CN112321629A - Spiro dibenzosuberene acridine compound and application thereof - Google Patents
Spiro dibenzosuberene acridine compound and application thereof Download PDFInfo
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Abstract
The invention relates to a spirodibenzoheptene acridine compound and application thereof. The spirodibenzohepteneacridine compound has a structure shown in a formula I, has good hole transmission capacity, good film forming property and thermal stability and a high triplet state energy level, is used as a hole transmission material or a light-emitting layer main body material of an OLED device, and can effectively improve the performance of the OLED devicePhotoelectric property and the service life of the OLED device, and meets the requirements of the panel industry.
Description
Technical Field
The invention relates to the field of light-emitting devices, in particular to a spirodibenzohepteneacridine compound and application thereof.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The conventional OLED light emitting device is a sandwich-like structure, and is an electroluminescent device composed of a cathode and an anode and an organic functional layer interposed between the electrodes. The OLED light-emitting device is a current type device, electrons are injected through an electron injection layer and are transmitted through an electron transmission layer; holes are injected through the hole injection layer and transported through the hole transport layer. The electrons and holes recombine in the light-emitting layer and emit light, i.e., the OLED emits electroluminescence.
Therefore, in order to improve the performance of the OLED device, the efficiency and the lifetime of the device can be improved by optimizing the electrodes, the hole injection layer, the hole transport layer, the electron injection layer, the electron transport layer, and the light emitting layer.
The choice of currently available electrodes and hole injection layers is not so many, and therefore, it is necessary to improve the material of the hole transport layer or the material of the light emitting layer.
Disclosure of Invention
The invention provides a spirodibenzoheptene acridine compound. The spirodibenzoheptene acridine compound has good hole transmission capacity, good film forming property and thermal stability and higher triplet state energy level, is used as a hole transmission material or a light-emitting layer main body material of an OLED device, can effectively improve the photoelectric property of the OLED device and the service life of the OLED device, and is suitable for and meets the requirements of the panel industry.
The technical scheme is as follows:
a spirodibenzosuberene acridine compound has a structure shown in a formula I:
wherein the content of the first and second substances,
Ar1selected from substituted or unsubstituted aryl groups having 6 to 60 carbon atoms;
R1and R2Each independently selected from one of the following structures:
Ar2selected from substituted or unsubstituted aryl or heteroaryl with 5-60 carbon atoms;
Ar3is selected from substituted or unsubstituted heteroaryl with 5-60 carbon atoms;
Ar4and Ar5Each independently selected from aryl groups having 6 to 60 carbon atoms.
The invention also provides a hole transport material which comprises the spirodibenzosuberene acridine compound.
The invention also provides a host material of the luminescent layer, which comprises the spirodibenzosuberene acridine compound.
The invention also provides an organic light-emitting diode which comprises a hole transport layer and a light-emitting layer, wherein the light-emitting layer is arranged on the hole transport layer;
the hole transport layer is made of the spirodibenzosuberene acridine compound or the hole transport material; and/or the presence of a gas in the gas,
the luminescent layer comprises the spirodibenzosuberene acridine compound or a host material comprising the luminescent layer.
Compared with the prior art, the invention has the following beneficial effects:
the spirodibenzoheptene acridine compound contains nitrogen atoms at specific sites, and the nitrogen atoms play a role in electron conjugation, so that the electron cloud density of a dibenzoheptene unit can be improved, and the structural unit is a structural unit with good hole transport performance. Furthermore, the external unit of the spirodibenzosuberene acridine unit is based on a condensed ring unit or a condensed ring unit with rich electron density, and the series of structural units all have good hole transport capability. In general, the spirodibenzohepteneacridine compound can be used as a good hole transport material or a host material in a light-emitting layer. Meanwhile, the spirodibenzoheptene acridine compound has good film-forming property and thermal stability, higher glass transition temperature and appropriate HOMO and LUMO energy levels, and the photoelectric property of an OLED device and the service life of the OLED device can be effectively improved through device structure optimization.
Drawings
FIG. 1 is a schematic diagram of the structure of an OLED device.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The present invention may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
A spirodibenzosuberene acridine compound has a structure shown in a formula I:
wherein the content of the first and second substances,
Ar1selected from substituted or unsubstituted aryl groups having 6 to 60 carbon atoms;
R1and R2Each independently selected from one of the following structures:
Ar2selected from substituted or unsubstituted aryl or heteroaryl with 5-60 carbon atoms;
Ar3is selected from substituted or unsubstituted heteroaryl with 5-60 carbon atoms;
Ar4and Ar5Each independently selected from aryl groups having 6 to 60 carbon atoms.
Preferably, the first and second electrodes are formed of a metal,ar is3Selected from one of the following substituted or unsubstituted structures:
wherein the content of the first and second substances,
X1each independently selected from C, N, S, Si or O.
Further preferably, Ar is3One selected from the following structures:
wherein the content of the first and second substances,
R3selected from hydrogen, alkyl with 1-3 carbon atoms or phenyl.
Still further preferably, Ar is3One selected from the following structures:
preferably, Ar is2Selected from one of the following substituted or unsubstituted structures:
wherein the content of the first and second substances,
X2each independently selected from C, N, S, Si or O.
Further preferably, Ar is2Selected from benzene or one of the following structures:
wherein the content of the first and second substances,
R3selected from hydrogen, alkyl with 1-3 carbon atoms or phenyl.
Preferably, Ar is4And Ar5Each independently selected from benzene, biphenyl, or naphthalene.
Preferably, Ar is1Selected from benzene, biphenyl or naphthalene.
The spirodibenzoheptene acridine compound contains nitrogen atoms at specific sites, and the nitrogen atoms play a role in electron conjugation, so that the electron cloud density of a dibenzoheptene unit can be improved, and the structural unit is a structural unit with good hole transport performance. Furthermore, the external unit of the spirodibenzosuberene acridine unit is based on a condensed ring unit or a condensed ring unit with rich electron density, and the series of structural units all have good hole transport capability.
The invention also provides a hole transport material which comprises the spirodibenzosuberene acridine compound.
The invention also provides a host material of the luminescent layer, which comprises the spirodibenzosuberene acridine compound.
The invention also provides an organic light-emitting diode which comprises a hole transport layer and a light-emitting layer, wherein the light-emitting layer is arranged on the hole transport layer;
the hole transport layer comprises the spirodibenzosuberene acridine compound or the hole transport material; and/or the presence of a gas in the gas,
the luminescent layer comprises the spirodibenzosuberene acridine compound or a host material of the luminescent layer.
It is understood that the organic light emitting diode further includes a first electrode, a hole injection layer disposed on the first electrode, an electron transport layer disposed on the hole injection layer, an electron injection layer disposed on the hole transport layer, an emission layer disposed on the hole transport layer, an electron transport layer disposed on the emission layer, an electron injection layer disposed on the electron transport layer, and a second electrode disposed on the electron injection layer.
Wherein the first electrode is an anode and the second electrode is a cathode.
The spirodibenzohepteneacridine compound can be used as a good hole-transport material or a host material in a light-emitting layer. Meanwhile, the spirodibenzoheptene acridine compound has good film-forming property and thermal stability, higher glass transition temperature and appropriate HOMO and LUMO energy levels, and the photoelectric property of an OLED device and the service life of the OLED device can be effectively improved through device structure optimization.
In some embodiments, the spirodibenzosuberene acridine compounds have the following structure, but are not limited thereto:
synthetic route
The following provides a preparation method of the spirodibenzosuberene acridine compound. The disclosure herein is not intended to be limited to any one of the methodologies recited herein. One skilled in the art can readily modify the methods described or utilize different methods for preparing one or more of the compounds disclosed herein. The following methods are exemplary only and are not intended to limit the scope of the present disclosure.
The general synthetic route of the spirodibenzosuberene acridine compound is as follows:
the synthesis route of the precursor is as follows:
2-Bromotriphenylamine (20mmol) was dissolved in 60ml of anhydrous THF, cooled to-78 deg.C, n-BuLi (24mmol) was added dropwise, and the mixture was incubated for 1 hour, dibenzocycloheptenone (19mmol) was dissolved in 30ml of THF, and the reaction was added dropwise overnight. Extraction with dichloromethane, drying and chromatography on silica gel column gave a white solid. And directly adding the obtained white solid into glacial acetic acid, heating and refluxing, adding 15ml of concentrated hydrochloric acid to generate solid precipitate, and performing suction filtration to obtain a white solid product 2 with the yield of 50%.
White solid product 2(10mmol) was dissolved in 50mL of glacial acetic acid and heated to reflux. 2-fold molar equivalent of liquid bromine (20mmol) was added and reacted overnight. Extraction with dichloromethane, washing with water, drying, removal of the solvent under reduced pressure gave precursor 3 in 85% yield.
M1-M7 monomer synthesis general formula:
precursor 3(1.5mmol), amine compound
(3.5mmol)，CuI(0.23g)，K2CO3(0.55g), 18-crown-6 (0.1g) was dissolved in N, N-Dimethylpropylurea (DMPU), heated at 180 ℃ overnight, extracted with dichloromethane, dried, extracted, and subjected to column chromatography to give Compound A1 in 80% yield.
M8-M15 monomer synthesis general formula:
weighing 3(5mmol) of precursor,
(12mmol) dissolved in a mixed solvent of toluene and ethanol in a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution and catalyst Pd (PPh)3)4(0.6 mmol); reacting the mixed solution of the reactants for 24 hours at the reaction temperature of 120 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target product B1; the yield is about 75%.
The specific synthetic route is as follows:
EXAMPLE 1 Compound M1
Precursor 3(1.5mmol), amine compound
(3.5mmol)，CuI(0.23g)，K2CO3(0.55g), 18-crown-6 (0.1g) was dissolved in N, N-Dimethylpropylurea (DMPU), heated at 180 ℃ overnight, extracted with dichloromethane, dried, extracted and chromatographed to give compound M1 in about 80% yield.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):8.55(d,2H),8.19(d,2H),7.94(d,2H),7.74(s,2H),7.59-7.58(m,4H),7.50-7.45(m,4H),7.35-7.31(t,6H),7.24-7.14(m,10H),7.08(d,2H),7.00-6.99(m,3H).
EXAMPLE 2 Compound M4
Precursor 3(1.5mmol), amine compound
(3.5mmol)，CuI(0.23g)，K2CO3(0.55g), 18-crown-6 (0.1g) was dissolved in N, N-Dimethylpropylurea (DMPU), heated at 180 ℃ overnight, extracted with dichloromethane, dried, extracted and chromatographed to give compound M4 in about 75% yield.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):7.45(d,2H),7.32(t,2H),7.24-7.20(m,10H),7.18-7.13(m,8H),7.08-7.04(m,4H),7.00-6.97(m,7H).
EXAMPLE 3 Compound M6
Precursor 3(1.5mmol), amine compound
(3.5mmol)，CuI(0.23g)，K2CO3(0.55g), 18-crown-6 (0.1g) was dissolved in N, N-Dimethylpropylurea (DMPU), heated at 180 ℃ overnight, extracted with dichloromethane, dried, extracted and chromatographed to give compound M6 in about 80% yield.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):7.45(d,2H),7.32(t,2H),7.24-7.23(m,12H),7.18-7.13(m,6H),7.08-7.04(m,12H),7.00-6.99(m,7H).
EXAMPLE 4 Compound M7
Precursor 3(1.5mmol), amine compound
(3.5mmol)，CuI(0.23g)，K2CO3(0.55g), 18-crown-6 (0.1g) was dissolved in N, N-Dimethylpropylurea (DMPU), heated at 180 ℃ overnight, extracted with dichloromethane, dried, extracted and chromatographed to give compound M7 in about 80% yield.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):7.45(d,2H),7.32(t,2H),7.24-7.23(m,8H),7.18-7.13(m,14H),7.08-7.04(m,8H),7.00-6.99(m,5H)，6.95(m,8H).
EXAMPLE 5 Compound M8
Weighing 3(5mmol) of precursor,
(12mmol) dissolved in a mixed solvent of toluene and ethanol in a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution and catalyst Pd (PPh)3)4(0.6 mmol); mixing the above reactant solution in the reactionReacting at 120 ℃ for 24 hours, cooling and filtering the reaction solution, evaporating the filtrate in a rotary manner, and passing the filtrate through a silica gel column to obtain the target product M8 with the yield of about 75%.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):8.55(d,1H),8.30(d,1H),8.30(d,1H),8.19(d,1H),7.99(t,1H),7.94(m,1H),7.89(s,1H),7.77(d,2H),7.62(t,2H),7.58(t,3H),7.50(m,5H),7.45(m,4H),7.36-7.35(m,4H),7.24-7.14(m,8H),7.08(d,8H),7.00-6.99(m,3H).
EXAMPLE 6 Compound M9
Weighing 3(5mmol) of precursor,
(12mmol) dissolved in a mixed solvent of toluene and ethanol in a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution and catalyst Pd (PPh)3)4(0.6 mmol); and (3) reacting the mixed solution of the reactants for 24 hours at the reaction temperature of 120 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain the target product M9, wherein the yield is about 75%.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):7.76(s,2H),7.55(d,4H),7.45(d,4H),7.37-7.32(m,8H),7.24(t,10H),7.18-7.14(m,4H),7.08(d,10H)，7.00-6.99(m,7H).
EXAMPLE 7 Compound M10
Weighing 3(5mmol) of precursor,
(12mmol) dissolved in a mixed solvent of toluene and ethanol in a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution and catalyst Pd (PPh)3)4(0.6 mmol); will be reversedReacting the mixed solution of the reactants at the reaction temperature of 120 ℃ for 24 hours, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain the target product M10, wherein the yield is about 75%.
1H NMR(500MHz,CDCl3),δ(TMS,ppm):8.18(s,2H),7.9-7.89(m,6H),7.76-7.74(m,4H),7.68(d,2H),7.55(d,4H),7.45(d,8H),7.38-7.32(m,6H),7.28-7.24(m,12H),7.18-7.14(m,4H),7.08(d,2H)，7.00-6.99(m,3H).
EXAMPLE 8 Compound M15
Weighing 3(5mmol) of precursor,
(12mmol) dissolved in a mixed solvent of toluene and ethanol in a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution and catalyst Pd (PPh)3)4(0.6 mmol); reacting the mixed solution of the reactants for 24 hours at the reaction temperature of 120 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target product M15; the yield is about 75 percent;
1H NMR(500MHz,CDCl3),δ(TMS,ppm):7.76(s,2H),7.55(d,4H),7.45(m,4H),7.37-7.32(m,8H),7.24(t,6H),7.18-7.14(m,12H),7.08(d,6H),7.00-6.99(m,13H).
preparation of OLED device
The preparation method comprises the following steps:
firstly, the ITO substrate is cleaned according to the following sequence: 5% KOH solution is subjected to ultrasonic treatment for 15min, pure water is subjected to ultrasonic treatment for 15min, isopropanol is subjected to ultrasonic treatment for 15min, and the mixture is dried in an oven for 1 h; the substrate was then transferred to a UV-ozon apparatus for surface treatment for 15min and immediately transferred to a glove box after treatment.
And (3) evaporating a hole injection layer material, namely HAT-CN (2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene) material on the clean ITO substrate to form a hole injection layer with the thickness of 30 nm.
On the above hole injection layer, using the compounds of examples 1 to 8 and the compound of comparative example as hole transport materials, respectively, and then continuing vapor deposition, a hole transport layer having a thickness of 50nm was formed;
then, a host material TCTA and a guest material Ir (ppy) are evaporated in a mixed evaporation mode2acac, forming a light emitting layer with a total thickness of 60 nm;
then, continuously evaporating an electron transport material TPBi to form an electron transport layer with the thickness of 50 nm;
then, continuously evaporating an electron injection material LiQ to form an electron injection layer with the thickness of 2 nm;
then, continuously evaporating cathode Al, wherein the thickness is 120 nm;
finally, packaging is carried out through UV curing, and heating and baking are carried out for 20min, so that OLED devices corresponding to examples 1-8 and comparative examples can be prepared.
The schematic structural diagram of one of the OLED devices is shown in fig. 1, and the structure is as follows: ITO/HAT-CN (30nm)/M1(50nm)/TCTA Ir (ppy)2acac,7wt％(60nm)/TPBi(50nm)//LiQ(2nm)/Al(120nm)。
Among them, HAT-CN as a hole injection layer material, the spiro dibenzosuberene acridine unit derivative M1 of example 1 as a hole transport layer material, TCTA as a host material, Ir (ppy)2acac is used as a guest material, TPBi is used as an electron transport layer material, LiQ is used as an electron injection layer material, and Al is used as a cathode.
Comparative example
The comparative example device has the same structure as other devices except that a common hole transport layer material NPB is adopted as the hole transport layer.
The structure of the device is ITO/HAT-CN (30nm)/NPB (50nm)/TCTA Ir (ppy)2acac,7wt％(60nm)/TPBi(50nm)//LiQ(2nm)/Al(120nm)。
The structure of the organic material is as follows:
the device properties are shown in table 1.
TABLE 1
Wherein (CIE)x,CIEy) Coordinates representing the color of the emitted light;
as can be seen from Table 1, the spirodibenzosuberene acridine compound provided by the invention has good hole transport capability as a hole transport material, and effectively improves the photoelectric property of an OLED device and the service life of the OLED device.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A spirodibenzosuberene acridine compound is characterized by having a structure shown in a formula I:
wherein the content of the first and second substances,
Ar1selected from substituted or unsubstituted aryl groups having 6 to 60 carbon atoms;
R1and R2Each independently selected from one of the following structures:
Ar2selected from substituted or unsubstituted aryl or heteroaryl with 5-60 carbon atoms;
Ar3is selected from substituted or unsubstituted heteroaryl with 5-60 carbon atoms;
Ar4and Ar5Each independently selected from aryl groups having 6 to 60 carbon atoms.
2. The spirodibenzosuberene acridine compound according to claim 1, wherein Ar is3Selected from one of the following substituted or unsubstituted structures:
wherein the content of the first and second substances,
X1each independently selected from C, N, S, Si or O.
3. The spirodibenzosuberene acridine compound according to claim 2, wherein Ar is3One selected from the following structures:
wherein the content of the first and second substances,
R3selected from hydrogen, alkyl with 1-3 carbon atoms or phenyl.
4. The spirodibenzosuberene acridine compound according to claim 3, wherein Ar is selected from the group consisting of3One selected from the following structures:
5. the spirodibenzosuberene acridine compound according to claim 1, wherein Ar is2Selected from one of the following substituted or unsubstituted structures:
wherein the content of the first and second substances,
X2each independently selected from C, N, S, Si or O.
6. The spirodibenzosuberene acridine compound according to claim 5, wherein Ar is selected from the group consisting of2Selected from benzene or one of the following structures:
wherein the content of the first and second substances,
R3selected from hydrogen, alkyl with 1-3 carbon atoms or phenyl.
7. The spirodibenzosuberene acridine compound according to any one of claims 1 to 6, wherein Ar is Ar4And Ar5Each independently selected from benzene, biphenyl, or naphthalene; and/or the presence of a catalyst in the reaction mixture,
ar is1Selected from benzene, biphenyl or naphthalene.
8. A hole transport material comprising the spirodibenzosuberene acridine compound according to any one of claims 1 to 7.
9. A host material for a light-emitting layer, comprising the spirodibenzosuberene acridine compound according to any one of claims 1 to 7.
10. An organic light emitting diode comprising a hole transport layer and a light emitting layer;
the hole-transporting layer comprising the spirodibenzosuberene acridine compound according to any one of claims 1 to 7, or comprising the hole-transporting material according to claim 8; and/or the presence of a gas in the gas,
the light-emitting layer includes the spirodibenzosuberene acridine compound according to any one of claims 1 to 7, or a host material including the light-emitting layer according to claim 9.
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