CN111018863B - Compound taking pyrrole [1, 2-a ] quinoxaline as receptor and application thereof - Google Patents

Compound taking pyrrole [1, 2-a ] quinoxaline as receptor and application thereof Download PDF

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CN111018863B
CN111018863B CN201911158566.6A CN201911158566A CN111018863B CN 111018863 B CN111018863 B CN 111018863B CN 201911158566 A CN201911158566 A CN 201911158566A CN 111018863 B CN111018863 B CN 111018863B
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luminous
quinoxaline
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孙军
张宏科
刘凯鹏
杨燕
郭静
王小伟
刘骞峰
高仁孝
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Xi'an Manareco New Materials Co ltd
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Abstract

The invention discloses a pyrrole [1, 2-a ]]A structural general formula of the compound is shown as a formula (I), wherein A is an electron donating group or a hydrogen atom, B is an electron donating group, and when A is an electron donating group, the A and B can be the same as or different from each other; the invention provides pyrrole [1, 2-a ]]The compound with quinoxaline as an acceptor has a donor-acceptor structure, a small delta Est energy value and a proper HOMO/LUMO value, can realize high brightness, low voltage, high efficiency and long service life of an organic EL element, and meanwhile, the material prepared by the compound has high thermal stability, can obviously improve the luminous stability of a luminous device, and can be widely applied to OLED luminous devices and display devices as a luminous layer main body material or a thermal activity delayed fluorescence luminous material or a hole blocking material;
Figure DDA0002285447110000011

Description

Compound taking pyrrole [1, 2-a ] quinoxaline as receptor and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent functional materials and devices, and particularly relates to a compound taking pyrrole [1, 2-a ] quinoxaline as an acceptor and application thereof.
Background
The luminous mechanism of display and lighting elements of Organic Light Emitting Diodes (OLEDs), which are self-luminous electronic elements, is a novel optoelectronic information technology that converts electrical energy directly into Light energy with the help of Organic semiconductor functional materials under the action of a direct current electric field. The light emission color can be red, green, blue, yellow alone or combined white. The biggest characteristics of the OLED light-emitting display technology are ultrathin, high response speed, ultralight weight, surface light-emitting and flexible display, can be used for manufacturing monochromatic or panchromatic displays, can be used as a novel light source technology, and can also be used for manufacturing illumination and display products or a novel backlight source technology for manufacturing liquid crystal displays.
Organic electroluminescent elements (organic EL elements) can be classified into two types, i.e., fluorescent type and phosphorescent type, according to the principle of light emission. When a voltage is applied to the organic EL element, holes from the anode and electrons from the cathode are injected, and they are recombined in the light-emitting layer to form excitons. According to the electron spin statistical method, singlet excitons and triplet excitons are 25%: a proportion of 75% was produced. The fluorescent type uses singlet excitons to emit light, and thus its internal quantum efficiency can only reach 25%. The phosphorescent material is composed of heavy metal elements, and can utilize singlet state energy and triplet state energy simultaneously through interstitial crossing, and the internal quantum efficiency can reach 100%. A Thermally Active Delayed Fluorescence (TADF) material is a third generation organic light emitting material developed after organic fluorescent materials and organic phosphorescent materials. The material generally has smaller singlet-triplet energy level difference (delta Est), triplet excitons can be converted into singlet excitons through reverse gap crossing to emit light, the singlet excitons and the triplet excitons formed under electric excitation can be fully utilized, the internal quantum efficiency of the device can reach 100 percent, meanwhile, the material has controllable structure and stable property, is low in price, does not need noble metals such as iridium, platinum and the like, and has wide application prospect in the field of OLEDs. The research results in recent years show that: the TADF material can be used not only as a luminescent material (emitter) in a luminescent layer, but also as a host material or an auxiliary host material in the luminescent layer to sensitize the emitter, which is helpful for improving the efficiency of a conventional device, improving the color purity of the device, and prolonging the service life of the device, and is an organic electroluminescent functional material with a wide application prospect. The TADF material is generally structurally formed by connecting an electron donating group and an electron withdrawing group through a pi bond, but the types of the electron withdrawing groups which can be utilized at present are few, so that the design and the development of the novel electron withdrawing group for developing the novel TADF material are very important.
Pyrrole [1, 2-a ] quinoxaline has higher thermal stability and electron affinity potential energy due to a specific molecular conjugated structure in a molecule, and can be used as an electron transport material of an OLED (KR1020140064988) through connecting donor group modification. Compared with the traditional electron transport material Alq3, the material is used as the electron transport material, so that the service life of the device is prolonged, and the driving voltage is reduced. However, the previous research on pyrrole [1, 2-a ] quinoxaline is still limited to the application of an electron transport material, and no research is carried out on the development of a host material with bipolar characteristics, a light emitting material with TADF (TADF) property and a hole blocking layer material.
Disclosure of Invention
The invention aims to provide a compound taking pyrrole [1, 2-a ] quinoxaline as an acceptor and application thereof, wherein the compound is applied to an organic electroluminescent device as a luminescent layer material or a hole blocking layer material, and can obviously improve the device performance of the organic electroluminescent device.
The invention provides a compound taking pyrrole [1, 2-a ] quinoxaline as an acceptor, which has a structural general formula shown in formula (I):
Figure BDA0002285447090000021
wherein L is1Is H or arylene, A and B are respectively independent electron-donating groups or hydrogen, A and B are not simultaneously hydrogen, and the electron-donating groups have structures shown as formula (II), formula (III), formula (IV), formula (V), formula (VI), formula (VII) or formula (VIII):
Figure BDA0002285447090000031
in the formula (III), X is oxygen atom, sulfur atom, C-m1m2、Si-m1m2Or N-m3(ii) a Wherein m is1、m2Each independently selected from a hydrogen atom, a methyl group, a phenyl group or a biphenyl group; m is3Is phenyl;
in the formulae (IV) and (V), Y is a carbon atom or a silicon atom.
Preferably, the compound taking the pyrrole [1, 2-a ] quinoxaline as the acceptor is specifically one of the following compounds:
Figure BDA0002285447090000032
Figure BDA0002285447090000041
Figure BDA0002285447090000051
Figure BDA0002285447090000061
the second purpose of the invention is to provide the application of the compound taking the pyrrole [1, 2-a ] quinoxaline as the acceptor in the organic electroluminescent device.
A third object of the present invention is to provide an organic electroluminescent device comprising a light-emitting layer, the light-emitting layer material comprising the compound having pyrrolo [1, 2-a ] quinoxaline as an acceptor according to claim 1 or 2.
Preferably, the organic electroluminescent device further comprises a hole blocking layer, and the hole blocking layer is made of the compound with pyrrolo [1, 2-a ] quinoxaline as an acceptor according to claim 1 or 2.
A fourth object of the present invention is to provide an application of the above organic electroluminescent device in an organic electroluminescent display device.
Compared with the prior art, the invention has the beneficial effects that:
the compound taking pyrrole [1, 2-a ] quinoxaline as an acceptor has a donor-acceptor structure, a small delta Est energy value and a proper HOMO/LUMO value, can realize high brightness, low voltage, high efficiency and long service life of an organic electroluminescent device, and meanwhile, a material prepared from the compound has high thermal stability, can remarkably improve the luminous stability of the luminous device, and can be widely applied to OLED luminous devices and display devices as a luminous layer main body material, a thermal activity delay fluorescence luminous material or a hole blocking layer material.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided in an embodiment of the present invention.
Description of reference numerals:
1. the cathode layer comprises a substrate, 2, an anode layer, 3, a hole injection layer, 4, a first hole transport layer, 5, a second hole transport layer, 6, a light emitting layer, 7, a hole blocking layer, 8, an electron transport layer, 9, an electron injection layer, 10 and a cathode layer.
Detailed Description
In order to make the technical solutions of the present invention better understood and implemented by those skilled in the art, the present invention is further described below with reference to the following specific embodiments and the accompanying drawings, but the embodiments are not meant to limit the present invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
The invention provides a compound taking pyrrole [1, 2-a ] quinoxaline as an acceptor, which has a structural general formula shown in formula (I):
Figure BDA0002285447090000071
wherein L is1Is H or arylene, A and B are respectively independent electron-donating groups or hydrogen, A and B are not simultaneously hydrogen, and the electron-donating groups have structures shown as formula (II), formula (III), formula (IV), formula (V), formula (VI), formula (VII) or formula (VIII):
Figure BDA0002285447090000081
in the formula (III), X is oxygen atom, sulfur atom, C-m1m2、Si-m1m2Or N-m3(ii) a Wherein m is1、m2Each independently selected from a hydrogen atom, a methyl group, a phenyl group or a biphenyl group; m is3Is phenyl; in the formulae (IV) and (V), Y is a carbon atom or a silicon atom.
In the following, we provide specific synthetic methods for the preparation of several intermediates corresponding to the above compounds.
(1) Synthesis of intermediate 1
Figure BDA0002285447090000082
Adding 31.6g of intermediate 1-2, 500ml of dichloromethane and 40.5g of triethylamine into a 1L three-necked bottle, cooling to 0 ℃ in an ice water bath, adding 48.3g of intermediate 1-1 under stirring, naturally heating to room temperature after the addition is finished, stirring for 2 hours, adding a saturated sodium carbonate aqueous solution after TLC monitoring reaction is completed to adjust the system to be neutral, washing an organic phase for 2 times after layering, and drying with anhydrous sodium sulfate;
the solvent is dried by spinning, the obtained solid is added with 600ml of phosphorus oxychloride, and the mixture is heated to reflux and stirred for reaction for 4 hours. After TLC monitoring reaction, solvent is evaporated, residual solid is added into cold water, sodium carbonate is added to adjust the system to be neutral, toluene is added into the system for extraction, organic phase is dried by anhydrous sodium sulfate, solvent is dried by spinning, intermediate 47.3g is obtained, and yield is 73.2%.
Nuclear magnetic spectrum data of intermediate 1:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.8,2H),7.94(d,J＝8.8,1H),7.73(d,J＝8.0,2H),7.67(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.49(d,J＝6.0,2H),7.37(d,J＝6.0,2H)。
(2) synthesis of intermediate 2
Figure BDA0002285447090000091
The synthesis method of the intermediate 2 is the same as that of the intermediate 1, except that the reaction raw material is replaced by the intermediate 2-1 from the intermediate 1-1, 0.22mol of the intermediate 2-1 is added to obtain 42.6g of the intermediate 2, and the yield is 65.9%;
nuclear magnetic spectrum data of intermediate 2:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.8,2H),7.94(d,J＝8.8,1H),7.73(d,J＝8.0,2H),7.67-7.65(m,2H),7.60(d,J＝6.8,1H),7.42-7.39(m,2H),7.21(t,J＝6.0,1H)。
(3) synthesis of intermediate 3
Figure BDA0002285447090000092
The synthesis method of the intermediate 3 is the same as that of the intermediate 2, except that the reaction raw material is replaced by the intermediate 3-1 from the intermediate 1-2, and 0.22mol of the intermediate 2-1 is added to obtain 51.6g of the intermediate 3, and the yield is 64.2%;
nuclear magnetic spectrum data of intermediate 3:1H NMR(400MHz,CDCl3)δ8.23(s,1H),8.08(d,J＝8.8,1H),8.03(d,J＝8.8,1H),7.82(d,J＝8.8,1H),7.67-7.65(m,2H),7.60(d,J＝6.8,1H),7.42-7.39(m,2H),7.21(t,J＝6.0,1H)。
(4) synthesis of intermediate 4
Figure BDA0002285447090000101
The synthesis method of the intermediate 4 is the same as that of the intermediate 3, except that the reaction raw material is replaced by the intermediate 4-1 from the intermediate 2-1, and 0.22mol of the intermediate 4-1 is added to obtain 54.1g of the intermediate 4, and the yield is 67.3%;
nuclear magnetic spectrum data of intermediate 4:1H NMR(400MHz,CDCl3)δ8.23(s,1H),8.08(d,J＝8.8,1H),8.03(d,J＝8.8,1H),7.82(d,J＝8.8,1H),7.67(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.49(d,J＝6.4,1H),7.37(d,J＝6.0,1H),7.26(t,J＝6.0,1H),7.11(t,J＝6.0,1H)。
(5) synthesis of intermediate 5
Figure BDA0002285447090000102
The synthesis method of the intermediate 5 is the same as that of the intermediate 1, except that the reaction raw material is replaced by the intermediate 5-1 from the intermediate 1-2, and 0.22mol of the intermediate 1-1 is added to obtain 54.6g of the intermediate 5, and the yield is 57.1%;
nuclear magnetic spectrum data of intermediate 5:1H NMR(400MHz,CDCl3)δ8.32(s,1H),8.16(d,J＝8.8,1H),8.03(d,J＝8.8,1H),7.92(d,J＝8.4,1H),7.67(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.49(d,J＝6.4,4H),7.37(d,J＝6.4,4H)。
(6) synthesis of intermediate 6
Figure BDA0002285447090000111
The synthesis method of the intermediate 6 is the same as that of the intermediate 2, except that the reaction raw material is replaced by the intermediate 6-1 from the intermediate 1-2, 0.22mol of the intermediate 2-1 is added to obtain 60.5g of the intermediate 6, and the yield is 63.3%;
nuclear magnetic spectrum data of intermediate 6:1H NMR(400MHz,CDCl3)δ8.32(s,1H),8.16(d,J＝8.8,1H),8.03(d,J＝8.8,1H),7.92(d,J＝8.4,1H),7.67-7.65(m,3H),7.60(d,J＝6.8,1H),7.42-7.39(m,4H),7.21(t,J＝6.4,2H)。
(7) synthesis of intermediate 7
Figure BDA0002285447090000112
The synthesis method of the intermediate 7 is the same as that of the intermediate 1, except that the reaction raw material is replaced by the intermediate 7-1 from the intermediate 2-1, 0.22mol of the intermediate 7-1 is added to obtain 50.6g of the intermediate 7, and the yield is 71.2%;
nuclear magnetic spectrum data of intermediate 7:1H NMR(400MHz,CDCl3)δ8.45(s,1H),8.27(d,J＝8.8,1H),8.13(d,J＝8.8,1H),7.96(d,J＝8.4,1H),7.66(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.48(d,J＝6.4,2H),7.32(d,J＝6.4,2H),7.22(d,J＝6.4,1H)。
(8) synthesis of intermediate 8
Figure BDA0002285447090000121
The synthesis method of the intermediate 8 is the same as that of the intermediate 7, except that the reaction raw material is replaced by the intermediate 5-1 from the intermediate 3-1, and 0.22mol of the intermediate 7-1 is added to obtain 50.9g of the intermediate 8, and the yield is 63.8%;
nuclear magnetic spectroscopy data for intermediate 8:1H NMR(400MHz,CDCl3)δ8.42(s,1H),8.23(d,J＝8.8,1H),8.15(d,J＝8.8,1H),7.96(d,J＝8.4,1H),7.66(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.47-7.50(m,4H),7.37(d,J＝6.8,2H),7.32(J,J＝6.4,2H),7.22(J,J＝6.4,1H)。
we now present specific synthetic methods for several of the compounds described below.
(1) Synthesis of Compound 1
Figure BDA0002285447090000122
10g of intermediate 1, 5.7g of compound 1-1, 0.44g of 1, 10-phenanthroline, 6.4g of potassium carbonate and 200ml of toluene are added into a 500ml three-necked bottle, a nitrogen protection reaction system is introduced, 0.44g of cuprous bromide is continuously added, and the reaction system is heated to reflux and stirred for reaction for 8 hours. And (3) monitoring by TLC, cooling the reaction system to room temperature after the reaction is completed, washing with water to be neutral, drying an organic phase with anhydrous sodium sulfate, concentrating and spin-drying, and purifying the obtained solid by a column to obtain 10.4g of a compound 1 with the yield of 82.3%.
Nuclear magnetic spectroscopy data for compound 1:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.4,2H),7.92(d,J＝8.8,1H),7.73(d,J＝8.4,2H),7.66(t,J＝7.6,1H),7.60(d,J＝6.0,1H),7.55-7.52(m,4H),7.40(d,J＝6.8,2H),7.32(d,J＝6.0,2H),7.08(t,J＝6.8,2H),7.00(t,J＝6.8,2H)。
(2) synthesis of Compound 3
Figure BDA0002285447090000131
10g of intermediate 1, 6.2g of compound 3-1, 5.9g of sodium tert-butoxide and 200ml of toluene are added into a 500ml three-necked bottle, nitrogen is introduced to protect the reaction system, 0.35g of palladium acetate and 0.06g of tri-tert-butylphosphine are added, and the reaction system is heated to reflux and stirred for reaction for 12 hours. Monitoring by TLC, cooling the reaction system to room temperature after the reaction is completed, washing with water to be neutral, drying an organic phase with anhydrous sodium sulfate, concentrating and spin-drying, and purifying the obtained solid by a column to obtain 10.5g of a compound 3 with a yield of 79.6%;
nuclear magnetic spectroscopy data for compound 3:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.4,2H),7.92(d,J＝8.8,1H),7.73(d,J＝8.4,2H),7.66(t,J＝7.6,1H),7.60(d,J＝6.0,1H),7.23(d,J＝6.0,2H),6.73-6.67(m,4H),6.58(t,J＝6.8,2H),6.52(t,J＝6.0,2H),6.42(d,J＝6.8,2H)。
(3) synthesis of Compound 9
Figure BDA0002285447090000132
The synthesis method of the compound 9 is the same as that of the compound 3, except that the reaction raw material is replaced by the compound 5-1 from the compound 3-1, 10g of the intermediate 1 is added, 13.7g of the compound 9 is obtained, and the yield is 83.2%;
nuclear magnetic spectroscopy data for compound 9:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.4,2H),7.92(d,J＝8.8,1H),7.73(d,J＝8.4,2H),7.66(m,2H),7.60(t,J＝7.6,1H),7.47(d,J＝6.0,2H),7.40(d,J＝6.0,2H),7.32-7.26(m,8H),7.08(m,2H),7.00(d,J＝6.0,1H)。
(4) synthesis of Compound 11
Figure BDA0002285447090000141
The synthesis method of compound 11 was the same as that of compound 3, except that the reaction raw material was replaced from intermediate 1 to intermediate 2, from compound 3-1 to compound 2-1, and 10g of intermediate 1 was added to give 10.0g of compound 11 with a yield of 71.8%.
Nuclear magnetic spectroscopy data for compound 11:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.4,2H),7.92(d,J＝8.8,1H),7.73(d,J＝8.4,2H),7.66(t,J＝7.6,1H),7.60(d,J＝6.0,1H),7.07(t,J＝6.0,1H),6.88-6.83(m,5H),6.68(s,1H),6.54(t,J＝6.8,2H),6.42(d,J＝6.0,1H),6.38(d,J＝6.8,2H),1.67(s,6H)。
(5) synthesis of Compound 15
Figure BDA0002285447090000142
The synthesis method of the compound 15 is the same as that of the compound 11, except that the reaction raw material is replaced by the compound 4-1 from the compound 2-1, 10g of the intermediate 2 is added, 12.0g of the compound 15 is obtained, and the yield is 67.5%;
nuclear magnetic spectroscopy data for compound 15:1H NMR(400MHz,CDCl3)δ8.16(d,J＝8.4,2H),7.92(d,J＝8.8,1H),7.73(d,J＝8.4,2H),7.66(d,J＝7.6,1H),7.60(t,J＝7.6,1H),7.14-7.06(m,11H),6.84-6.68(m,6H),6.50(t,J＝6.8,2H),6.42(d,J＝6.0,1H),6.34(d,J＝6.8,2H)。
(6) synthesis of Compound 20
Figure BDA0002285447090000151
The synthesis method of the compound 20 is the same as that of the compound 1, except that the reaction raw material is replaced by an intermediate 4 from the intermediate 1,10 g of the intermediate 4 is added, 12.2g of the compound 20 is obtained, and the yield is 85.6%;
nuclear magnetic spectroscopy data for compound 20:1H NMR(400MHz,CDCl3)δ8.12(s,1H),7.96(d,J＝8.8,1H),7.83(d,J＝8.4,1H),7.72(d,J＝8.4,1H),7.46-7.55(m,8H),7.40(d,J＝6.0,4H),7.32(m,1H),7.00-7.18(m,9H)。
(7) synthesis of Compound 22
Figure BDA0002285447090000152
The synthesis method of the compound 22 is the same as that of the compound 11, except that the intermediate 2 is replaced by the intermediate 3, and 10g of the intermediate 3 is added to obtain 11.9g of the compound 22, wherein the yield is 72.8%;
nuclear magnetic spectroscopy data for compound 22:1H NMR(400MHz,CDCl3)δ7.82(s,1H),7.66(d,J＝8.8,1H),7.53(d,J＝8.8,1H),7.42(d,J＝8.4,1H),7.17(t,J＝6.8,1H),7.08(m,2H),6.88-6.83(m,9H),6.68(s,1H),6.54(t,J＝7.2,4H),6.42(d,J＝6.0,1H),6.38(d,J＝7.2,4H),1.67(s,12H)。
(8) synthesis of Compound 23
Figure BDA0002285447090000161
The synthesis method of the compound 23 is the same as that of the compound 1, except that the reaction raw material is replaced by the intermediate 6 from the intermediate 1, and 10g of the intermediate 6 is added to obtain 10.8g of the compound 23, wherein the yield is 79.3%;
nuclear magnetic spectroscopy data for compound 23:1H NMR(400MHz,CDCl3)δ8.32(s,1H),8.16(d,J＝8.8,1H),8.03(d,J＝8.8,1H),7.92(d,J＝8.4,1H),7.67(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.52-7.55(m,8H),7.40(d,J＝6.0,4H),7.31(t,J＝6.0,2H),7.22(d,J＝6.0,2H),7.08-7.00(m,8H)。
(9) synthesis of Compound 30
Figure BDA0002285447090000162
The synthesis method of the compound 30 is the same as that of the compound 1, except that the reaction raw material is replaced by an intermediate 7 from the intermediate 1,10 g of the intermediate 7 is added, 10.9g of the compound 10 is obtained, and the yield is 85.8%;
nuclear magnetic spectroscopy data for compound 30:1H NMR(400MHz,CDCl3)δ8.12(s,1H),7.99(d,J＝8.8,1H),7.83(d,J＝8.4,1H),7.72(d,J＝8.4,1H),7.48-7.55(m,6H),7.40(d,J＝6.0,2H),7.32(t,J＝6.0,2H),7.22(t,J＝6.0,1H),7.08(t,J＝6.0,2H),7.00(t,J＝6.0,2H)。
(10) synthesis of Compound 43
Figure BDA0002285447090000171
10g of the intermediate 8, 7.7g of the compound 43-1, 200ml of toluene, 80ml of ethanol, 40ml of water, 6.9g of potassium carbonate and 1.6g of tetrabutylammonium bromide are sequentially added into a 500ml three-necked flask, nitrogen is introduced for 10min, then 0.53g of tetrakis (triphenylphosphine) palladium is added, the mixture is heated to (78-80 ℃) and reacts for 6h, sampling detection is carried out, heating is stopped when the raw materials completely react, and the temperature is reduced to the room temperature. And filtering the reaction solution, washing an organic phase to be neutral by water, drying the organic phase for 1h by anhydrous sodium sulfate, passing through a column to remove the catalyst, carrying out spin drying on eluent, and recrystallizing the obtained crude product by using toluene to obtain a product of 10.9g of a compound 43 with the yield of 75.3%.
Nuclear magnetic spectroscopy data for compound 43:1H NMR(400MHz,CDCl3)δ8.42(s,1H),8.23(d,J＝8.8,1H),8.15(d,J＝8.8,1H),7.96(d,J＝8.4,1H),7.66(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.42-7.54(m,11H),7.32(t,J＝6.4,2H),7.19-7.22(m,3H),7.13(J,J＝6.4,2H)；
(11) synthesis of Compound 48
Figure BDA0002285447090000172
The synthesis method of the compound 48 is the same as that of the compound 3, except that the reaction raw material is replaced by an intermediate 5 from an intermediate 1,10 g of the intermediate 5 is added, 10.9g of the compound 48 is obtained, and the yield is 76.1%;
nuclear magnetic spectroscopy data for compound 48:1H NMR(400MHz,CDCl3)δ8.32(s,1H),8.16(d,J＝8.8,1H),8.03(d,J＝8.8,1H),7.92(d,J＝8.4,1H),7.67(t,J＝6.8,1H),7.60(d,J＝6.8,1H),7.23(d,J＝6.0,4H),6.73-6.67(m,8H),6.58-6.52(m,8H),6.42(d,J＝6.0,4H)。
t was performed on some of the compounds provided in the above examples and the existing materials, respectively1Energy levels and HOMO, LUMO energy levels were tested and the results are shown in table 1:
TABLE 1 Compounds T of the invention1Energy level and HOMO, LUMO
Figure BDA0002285447090000181
Note: data obtained by the triplet state energy (T1) of the highest molecular occupied orbital (HOMO) and the lowest molecular unoccupied orbital (LUMO) are calculated by a Gaussian 09 software simulation method, and a B3LYP hybridization functional is adopted as a calculation method, and the group is 6-31g (d, p).
As shown in table 1, the organic compounds of the present invention have higher triplet energy and more suitable HOMO/LUMO, which are favorable for carrier transport and energy transfer in OLED devices, and can be used as phosphorescent host material, fluorescent host material or TADF host material, and also can be used as TADF light emitting material or hole blocking material. The organic electroluminescent device may be, without particular limitation, a phosphorescent device, a fluorescent device or a device containing a Thermally Active Delayed Fluorescence (TADF) material. Therefore, after the compound taking the pyrrole [1, 2-a ] quinoxaline as the acceptor is applied to the light-emitting layer of the OLED device, the light-emitting efficiency, the service life and other properties of the device can be effectively improved.
In the following, some of the compounds provided by the present invention are taken as examples, and applied to an organic electroluminescent device as a light emitting layer material (host material and/or doped dye) or a hole blocking layer material to verify the excellent effects obtained by the compounds.
The excellent effect of the inventive OLED materials in devices is detailed in particular by the device properties of device examples 1-12 and comparative examples 1-2. The manufacturing processes of the device examples 1 to 12 and the device comparative examples 1 to 2 are completely the same, the same glass substrate and the same electrode material are adopted, the thickness of the electrode material film is also kept consistent, and the difference is that the material of the luminescent layer or the material of the hole blocking layer is adjusted as follows.
Device application example
Device example 1
The present embodiment provides an organic electroluminescent device, which has a structure as shown in fig. 1, and includes a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10, which are sequentially stacked.
Wherein, the anode layer 2 is made of Indium Tin Oxide (ITO) with high common function, the hole injection layer 3 is made of HAT-CN with the thickness of 5 nm; NPB is selected as the material of the first hole transport layer 4, and the thickness is 60 nm; TCTA is selected as the material of the second hole transport layer 5, and the thickness is 15 nm; the luminescent layer 6 used RD01 as the luminescent material and compound 1 as the host material, the doping ratio was 3%, and the thickness was 30 nm; TPBI is selected as the material of the hole blocking layer 7, and the thickness is 10 nm; the material of the electron transport layer 8 is ET-1, and the thickness is 35 nm; liq is selected as the material of the electron injection layer 9, and the thickness is 2 nm; the cathode layer is made of Al and has a thickness of 120 nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
Figure BDA0002285447090000201
the organic electroluminescent device is prepared by the following specific steps:
1) cleaning an ITO anode on a transparent glass substrate, respectively ultrasonically cleaning the ITO anode for 20 minutes by using deionized water, acetone and ethanol, and then carrying out Plasma (Plasma) treatment for 5 minutes in an oxygen atmosphere;
2) evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the hole injection layer is used as a hole injection layer;
3) evaporating a hole transport material NPB on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 60nm, and the hole transport layer is used as a first hole transport layer;
4) evaporating a hole transport material TCTA on the first hole transport layer NPB in a vacuum evaporation mode, wherein the thickness of the TCTA is 15nm, and the TCTA serves as a second hole transport layer;
5) co-evaporating a light-emitting layer on the second hole transport layer by a vacuum evaporation mode, wherein the compound 1 is used as a host material, the RD01 is used as a light-emitting material, the doping amount ratio is 3%, and the thickness is 30 nm;
6) evaporating a hole blocking material TPBI on the light-emitting layer in a vacuum evaporation mode, wherein the thickness of the hole blocking material TPBI is 10nm, and the layer is used as a hole blocking layer;
7) evaporating an electron transport material ET-1 on the hole blocking layer in a vacuum evaporation mode, wherein the thickness of the electron transport material ET-1 is 35nm, and the electron transport material ET-1 serves as an electron transport layer;
8) evaporating an electron injection material Liq on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the electron injection material Liq is 2nm, and the electron injection layer is used as an electron injection layer;
9) on the electron injection layer, a cathode Al was deposited by vacuum deposition to a thickness of 120nm, and the layer was used as a cathode conductive electrode.
Device example 2
Same as device example 1, except that: compound 3 was used as the host instead of compound 1.
Device example 3
Same as device example 1, except that: compound 9 was used as the host instead of compound 1.
Device example 4
Same as device example 1, except that: compound 11 was used as the host instead of compound 1.
Device example 5
Same as device example 1, except that: compound 15 was used as the host instead of compound 1.
Device example 6
Same as device example 1, except that: compound 20 was used as the host instead of compound 1.
Device example 7
Same as device example 1, except that: compound 22 was used as the host instead of compound 1.
Device example 8
Same as device example 1, except that: compound 23 was used as the host instead of compound 1.
Device example 9
Same as device example 1, except that: compound 30 was used as the host instead of compound 1.
Device example 10
Same as device example 1, except that: compound 48 was used as the host in place of compound 1.
Device example 11
Same as device example 1, except that: the compound CBP was used as a main body instead of the compound 1, and the compound 1 was used as a dose to fabricate a TADF device.
Device example 12
Same as device example 11, except that: compound 43 was used as a hole blocking material in place of TPBI.
Comparative example 1
Same as device example 1, except that: CPB was used as host material instead of compound 1.
Comparative example 2
Same as device example 11, except that: PTZ-DCPP as a doping material instead of compound 1.
The composition of the various devices prepared in inventive device examples 1-12 and comparative examples 1-2 is shown in Table 2:
TABLE 2 comparison table of organic electroluminescent element components of each device example
Figure BDA0002285447090000221
Figure BDA0002285447090000231
Connecting the cathode and the anode of each group of organic electroluminescent devices by using a known driving circuit, and testing the voltage-efficiency-current density relation of the OLED devices by adopting a Keithley2400 power supply and a PR670 photometer through a standard method; the service life of the device is tested by a constant current method under the condition that the constant current density is 50mA/cm2The time for the test brightness to decay to 95% of the initial brightness is the device LT95Lifetime, test results are shown in table 3:
table 3 performance results for each group of organic electroluminescent devices
Figure BDA0002285447090000232
Figure BDA0002285447090000241
As can be seen from Table 3, the compounds provided by the present invention are excellent in performance when applied to OLED emitters as host materials and light-emitting materials for light-emitting layers. Compared with the CPB of the comparative example 1, the compound 9 in the device example 3 serving as the phosphorescent main body material has the advantages that the luminous efficiency and the service life are remarkably improved, the luminous efficiency is improved by about 34%, and the service life is improved by 80%; compared with the PTZ-DCPP in the comparative example 2, the TADF luminescent material of the compound 1 in the embodiment 11 has the advantages that the luminous efficiency is improved by about 18 percent, the service life is improved by 33 percent, and the color coordinate is excellent. Compared with the conventional material TPBI, the compound 43 used as a hole blocking material in the device example 12 has the advantage that the service life of the device is improved by 18.7%. Therefore, the compound provided by the invention is used as a main material or a luminescent material or a hole blocking material of an OLED device, and compared with an OLED luminescent device applied by the existing material, the photoelectric properties of the device, such as luminous efficiency, service life, color purity and the like, have good performances, and have great application value in the application of the OLED device and good industrial prospect.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the appended claims and their equivalents.

Claims (5)

1. A compound taking pyrrole [1, 2-a ] quinoxaline as an acceptor is characterized by being one of the following compounds:
Figure FDA0002968344300000011
Figure FDA0002968344300000021
2. use of a compound according to claim 1 with pyrrolo [1, 2-a ] quinoxaline as an acceptor in an organic electroluminescent device.
3. An organic electroluminescent device comprising a light-emitting layer, wherein a host material in the light-emitting layer comprises the compound having pyrrolo [1, 2-a ] quinoxaline as an acceptor according to claim 1 and/or a light-emitting material in the light-emitting layer comprises the compound having pyrrolo [1, 2-a ] quinoxaline as an acceptor according to claim 1.
4. The organic electroluminescent device according to claim 3, further comprising a hole blocking layer, wherein the hole blocking layer is a compound having pyrrolo [1, 2-a ] quinoxaline as an acceptor according to claim 1.
5. Use of the organic electroluminescent device as claimed in claim 3 or 4 in an organic electroluminescent display device.
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