CN111393417A - Red phosphorescent host compound and organic light-emitting device using same - Google Patents
Red phosphorescent host compound and organic light-emitting device using same Download PDFInfo
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- CN111393417A CN111393417A CN202010226792.XA CN202010226792A CN111393417A CN 111393417 A CN111393417 A CN 111393417A CN 202010226792 A CN202010226792 A CN 202010226792A CN 111393417 A CN111393417 A CN 111393417A
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- red phosphorescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- -1 1-dialkyl-1H-indene Chemical compound 0.000 claims description 2
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical class CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 37
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 5
- 229940126543 compound 14 Drugs 0.000 description 5
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 4
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229940126208 compound 22 Drugs 0.000 description 4
- 229940125844 compound 46 Drugs 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000002346 layers by function Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 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 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 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
- 238000004020 luminiscence type Methods 0.000 description 2
- 229940078552 o-xylene Drugs 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 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
- IVURTNNWJAPOML-UHFFFAOYSA-N 5,10-dihydrophenazine Chemical compound C1=CC=C2NC3=CC=CC=C3NC2=C1 IVURTNNWJAPOML-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000006872 improvement Effects 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 235000015320 potassium carbonate Nutrition 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
- 239000000243 solution Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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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
- C07D403/14—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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- 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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Abstract
The invention provides a red phosphorescent host compound and an organic light-emitting device using the same, and particularly relates to a soluble phosphorescent host compound with excellent color purity, high brightness and luminous efficiency and an O L ED device using the same, wherein the structure of the red phosphorescent host compound is shown as the formula 1:
in the above structural formula, Ar1And Ar2Each independently selected from substituted or unsubstitutedSubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; r1～R4Independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 nitrogen-containing heteroaryl, or combination thereof.
Description
Technical Field
The present invention relates to a red phosphorescent host compound and an organic light emitting device using the same, and more particularly, to a soluble phosphorescent host compound having excellent color purity and high luminance and luminous efficiency and an O L ED device using the same.
Background
The O L ED has a series of advantages of self-luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich color and the like, and has wide application prospect due to potential application in a new generation of display and lighting technology, wherein the organic electroluminescent device is a spontaneous light-emitting device, the O L ED emits light by the mechanism that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and attenuate in an organic material under the action of an external electric field to generate light, and the typical structure of the O L ED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron 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 commercially used due to their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to the triplet energy level higher than that of the guest materials 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
An object of the present invention is to provide a red phosphorescent host compound having excellent pure chromaticity, high luminance and excellent luminous efficiency, and an organic light emitting device using the same
The invention provides a red phosphorescent host compound, the structural formula of which is shown as 1,
in the above structural formula, Ar in the above structural formula1And Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; r1～R4Independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 nitrogen-containing heteroaryl, or combination thereof
Preferably, Ar is1And Ar2Independently selected from substituted or unsubstituted benzofuran, benzothiophene, 1-dialkyl-1H-indene, 2, 3-benzopyrrole, benzo [ b]Silanes, benzothiazines, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted
A group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted naphthalene groupPyridine group, or a combination thereof.
In a more preferred embodiment, Ar in the red phosphorescent host compound of formula 1 is Ar1Pyrimidine complex and Ar2The pyrimidine complexes of (a) are independently selected from the following structures:
wherein R is1、R5、R6Independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 nitrogen-containing heteroaryl, or combination thereof.
In a further preferred embodiment, the red phosphorescent host compound is independently selected from the following compounds:
the invention also provides application of the pyrimidine complex-containing compound in an organic light-emitting device.
Preferably, the organic light-emitting device comprises an anode, a cathode and a plurality of organic functional layers positioned between the anode and the cathode, wherein the organic functional layers contain the compound containing the pyrimidine complex.
The invention has the beneficial effects that:
the invention provides a compound containing a pyrimidine complex, which has a structure shown in a formula 1, wherein the photoelectric properties of the whole compound molecule of two pyrimidine linking structures rich in electrons in the structure of the compound of the pyrimidine complex are greatly influenced, so that unnecessary vibration energy loss is reduced, and efficient luminous performance is realized. By adjusting substituent groups, the complex has better thermal stability and chemical properties. The pyrimidine complex-containing compound disclosed by the invention is simple in preparation method, easily available in raw materials and capable of meeting the industrial requirements.
The pyrimidine complex compound is prepared into a device, particularly used as a host material, the device has the advantages of low driving voltage and high luminous efficiency, and is superior to the existing common O L ED device.
In the present invention, the organic electroluminescent device preferably includes an anode, a cathode, and several organic layers located between the anode and the cathode, and the "organic layer" refers to a term of all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole characteristic and a layer having an electron characteristic. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a technical layer having both hole injection and hole transport, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a technical layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties may be formed using a conventional hole injection material, a hole transport material, or a material having both hole injection and hole transport properties, and may further include an electron-generating material.
For example, the organic layer includes a light emitting layer, and the light emitting layer includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. In the present invention, the compound for an organic electroluminescent device can be used as a fluorescent host, as a fluorescent dopant, and as both a fluorescent host and a fluorescent dopant.
In the present invention, the light emitting layer may be a red, yellow or blue light emitting layer. In the present invention, when the light-emitting layer is a red light-emitting layer, an organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-mentioned compound for an organic electroluminescent device as a red host.
In the present invention, the organic electroluminescent diode device of the red phosphorescent host compound is characterized in that 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, and the red phosphorescent compound is used as a host material.
The method for preparing the organic electroluminescent device is not particularly limited, and the organic electroluminescent device can be prepared by using the method and materials for preparing the light emitting device, which are well known to those skilled in the art, in addition to the organic compound of formula 1.
Drawings
FIG. 1 is a graph of chromaticity and visibility of light emitted from an organic electroluminescent diode. Indicating that the visibility decreases as the color purity of the organic electroluminescent device increases (i.e., as the X value of the chromaticity coordinate becomes larger).
Detailed Description
In order to make the technical means, the original characteristics, the achieved purposes and the effects of the invention easy to understand, the invention is further described with reference to the figures and the specific embodiments.
The compounds of the respective organic layers used in the device examples are as follows:
examples of formation
Example 1: synthesis of Compound 1
Synthesis of intermediate Sub-1
Adding 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 (200M L) and water (50M L) into a 500M L reaction bottle, heating the reaction system to 80 ℃, reacting for 12 hours under the protection of nitrogen, cooling the reaction liquid to room temperature after the reaction is completed, extracting with o-dichlorobenzene and water, drying the organic layer with anhydrous magnesium sulfate, concentrating, recrystallizing the obtained crude product, and passing through a silica gel column to obtain intermediate Sub-1(13.13g, yield 75%) L C-MS: M/Z283.99 (M + H) +
Synthesis of Compound 1
Adding an intermediate 5, 10-dihydrophenazine (1.82g, 10.0mmol), an intermediate Sub-1(5.99g,21.0mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80M L) into a 250M L three-neck flask, heating the reaction system to 120 ℃, reacting for 12 hours under the protection of nitrogen, cooling the reaction solution to room temperature after the reaction is completed, extracting with o-dichlorobenzene and water, drying an organic layer with anhydrous magnesium sulfate, concentrating, recrystallizing to obtain a crude product, and passing the crude product through a silica gel column to obtain the compound 1(4.72g, the yield is 80%). L C-MS: M/Z590.22 (M + H) +.
Example 2: synthesis of Compound 14
Synthesis of intermediate Sub-2
Adding an intermediate 2, 4-dibromobenzo [4,5] thieno [3,2-d ] pyrimidine (3.85g, 11.2mmol), an 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 (80M L) into a 250M L three-neck flask, heating the reaction system to 120 ℃, reacting for 12 hours under the protection of nitrogen, cooling the reaction liquid to room temperature after the reaction is finished, extracting with o-dichlorobenzene and water, drying an organic layer with anhydrous magnesium sulfate, concentrating, recrystallizing the obtained crude product to obtain Sub-2(3.86g, 80% yield), L C-MS, M/Z430.32(M + H) +.
Synthesis of Compound 14
Compound 14 was synthesized according to the method of example 1, and the other steps were carried out according to the synthesis of Compound 1 to give Compound 14(5.08g, 59% yield.) L C-MS M/Z768.27 (M + H) +.
Example 3: synthesis of Compound 22
Compound 22 was synthesized according to the procedure of example 2, and the other steps were carried out according to the synthesis of example 2, to give compound 22(6.55g, yield 55%). L C-MS: M/Z1062.30 (M + H) +.
Example 4: synthesis of Compound 45
Compound 45 was synthesized according to the method of example 2, and the other steps were carried out according to the synthesis of example 2, to give compound 45(5.68g, yield 51%). L C-MS: M/Z768.27 (M + H) +.
Example 5: synthesis of Compound 46
Compound 46 was synthesized according to the procedure of example 2, and the other steps were carried out according to the synthesis of example 2, to give compound 46(5.46g, yield 51%). L C-MS: M/Z954.33 (M + H) +.
Device embodiments
1. First embodiment
The ITO glass substrate was patterned to have a light emitting area of 3mm × 3mm then, the patterned ITO glass substrate was washed.
The substrate was then placed in a vacuum chamber with a standard pressure set at 1 × 10-6 torr, and thereafter, on an ITO substrate
Compound (I)
And
the sequence of (a) and (b) forming layers of organic material.
2. Second embodiment
An organic light-emitting 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 light-emitting device was replaced with compound 14 from compound 1 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the third embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 22 from compound 1 of the first embodiment.
4. Fourth embodiment
An organic light-emitting 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 light-emitting device was replaced with compound 45 from compound 1 of the first embodiment.
5. Fifth embodiment
An organic light-emitting 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 light-emitting device was replaced with compound 46 from compound 1 of the first embodiment.
Comparative example
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH-1 instead of the compound 1 of the first embodiment.
The prepared organic light-emitting device is at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 1 shows the performance test results of the organic light emitting devices prepared in the examples of the present invention and the comparative examples.
TABLE 1
As shown in table 1, the device also operated efficiently at low voltage. And the current efficiency of the embodiment is significantly increased compared to the comparative example, and in addition, the lifetime is increased by at least 34% or more.
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. A red phosphorescent host compound characterized in that: the structural formula of the compound is shown as 1,
in the above structural formula, Ar1And Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; r1～R4Independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 nitrogen-containing heteroaryl, or combination thereof.
2. A red phosphorescent host compound according to claim 1, wherein: ar (Ar)1And Ar2Independently selected from substituted or unsubstituted benzofuran, benzothiophene, 1-dialkyl-1H-indene, 2, 3-benzopyrrole, benzo [ b]Silanes, benzothiazines, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenylOr unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted
A group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted naphthyridinyl group, or a combination thereof.
3. A red phosphorescent host compound according to claim 1, wherein: ar is1Pyrimidine complex and Ar2The pyrimidine complexes of (a) are independently selected from the following structures:
wherein R is1、R5、R6Independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 nitrogen-containing heteroaryl, or combination thereof.
4. A red phosphorescent host compound according to any one of claims 1 to 3, wherein the red phosphorescent host compound is independently selected from the following compounds:
5. an organic electroluminescent diode device using the red phosphorescent host compound according to any one of claims 1 to 4, wherein 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 deposited in this order, and the red phosphorescent compound is used as a host material.
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