CN113816942A - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- CN113816942A CN113816942A CN202111139787.6A CN202111139787A CN113816942A CN 113816942 A CN113816942 A CN 113816942A CN 202111139787 A CN202111139787 A CN 202111139787A CN 113816942 A CN113816942 A CN 113816942A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 23
- 239000010410 layer Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 42
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 239000002346 layers by function Substances 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MKEJZKKVVUZXIS-UHFFFAOYSA-N 2,4-dibromo-1,3-thiazole Chemical compound BrC1=CSC(Br)=N1 MKEJZKKVVUZXIS-UHFFFAOYSA-N 0.000 description 1
- CQBMSTJROIULOR-UHFFFAOYSA-N 2,4-dibromo-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C1=CC=C2C(=C1)C3=C(S2)C(=NC(=N3)Br)Br CQBMSTJROIULOR-UHFFFAOYSA-N 0.000 description 1
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical group NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 238000003775 Density Functional Theory Methods 0.000 description 1
- WGCOQYDRMPFAMN-ZDUSSCGKSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyrimidin-5-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=NC=1 WGCOQYDRMPFAMN-ZDUSSCGKSA-N 0.000 description 1
- YQYBUJYBXOVWQW-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical group NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC2=CC=CC=C2CC1 YQYBUJYBXOVWQW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Abstract
The present invention provides an organic compound and an organic electroluminescent device including the same, the organic compound being represented by the following formula 1:
Description
Technical Field
The present invention relates to an organic compound, and more particularly, to an organic compound and an organic electroluminescent device including the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The organic electroluminescent device (OLED) has a series of advantages of self-luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich color and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from a positive electrode and a negative electrode and then migrate, recombine and attenuate in an organic material to generate light. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
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.
At present, some organic electroluminescent materials have been applied in the market due to their excellent performance, but as host materials in organic electroluminescent devices, in addition to the triplet energy level being higher than the guest materials, it is more important to have good hole transport performance to prevent the energy reverse transfer of exciton transition release. Currently, materials having both a high triplet level and good hole mobility in the host material are still lacking. Therefore, how to design a new host material with better performance is a problem to be solved by those skilled in the art.
Disclosure of Invention
The invention aims to provide an organic compound and an organic electroluminescent device comprising the same. The organic electroluminescent device of the present invention has a reduced driving voltage, excellent luminous efficiency and a lifetime.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
the invention provides an organic compound, the structure of which is shown as formula 1:
wherein R1 is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl.
Ar1 is selected from the group consisting of:
wherein R is2、R3And R4Independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
Preferably, the organic compound is selected from the group consisting of:
the present invention also provides an organic electroluminescent device comprising an anode, an organic layer and a cathode deposited in this order, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer, wherein the organic layer comprises the organic compound of the present invention.
Preferably wherein the organic layer further comprises a doping compound.
More preferably wherein the weight ratio of the organic compound to the doping compound is 1: 99-99: 1.
the invention provides an organic compound, which has a structure shown in formula 1, wherein the photoelectric properties of the whole compound molecule of an electron-rich heterocyclic chain structure in the organic compound structure are greatly influenced, so that unnecessary vibration energy loss is reduced, and high-efficiency light-emitting performance is realized. By adjusting substituent groups, the complex has better thermal stability and chemical properties. The organic compound provided by the invention is simple in preparation method, easily available in raw materials and capable of meeting the industrial requirements.
The organic compound is prepared into a device, and particularly used as a main material, the device has the advantages of low driving voltage and high luminous efficiency, and is superior to the conventional common OLED device.
Detailed Description
The invention also provides application of the organic compound in an organic electroluminescent device.
Preferably, the organic electroluminescent device comprises an anode, a cathode and a plurality of organic energy layers positioned between the anode and the cathode, wherein the organic functional layer contains the organic compound.
The organic electroluminescent device of the present invention preferably comprises an anode, a cathode and a plurality of organic functional layers located between the anode and the cathode. The term "organic functional layer" refers to all layers disposed between an anode and a cathode in an organic electroluminescent device, and the organic functional layer may be a layer having a hole property and a layer having an electron property, for example, the organic functional layer includes one or more of a hole injection layer, a hole transport layer, a hole injection and transport functional layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport and injection functional layer.
The hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties of the present invention may include an electron-generating substance in addition to a conventional hole injection substance, a conventional hole transport substance, and a substance having both hole injection and hole transport properties. For example, the organic functional layer is an emissive layer, and the emissive layer includes one or more of phosphorescent hosts, fluorescent hosts, phosphorescent dopants, and fluorescent dopants. The compound for the organic electroluminescent device can be used as a fluorescent main body, can also be used as fluorescent doping, and can be used as the fluorescent main body and the fluorescent doping at the same time.
The light-emitting layer of the present invention may be a red, yellow or blue light-emitting layer. And when the luminescent layer is a red luminescent layer, the compound for the organic electroluminescent device is used as a red main body, so that the organic electroluminescent device with high efficiency, high resolution, high brightness and long service life can be obtained.
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 sequentially deposited, wherein the red phosphorescent compound is used as a host material of the light-emitting layer.
The method for preparing the organic electroluminescent device of the present invention is not particularly limited, and other methods and materials for preparing the organic electroluminescent device known to those skilled in the art may be used in addition to the host compound represented by formula 1.
Examples
Example 1: synthesis of Compound 1-1
Synthesis of intermediate Sub-1
A500 mL reaction flask was charged with intermediate phenylboronic acid (7.49g,61.4mmol), 2, 4-dibromothiazole (17.68g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ 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 intermediate Sub-1(13.13g, yield 75%). LC-MS: M/Z283.99 (M + H) +.
2. Synthesis of intermediate Sub-4
A250 mL three-necked flask was charged with intermediate Sub-3(1.82g, 10mmol), bromobenzene (1.65g,10.5mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column to obtain Compound Sub-4(0.73g, yield 28%). LC-MS: M/Z258.12 (M +).
3. Synthesis of Compound 1-1
A250 mL three-necked flask was charged with intermediate Sub-4(4.23g, 10mmol), intermediate Sub-1(2.99g,10.5mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain Compound 1-1(3.47g, yield 75%). LC-MS: M/Z462.18(M +).
Example 2: synthesis of Compounds 1-5
1. Synthesis of intermediate Sub-5
A250 mL three-necked flask was charged with intermediate 2, 4-dibromobenzo [4,5] thieno [3,2-d ] pyrimidine (3.85g, 11.2mmol), intermediate carbazole (3.0g,12.3mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was then passed through a silica gel column to give Sub-5(3.86g, yield 80%). LC-MS: M/Z430.32 (M +).
2. Synthesis of Compounds 1-5
Compounds 1-5 were synthesized according to the method of example 1, and the other steps were carried out according to the synthesis of compound 1-1 to obtain compounds 1-5(3.42g, yield 62%). LC-MS: M/Z551.21(M +).
Example 3: synthesis of Compounds 1-10
Compounds 1 to 10 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1-1, to give compounds 1 to 10(3.12g, yield 54%). LC-MS: M/Z578.25 (M +).
Example 4: synthesis of Compounds 1-11
Compounds 1 to 11 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1-1, to give Compound 1 to 11(2.84g, yield 45%). LC-MS: M/Z552.20 (M +).
Example 5: synthesis of Compounds 1-50
Compounds 1 to 50 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1-1, to give compounds 1 to 50(1.97g, yield 35%). LC-MS: M/Z562.22 (M +)
Example 6: synthesis of Compounds 4-17
Compounds 4 to 17 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1-1, to give Compound 4 to 17(3.30g, yield 54%). LC-MS: M/Z611.21 (M +).
Example 7: synthesis of Compounds 4-21
Compounds 4 to 21 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compound 1 to 1, to give compounds 4 to 21(3.29g, yield 51%). LC-MS: M/Z644.24 (M +).
Example 8: synthesis of Compounds 4-24
Compounds 4-24 were synthesized according to the procedure of example 1, and the other procedures were carried out according to the synthesis of compound 1-1, to give compounds 4-24(4.14g, yield 56%). LC-MS: M/Z560.24 (M +).
Table 1: evaluation results of HOMO, LUMO, triplet energy level and S1-T1 energy level of organic compound of the present invention (DFT calculation by Gaussian software/based on B3LYP functional)
As can be seen from Table 1, the HOMO value of the compound of the present invention is reduced as compared with that of the comparative compound, the Eg (eV) value is more suitable for the RH (phosphorescent host) condition, and the delayed fluorescence property (S1-T1) is enhanced.
Device embodiments
1. First embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set at 1X 10-6 Torr. Thereafter on an ITO substrate
Compound (I)
And
the sequence of (a) and (b) forming layers of organic material.
2. Second embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compound 1-5 instead of compound 1-1 of the first embodiment.
3. Third embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound 1-10 instead of the compound 1-1 of the first embodiment.
4. Fourth embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compound 1-11 instead of compound 1-1 of the first embodiment.
5. Fourth embodiment
An organic electroluminescent device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound 1-50 instead of the compound 1-1 of the first embodiment.
6. Third embodiment
An organic electroluminescent device of the third embodiment was fabricated in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compounds 4 to 17 from compound 1 to 1 of the first embodiment.
7. Fourth embodiment
An organic electroluminescent device of the fourth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compounds 4 to 21 instead of compound 1 to 1 of the first embodiment.
8. Fifth embodiment
An organic electroluminescent device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with compounds 4 to 24 from compound 1 to 1 of the first embodiment.
9. Comparative example 1
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-1 instead of the compound 1-1 of the first embodiment.
10. Comparative example 2
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-2 instead of the compound 1-1 of the first embodiment.
11. Comparative example 3
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-3 instead of the compound 1-1 of the first embodiment.
12. Comparative example 4
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-4 instead of the compound 1-1 of the first embodiment.
13. Comparative example 5
An organic electroluminescent device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic electroluminescent device was replaced with the compound Ref-5 instead of the compound 1-1 of the first embodiment.
The prepared organic electroluminescent device is at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 2 shows the performance test results of the organic electroluminescent devices prepared in the examples and comparative examples of the present invention.
TABLE 2
As shown in table 2, the organic electroluminescent device comprising the compound according to the present disclosure as a host material has higher luminous efficiency and longer life characteristics than the organic electroluminescent device of the comparative substance.
The foregoing has described the general principles, principal 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 (5)
1. An organic compound having a structure represented by formula 1:
wherein R is1Is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
ar1 is selected from the group consisting of:
wherein R is2、R3And R4Each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.
2. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of:
3. an organic electroluminescent device comprising an anode, an organic layer and a cathode deposited in this order, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer, wherein the organic layer comprises the organic compound of any one of claims 1-2.
4. The organic electroluminescent device according to claim 3, wherein the organic layer further comprises a doping compound.
5. The organic electroluminescent device according to claim 4, wherein the weight ratio of the organic compound to the dopant compound is 1: 99-99: 1.
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