CN112920058A - High-refractive-index organic small molecule material and application thereof - Google Patents

High-refractive-index organic small molecule material and application thereof Download PDF

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CN112920058A
CN112920058A CN202110117037.2A CN202110117037A CN112920058A CN 112920058 A CN112920058 A CN 112920058A CN 202110117037 A CN202110117037 A CN 202110117037A CN 112920058 A CN112920058 A CN 112920058A
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朱旭辉
黄小兰
彭俊彪
曹镛
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South China University of Technology SCUT
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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a high-refractive-index organic small molecular material and application thereof. The structure of the high-refractive-index organic micromolecule material is shown as formula I, Ar1,Ar2Independently phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl and furyl. The refractive index of the organic small molecule material in the visible light wavelength range is more than 1.9The transparent film is transparent in a visible light range after 460nm wavelength, and the extinction coefficient tends to be 0. The material of the invention is beneficial to improving the light extraction efficiency of the device. The organic micromolecule material with high refractive index is applied to a high-performance top-emitting organic light-emitting diode.

Description

High-refractive-index organic small molecule material and application thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a high-refractive-index organic micromolecule material applied to a top-emission organic light-emitting diode device.
Background
Top-emitting organic light-emitting diodes (TEO LEDs) are generally composed of a fully reflective anode and a transparent or translucent cathode. Since light is emitted from the top of the OLED device, it does not pass through the TFT backplane at the bottom, and thus has a high aperture ratio relative to bottom-emitting devices. On the other hand, top-emitting OLED structures containing a semi-transparent cathode lead to microcavity effects, causing viewing angle dependence of the light emission characteristics of the device. To overcome the above problem, a high refractive index light extraction layer is generally added on a translucent cathode. The design and preparation of the high-refractive-index and hole-transport organic molecular material which has high glass transition temperature and is transparent in a visible light region have challenges.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a high-refractive-index hole-transport organic small molecule material.
The invention also aims to provide application of the high-refractive-index organic small molecule material. The organic micromolecule material with high refractive index is applied to a high-performance top-emitting organic light-emitting diode and is used as a light extraction layer.
The object of the present invention is achieved by the following means.
A high refractive index organic small molecule material has a structure shown in formula I:
Figure BDA0002924180190000011
Ar1,Ar2independently phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl and furyl.
The biphenyl is 1, 1' -biphenyl, and the naphthyl is 2-naphthyl.
The high-refractive-index organic small molecule material disclosed by the invention preferably has the following specific structure:
Figure BDA0002924180190000021
Figure BDA0002924180190000031
the high-refractive-index organic small molecule material is also a hole transport material.
The high-refractive-index organic small molecule material is applied to a top-emitting organic light-emitting diode device.
The organic micromolecule material with high refractive index is applied to a high-performance top-emitting organic light-emitting diode and is used as a light extraction layer.
The high-refractive-index organic small molecule material is deposited on a cathode of the top-emitting organic light-emitting diode.
The principle of the invention is as follows:
the organic material disclosed by the invention is based on 2,2 '-binaphthyl-6, 6' -diamine, has a typical arylamine structure, and can transmit hole carriers. Relative to 1,1 '-biphenyl, 2,2' -binaphthyl helps to promote intermolecular forces, enhance molecular packing, and thus increase the refractive index. On the side group, groups such as 1, 1' -biphenyl, naphthyl, fluorenyl, carbazolyl and furyl are introduced, so that intermolecular force can be further increased, and the refractive index can be improved.
The hole-transport organic small molecule material with high refractive index applied to the high-performance top-emission organic light-emitting diode is beneficial to improving the light extraction efficiency of the device.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) compared with the light extraction layer NPB of a common top-emitting organic light-emitting diode device, the organic micromolecule material disclosed by the invention generally has a high refractive index in a visible light region.
(2) The organic micromolecular material disclosed by the invention has low absorption in a visible light region.
(3) The organic micromolecular material has high glass transition temperature.
Drawings
FIG. 1 is a refractive index curve of an organic small molecule material XL 10;
FIG. 2 is an extinction coefficient curve (k) of an organic small molecular material XL 10;
FIG. 3 is a refractive index curve of an organic small molecule material XL 11;
FIG. 4 is an extinction coefficient curve (k) of an organic small molecule material XL 11;
FIG. 5 is a refractive index profile of an organic small molecule material NPB;
fig. 6 is an extinction coefficient curve (k) of the organic small molecule material NPB.
Detailed Description
The present invention will be further described with reference to the following specific examples and drawings, but the embodiments of the present invention are not limited thereto.
Example 1
The organic small molecule material XL10 is prepared by the following method, comprising the following steps:
step 1: preparation of 6-bromo-N-phenyl-2-naphthylamine (Compound II), equation:
Figure BDA0002924180190000041
dissolving p-toluenesulfonic acid (1.7g,9mmol), aniline (12.6g,0.135mol) and 6-bromo-2-naphthol (10.0g,0.045mol) in 10ml p-xylene, heating to 190 ℃ in nitrogen atmosphere to react for 7h, then cooling to 70 ℃, adding a proper amount of sodium acetate (making the reaction system alkaline) and 100ml of ethanol, continuing stirring for 10min, then carrying out reduced pressure distillation on the reaction solution to remove the solvent, adding warm water to stir, carrying out suction filtration, then carrying out reflux washing on the filter cake with ethanol, carrying out suction filtration after ice bath to obtain a white solid product, wherein the yield is about 90% (12 g);
step 2: preparation of N- (6-bromonaphthalen-2-yl) -9, 9-dimethyl-N-phenyl-9H-fluoren-2-amine (compound 3), reaction equation:
Figure BDA0002924180190000042
adding a compound II (6.0g,0.02mol), 2-iodine-9, 9-dimethyl-9H-fluorene (7.7g,0.024mol), 1, 10-phenanthroline (0.725g,4mmol), CuI (0.38g,2mmol) and sodium tert-butoxide (7.7g,0.08mol) into a reaction bottle filled with 90mL of anhydrous toluene, heating to 115 ℃ under the nitrogen atmosphere for reaction for 12 hours, cooling, concentrating to remove toluene, adding deionized water and dichloromethane for extraction, drying an organic layer obtained by liquid separation with anhydrous magnesium sulfate, performing suction filtration and reduced pressure distillation, and performing column chromatography separation and purification by using a mixed solvent of petroleum ether and dichloromethane as a developing agent to obtain a solid product with the yield of about 88% (8.6 g);
and step 3: preparation of 9, 9-dimethyl-N-phenyl-N- (6- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-2-yl) -9H-fluoren-2-amine (compound 4), reaction equation:
Figure BDA0002924180190000051
in N2Compound 3(6.0g,0.012mol), bis (pinacolato) borate (3.73g,0.014mol), bis (triphenylphosphine) palladium dichloride (Pd (PPh)3)2Cl2) (85mg,0.12mmol) and anhydrous potassium acetate (3.6g,0.037mol) were added to anhydrous tetrahydrofuran (80mL), the reaction was heated to 95 ℃ for 10h, after the reaction was completed, the crude product was concentrated under reduced pressure to remove tetrahydrofuran, then extracted with distilled water and dichloromethane and separated, the organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and then treated with petroleum ether: the volume ratio of the dichloromethane is 2: 1 as developing solvent to obtain solid product with 91% yield (5.98 g);
and 4, step 4: preparation of N ', N "-bis (9, 9-dimethyl-9H-fluoren-2-yl) -N', N" -diphenyl- [2,2 '-binaphthyl ] -6,6' -diamine (organic small molecule material XL10), reaction equation:
Figure BDA0002924180190000052
pd (PPh) under the protection of nitrogen3)4(48mg,0.041mmol), Compound 3(2.1g,4.28mmol), Compound 4(2.2g,4.07mmol) and K2CO3Adding an aqueous solution (2mol/L,12mL) into a mixed solvent of toluene (70mL) and ethanol (12mL), heating to 108 ℃, reacting for 10h, cooling, concentrating to remove toluene, and adding a solvent with a volume ratio of 1: 1, extracting with dichloromethane, drying an organic layer with anhydrous magnesium sulfate, filtering, concentrating under reduced pressure, and separating and purifying by column chromatography to obtain a solid product, wherein a developing agent of the column chromatography is a solvent with a volume ratio of 4: 1 petroleum ether: and (3) carrying out reflux washing on a solid product obtained by column chromatography separation by using a mixed solvent of dichloromethane and ethanol, carrying out suction filtration and drying to obtain a pure solid product, wherein the yield is about 86% (2.9 g).
Example 2
The organic small molecule material XL11 is prepared by the following method, comprising the following steps:
step 1: preparation of 6-bromo-N-phenyl-2-naphthylamine (II), reaction equation:
Figure BDA0002924180190000061
the step (1) is completely the same as the step (1) in the embodiment 1, and is not described again;
step 2: preparation of N- (6-bromonaphthalen-2-yl) -9-methyl-N-phenyl-9H-carbazol-3-amine (5), reaction equation:
Figure BDA0002924180190000062
the operation process of the step (2) is different from that of the step (2) in the example 1 in that one reactant 2-iodo-9, 9-dimethyl-9H-fluorene in the step (2) in the example 1 is replaced by 3-iodo-9-methyl-9H-carbazole, petroleum ether is used at the beginning of column chromatography separation developing agent, after unreacted 3-iodo-9-methyl-9H-carbazole is removed, the developing agent is changed into a mixed solvent of petroleum ether and dichloromethane, and the volume ratio is about 4: 1; yield about 90% (10.1 g);
and step 3: preparation of 9-methyl-N-phenyl-N- (6- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalen-2-yl) -9H-carbazol-3-amine (6) reaction equation:
Figure BDA0002924180190000063
the procedure of step (3) differs from that of step (3) in example 1 in that one of the reactants, compound 3, of step (3) in example 1 is replaced with compound 5 in a yield of 93% (8.37 g);
and 4, step 4: preparation of N ', N' -bis (9, 9-dimethyl-9H-carbazol-3-yl) -N ', N' -diphenyl- [2,2 '-binaphthyl ] -6,6' -diamine (organic small molecule material XL11), the reaction equation is as follows:
Figure BDA0002924180190000071
the procedure of step (4) differs from that of step (4) in example 1 in that the reactant compound 3 of step (3) in example 1 is replaced with compound 5 and compound 4 is replaced with compound 6, in 88% yield (7 g).
Example 3
And respectively evaporating 30nm organic small molecular materials XL10 and XL11 on a silicon chip by adopting a vacuum evaporation method, characterizing the refractive index and the extinction coefficient, and comparing the refractive index and the extinction coefficient with a hole transport type material NPB on the current market. The chemical structural formulas of XL10, XL11 and NPB are as follows:
Figure BDA0002924180190000072
the refractive index and extinction coefficient characterization results are as follows:
FIG. 1 is a refractive index curve of an organic small molecule material XL 10;
FIG. 2 is an extinction coefficient curve (k) of an organic small molecular material XL 10;
FIG. 3 is a refractive index curve of an organic small molecule material XL 11;
FIG. 4 is an extinction coefficient curve (k) of an organic small molecule material XL 11;
FIG. 5 is a refractive index profile of an organic small molecule material NPB;
fig. 6 is an extinction coefficient curve (k) of the organic small molecule material NPB.
Table 1 shows refractive indexes n of the organic small molecular material at wavelengths of 460nm, 530nm and 630nm, respectively.
TABLE 1 refractive index data for deposition of 30nm organic small molecule materials on silicon wafers
Figure BDA0002924180190000081
As can be seen from fig. 1, fig. 3 and table 1, the high refractive index, hole transport type organic materials XL10 and XL11 applied to the high performance top emission organic light emitting diode provided by the present embodiment have refractive indexes greater than 1.9 at wavelengths of 460nm, 530nm and 630nm, and have refractive indexes higher than corresponding values of the commercially available hole transport type organic material NPB (fig. 5 and table 1).
In addition, as can be seen from fig. 2 and 4, after the wavelength of 460nm, the extinction coefficients of the high refractive index, hole transport type organic materials XL10 and XL11 provided by the present embodiment and applied to the high performance top emission organic light emitting diode tend to 0, indicating that it has no absorption for visible light with the wavelength after 460 nm.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.

Claims (6)

1. A high refractive index organic small molecule material is characterized in that: the structure is shown as formula I:
Figure FDA0002924180180000011
Ar1，Ar2independently phenyl, biphenyl, naphthyl, fluorenyl, carbazolyl and furyl.
2. The high refractive index organic small molecule material of claim 1, wherein: the biphenyl is 1, 1' -biphenyl, and the naphthyl is 2-naphthyl.
3. The high refractive index organic small molecule material of claim 1, wherein: is more than one of the following structures;
Figure FDA0002924180180000012
Figure FDA0002924180180000021
4. the use of the high refractive index organic small molecule material according to any one of claims 1 to 3, wherein: the organic micromolecule material with high refractive index is applied to a top-emitting organic light-emitting diode.
5. Use according to claim 4, characterized in that: the high refractive index organic small molecule material is used as a light extraction layer.
6. Use according to claim 5, characterized in that: the high-refractive-index organic small molecule material is deposited on a cathode of the top-emitting organic light-emitting diode.
CN202110117037.2A 2021-01-29 2021-01-29 High-refractive-index organic small molecule material and application thereof Pending CN112920058A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003081923A (en) * 2001-09-17 2003-03-19 Mitsui Chemicals Inc Amine compound and organic electroluminescent element containing the same
US20100156285A1 (en) * 2007-06-18 2010-06-24 Idemitsu Kosan Co., Ltd. Trinaphthyl monoamine or derivative thereof, organic electroluminescent device using the same, and organic electroluminescent material-containing solution
KR20140096227A (en) * 2013-01-25 2014-08-05 주식회사 삼양사 Binaphthyl diamine derivatives, method of making the same and the organic electronic device comprising the same
CN107954884A (en) * 2017-11-16 2018-04-24 华南理工大学 High glass-transition temperature hole-injecting material and its preparation and application
CN111233676A (en) * 2020-01-17 2020-06-05 华南理工大学 High-performance hole transport material and preparation and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003081923A (en) * 2001-09-17 2003-03-19 Mitsui Chemicals Inc Amine compound and organic electroluminescent element containing the same
US20100156285A1 (en) * 2007-06-18 2010-06-24 Idemitsu Kosan Co., Ltd. Trinaphthyl monoamine or derivative thereof, organic electroluminescent device using the same, and organic electroluminescent material-containing solution
KR20140096227A (en) * 2013-01-25 2014-08-05 주식회사 삼양사 Binaphthyl diamine derivatives, method of making the same and the organic electronic device comprising the same
CN107954884A (en) * 2017-11-16 2018-04-24 华南理工大学 High glass-transition temperature hole-injecting material and its preparation and application
CN111233676A (en) * 2020-01-17 2020-06-05 华南理工大学 High-performance hole transport material and preparation and application thereof

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