CN114213377B - Anthracene-based fluorescent luminous main body material and application thereof - Google Patents

Anthracene-based fluorescent luminous main body material and application thereof Download PDF

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CN114213377B
CN114213377B CN202111508950.1A CN202111508950A CN114213377B CN 114213377 B CN114213377 B CN 114213377B CN 202111508950 A CN202111508950 A CN 202111508950A CN 114213377 B CN114213377 B CN 114213377B
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anthracene
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王湘成
何为
何睦
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention discloses an anthracene-based fluorescent luminous main body material and application thereof, the general structure of the anthracene-based fluorescent luminous main body material is composed of
Figure DDA0003404525820000011
Intermediate junction sites m and n and
Figure DDA0003404525820000012
middle X 1 And X 2 、X 2 And X 3 、X 3 And X 4 Optionally connected in a ring, Z 1 ～Z 8 Each independently hydrogen or deuterium, ar 1 Selected from deuterium substituted, alkyl substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, Y 1 Selected from O, S, -C (CH) 3 ) 2 ‑、‑C(CD 3 ) 2 -phenyl substituted or unsubstituted imino; x is X 1 ～X 4 All are carbon, R 1 ～R 3 Each independently hydrogen, deuterium, alkyl or phenyl, a, b and c are independently selected from 1, 2, 3 and 4, Y 2 Selected from the group consisting of absence, O, S, -C (CH) 3 ) 2 ‑、‑C(CD 3 ) 2 Phenyl substituted or unsubstituted imino groups, the material has good crystallization resistance and solubility, and can balance hole and electron transport for OLED devices, thereby reducing the power consumption of OLED devices.

Description

Anthracene-based fluorescent luminous main body material and application thereof
Technical Field
The invention belongs to the field of organic electroluminescent materials, and particularly relates to an anthracene-based fluorescent luminescent main body material and application thereof.
Background
With the development of electronic display technology, organic Light Emitting Devices (OLEDs) are widely used in various display devices, and research and application of OLED light emitting materials are increasing. According to the light emission mechanism, the materials used as OLED light emitting materials mainly include the following four types: (1) a fluorescent material; (2) a phosphorescent material; (3) triplet-triplet annihilation (TTA) material; (4) Thermally Activated Delayed Fluorescence (TADF) materials. The anthracene has strong chemical modification property, and substitution modification is carried out on 9, 10 positions or other carbon atoms, so that aggregation among anthracene molecules can be effectively reduced, and researches show that the anthracene derivative has good film forming property, stability and proper carrier transmission property, and simultaneously has good photoelectric property, and has practical application value as a luminescent material of an organic electroluminescent device. Based on the above, the invention starts from molecular structural design, and an anthracene-based derivative is tried and proposed for the first time as a fluorescent light-emitting main body material of an OLED device, and the specific steps are as follows.
Disclosure of Invention
The invention provides an anthracene-based fluorescent light-emitting main body material, which is formed by connecting a structure shown in a formula 1 with a chemical structure shown in a formula 2 through chemical bonds:
Figure BDA0003404525800000011
in formula 1, Z 1 ～Z 8 Each independently hydrogen or deuterium, ar 1 Selected from deuterium substituted, alkyl substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, Y 1 Selected from O, S, -C (CH) 3 ) 2 -、-C(CD 3 ) 2 -phenyl substituted or unsubstituted imino;
in formula 2, X 1 ～X 4 All are carbon, R 1 ～R 3 Each independently hydrogen, deuterium, alkyl or phenyl, a, b and c each independently represent R 1 、R 2 And R is 3 Is independently selected from 1, 2, 3 and 4, Y 2 Selected from the group consisting of absence, O, S, -C (CH) 3 ) 2 -、-C(CD 3 ) 2 -phenyl substituted or unsubstituted imino;
in formula 1, m and n represent the attachment site, and X in formula 2 1 And X 2 、X 2 And X 3 、X 3 And X 4 One group of which is optionally connected in a ring.
Compared with the prior art, the invention has the beneficial effects that: the anthracene-based fluorescent light-emitting main material provided by the invention has good crystallization resistance and solubility, and hole and electron transmission are balanced better, so that the power consumption of an OLED device is reduced better.
Drawings
Fig. 1 is a schematic structural view of a bottom-emission organic electroluminescent device in an embodiment.
Fig. 2 is a schematic structural view of a top-emission organic electroluminescent device in an embodiment.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings of the embodiments of the present invention. It will be apparent that the described embodiments are some, but not all, embodiments of the invention. All other embodiments, which can be made by a person skilled in the art without creative efforts, based on the described embodiments of the present invention fall within the protection scope of the present invention.
The general structure of the anthracene-based fluorescent light-emitting main material provided by the invention is formed by connecting a structure shown in a formula 1 with a chemical structure shown in a formula 2 through chemical bonds:
Figure BDA0003404525800000021
in formula 1, Z 1 ～Z 8 Each independently hydrogen or deuterium, ar 1 Selected from deuterium substituted, alkyl substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, Y 1 Selected from O, S, -C (CH) 3 ) 2 -、-C(CD 3 ) 2 -phenyl substituted or unsubstituted imino;
in formula 2, X 1 ～X 4 All are carbon, R 1 ～R 3 Each independently hydrogen, deuterium, alkyl or phenyl, a, b and c each independently represent R 1 、R 2 And R is 3 Is independently selected from 1, 2, 3 and 4, Y 2 Selected from the group consisting of absence, O, S, -C (CH) 3 ) 2 -、-C(CD 3 ) 2 -phenyl substituted or unsubstituted imino;
in formula 1, m and n represent the attachment site, and X in formula 2 1 And X 2 、X 2 And X 3 、X 3 And X 4 One group of which is optionally connected in a ring.
The above description of "aryl" may be a monocyclic aryl group including phenyl, biphenyl, terphenyl, tetrabiphenyl, or a polycyclic aryl group including naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, and the above description of aryl may be applied to arylene groups, except that arylene groups are divalent.
According to some embodiments, the anthracene-based fluorescent light-emitting host material has a general structure as shown in chemical formulas a-f:
Figure BDA0003404525800000031
according to some embodiments, ar in the above formulas a-f 1 Selected from deuterium substituted, alkyl substituted or unsubstituted phenyl, naphthyl or biphenyl.
According to some embodiments, in the above formulas a-f, Y 1 Selected from O or S.
According to some embodiments, in the above formulas a-f, Y 2 Selected from O or absent.
According to some embodiments, in the above formulas a-f, R 1 ～R 3 All are hydrogen, and a, b and c are all 1.
According to some embodiments, the anthracene-based fluorescent host material described above is selected from any one of the following chemical structures:
Figure BDA0003404525800000032
/>
Figure BDA0003404525800000041
/>
Figure BDA0003404525800000051
/>
Figure BDA0003404525800000061
the general synthetic route for the anthracene-based fluorescent host materials described above is shown below, with appropriate starting materials selected according to the molecular structure of the final product, and the following route and the materials referred to in table 1 are all commercially available chemicals.
Figure BDA0003404525800000062
The following synthesis examples 1 to 10 respectively describe in detail the raw materials or intermediates employed in the preparation methods of the above-mentioned anthracene-based fluorescent light-emitting host materials H1, H5, H7, H8, H16, H31, H32, H42, H47 and H53, the raw materials of the preparation methods not being noted being commercial products, the synthesis example 1 being described below, and the preparation methods of the other examples being similar thereto.
TABLE 1
Figure BDA0003404525800000071
Figure BDA0003404525800000081
/>
Synthesis example 1: synthesis of Compound H1
Figure BDA0003404525800000082
Synthesis of H1-3: h1-1 (15 g,51.5 mmol), H1-2 (6.3 g,51.5 mmol), potassium carbonate (10.3 g,77.2 mmol) and tetrakis (triphenylphosphine) palladium (0.6 g,0.51 mmol) were sequentially added to a three-necked flask, 110mL of toluene, 20mL of ethanol and 20mL of water were further added, the system was replaced with nitrogen for 3 times, the reaction solution was heated to reflux, and the reaction was continued with stirring for 4 hours. The reaction solution was cooled to 70℃and allowed to stand for separation, the upper organic phase was washed with 50mL of water and separated, and the upper organic phase was passed through a silica gel column. The organic phase was concentrated to 50mL, 100mL of petroleum ether was gradually added, solids precipitated, stirred for 2 hours, suction filtration, washing the cake with a small amount of petroleum ether, heating the mixed solution of 50mL of toluene and 100mL of ethanol for 2 hours at 40℃and stirring the solid, and drying the solid to obtain 12g of H1-3 compound in 81% yield.
Synthesis of H1: h1-3 (10 g,34.6 mmol), H1-4 (15.6 g,34.6 mmol), potassium carbonate (9.2 g,69.2 mmol) and tetrakis (triphenylphosphine) palladium (0.4 g,0.35 mmol) were sequentially added to a three-necked flask, 120mL of toluene, 20mL of ethanol and 20mL of water were further added, the system was replaced with nitrogen for 3 times, the reaction solution was heated to reflux, and the reaction was continued with stirring for 6 hours. The reaction solution was cooled to 70℃and allowed to stand for separation, the upper organic phase was washed with 50mL of water and separated, and the upper organic phase was passed through a silica gel column. The organic phase was concentrated to 70mL, 100mL of petroleum ether was gradually added, solids precipitated, stirred for 2 hours, suction filtration, washing of the cake with a small amount of petroleum ether, heating of a mixed solution of 70mL of toluene and 100mL of ethanol was carried out, stirring for 2 hours at 40℃and filtration of the solids was carried out, drying was carried out, 18g of H1 compound was obtained, yield 79%.
The anthracene-based fluorescent light-emitting host material needs to be matched with a blue light guest material for use, and the guest material is selected from the following materials:
Figure BDA0003404525800000091
as shown in fig. 1 and 2, the present invention also provides the application of the anthracene-based fluorescent light-emitting host material in an organic electroluminescent device, as shown in device embodiments 1 to 10.
Device example 1
The blue light non-series organic electroluminescent device is manufactured according to the structure shown in figure 1, and the preparation process comprises the following steps: forming a transparent anode ITO film layer with a film thickness of 150nm on a glass substrate 101 to obtain a first electrode 102 as anode, and evaporating
Figure BDA0003404525800000101
And the compound->
Figure BDA0003404525800000102
As the hole injection layer 103, the mixing ratio was 3:97 (mass ratio), followed by evaporation of 100nm thick compound +.>
Figure BDA0003404525800000103
A first hole transport layer 104 was obtained, followed by evaporation of a 20nm thick compound +.>
Figure BDA0003404525800000104
Obtaining a second hole transport layer 105, then evaporating the compound H1 of the invention as anthracene-based fluorescent light-emitting host material and guest material BD230nm at an evaporation rate of 97:3 to prepare a blue light-emitting unit 106, and then evaporating a compound +.>
Figure BDA0003404525800000105
An electron blocking layer 107 is formed, and then a compound is evaporated>
Figure BDA0003404525800000106
And->
Figure BDA0003404525800000107
An electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then ytterbium metal having a thickness of 1nm was vapor deposited, and then silver metal having a thickness of 100nm was formed as a double-layered ytterbium/silver metal as the second electrode 109.
The anthracene-based fluorescent light-emitting host materials H5, H7, H8, H16, H31, H32, H42, H47, and H53 described above were used in device examples 2 to 10, and the compounds used in comparative examples 1 and 2, respectively
Figure BDA0003404525800000111
And a compound
Figure BDA0003404525800000112
Alternative device example 1, compound H1 was doped simultaneously with guest material BD2 (guest weight3%) as the light-emitting layer 106 to produce a blue organic electroluminescent device, the anthracene-based fluorescent light-emitting host materials H1, H5, H7, H8, H16, H31, H32, H42, H47, and H53 described above were used in device examples 11 to 20, respectively, and the compounds>
Figure BDA0003404525800000113
And the compound->
Figure BDA0003404525800000114
Instead of the compound H1 of device example 1, a blue organic electroluminescent device was fabricated while using a guest material BD16 doping (guest weight ratio of 3%) as the light emitting layer 106, and the resulting organic electroluminescent device was subjected to performance test as shown in table 2.
TABLE 2
Figure BDA0003404525800000115
Figure BDA0003404525800000121
As can be seen from Table 2, the anthracene-based fluorescent light-emitting host material provided by the invention is used for an organic electroluminescent device and has the advantages of low driving voltage, high light-emitting efficiency and long service life.
In addition, the invention also provides a display device comprising any one of the organic electroluminescent devices.

Claims (4)

1. The anthracene-based fluorescent luminescent host material is characterized by having a general structure shown in chemical formulas a-f:
Figure FDA0004173474450000011
in the formulae a-f, Z 1 ～Z 8 Are deuterium;
Ar 1 selected from deuterium substitutedPhenyl or naphthyl;
Y 1 selected from O, S or-C (CD) 3 ) 2 -；
R 1 ～R 3 Each independently hydrogen or deuterium, a, b and c each represent R 1 、R 2 And R is 3 Is independently selected from 1, 2, 3 and 4; y is Y 2 Selected from single bonds or O.
2. The anthracene-based fluorescent light-emitting host material according to claim 1, characterized by any one of the chemical structures selected from:
Figure FDA0004173474450000021
/>
Figure FDA0004173474450000031
/>
Figure FDA0004173474450000041
3. a display panel comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting material of the light-emitting layer comprises a host material and a guest material, and the host material of the light-emitting layer is one or more than one of the anthracene-based fluorescent host materials according to claim 1 or 2.
4. A display device comprising the display panel of claim 3.
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Inventor before: Wang Xiangcheng

Inventor before: He Wei

Inventor before: He Mu

CB03 Change of inventor or designer information