CN109593097B - Phosphorescent host compound and organic electroluminescent device using same - Google Patents
Phosphorescent host compound and organic electroluminescent device using same Download PDFInfo
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Abstract
The present invention relates to a phosphorescent host compound and an organic electroluminescent device using the same. A phosphorescent host compound has a structural formula shown as I,
in the above formula I, Z is independently selected from the following structures:
wherein Ar is independently selected from one of C6-C30 aryl and C2-C30 heteroaryl. The present invention uses the chemical formula shown in I as a host material of a light emitting layer of an organic light emitting diode device (organic electroluminescent device), and has excellent color purity and luminance and a prolonged durability effect.
Description
Technical Field
The present invention relates to a phosphorescent host compound and an organic electroluminescent device using the same. And more particularly, to a soluble phosphorescent host compound having excellent color purity and high luminance and luminous 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 0LED device may be formed on a flexible substrate (e.g., 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 a phosphorescent host compound and an organic electroluminescent device using the same. Which substantially overcome one or more of the problems due to the limitations and disadvantages of the related art.
An object of the present invention is to provide a phosphorescent host compound having excellent pure chromaticity, high luminance, and excellent luminous efficiency.
It is another object of the present invention to provide an OLED with improved luminous efficiency.
Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objectives and other advantages of the invention will be realized and attained by the structure particularly pointed out in the written description and claims hereof as well as the appended drawings.
To achieve these and other advantages and in accordance with the purpose of the present invention, as embodied and broadly described herein, there is provided a phosphorescent host compound of the formula:
the invention provides a phosphorescent host compound, which has a structural formula shown as I,
in the above formula I, Z is independently selected from the following structures:
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 host compound is used as a host material of the light emitting layer.
The invention has the advantages that: the present invention uses the chemical formula shown in I as a light emitting layer of an 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 formula I all 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 preparation methods and test results of RH-001, RH-007, RH-091 and RH-097 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. Synthesis of intermediate I-1:
in a 2000mL flask 8-bromo-2, 4-dimethoxyquinoline (40g,148.6mmol), dimethyl [2(4-,4-,5-, 5-tetramethyl-1, 3-dioxaborolan-2-yl) phenyl ] silane (42.9g,163.5mmol), potassium carbonate (51.4g,371.6mmol), tetrakis triphenylphosphine palladium (5 mol%) were dissolved in 1,4 dioxane (400mL) and water (200 mL). The mixture was heated to reflux under nitrogen for 12 hours.
The resulting mixture was added to 750ml of methanol, and the precipitated solid was filtered and dissolved in chlorobenzene, filtered through silica gel/celite, concentrated to remove the organic solvent, and recrystallized from methanol to give intermediate I-1(31.3g, yield 65%). LC-MS: M/Z325.5 (M + H))+。
2. Synthesis of intermediate I-2:
intermediate I-1(31g,95.5mmol), Triphenylphosphine rhodium chloride (0.44g,0.48mmol) and 1, 4-dioxane (100mL) were added to a 250mL sealInside the tube. Stirring was carried out at 135 ℃ for 1 hour. When the reaction is completed, the product is separated and purified by a silica gel column with an eluent of n-hexane and dichloromethane (2: 1). The solvent was distilled off under reduced pressure to give intermediate I-2(24.6g, yield 80%). LC-MS: M/Z323.4 (M + H)+。
3. Synthesis of intermediate I-3:
intermediate I-2(24g,74.4mmol) was dissolved in glacial acetic acid (300mL) in a 1000mL round bottom flask, then sodium iodide (44.6g,297.7mmol) was added, and after the mixture was stirred at 60 ℃ for 1 hour, the solvent was removed by distillation under pressure. The residue extracted therefrom was dissolved in methylene chloride (350mL) and then washed with an aqueous solution of sodium thiosulfate. The organic layer obtained by the extraction was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting mixture was charged without purification to a 150ml flask containing phosphorus oxychloride (69.5g,521.0mmol) and refluxed at 120 ℃ for 4 hours under nitrogen. The reaction mixture was slowly poured into excess ice to complete the reaction and the precipitated solid was filtered. The resulting solid was washed with water and methanol and dried to give intermediate I-3(20.0g, yield 81%). LC-MS: M/Z332.3 (M + H)+。
4. Synthesis of intermediate I-4:
a500 mL reaction flask was charged with intermediate I-3(10.0g,30.2mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (8.7g,30.2mmol), potassium carbonate (10.4g,75.5mmol), tetrakistriphenylphosphine palladium (5 mol%), 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 give intermediate I-4(10.6g, yield 65%) LC-MS: M/Z539.1 (M + H))+。
Synthesis of RH-001:
a250 mL three-necked flask was charged with intermediate I-4(5g,9.3mmol), 7H-dibenzo [ c, g]Carbazole (3.0g,11.2mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.1g,27.9mmol) 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(5.7g, yield 80%) through silica gel column. LC-MS: M/Z770.0 (M + H)+。
6. Synthesis of intermediate I-5:
a500 mL reaction flask was charged with intermediate I-3(10.0g,30.2mmol), carbazole 9- (4-biphenyl) -3-borate (11.0g,30.2mmol), potassium carbonate (10.4g,75.5mmol), tetrakis triphenylphosphine palladium (5 mol%), 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 give intermediate I-5(11.1g, yield 60%). LC-MS: M/Z615.2 (M + H)+。
Synthesis of RH-007:
a250 mL three-necked flask was charged with intermediate I-5(5g,8.1mmol), 7H-dibenzo [ c, g]Carbazole (2.6g,9.8mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (2.3g,20.4mmol) and o-dimethylBenzene (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-007(5.3g, yield 78%). LC-MS: M/Z846.1 (M + H)+。
8. Synthesis of intermediate I-6:
a500 mL reaction flask was charged with intermediate I-3(10.0g,30.2mmol), (9-phenyl-9H-carbazol-2-yl) boronic acid (8.7g,30.2mmol), potassium carbonate (10.4g,75.5mmol), tetrakistriphenylphosphine palladium (5 mol%), 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 give intermediate I-6(10.2g, yield 63%) LC-MS: M/Z539.1 (M + H)+。
Synthesis of RH-091:
a250 mL three-necked flask was charged with intermediate I-6(5g,9.3mmol), 7H-dibenzo [ c, g]Carbazole (3.0g,11.2mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.1g,27.9mmol) 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 product which was passed through silica gel column to give RH-091(5.4g, yield 78%). LC-MS: M/Z770.0 (M + H)+。
10. Synthesis of intermediate I-7:
a500 mL reaction flask was charged with intermediate I-3(10.0g,30.2mmol), carbazole 9- (4-biphenyl) -2-borate (11.0g,30.2mmol), potassium carbonate (10.4g,75.5mmol), tetrakis triphenylphosphine palladium (5 mol%), 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 give intermediate I-7(11.1g, yield 60%). LC-MS: M/Z615.2 (M + H)+。
Synthesis of RH-097:
a250 mL three-necked flask was charged with intermediate I-7(5g,8.1mmol), 7H-dibenzo [ c, g]Carbazole (2.6g,9.8mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (2.3g,20.4mmol) 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 a crude product, which was then passed through a silica gel column to obtain RH-097(5.1g, yield 75%). LC-MS: M/Z846.1 (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 is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
At 0.9mA, the luminance is equal to 1237cd/m2(5.8V). In this case, CIEx is 0.659 and y 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 is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
At 0.9mA, the luminance is equal to 1184cd/m2(5.9V). In this case, CIEx is 0.660 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 is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
At 0.9mA, the luminance is equal to 1259cd/m2(5.9V). 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 is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
At 0.9mA, the luminance was equal to 1193cd/m2(6.0V). In this case, CIEx is 0.660 and y is 0.330.
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 is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. On an ITO substrate
At 0.9mA, the luminance is equal to 780cd/m2(7.5V)。In this case, CIEx is 0.659 and y is 0.329.
As shown in fig. 1, the visibility decreases as the color purity of the organic electroluminescent device increases (i.e., as the X value of the chromaticity coordinate becomes larger).
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
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 present invention provides an organic electroluminescent device having excellent color purity and brightness and prolonged durability by using the compound represented by formula 1 as a light emitting layer of the organic electroluminescent device.
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 (2)
1. A phosphorescent host compound characterized by: the structural formula is one of the following structural formulas,
2. an organic electroluminescent device using the phosphorescent host compound of claim 1, 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 main body compound is used as a main body material of the luminescent layer.
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| CN109438468A (en) * | 2018-11-26 | 2019-03-08 | 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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| KR102008134B1 (en) * | 2011-05-30 | 2019-08-09 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
| KR101887003B1 (en) * | 2011-07-21 | 2018-08-13 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
| KR101884173B1 (en) * | 2014-05-23 | 2018-08-02 | 롬엔드하스전자재료코리아유한회사 | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| KR101763222B1 (en) * | 2014-06-27 | 2017-07-31 | 희성소재 (주) | Hetero-cyclic compound and organic light emitting device using the same |
| KR102377221B1 (en) * | 2015-01-20 | 2022-03-22 | 에스에프씨주식회사 | Novel heterocyclic compounds and organic light-emitting diode including the same |
| KR101844672B1 (en) * | 2015-09-14 | 2018-04-03 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20180095916A (en) * | 2015-12-21 | 2018-08-28 | 이데미쓰 고산 가부시키가이샤 | Heterocondensated phenylquinazolines and their use in electronic devices |
| CN107011360B (en) * | 2017-03-14 | 2020-08-11 | 上海大学 | Heterocyclic-carboline derivative and application thereof |
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