,2-D ] was added to a 500ml reaction flask]Pyrimidine (10.0g,41.8mmol), carbazole 9- (4-biphenyl) -3-borate (15.2g,41.8mmol), potassium carbonate (14.5g,104.6mmol), palladium tetrakistriphenylphosphine (2.4g,2.1mmol),1, 4-dioxane (140mL) and water (70 mL). The reaction system is heated to 60 ℃ and reacts for ten hours under the protection of nitrogen. The reaction solution was poured into 450mL of methanol, and the precipitated solid was filtered. The precipitated solid was dissolved in chlorobenzene and filtered through a funnel containing celite and silica gel powder. The orange liquid obtained by filtration was concentrated to dryness and recrystallized from methanol to yield intermediate Sub-6(14.4g, yield 66%). LC-MS: M/Z523.0 (M + H)+。
Synthesis of RH-007:
a250 mL three-necked flask was charged with intermediate Sub-6(5g,9.6mmol), intermediate Sub-4(3.3g,11.5mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.2g,28.7mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give RH-007(5.2g, yield 70%). LC-MS: M/Z777.9 (M + H)+。
9. Synthesis of intermediate Sub-7:
2, 4-Dichlorobenzofuran [3,2-D ] was added to a 500ml reaction flask]Pyrimidine (10.0g,41.8mmol), (9-phenyl-9H-carbazol-2-yl) boronic acid (12.0g,41.8mmol), potassium carbonate (14.5g,104.6mmol), palladium tetrakistriphenylphosphine (2.4g,2.1mmol),1, 4-dioxane (140mL) and water (70 mL). The reaction system is heated to 60 ℃ and reacts for ten hours under the protection of nitrogen. The reaction solution was poured into 450mL of methanol, and the precipitated solid was filtered. The precipitated solid was dissolved in chlorobenzene and filtered through a funnel containing celite and silica gel powder. The orange liquid obtained by filtration was concentrated to dryness and recrystallized from methanol to yield intermediate Sub-7(12.3g, yield 66%). LC-MS: M/Z446.9 (M + H)+。
Synthesis of RH-073:
a250 mL three-necked flask was charged with intermediate Sub-7(5g, 11.2mmol), intermediate Sub-4(3.6g,12.3mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude RH-073(6.3g, yield 80%). LC-MS: M/Z701.8 (M + H)+。
11. Synthesis of intermediate Sub-8:
2, 4-Dichlorobenzofuran [3,2-D ] was added to a 500ml reaction flask]Pyrimidine (10.0g,41.8mmol), carbazole 9- (4-biphenyl) -2-borate (15.2g,41.8mmol), potassium carbonate (14.5g,104.6mmol), palladium tetrakistriphenylphosphine (2.4g,2.1mmol),1, 4-dioxane (140mL) and water (70 mL). Reaction System literThe temperature is raised to 60 ℃, and the reaction is carried out for ten hours under the protection of nitrogen. The reaction solution was poured into 450mL of methanol, and the precipitated solid was filtered. The precipitated solid was dissolved in chlorobenzene and filtered through a funnel containing celite and silica gel powder. The orange liquid obtained by filtration was concentrated to dryness and recrystallized from methanol to yield intermediate Sub-8(14.2g, yield 65%). LC-MS: M/Z523.0 (M + H)+。
Synthesis of RH-079:
a250 mL three-necked flask was charged with intermediate Sub-8(5g,9.6mmol), intermediate Sub-4(3.3g,11.5mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.2g,28.7mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain RH-079(5.2g, yield 70%). LC-MS: M/Z777.9 (M + H)+。
Detailed description of the preferred embodiments
1. First embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate was then placed in a vacuum chamber with a standard pressure setting of 1 × 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material.
At 0.9mA, the luminance is equal to 1032cd/m2(6.2V). In this case, CIEx is 0.659y is 0.330.
2. Second embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate was then placed in a vacuum chamber with a standard pressure setting of 1 × 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material.
At 0.9mA, the luminance was equal to 1119cd/m2 (6.0V). In this case, CIEx is 0.659 and y is 0.329.
3. Third embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate was then placed in a vacuum chamber with a standard pressure setting of 1 × 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material.
At 0.9mA, the luminance was equal to 1119cd/m2 (6.0V). In this case, CIEx is 0.659 and y is 0.329.
4. Fourth embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate was then placed in a vacuum chamber with a standard pressure setting of 1 × 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material.
At 0.9mA, the luminance was equal to 1078cd/m2 (6.3V). In this case, CIEx is 0.660 and y is 0.329.
5. Comparative example
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate was then placed in a vacuum chamber with a standard pressure setting of 1 × 10-6And (4) supporting. On an ITO substrate
And
the sequence of (a) and (b) forming layers of organic material.
At 0.9mA, the luminance is equal to 780cd/m2(7.5V). In this case, CIEx is 0.659 and y is 0.329.
It is shown in fig. 1 that the color purity of the organic electroluminescent device increases (i.e., the X value becomes larger as the chromaticity coordinate becomes larger) and the visibility decreases.
The characteristics of efficiency, chromaticity coordinates, and luminance according to the above-described embodiments and comparative examples are shown in table 1 below.
TABLE 1
| Device with a metal layer | Voltage (V) | Current (mA) | Luminance (cd/m2) | Current efficiency (cd/A) | Power efficiency (Im/W) | CIE(x) | CIE(y) |
| First embodiment | 6.1 | 0.9 | 1107 | 11.1 | 5.7 | 0.659 | 0.329 |
| Second embodiment | 6.2 | 0.9 | 1032 | 10.3 | 5.2 | 0.659 | 0.330 |
| Third embodiment | 6.0 | 0.9 | 1119 | 11.2 | 5.9 | 0.659 | 0.329 |
| Fourth embodiment | 6.3 | 0.9 | 1078 | 10.8 | 5.4 | 0.660 | 0.329 |
| For this example | 7.5 | 0.9 | 780 | 7.8 | 3.3 | 0.659 | 0.329 |
As shown in table 1, the device operates at high efficiency at low voltage even when the color purity is high. Also, the current efficiency of the second embodiment is increased by 40% or more compared to the comparative example.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (6)
1. A phosphorescent compound characterized by: the structural formula is shown as formula 1 and formula 2,
in the above structural formulae 1 and 2, Z is independently selected from the following structures:
x1 to X6 are independently selected from N atoms or C atoms, wherein at least one of X1 to X6 is N wherein Y is selected from O, S and Se
Wherein Ar is independently selected from the group consisting of C6-C30 aryl, C2-C30 heteroaryl.
2. The phosphorescent compound according to claim 1, wherein: the C6-C30 aryl is selected from one of phenyl, naphthyl, biphenyl, terphenyl and phenanthryl.
3. The phosphorescent compound according to claim 1, wherein: the C2-C30 heteroaryl is selected from one of pyridyl, bipyridyl, quinolyl, isoquinolyl, phenanthrolinyl and triazinyl.
4. The phosphorescent compound according to claim 1, wherein Ar is independently selected from the group consisting of:
5. phosphorescent compound according to any of claims 1 to 4, characterized in that: the phosphorescent compounds are independently selected from the following compounds:
6. an organic electroluminescent diode device using the phosphorescent compound according to any one of claims 1 to 5, characterized in that: the organic electroluminescent device sequentially comprises a deposited anode, a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode, and the phosphorescent compound is used as a main material of the luminescent layer.
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| CN109678867A (en) * | 2018-11-08 | 2019-04-26 | 浙江华显光电科技有限公司 | A kind of phosphorescent compound and the organic light emitting diode device using the compound |
| CN109678868A (en) * | 2018-11-08 | 2019-04-26 | 浙江华显光电科技有限公司 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
| CN109678876A (en) * | 2018-11-08 | 2019-04-26 | 浙江华显光电科技有限公司 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
| CN109694371A (en) * | 2018-11-26 | 2019-04-30 | 浙江华显光电科技有限公司 | A kind of phosphorescence host compound and its organic electroluminescence device using the compound |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109678867A (en) * | 2018-11-08 | 2019-04-26 | 浙江华显光电科技有限公司 | A kind of phosphorescent compound and the organic light emitting diode device using the compound |
| CN109678868A (en) * | 2018-11-08 | 2019-04-26 | 浙江华显光电科技有限公司 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
| CN109678876A (en) * | 2018-11-08 | 2019-04-26 | 浙江华显光电科技有限公司 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
| CN109694371A (en) * | 2018-11-26 | 2019-04-30 | 浙江华显光电科技有限公司 | A kind of phosphorescence host compound and its organic electroluminescence device using the compound |
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