CN115504858A - Compound and application thereof in organic photoelectric device - Google Patents

Compound and application thereof in organic photoelectric device Download PDF

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CN115504858A
CN115504858A CN202211198735.0A CN202211198735A CN115504858A CN 115504858 A CN115504858 A CN 115504858A CN 202211198735 A CN202211198735 A CN 202211198735A CN 115504858 A CN115504858 A CN 115504858A
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王鹏
王湘成
何睦
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention discloses a compound and application thereof in an organic photoelectric device, wherein the compound has a structure shown as a formula (1), X is selected from O, S and C (R) 9 R 10 ) Or N (R) 11 )，R 1 ‑R 15 Independently selected from hydrogen, deuterium, substituted or unsubstituted straight or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, or a group adjacent to the ringSublinked to form a ring, R 1 ‑R 8 At least one is selected from the group A or C and at least one is selected from the group B. The compound of the invention is used as a hole transport material and an electron transport material of an OLED device and a light-emitting main body material of a red and green phosphorescent organic photoelectric device, reduces the driving voltage, and simultaneously improves the light-emitting efficiency and prolongs the service life.

Description

Compound and application thereof in organic photoelectric device
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to a compound and application thereof in organic photoelectric devices.
Background
Organic electroluminescent devices (OLEDs), which are devices having a sandwich-like structure, include positive and negative electrode films and organic functional material layers sandwiched between the electrode films, have been widely used for display panels of products such as novel lighting fixtures, smart phones and tablet computers, and further will be expanded to the application field of large-size display products such as televisions, are novel display technologies with fast development and high technical requirements, and have great research values and application prospects in the fields of information display materials, organic optoelectronic materials, and the like.
With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The current main display technologies include plasma display devices, field emission display devices and organic electroluminescent display devices (OLEDs), wherein the OLEDs have a series of advantages of self-luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with liquid crystal display devices, the OLEDs do not need backlight sources, have wider viewing angles and low power consumption, have response speeds 1000 times that of the liquid crystal display devices, and have wider application prospects. Since the first time OLEDs were reported, many scholars have been devoted to studying how to improve device efficiency and stability. At present, OLED display and illumination are widely applied in commercialization, the requirements of a client terminal on photoelectricity and service life of an OLED screen body are continuously improved, in order to meet the requirements, refinement is required in the process of OLED panel manufacturing, and development of OLED materials capable of meeting higher device indexes is particularly important. So far, the development of the existing OLED materials is far behind the requirements of panel manufacturing enterprises on the OLED materials, and it is particularly urgent to develop organic functional materials with better performance to meet the development requirements of the current industry.
At present, aromatic amine compounds with good hole transport characteristics are mainly adopted as hole transport materials, and N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB) is widely used for organic electroluminescent devices with various colors due to moderate highest occupied orbital energy level and good hole mobility, however, the glass transition temperature of the molecules is low (98 ℃), the devices are easy to generate phase change under the action of accumulated joule heat during long-time work, the service life of the devices is greatly influenced, and the design of the hole transport materials with high mobility and glass transition temperature is necessary. In addition, the host material is used as a key luminescent material of the device, and has more strict requirements on the performance of the device, such as thermal stability, electrical stability, high luminous efficiency, service life and the like, and the development of the stable and efficient host material has important practical application value for reducing driving voltage, improving luminous efficiency of the device and prolonging service life of the device.
Disclosure of Invention
Based on this, the present invention provides a compound having a chemical structure represented by formula (1):
Figure BDA0003871605290000021
in the formula (1), X is selected from O, S and C (R) 9 R 10 ) Or N (R) 11 )；
R 1 -R 15 Identical or different from each other, each independently selected from hydrogen, deuterium, substituted or unsubstituted linear or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl or bonded to an adjacent atom to form a ring, wherein R is 1 -R 8 At least one is selected from substituted or unsubstituted groups a or C, and at least one is selected from substituted or unsubstituted groups B:
Figure BDA0003871605290000022
in the groups A and B, L 1 And L 2 Selected from the group consisting of a single bond, O, S, N (R) 12 ) Substituted or unsubstituted straight or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
Ar 1 selected from substituted or unsubstituted C6-C60 aryl, or substituted orUnsubstituted C5-C60 heteroaryl;
the group C is selected from one or more of the structures shown in the formula (2):
Figure BDA0003871605290000023
z in the formula (2) 1 -Z 9 Are identical or different from each other and are each independently selected from O, S, C (R) 13 R 14 ) Or N (R) 15 )，Ar 2 Selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
the term "substituted 8230" in said "substituted 8230", means substituted with one or more substituents independently selected from deuterium, fluorine, cyano, C1-C12 alkyl, C6-C18 aryl, C5-C18 heteroaryl;
* Is a linking site.
The invention also provides an organic photoelectric device comprising the compound.
The invention also provides a display or lighting device comprising the organic photoelectric device.
Compared with the prior art, the invention has the beneficial effects that: due to the introduction of rigid spirocycloalkane compounds or acenaphthene, the compound of the invention can adjust the HOMO energy level of molecules on one hand, and the electron transport capability is enhanced due to the power supply property of alkane on the other hand, the integral rigidity of the compound is enhanced due to the introduction of rigid groups, and the compound has good thermal stability. In addition, the alkyl structure in the compound of the present invention makes the intermolecular packing more loose, thereby lowering the deposition temperature. The compound has higher triplet state energy level, better carrier mobility, higher thermal stability and film forming stability, can be matched with adjacent energy levels, is used as a stable and efficient hole transport material and an electron transport material, is used for corresponding OLED devices as well as a novel organic material for red and green phosphorescent organic photoelectric devices, can reduce driving voltage and simultaneously improve the luminous efficiency and the service life of the devices.
Detailed Description
The invention provides a compound based on fluorene acenaphthene substituted fluorene dianthracene derivatives, which has higher device efficiency when applied to organic photoelectric devices, has high stability of molecules, further improves the luminous efficiency and the service life of the device, and completes the invention on the basis.
The compound provided by the invention has a chemical structure shown as a formula (1):
Figure BDA0003871605290000031
in the formula (1), X is selected from O, S and C (R) 9 R 10 ) Or N (R) 11 )；
R 1 -R 15 Identical or different from each other, each independently selected from hydrogen, deuterium, substituted or unsubstituted linear or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl or bonded to an adjacent atom to form a ring, wherein R is 1 -R 8 At least one is selected from substituted or unsubstituted groups a or C, and at least one is selected from substituted or unsubstituted groups B:
Figure BDA0003871605290000032
in the groups A and B, L 1 And L 2 Selected from the group consisting of a single bond, O, S, N (R) 12 ) Substituted or unsubstituted straight or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
Ar 1 selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
the group C is selected from one or more of the structures shown in the formula (2):
Figure BDA0003871605290000041
z in the formula (2) 1 -Z 9 Are identical or different from each other and are each independently selected from O, S, C (R) 13 R 14 ) Or N (R) 15 )，Ar 2 Selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
the term "substituted 8230" as used herein means substituted with one or more substituents independently selected from deuterium, fluorine, cyano, C1-C12 alkyl, C6-C18 aryl, and C5-C18 heteroaryl;
* Is a linking site.
Examples of the substituent in the present invention are described below, but the substituent is not limited thereto:
[ substituted or unsubstituted ] means substituted with one or more substituents selected from: deuterium, halogen, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylphosphine group, and heteroaryl group, acenaphthylene group, or unsubstituted; or substituted with a substituent linking two or more of the substituents exemplified above, or unsubstituted; for example, "a substituent linking two or more substituents" may include a biphenyl group, i.e., a biphenyl group may be an aryl group, or a substituent linking two phenyl groups.
[ alkyl ] may be linear or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl.
The above description of alkyl groups also applies to alkyl groups in aralkyl, aralkylamino, alkylaryl, and alkylamino groups.
[ heteroalkyl ] may be a linear or branched alkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl includes, but is not limited to, alkoxy, alkylthio, alkylsulfonyl, alkoxy including, but not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy; alkylthio includes, but is not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio.
[ cycloalkyl ] may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl.
[ heterocycloalkyl ] may be a cycloalkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heterocycloalkyl includes, but is not limited to
Figure BDA0003871605290000051
And the like.
[ aryl ] is not particularly limited, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthracyl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group can be substituted, such as 9,9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. Further, two of the substituents may be bonded to each other to form a spiro ring structure, such as 9,9' -spirobifluorenyl group and the like.
The description above for aryl groups applies to arylene groups except that arylene groups are divalent.
The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
[ heteroaryl ] comprises one or more of N, O, P, S, si and Se as heteroatoms. Heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazainonyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, furanyl, thienyl, thiazolyl, and the like pyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophenanthridinyl, spiro [ fluorene-9, 9' -xanthene ], benzidinaphthyl, dinaphthofuranyl, naphthofuranyl, dinaphthothiophenyl, naphthothienyl, triphenylphosphine oxide, triphenylborane.
The above description of heteroaryl groups applies to heteroaryl groups in heteroarylamino and arylheteroarylamino groups.
The above description of heteroaryl groups can be used for heteroarylenes, except that the heteroarylene group is divalent.
Specifically, the aforementioned compounds of the present invention may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following. For example, deuterium, halogen, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylheteroarylamino group, arylphosphine group, heteroaryl group and the like can be cited.
In some embodiments, in formula (1), R 3 、R 4 、R 5 And R 6 One of them is selected from substituted or unsubstituted groups a.
In some embodiments, in formula (1), R 3 、R 4 、R 5 And R 6 One of them is selected from substituted or unsubstituted groups C.
In some embodiments, in formula (1), ar 1 One or more selected from substituted or unsubstituted structures represented by formula (3):
Figure BDA0003871605290000061
wherein the term "substituted or unsubstituted" \8230 "" substituted \8230 "in" means substituted with one or more substituents independently selected from deuterium, fluorine, cyano, C1-C12 alkyl, C6-C18 aryl, and C5-C18 heteroaryl, and is a linking site.
In some embodiments, the groups C and Ar 2 Form aThe alkyl groups of the ring are selected from one or more of the structures shown in the formula (4):
Figure BDA0003871605290000062
Figure BDA0003871605290000071
in the formula (4), R c Selected from C6-C30 aryl or C5-C30 heteroaryl, which is a linking site.
In some embodiments, in formulas (1) - (4), the hydrogen atom on any one of the phenyl rings can be replaced by deuterium, and the hydrogen atom on any one of the alkyl groups can be replaced by deuterium.
In some embodiments, the aforementioned compound is selected from one or more of the following chemical structures:
Figure BDA0003871605290000072
Figure BDA0003871605290000081
Figure BDA0003871605290000091
Figure BDA0003871605290000101
Figure BDA0003871605290000111
Figure BDA0003871605290000121
Figure BDA0003871605290000131
Figure BDA0003871605290000141
the fluorene derivative is used as a matrix of the compound, the matrix structure has good thermal stability, appropriate HOMO, LUMO energy levels and Eg, higher triplet state energy level and carrier mobility, can be matched with adjacent energy levels, has higher thermal stability and film forming stability, can be used as a hole transport material, an electron transport material and a main body material and applied to OLED devices, and effectively improves the efficiency and the service life of the devices.
The organic photoelectric device provided by the invention comprises a first electrode, a second electrode and one or more organic layers arranged between the first electrode and the second electrode, and is of a bottom or top light-emitting device structure, wherein the organic layers can be of a single-layer structure or a multi-layer series structure laminated with two or more organic layers, and the organic layers such as the organic layers with at least one layer of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer can be prepared by using common methods and materials for preparing the organic photoelectric device.
In the organic photoelectric device provided by the present invention, the first electrode is used as an anode layer, and the anode material may be, for example, a material having a large work function, so that holes are smoothly injected into the organic layer, such as a metal, a metal oxide, a combination of a metal and an oxide, a conductive polymer, and the like, and a metal oxide such as Indium Tin Oxide (ITO), zinc oxide, indium Zinc Oxide (IZO), and the like.
In the organic photoelectric device provided by the present invention, the second electrode serves as a cathode layer, the cathode material may be, for example, a material having a small work function so that electrons are smoothly injected into the organic layer, the cathode material may be, for example, a metal such as magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead, or an alloy thereof, or a material having a multilayer structure, and the cathode material is preferably magnesium and silver.
In the organic opto-electronic device provided by the present invention, the material of the hole injection layer, preferably the material having the Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer, is the material that advantageously receives holes from the anode at low voltage.
In the organic photoelectric device provided by the invention, the material of the hole transport layer is a material with high mobility for holes, and is suitable for being used as a material for receiving the holes from the anode or the hole injection layer and transporting the holes to the light emitting layer. Materials for the hole transport layer include, but are not limited to, organic materials of arylamines, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
In the organic photoelectric device provided by the invention, the compound provided by the invention can be applied to a light-emitting layer of the device.
In the organic photoelectric device provided by the present invention, the material of the electron transport layer is a material having high mobility to electrons and suitable as a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer.
In the organic photoelectric device provided by the invention, the material of the covering layer generally has high refractive index, so that the organic photoelectric device can contribute to the improvement of the light efficiency of the organic light-emitting device, particularly the improvement of the external light-emitting efficiency.
In the organic photoelectric device provided by the invention, the organic photoelectric device is an organic photovoltaic device, an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor and the like.
Synthesis examples:
the synthesis of the compound represented by the above formula (I) can be carried out by a known method, for example, a cross-coupling reaction using a transition metal such as nickel or palladium. Other synthesis methods are C-C, C-N coupling reactions using transition metals such as magnesium or zinc. The above reaction is limited to mild reaction conditions and superior selectivity of various functional groups, and Suzuki and Buchwald reactions are preferred. The invention is realized byThe compounds are illustrated by, but not limited to, the compounds and methods of synthesis exemplified in the following examples. The initial raw materials and solvents of the invention and products such as common OLED intermediates are purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. are available from sigma-Aldrich, 1 h NMR data were measured using a JEOL (400 MHz) nuclear magnetic resonance apparatus, and HPLC data were measured using a Shimadzu LC-20AD HPLC apparatus.
The materials used in the examples were:
Figure BDA0003871605290000151
Figure BDA0003871605290000161
example 1
Synthesis of Compound 1
Figure BDA0003871605290000162
1) Synthesis of intermediate 1-1
Under an argon atmosphere, 33.6g (100 mmol) of 1-A, 12.1g (100 mmol) of 1-B, 1.16g (1.0 mmol) of tetrakis (triphenylphosphine) palladium, 200ml (300 mmol) of a 1.5M aqueous solution of sodium carbonate and 800ml (DME) were charged into a reactor, and the mixture was stirred with heating at 80 ℃ overnight. After cooling to room temperature, 500ml of water was added, a solid was precipitated and filtered, and the obtained solid was washed with ethanol to obtain 22.0g of compound 1-1, yield 66%, and HPLC purity 98.9%. LC MS M/Z332.02 (M +); 1 H NMR(400MHz,DMSO-d6)δ7.34-7.43(m,1H),7.43-7.53(m,4H),7.50-7.60(m,2H),7.61-7.69(m,2H),8.13-8.22(m,2H),8.22-8.31(m,2H)。
2) Synthesis of Compound 1
Under an argon atmosphere, 1 to 1.3 g (100 mmol), 1 to C39.0 g (100 mmol), 1.16g (1.0 mmol) of tetrakis (triphenylphosphine) palladium, 200ml (300 mmol) of 1.5M aqueous sodium carbonate solution and 800ml of ethylene glycol dimethyl ether (DME) were added to a reactor, and the mixture was heated and stirred at 80 ℃One night. After cooling to room temperature, 500ml of water was added, a solid precipitated and filtered, the resulting solid was washed with ethanol, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane), yielding 45.5g of compound 1-1, 76% yield, 99.9% purity by HPLC. LC MS M/Z598.27 (M +); 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),7.16-7.28(m,2H),7.30-7.40(m,2H),7.35-7.46(m,6H),7.40-7.50(m,3H),7.50-7.60(m,3H),7.61-7.69(m,2H),7.84-7.92(m,1H),8.06(d,1H),8.16-8.26(m,4H)。
example 2
Synthesis of Compound 12
Figure BDA0003871605290000171
The procedure of example 1 was repeated, except that the starting materials were changed to 12-B and 12-C. LC MS M/Z750.33 (M +) HPLC purity: 99.9%, total yield: 49 percent; 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),7.16-7.28(m,2H),7.29-7.35(m,1H),7.35-7.53(m,14H),7.67(m,1H),7.70-7.81(m,6H),8.04-8.12(m,1H),8.15-8.26(m,5H),8.80(s,2H)。
example 3
Synthesis of Compound 23
Figure BDA0003871605290000172
The procedure of example 1 was repeated, except that the starting materials were changed to 23-B and 23-C. LC MS M/Z738.29 (M +). The total synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.82(s,6H),3.52(s,4H),7.16-7.27(m,2H),7.31(m,1H),7.35-7.41(m,3H),7.36-7.62(m,9H),7.57-7.66(m,2H),7.76(m,1H),7.80-7.87(m,2H),7.94-8.02(m,1H),8.06-8.15(m,2H),8.16-8.28(m,5H)。
Example 4
Synthesis of Compound 42
Figure BDA0003871605290000173
The procedure was as in example 1 except that the starting materials were changed to 42-B and 42-C. LC MS M/Z724.31 (M +). The total synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),7.16-7.28(m,2H),7.29-7.35(m,1H),7.35-7.59(m,14H),7.63(m,1H),7.73-7.83(m,4H),8.00-8.12(m,3H),8.16-8.26(m,4H),8.97-9.05(m,1H).
Example 5
Synthesis of Compound 45
Figure BDA0003871605290000181
The procedure of example 1 was repeated, except that the starting materials were changed to 45-B and 45-C. LC MS M/Z674.30 (M +). The total synthesis yield is as follows: 52 percent; HPLC purity: 99.9 percent.
Example 6
Synthesis of Compound 73
Figure BDA0003871605290000182
The procedure of example 1 was repeated, except that the starting materials were changed to 73-B and 73-C. LC MS M/Z737.27 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.14-7.24(m,2H),7.19-7.28(m,1H),7.31-7.52(m,11H),7.52-7.66(m,5H),7.66-7.83(m,6H),7.87-7.95(m,1H),8.16-8.26(m,5H).
Example 7
Synthesis of Compound 87
Figure BDA0003871605290000183
The procedure was as in example 1 except that the starting materials were changed to 87-B and 87-C. LC MS M/Z712.24 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.16-7.51(m,12H),7.51-7.58(m,2H),7.62-7.76(m,3H),7.76(m,1H),7.79-7.89(m,3H),7.94-8.02(m,1H),8.07-8.15(m,1H),8.16-8.26(m,5H).
Example 8
Synthesis of Compound 100
Figure BDA0003871605290000191
The procedure was as in example 1 except that the starting materials were changed to 100-B and 100-C. LC MS M/Z764.25 (M +). The total synthesis yield is as follows: 49 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.16-7.28(m,2H),7.34-7.53(m,10H),7.69-7.77(m,2H),7.84(s,2H),7.87(m,1H),7.95-8.05(m,2H),8.08-8.21(m,3H),8.16-8.26(m,6H),8.44(d,2H),9.76(d,2H).
Example 9
Synthesis of Compound 102
Figure BDA0003871605290000192
The procedure was as in example 1 except that the starting materials were changed to 102-B and 102-C. LC MS M/Z812.31 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.03-7.11(m,4H),7.13-7.52(m,20H),7.54-7.63(m,2H),7.73-7.84(m,2H),7.84-7.94(m,2H),7.98-8.05(m,1H),8.05-8.12(m,1H),8.16-8.26(m,4H).
Example 10
Synthesis of Compound 112
Figure BDA0003871605290000193
The procedure of example 1 was repeated, except that the starting materials were changed to 112-B and 112-C. LC MS M/Z695.36 (M +). The total synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.16-7.28(m,2H),7.34-7.60(m,11H),7.64(m,2H),7.70(m,2H),7.87-7.95(m,1H),8.01(m,2H),8.16-8.26(m,4H),8.26(d,1H),8.27-8.37(m,2H),8.45(m,1H),9.56-9.64(m,1H),9.76(m,1H).
Example 11
Synthesis of Compound 127
Figure BDA0003871605290000201
The procedure of example 1 was repeated, except that the starting materials were changed to 127-B and 127-C. LC MS M/Z890.30 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.16-7.28(m,2H),7.34-7.44(m,5H),7.39-7.51(m,2H),7.54-7.62(m,4H),7.59-7.68(m,3H),7.63-7.73(m,1H),7.68-7.79(m,1H),7.79-7.94(m,7H),7.97-8.07(m,4H),8.11-8.20(m,1H),8.15-8.26(m,4H),8.30(d,1H),8.44(m,1H),8.81-8.89(m,1H),9.73-9.79(m,1H).
Example 12
Synthesis of Compound 135
Figure BDA0003871605290000202
The procedure of example 1 was repeated, except that the starting materials were changed to 135-B and 135-C. LC MS M/Z737.27 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.12-7.67(m,22H),7.76(m,1H),7.84(m,2H),7.98(m,1H),8.16-8.26(m,4H),8.54-8.64(m,1H).
Example 13
Synthesis of Compound 142
Figure BDA0003871605290000203
The procedure of example 1 was repeated, except that the starting materials were changed to 142-B and 142-C. LC MS M/Z773/31 (M +). The total synthesis yield is as follows: 46 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.14(m,1H),7.17-7.28(m,2H),7.34-7.52(m,12H),7.58(s,4H),7.52-7.67(m,3H),7.71-7.81(m,3H),7.93(m,1H),7.99-8.09(m,1H),8.16-8.28(m,4H),8.28-8.37(m,2H),8.45-8.55(m,1H),8.90-9.00(m,1H).
Example 14
Synthesis of Compound 156
Figure BDA0003871605290000211
The procedure was as in example 1 except that the starting materials were changed to 156-B and 156-C. LC MS M/Z849.34 (M +). The total synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.16-7.27(m,2H),7.29(s,1H),7.34-7.46(m,8H),7.42-7.55(m,10H),7.52-7.67(m,3H),7.69-7.77(m,4H),8.03(d,1H),8.16-8.26(m,4H),8.32(m,1H),8.80(s,2H),8.97(m,2H),9.34-9.40(m,1H).
Example 15
Synthesis of Compound 167
Figure BDA0003871605290000212
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 167-B and 167-C. LC MS M/Z813.30 (M +). The total synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ3.52(s,4H),7.12-7.28(m,4H),7.34-7.67(m,19H),7.69-7.80(m,4H),7.84(m,3H),8.16-8.26(m,4H),8.54-8.64(m,1H).
Example 16
Synthesis of Compound 188
Figure BDA0003871605290000213
The procedure was as in example 1 except that the starting materials were changed to 188-B and 188-C. LC MS M/Z975.39 (M +). The total synthesis yield is as follows: 49 percent; HPLC purity: 99.9 percent.
Example 17
Synthesis of Compound 196
Figure BDA0003871605290000221
The procedure of example 1 was repeated, except that the starting materials were changed to 196-B and 196-C. LC MS M/Z718.36 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ0.95-1.05(m,1H),1.08-1.23(m,2H),1.20-1.30(m,1H),1.40(m,2H),1.48-1.81(m,10H),1.87(m,1H),1.96(m,1H),2.05(m,1H),2.21(m,1H),5.70(m,1H),6.26(m,1H),7.28-7.40(m,2H),7.35-7.44(m,6H),7.45-7.52(m,1H),7.59-7.72(m,2H),7.72-7.81(m,2H),7.81-7.94(m,3H),8.05-8.12(m,1H),8.16-8.26(m,4H),8.44(m,1H),8.81-8.89(m,1H),9.76(m,1H).
Example 18
Synthesis of Compound 203
Figure BDA0003871605290000222
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 203-B and 203-C. LC MS M/Z755.02 (M +). The total synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.33-1.51(m,4H),1.58-1.74(m,4H),1.69(s,6H),2.75(m,2H),6.67(m,1H),7.04(m,1H),7.27(t,1H),7.30-7.35(m,1H),7.35-7.44(m,5H),7.44-7.53(m,2H),7.63-7.81(m,1H),8.05-8.12(m,1H),8.15-8.26(m,5H),8.67-8.73(m,2H).
Example 19
Synthesis of Compound 207
Figure BDA0003871605290000223
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 207-B and 207-C. LC MS M/Z740.31 (M +). The total synthesis yield is as follows: 50 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),4.63(d,4H),7.31-7.53(m,8H),7.49-7.72(m,6H),7.75(m,1H),7.81-7.94(m,6H),7.97-8.04(m,1H),8.06(d,1H),8.16-8.26(m,4H),8.44(m,1H),8.81-8.89(m,1H),9.76(m,1H).
Example 20
Synthesis of Compound 212
Figure BDA0003871605290000231
The procedure of example 1 was repeated, except that the starting materials were changed to 212-B and 212-C. LC MS M/Z768.38 (M +). The total synthesis yield is as follows: 49 percent; HPLC purity: 99.9 percent.
Example 21
Synthesis of Compound 217
Figure BDA0003871605290000232
The procedure of example 1 was repeated, except that the starting materials were changed to 217-B and 217-C. LC MS M/Z821.38 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent.
Example 22
Synthesis of Compound 224
Figure BDA0003871605290000233
The procedure of example 1 was repeated, except that the starting materials were changed to 224-B and 224-C. LC MS M/Z858.42 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent.
Example 23
Synthesis of Compound 243
Figure BDA0003871605290000241
The procedure of example 1 was repeated, except that the starting materials were changed to 243-B and 243-C. LC MS M/Z772.32 (M +). The total synthesis yield is as follows: 49 percent; HPLC purity: 99.9 percent.
Example 24
Synthesis of Compound 255
Figure BDA0003871605290000242
The procedure of example 1 was repeated, except that the starting materials were changed to 255-B and 255-C. LC MS M/Z907.42 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent.
Example 25
Synthesis of Compound 261
Figure BDA0003871605290000243
The procedure of example 1 was repeated, except that the starting materials were changed to 261-B and 261-C. LC MS M/Z712.30 (M +). The total synthesis yield is as follows: 47%; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.69(s,6H),3.52(s,4H),7.16-7.28(m,2H),7.30-7.61(m,9H),7.67(m,1H),7.84-7.96(m,3H),7.97-8.09(m,2H),8.45(m,1H).
Example 26
Synthesis of Compound 264
Figure BDA0003871605290000244
The procedure of example 1 was repeated, except that the starting materials were changed to 264-B and 264-C. LC MS M/Z886.30 (M +). The total synthesis yield is as follows: 49 percent; HPLC purity: 99.9 percent.
Example 27
Synthesis of Compound 276
Figure BDA0003871605290000251
The procedure of example 1 was repeated, except that the starting materials were changed to 276-B and 276-C. LC MS M/Z942.47 (M +). The total synthesis yield is as follows: 47%; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.22(s,12H),3.52(s,4H),6.67(m,1H),7.14(m,1H),7.26(s,4H),7.32(m,3H),7.38(m,1H),7.41-7.51(m,2H),7.51-7.64(m,3H),7.61-7.69(m,1H),7.64-7.89(m,7H),7.84-7.94(m,3H),7.97-8.05(m,1H),8.44(m,1H),8.81-8.89(m,1H),9.76(m,1H).
Example 28
Synthesis of Compound 294
Figure BDA0003871605290000252
The procedure of example 1 was repeated, except that the starting materials were changed to 294-B and 294-C. LC MS M/Z894.48 (M +). The synthesis yield is as follows: 49 percent; HPLC purity: 99.9 percent.
Example 29
Synthesis of Compound 296
Figure BDA0003871605290000253
The procedure of example 1 was repeated, except that the starting materials were changed to 296-B and 296-C. LC MS M/Z884.40 (M +). The synthesis yield is as follows: 51 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ1.33-1.52(m,16H),2.69-2.82(m,4H,),6.67(m,2H),7.04(m,2H),7.27(t,2H),7.34-7.44(m,5H),7.44-7.52(m,2H),7.54(m,1H),7.63-7.77(m,8H),7.76(m,1H),7.79-7.89(m,3H),8.16-8.26(m,4H),8.70(t,2H).
Example 30
Synthesis of Compound 299
Figure BDA0003871605290000261
The procedure of example 1 was repeated, except that the starting materials were changed to 299-B and 299-C. LC MS M/Z852.23 (M +). The total synthesis yield is as follows: 48 percent; HPLC purity: 99.9 percent. 1 H NMR(400MHz,DMSO-d6)δ6.11(d,4H),6.98-7.06(m,4H),7.31(m,2H),7.35-7.44(m,5H),7.44-7.53(m,2H),7.69-7.77(m,2H),7.84(s,2H),7.87(m,1H),7.96-8.05(m,3H),8.12(m,2H),8.16-8.26(m,4H),8.30(d,1H),8.44(d,2H),9.76(d,2H).
Device example 1: preparation of organic electroluminescent device
Figure BDA0003871605290000262
The preparation process comprises the following steps:
1) A transparent anode ITO film layer (thickness 150 nm) was formed on a glass substrate to obtain a first electrode as an anode.
2) The compound F4-TCNQ was evaporated on the surface of the anode by vacuum evaporation to form a hole injection layer having a thickness of 10nm, and the compound NPB was vacuum evaporated on the hole injection layer to form a Hole Transport Layer (HTL) having a thickness of 110 nm.
3) Compound EB-01 was evaporated on the hole injection layer to a thickness of 10nm to obtain an electron blocking layer.
4) BD-1 was doped on the EBL with the compound 1 as the host at a film thickness ratio of 100.
5) An Electron Transport Layer (ETL) having a thickness of 30nm was formed on the EML by vapor deposition of ET-01 and LiQ at a film thickness ratio of 1.
6) Mixing magnesium (Mg) and silver (Ag) in a ratio of 1: the thickness of 9 was larger than that of the electron injection layer by vacuum vapor deposition, and a cathode having a thickness of 11nm was formed.
7) And (3) evaporating and plating CP-1 with the thickness of 65nm on the cathode to be used as an organic Coating (CPL) to finish the manufacture of the organic light-emitting device.
Device examples 2 to 12
An organic electroluminescent device was produced in the same manner as in device example 1, except that compound 1 was replaced with compounds 12, 23, 42, 45, 73, 87, 100, 102, 112, 127, 135, 142, 156, 167, 188, 196, 203, 207, 212, 217, 224, 243, 255, 261, 264, 276, 294, 296, and 299, respectively, at the time of forming the light-emitting layer.
Comparative device examples 1-2
An organic electroluminescent device was fabricated in the same manner as in device example 1, except that in the formation of the light-emitting layer, compound BH-1 and compound BH-2 were used instead of compound 1, respectively.
Each of the above device examples and device comparative example 1 was produced and tested in the same batch as the device of device comparative example 2, the operating voltage, efficiency and lifetime of the device of device comparative example 1 were each noted as 1, and the ratio of the respective indices of device examples 1 to 20, device comparative example and device comparative example 1 was calculated as shown in table 1.
TABLE 1
EML Relative operating voltage Relative efficiency Relative life time CIE-x CIE-y
Comparative device example 1 BH-1 1 1 1 0.14 0.05
Comparative device example 2 BH-2 1.071 0.981 1.045 0.14 0.05
Device example 1 1 0.971 1.135 1.234 0.14 0.05
Device example 2 12 0.962 1.133 1.242 0.14 0.05
Device example 3 23 0.971 1.142 1.132 0.14 0.05
Device example 4 42 0.942 1.133 1.244 0.14 0.05
Device example 5 45 0.925 1.157 1.213 0.14 0.05
Device example 6 73 0.923 1.146 1.225 0.14 0.05
Device example 7 87 0.952 1.151 1.186 0.14 0.05
Device example 8 100 0.957 1.160 1.204 0.14 0.05
Device example 9 102 0.967 1.130 1.115 0.14 0.05
Device example 10 112 0.943 1.153 1.228 0.14 0.05
Device example 11 127 0.962 1.194 1.233 0.14 0.05
Device example 12 135 0.973 1.165 1.214 0.14 0.05
Device example 13 142 0.980 1.137 1.204 0.14 0.05
Device example 14 156 0.953 1.138 1.225 0.14 0.05
Device example 15 167 0.961 1.135 1.112 0.14 0.05
Device example 16 188 0.963 1.128 1.134 0.14 0.05
Device example 17 196 0.944 1.156 1.233 0.14 0.05
Device example 18 203 0.935 1.148 1.205 0.14 0.05
Device example 19 207 0.954 1.156 1.187 0.14 0.05
Device example 20 212 0.961 1.166 1.234 0.14 0.05
Device example 21 217 0.967 1.135 1.205 0.14 0.05
Device example 22 224 0.961 1.148 1.208 0.14 0.05
Device example 23 243 0.982 1.164 1.211 0.14 0.05
Device example 24 255 0.973 1.161 1.221 0.14 0.05
Device example 25 261 0.964 1.155 1.187 0.14 0.05
Device example 26 264 0.957 1.163 1.214 0.14 0.05
Device example 27 276 0.977 1.138 1.215 0.14 0.05
Device example 28 294 0.942 1.145 1.208 0.14 0.05
Device example 29 296 0.963 1.189 1.211 0.14 0.05
Device example 30 299 0.972 1.167 1.221 0.14 0.05
From the results of table 1, it is understood that the compounds used in device examples 1 to 30 as the light emitting layer of the light emitting device all have a reduced voltage, improved luminous efficiency (up to 19%), and a lifetime as high as 20% or more, as compared with the devices formed of the commercial products used in device comparative examples 1 to 2.
Therefore, the device structures of the above embodiments and comparative examples are all the same except that the light emitting layers are different, and based on the device performance of the comparative material as reference, the current efficiency of the device comprising the compound of the present invention is significantly improved, and the lifetime of the device is also improved.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (12)

1. A compound having a chemical structure according to formula (1):
Figure FDA0003871605280000011
in the formula (1), X is selected from O, S and C (R) 9 R 10 ) Or N (R) 11 )；
R 1 -R 15 Identical or different from each other, each independently selected from hydrogen, deuterium, substituted or unsubstituted linear or branched C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl or bonded to an adjacent atom to form a ring, wherein R is 1 -R 8 At least one is selected from substituted or unsubstituted groups a or C, and at least one is selected from substituted or unsubstituted groups B:
Figure FDA0003871605280000012
in the groups A and B, L 1 And L 2 Selected from the group consisting of a single bond, O, S, N (R) 12 ) Substituted or unsubstituted, linear or branched C1-C30 alkyl, substituted or unsubstitutedSubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl; ar (Ar) 1 Selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
the group C is selected from one or more of the structures shown in the formula (2):
Figure FDA0003871605280000013
in the formula (2), Z 1 -Z 9 Are identical or different from each other and are each independently selected from O, S, C (R) 13 R 14 ) Or N (R) 15 )，Ar 2 Selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C5-C60 heteroaryl;
the term "substituted 8230" in said "substituted 8230", means substituted with one or more substituents independently selected from deuterium, fluorine, cyano, C1-C12 alkyl, C6-C18 aryl, C5-C18 heteroaryl;
* Is a linking site.
2. The compound of claim 1, wherein R in formula (1) 3 、R 4 、R 5 And R 6 One of them is selected from substituted or unsubstituted groups a.
3. The compound of claim 1, wherein R in formula (1) 3 、R 4 、R 5 And R 6 One of them is selected from substituted or unsubstituted groups C.
4. The compound of claim 1, wherein Ar is Ar 1 One or more selected from the group consisting of substituted or unsubstituted structures represented by formula (3):
Figure FDA0003871605280000021
in the formula (3), the substituted or unsubstituted (8230) ' substituted (8230) ' in the formula (3) means that the substituted (8230) ' is substituted by one or more groups independently selected from deuterium, fluorine, cyano, C1-C12 alkyl, C6-C18 aryl and C5-C18 heteroaryl, and is a linking site.
5. The compound of claim 1, wherein the groups C and Ar 2 The alkyl groups forming the ring are selected from one or more of the structures shown in formula (4):
Figure FDA0003871605280000022
Figure FDA0003871605280000031
in the formula (4), R c Selected from C6-C30 aryl or C5-C30 heteroaryl, which is a linking site.
6. The compound of any one of claims 1 to 5, wherein the hydrogen atom of any one of the phenyl rings and the hydrogen atom of any one of the alkyl groups in formulae (1) to (4) are each replaced by deuterium.
7. The compound of claim 1, wherein the compound is selected from one or more of the following chemical structures:
Figure FDA0003871605280000032
Figure FDA0003871605280000041
Figure FDA0003871605280000051
Figure FDA0003871605280000061
Figure FDA0003871605280000071
Figure FDA0003871605280000081
Figure FDA0003871605280000091
Figure FDA0003871605280000101
8. use of a compound according to any one of claims 1 to 7 in an organic opto-electronic device.
9. An organic opto-electrical device comprising one or more of the compounds of any one of claims 1 to 7.
10. The organic optoelectronic device according to claim 9, comprising a substrate, a first electrode, an organic layer and a second electrode, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the material thereof comprises one or more compounds according to any one of claims 1 to 6.
11. The organic optoelectronic device according to claim 9, wherein the organic optoelectronic device is at least one of an organic photovoltaic device, an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, and an organic thin film transistor.
12. A display or lighting device comprising the organic optoelectronic device of claims 9 to 11.
CN202211198735.0A 2022-09-29 2022-09-29 Compound and application thereof in organic photoelectric device Withdrawn CN115504858A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112778253A (en) * 2019-11-07 2021-05-11 北京鼎材科技有限公司 Organic compound and organic electroluminescent device containing the same
CN113582909A (en) * 2021-07-30 2021-11-02 上海钥熠电子科技有限公司 Large steric hindrance carbazole compound and application thereof in organic electroluminescent display device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112778253A (en) * 2019-11-07 2021-05-11 北京鼎材科技有限公司 Organic compound and organic electroluminescent device containing the same
CN113582909A (en) * 2021-07-30 2021-11-02 上海钥熠电子科技有限公司 Large steric hindrance carbazole compound and application thereof in organic electroluminescent display device

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