CN109378397B - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN109378397B CN109378397B CN201811531439.1A CN201811531439A CN109378397B CN 109378397 B CN109378397 B CN 109378397B CN 201811531439 A CN201811531439 A CN 201811531439A CN 109378397 B CN109378397 B CN 109378397B
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Abstract
The invention provides an organic electroluminescent device, and belongs to the technical field of organic photoelectricity. The device has the compounds shown in the chemical formulas I and II, effectively realizes the injection balance of current carriers under the combined action of a hole transport layer and a hole blocking layer, and improves the generation and utilization rate of excitons. The organic light-emitting device provided by the invention has the advantages of low starting voltage, high light-emitting efficiency, long service life and the like.
Description
Technical Field
The invention relates to the technical field of organic photoelectricity, in particular to an organic electroluminescent device.
Background
With the advancement of the information industry, conventional displays have been unable to meet the requirements of people, such as: cathode Ray Tube (CRT) displays are bulky and have high drive voltages; a Liquid Crystal Display (LCD) has low brightness, a narrow viewing angle and a small working temperature range; plasma Display Panels (PDPs) are expensive, have low resolution, and consume a lot of power.
Organic light-emitting diodes (OLEDs) are novel electroluminescent devices using organic substances as luminescent materials, and as a brand new display technology, have the advantages that the existing display technology has no ethical ratio in various performances, and due to the fact that the organic light-emitting diodes have simple preparation process, all-solid-state property, self-luminescence, high brightness, high resolution, wide viewing angle (more than 170 degrees), high response speed, thin thickness, small size, light weight, flexible substrates, low-voltage direct current drive (3-10V), low power consumption, wide working temperature range and the like, the organic light-emitting diodes have wide application markets, such as lighting systems, communication systems, vehicle-mounted display, portable electronic equipment, high-definition display and even military fields.
Generally, OLEDs are layered or laminated structures, and a typical organic light emitting device has a structure generally including a cathode, an anode, and an organic layer between the electrodes. The device comprises a transparent ITO anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light Emitting Layer (EL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), LiF/Al and other functional layers. The organic electroluminescent device injects current by applying voltage across the cathode and the anode, and electrons and holes pass through each organic functional layer and are combined in the light-emitting layer to form excitons, and the excitons return to a stable ground state to generate radiation light emission.
Disclosure of Invention
The first electron transport layer material and the second electron transport layer material provided by the invention have the advantages of good compound stability, high electron mobility, high glass transition temperature, good film forming property, simple and easy synthetic method, and the prepared organic electroluminescent device has good luminous efficiency and service life performance.
The invention firstly provides an organic light-emitting device, which comprises a cathode, an anode and an organic layer positioned between the cathode and the anode, wherein the organic layer comprises a first electron transport layer and a second electron transport layer, and is characterized in that the first electron transport layer contains a compound shown in a chemical formula (I), and the second electron transport layer contains a compound shown in a chemical formula (II):
r, R therein3、R4One selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein R is1、R2One selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein X is the same or different and is selected from CR5Or N, wherein R5One selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and at least one is N;
wherein n1, n2, n3, n4 are independently the same or different and are selected from integers of 1 or more;
wherein L is selected from one of single bond, substituted or unsubstituted divalent aryl radical of C6-C30, and substituted or unsubstituted divalent heteroaryl radical of C3-C30.
Preferably, the organic light-emitting device, wherein R, R3、R4One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C3-C18 heteroaryl;
wherein R is1、R2Selected from hydrogen, substituted or notOne of substituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl;
wherein X is the same or different and is selected from CR5Or N, wherein R5One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, and at least one is N;
wherein n1, n2, n3 and n4 are independently the same or different and are selected from integers of 1 to 3;
wherein L is selected from one of single bond, substituted or unsubstituted divalent aryl radical of C6-C18, and substituted or unsubstituted divalent heteroaryl radical of C3-C18.
Preferably, the organic light emitting device, wherein R, R3, R4 are selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, spirobifluorenyl, carbazolyl, triazinyl, dibenzothienyl, pyridyl, acridinyl, dibenzofuranyl, quinolinyl or isoquinolinyl.
Preferably, the organic light emitting device, wherein L is selected from a single bond or any one of the following structures:
preferably, the organic light emitting device, wherein the hole transport layer material is selected from any one of the following structures:
preferably, the second hole blocking layer material is selected from any one of the following structures:
the hole transport layer of the present invention is located between the light emitting layer and the anode.
The hole blocking layer is positioned between the light-emitting layer and the cathode.
The invention has the beneficial effects that:
the invention provides an organic light-emitting device, which is prepared by designing a device structure and adopting a mode of combining a hole transport layer and a hole blocking layer.
The hole transport layer material introduces a structure of benzidine which is easy to accept electrons, so that the transport property of current carriers is improved; the carbazole structure is introduced at a specific position, so that the molecular weight of the compound can be increased, the obtained material has high glass transition temperature and can prevent crystallization, and the compound has certain distortion on a spatial three-dimensional structure and the film forming property of the compound is improved.
The fluorene compounds in the hole barrier layer material have the capacity of easily receiving holes, and the bridging structure is introduced, so that the molecular weight of the compounds can be increased, the obtained material has high glass transition temperature and can prevent crystallization, and the compounds have certain distortion on a spatial three-dimensional structure, and the film forming property of the compounds is improved. And a structure which is easy to accept electrons is introduced into a specific position of pyridine, pyrimidine and triazine at the other end, so that the carrier transport property is improved. In addition, such compounds localize the two moieties and control the flow of the conjugated system such that the compound has a bipolarity, L in turn interrupts the two moiety interaction, minimizing diffusion of excitons to adjacent other organic layers.
Detailed Description
For a further understanding of the invention, reference will now be made to the preferred embodiments of the invention by way of example, and it is to be understood that the description is intended to further illustrate features and advantages of the invention, and not to limit the scope of the claims.
It is to be understood that, unless defined otherwise, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The alkyl group in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group, a branched-chain alkyl group or a cyclic alkyl group, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, cyclopentyl, cyclohexyl, and the like.
The aryl group in the present invention refers to a general term of monovalent group left after one hydrogen atom is removed from the aromatic nucleus carbon of the aromatic hydrocarbon molecule, and may be monocyclic aryl group or condensed ring aryl group, and examples may include phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, etc., but are not limited thereto.
The heteroaryl group in the present invention refers to a general term of a group in which one or more aromatic core carbons in an aryl group are replaced with a heteroatom including, but not limited to, oxygen, sulfur, nitrogen or silicon atom, and the heteroaryl group may be a monocyclic or condensed ring, and examples may include, but are not limited to, pyridyl, phenothiazinyl, phenoxazinyl, pyrimidinyl, benzopyrimidinyl, carbazolyl, triazinyl, benzothiazolyl, benzimidazolyl, acridinyl and the like.
The divalent aryl group in the present invention refers to a general term of the divalent group remaining after removing one hydrogen atom from each of two aromatic core carbons of the aromatic hydrocarbon molecule, and may be a divalent monocyclic aryl group or a divalent condensed ring aryl group, and may be selected from, for example, phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, pyrenylene, fluorenylene, or benzophenanthrylene, but is not limited thereto.
The divalent heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic core carbons in a divalent aryl group with a heteroatom including but not limited to oxygen, sulfur or nitrogen atom, and the divalent heteroaryl group may be a divalent monocyclic heteroaryl group or a divalent fused cyclic heteroaryl group, and may be selected from, for example, a pyridylene group, a quinolylene group, a carbazolyl group, a thienylene group, a benzothiophenyl group, a furylene group, a benzofuranylene group, a pyrimidylene group, a benzopyrimidine group, an imidazolyl group or a benzimidazolyl group, and the like, but not limited thereto.
In the substituted alkyl group, substituted aryl group, substituted heteroaryl group and the like of the present invention, the substituents may be independently selected from deuterium atom, cyano group, nitro group, halogen atom, alkyl group of C1-C10, alkoxy group of C1-C10, alkylthio group of C1-C10, aryl group of C1-C30, aryloxy group of C1-C30, arylthio group of C1-C30, heteroaryl group of C3-C30, silyl group of C1-C30, alkylamino group of C2-C10, arylamine group of C6-C30 and the like, for example, deuterium atom, cyano group, nitro group, halogen, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, methoxy group, methylthio group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, benzophenanthryl group, perylene group, pyrenyl group, fluorenyl group, 9-dimethylfluorenyl group, benzyl group, phenoxy group, phenylthio group, dicarbanilino group, dimethylamino group, phenanthrenyl group and, 9-phenylcarbazolyl, furanyl, thienyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, phenothiazinyl, phenoxazinyl, acridinyl, piperidinyl, pyridinyl, pyrazinyl, triazinyl, pyrimidinyl, and the like, but are not limited thereto.
The invention firstly provides an organic light-emitting device, which comprises a cathode, an anode and an organic layer positioned between the cathode and the anode, wherein the organic layer comprises a hole transport layer and an electron blocking layer, and is characterized in that the hole transport layer contains a compound shown in a chemical formula (I), and the hole blocking layer contains a compound shown in a chemical formula (II):
r, R therein3、R4One selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein R is1、R2One selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein X is the same or different and is selected from CR5Or N, wherein R5One selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and at least one is N;
wherein n1, n2, n3, n4 are independently the same or different and are selected from integers of 1 or more;
wherein L is selected from one of single bond, substituted or unsubstituted divalent aryl radical of C6-C30, and substituted or unsubstituted divalent heteroaryl radical of C3-C30.
Preferably, in the organic light-emitting device, R, R3、R4One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C3-C18 heteroaryl;
wherein R is1、R2One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C3-C18 heteroaryl;
wherein X is the same or different and is selected from CR5Or N, wherein R5One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, and at least one is N;
wherein n1, n2, n3 and n4 are independently the same or different and are selected from integers of 1 to 3;
wherein L is selected from one of single bond, substituted or unsubstituted divalent aryl radical of C6-C18, and substituted or unsubstituted divalent heteroaryl radical of C3-C18.
Preferably, in the organic light-emitting device, R, R3、R4One selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, spirobifluorenyl, carbazolyl, triazinyl, dibenzothienyl, pyridyl, acridinyl, dibenzofuranyl, quinolinyl or isoquinolinyl.
Preferably, in the organic light emitting device, R1、R2Selected from hydrogen, substituted or unsubstituted one of the following groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, spirobifluorenyl, carbazolyl, triazinyl, dibenzothienyl, pyridyl, acridinyl, dibenzofuranyl, quinolinyl or isoquinolinyl.
Preferably, in the organic light emitting device, L is selected from a single bond or any one of the structures shown below:
preferably, the hole transport layer material is selected from any one of the following structures:
preferably, the hole blocking layer material is selected from any one of the following structures:
while specific structural forms of the compounds of the present invention have been illustrated above, the present invention is not limited to these listed chemical structures, and any of the various substituents defined above based on the structures of formula (I) and formula (II) should be included.
The preparation method of the hole transport layer material comprises the following steps:
the compound 1-a is coupled with the compound 1-b to obtain a compound 1-c, and the compound 1-c is coupled with the compound 1-d to obtain a compound 1-e.
The preparation method of the hole barrier layer material comprises the following steps:
the compound 2-a is coupled with the compound 2-b to obtain a compound 2-c, and the compound 2-c is coupled with the compound 2-d to obtain a compound 2-e.
The organic light-emitting device can be applied to the application fields of flat panel displays, illumination light sources, indicators, signal lamps and the like.
The invention is explained in more detail by the following examples, without wishing to restrict the invention accordingly. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue inventive effort.
The starting materials used in the following examples are not particularly limited in their source, and may be commercially available products or prepared by methods known to those skilled in the art.
Example 1:
preparation of Compound 1-1
Preparation of intermediates 1-1-3
Tri-tert-butylphosphine (4.4mL of a 1.0M solution in toluene, 1.48g, 0.05mmol), palladium acetate (0.4g, 1.83mmol) and sodium tert-butoxide (52.7g, 549mmol) were added to a solution of 1-1(33.42g, 100mmol) and 1-2(30.99g, 100mmol) in degassed toluene (500mL) and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue was filtered through silica gel (heptane/dichloromethane) and crystallized from isopropanol. Intermediate 1-1-345.13 g was obtained in 80% yield.
Preparation of Compound 1-1
Tri-tert-butylphosphine (4.4mL of a 1.0M solution in toluene, 1.48g, 0.05mmol), palladium acetate (0.4g, 1.83mmol) and sodium tert-butoxide (52.7g, 549mmol) were added to a solution of 1-1-3(56.41g, 100mmol) and 1-1-4(16.91g, 100mmol) in degassed toluene (500mL) and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue was filtered through silica gel (heptane/dichloromethane) and crystallized from isopropanol. 148.99 g of compound was obtained in 75% yield.
Example 2:
preparation of Compounds 1-32
Preparation of Compounds 1-32
Compound 1-32 is obtained by replacing 1-1-1 in example 1 with 1-32-1 as shown above and replacing 1-1-4 with 1-32-4 as shown above. Mass spectrum m/z: 845.38 (calculated value: 845.40). Theoretical element content (%) C63H47N3: c, 89.43; h, 5.60; n, 4.97 measured element content (%): c, 89.44; h, 5.61; and N, 4.98. The above confirmed that the obtained products were the objective products 1 to 32.
Example 3:
preparation of Compounds 1-63
Preparation of Compounds 1-63
Compound 1-63 is obtained by substituting 1-1-1 in example 1 with 1-63-1 as shown above and 1-1-4 with 1-63-4 as shown above. Mass spectrum m/z: 957.41 (calculated value: 957.43). Theoretical element content (%) C72H51N3: c, 90.25; h, 5.36; n, 4.39 measured element content (%): c, 90.26; h, 5.35; and N, 4.38. The above confirmed that the obtained products were the objective products 1 to 63.
Example 4:
preparation of Compounds 1-87
Preparation of Compounds 1-87
Compound 1-87 was obtained by replacing 1-1-1 in example 1 with 1-87-1 as shown above and replacing 1-1-4 with 1-87-4 as shown above. Mass spectrum m/z: 945.37 (calculated value: 945.38). Theoretical element content (%) C70H47N3O: c, 88.86; h, 5.01; n, 4.44; o, 1.69 measured elemental content (%): c, 88.88; h, 5.02; n, 4.454; o, 1.68. The above confirmed that the obtained products were the objective products 1 to 87.
Example 5:
preparation of Compounds 1-95
Preparation of Compounds 1-95
Compound 1-87 was obtained by replacing 1-1-1 in example 1 with 1-95-1 as shown above and replacing 1-1-4 with 1-95-4 as shown above. Mass spectrum m/z: 957.41 (calculated value: 957.42). Theoretical element content (%) C72H51N3: c, 90.25; h, 5.36; n, 4.39 measured element content (%): c, 90.26; h, 5.35; and N, 4.38. The above confirmed that the obtained products were 1 to 95 target products.
Example 6:
preparation of Compounds 1-111
Preparation of Compounds 1-111
Compound 1-111 was obtained by replacing 1-1-1 in example 1 with 1-111-1, 1-1-2 with 1-111-2, and 1-1-4 with 1-111-4, as shown above. Mass spectrum m/z: 779.33 (calculated value: 779.34). Theoretical element content (%) C58H41N3: c, 89.31; h, 5.30; n, 5.39 measured element content (%): c, 89.32; h, 5.31; n, 5.38. It was confirmed that the obtained product was the objective product1-111。
Example 7:
preparation of Compounds 1-125
Preparation of Compounds 1-125
Compounds 1 to 125 were obtained by replacing 1-1-1 in example 1 with 1-25-1, 1-1-2 with 1-125-2, and 1-1-4 with 1-125-4, as shown above. Mass spectrum m/z: 885.36 (calculated value: 885.38). Theoretical element content (%) C63H44N4: c, 88.29; h, 5.17; n, 6.54 measured elemental content (%): c, 88.28; h, 5.18; and N, 6.53. The above confirmed that the obtained products were the objective products 1 to 111.
Example 8:
preparation of Compound 2-1
Preparation of intermediates 2-1-3
Under the protection of nitrogen, 2-1-1(35.92g, 100.08mmol), 2-1-2(28.19g, 100.08mmol), potassium carbonate (1.24g, 9.00mmol) and 200mL of toluene were added to a 2L reaction vessel and stirred. The temperature in the reaction kettle is raised to 70 ℃, and Pd (PPh) is added3)4(1.04g, 0.90mmol) and 100mL of distilled water were stirred, and the mixture was refluxed for 11 hours to effect a complete reaction. After the reaction was terminated by adding 70mL of distilled water, filtration under reduced pressure was carried out, the solid was washed with distilled water, and then recrystallized from acetone, toluene, THF to give a solid which was then sublimed and toluene recrystallized to give 1 to 331.13 g of intermediate in 80.44% yield.
Preparation of Compound 2-1
The same procedure as that for the preparation of intermediate 2-1-3 gave compound 2-140.14 g in 75% yield. Mass spectrum m/z: 535.20 (calculated value: 535.21). Theoretical element content (%) C39H25N3: c, 87.45; h, 4.70; n, 7.84 measured elemental content (%): c, 8746; h, 4.71; n, 7.85 the above confirmation gave the product 2-1 as the desired product.
Example 9:
preparation of Compounds 2-11
Preparation of Compounds 2-11
Compound 2-11 was obtained by replacing 2-1-2 in example 1 with 2-11-2 as shown above and replacing 2-1-5 with 2-11-5 as shown above. Mass spectrum m/z: 699.29 (calculated value: 699.30). Theoretical element content (%) C54H37N: c, 92.67; h, 5.33; n, 2.00 measured element content (%): c, 92.68; h, 5.32; and N, 2.01. The above confirmed that the obtained products were the objective products 2 to 11.
Example 10:
preparation of Compounds 2-20
Preparation of Compounds 2-20
Compound 2-20 was obtained by replacing 2-1-1 in example 1 with 2-20-1, 2-1-2 with 2-20-2, and 2-1-5 with 2-20-5 as shown above. Mass spectrum m/z: 501.22 (calculated: 501.23). Theoretical element content (%) C36H27N3: c, 86.20; h, 5.43; n, 8.38 measured elemental content (%): c, 86.22; h, 5.42; n, 8.37. The above confirmed that the obtained products were 2 to 20 target products.
Example 11:
preparation of Compounds 2-30
Preparation of Compounds 2-30
Replacement of 2-1-1 in example 1 with 2-30-1, 2-1-2 as described aboveSubstitution of 2-30-2, 2-1-5 as shown above for 2-30-5 gave compound 2-30. Mass spectrum m/z: 625.25 (calculated value: 625.26). Theoretical element content (%) C46H31N3: c, 88.29; h, 4.99; n, 6.72 measured elemental content (%): c, 88.28; h, 4.98; n, 6.73. The above confirmed that the obtained products were 2 to 30 target products.
Example 12:
preparation of Compounds 2-47
Preparation of Compounds 2-47
Compound 2-47 is obtained by substituting 2-1-1 in example 1 with 2-47-1 as shown above, 2-1-2 with 2-47-2 as shown above, and 2-1-5 with 2-47-5 as shown above. Mass spectrum m/z: 701.28 (calculated value: 701.29). Theoretical element content (%) C52H35N3: c, 88.99; h, 5.03; n, 5.99 measured elemental content (%): c, 88.98; h, 5.02; and N, 5.98. The above confirmed that the obtained products were the objective products 2 to 47.
[ comparative application example ]
Respectively ultrasonically cleaning the transparent anode electrode ITO substrate with deionized water, acetone and ethanol for 15 minutes, cleaning the transparent anode electrode ITO substrate in a plasma cleaner for 2 minutes, drying and vacuumizing to 5 multiplied by 10-5Pa. And then evaporating the processed ITO substrate. Evaporating a hole injection layer HAT-CN/50nm, an evaporated hole transport layer NPB/30nm and an evaporated main body CBP layer by layer: doped Ir (ppy)310% mixing/30 nm, then evaporating and plating a first electron transport layer TPBi/30nm, an electron injection layer LiF/0.5nm and a cathode Al/200 nm.
[ application examples 1 to 7]
The compounds in the hole transport layer in the comparative application example were changed to the compounds 1-1, 1-32, 1-63, 1-87, 1-95, 1-111, 1-125 shown in examples 1-7.
[ application examples 8 to 12]
In addition to application example 1, a hole blocking layer was added and located between the light-emitting layer and the electron transporting layer, and the compounds 2-1, 2-11, 2-20, 2-30, and 2-47 in examples 8-12 were evaporated.
Table 1 shows the results of the test of the light emitting characteristics of the light emitting devices prepared by the compounds prepared in the examples of the present invention and the comparative materials.
Table 1 test of light emitting characteristics of light emitting device
The above results show that the organic light emitting device provided by the invention designs the hole transport layer and the hole blocking layer by combining the compounds shown in the chemical formulas I and II, and then carries out reasonable device structure design, thereby effectively realizing carrier injection balance under the combined action of the hole transport layer and the hole blocking layer, and improving the generation and utilization rate of excitons. The organic light-emitting device provided by the invention has the advantages of low starting voltage, high light-emitting efficiency and long service life, and the compound for preparing the organic light-emitting device is easy to obtain raw materials, simple in synthesis method and easy to operate, and meets the requirements of industry and market to a great extent.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims.
Claims (7)
1. An organic light-emitting device comprising a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises a hole transport layer and a hole blocking layer, wherein the hole transport layer comprises a compound of formula (I), and the hole blocking layer comprises a compound of formula (II):
r, R therein3、R4One selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein R is1、R2One selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein X is different from CR5Or N, wherein R5One selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and at least one is N;
wherein n1, n2, n3, n4 are independently the same or different and are selected from integers of 1 or more;
wherein L is selected from one of single bond, substituted or unsubstituted divalent aryl radical of C6-C30, and substituted or unsubstituted divalent heteroaryl radical of C3-C30.
2. The organic light-emitting device as claimed in claim 1, wherein R, R is present3、R4One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C3-C18 heteroaryl;
wherein R is1、R2One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C3-C18 heteroaryl;
wherein X is the same or different and is selected from CR5Or N, wherein R5One selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, and at least one is N;
wherein n1, n2, n3 and n4 are independently the same or different and are selected from integers of 1 to 3;
wherein L is selected from one of single bond, substituted or unsubstituted divalent aryl radical of C6-C18, and substituted or unsubstituted divalent heteroaryl radical of C3-C18.
3. The organic light-emitting device as claimed in claim 1, wherein R, R is present3、R4One selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, spirobifluorenyl, carbazolyl, triazinyl, dibenzothienyl, pyridyl, acridinyl, dibenzofuranyl, quinolinyl or isoquinolinyl.
4. The organic light-emitting device of claim 1, wherein R is1、R2Selected from hydrogen, substituted or unsubstituted one of the following groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, spirobifluorenyl, carbazolyl, triazinyl, dibenzothienyl, pyridyl, acridinyl, dibenzofuranyl, quinolinyl or isoquinolinyl.
5. The organic light-emitting device of claim 1, wherein L is selected from a single bond or any of the following structures:
6. the organic light-emitting device according to claim 1, wherein the hole transport layer material is selected from any one of the following structures:
7. the organic light-emitting device according to claim 1, wherein the hole blocking layer material is selected from any one of the following structures:
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