CN115304496A - Fluoranthene compound and application thereof in organic photoelectric device - Google Patents

Fluoranthene compound and application thereof in organic photoelectric device Download PDF

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CN115304496A
CN115304496A CN202210925709.7A CN202210925709A CN115304496A CN 115304496 A CN115304496 A CN 115304496A CN 202210925709 A CN202210925709 A CN 202210925709A CN 115304496 A CN115304496 A CN 115304496A
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fluoranthene
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CN115304496B (en
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王湘成
何睦
王鹏
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention discloses a fluoranthene compound and application thereof in organic photoelectric devices, the fluoranthene compound has a chemical structure shown in a formula (1), a carbon atom of a fluoranthene group is represented, at least two adjacent carbon atoms are connected into a non-aromatic ring through a carbon atom or a heteroatom, A is selected from substituted or unsubstituted aryl or heteroaryl, -R a N(R b R c ) or-N (R) d R e )，R 1 Selected from hydrogenDeuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted, straight or branched alkyl, heteroalkyl, cycloalkyl, aryl or heteroaryl, and the like. The fluoranthene compound is connected with cycloalkyl or heterocycloalkyl at fluoranthene group, and can reduce vacuum evaporation temperature, improve comprehensive performance of the device and prolong service life when used as a functional layer of an organic photoelectric device.

Description

Fluoranthene compound and application thereof in organic photoelectric device
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to a fluoranthene compound and application thereof in an organic photoelectric device.
Background
Organic Light Emitting Diodes (OLEDs) are widely used in various display devices, such as displays for consumer products such as mobile phones and watches, medical displays, vehicle displays, industrial control displays, VR/AR displays, and the like, because of their characteristics of self-luminescence, solid state, flexibility, high efficiency, high pixel density, and the like. The production method of the OLED device mainly comprises a solution method and a solid vacuum evaporation method, and the solid vacuum evaporation method is commonly used at present, namely, a material is evaporated on a substrate used for the device by heating in a cavity with high vacuum, but the process generally needs hundreds of hours, the thermal stability of a plurality of materials is poor, and the purity of the materials is poor in the using process, so that the using performance of the OLED device is reduced.
Fluoranthene compounds can be used for OLED devices, but fluoranthene has a large conjugated plane and large acting force between molecules, so that the problems of high vacuum evaporation temperature, easy decomposition of materials and the like exist in the solid vacuum evaporation process of the compounds, and the application of the compounds is limited to a great extent. It has been reported that the molecular structure of fluoranthene compounds is improved by alkyl or heterocycloalkyl substitution, but after hydrogen is substituted by alkyl or heterocycloalkyl, the aryl-alkyl bond in the molecular structure vibrates greatly, and alkyl can rotate freely, resulting in poor stability of the compounds, thereby affecting the overall use performance of the OLED device.
Disclosure of Invention
The invention provides a fluoranthene compound, which has a chemical structure shown as a formula (1):
Figure BDA0003779452990000011
in formula (1), a carbon atom of a fluoranthene group is represented, and at least two adjacent carbon atoms are superposed with a carbon atom represented by formula (2) or formula (3) to form a non-aromatic ring;
in formulae (2) and (3), B 1 –B 7 Each independently selected from O, S and-CR 3 R 4 -or-NR 5 -，B 1 –B 4 Or B 5 –B 7 Any two groups in between can be connected to form a ring, R 3 –R 5 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl or heteroatom-containing alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine;
a is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl;
or A is selected from-R a N(R b R c )，R a And is linked to a member selected from the group consisting of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene, R b And R c Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R a 、R b And R c Any two are connected into a ring;
or A is selected from-N (R) d R e ) N is connected to R d And R e Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R d And R e Linked to form a ring, or R d Or R e To which is attached;
the heteroatom of A is selected from O, N, S, P, si, se or B;
R 1 each independently selected from hydrogen, deuterium, fluorine, a carbon trifluoride group, a cyano group, a nitro group, a substituted or unsubstituted C1-C10 linear or branched alkyl group, a substituted or unsubstituted C1-C10 heteroalkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group, or two or more adjacent groups are linked to each other to form a ring;
m is an integer from 0 to 7.
The present invention also provides an organic optoelectronic device comprising a first electrode, a second electrode, an organic layer and an optical coupling layer, wherein the organic layer and/or optical coupling layer comprises one or more of the fluoranthene-based compounds.
The invention also provides a display or lighting device comprising the organic photoelectric device.
Compared with the prior art, the invention has the beneficial effects that: the fluoranthene compound is connected with the naphthenic base or the heterocyclic alkyl on the fluoranthene group, the rotation or the vibration of the aryl-alkyl in the molecular structure is limited by the naphthenic base or the heterocyclic alkyl, the thermal stability of the compound can be well improved, and the compound can be used as an organic layer and/or an optical coupling layer of an organic photoelectric device to reduce the vacuum evaporation temperature in the processing process, thereby improving the comprehensive performance of the device and prolonging the service life.
Drawings
Fig. 1 is a schematic structural diagram of a bottom emission organic optoelectronic device in an example embodiment.
Fig. 2 is a schematic structural diagram of a top-emitting organic optoelectronic device in an example embodiment.
The reference numbers are as follows: 101 a base layer; 102-a first electrode (anode); 103 a hole injection layer; 104 a first hole transport layer; 105 a second hole transport layer; 106 an organic light-emitting layer; 107 hole blocking layers; 108 an electron transport layer; 109 a second electrode (cathode); 110, and covering the layer.
Detailed Description
Embodiments of the specifically disclosed compounds and their use in organic opto-electronic devices are described in detail below. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any number between the two endpoints are optional unless otherwise specified in the invention. 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. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples may be used in the practice of the invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and with the description of the invention.
The fluoranthene compound used in the following examples has a chemical structure represented by formula (1):
Figure BDA0003779452990000031
in formula (1), a carbon atom of a fluoranthene group is represented, and at least two adjacent carbon atoms are superposed with a carbon atom represented by formula (2) or formula (3) to form a non-aromatic ring;
in formulae (2) and (3), B 1 –B 7 Each independently selected from O, S and-CR 3 R 4 -or-NR 5 -，B 1 –B 4 Or B 5 –B 7 Any two groups in between can be connected to form a ring, R 3 –R 5 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl or heteroatom-containing alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine;
a is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl;
or A is selected from-R a N(R b R c )，R a To which is attached a member selected from the group consisting of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene, R b And R c Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R a 、R b And R c Any two are connected into a ring;
or A is selected from-N (R) d R e ) N is connected to R d And R e Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted heteroarylSubstituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R d And R e Linked to form a ring, or R d Or R e To which is attached;
the heteroatom of A is selected from O, N, S, P, si, se or B;
R 1 each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or two or more adjacent groups are linked together to form a ring, and m is selected from an integer of 0 to 7.
In some embodiments, the compound of formula (1) is selected from one of the following chemical structures:
Figure BDA0003779452990000041
in the formulae (1-1), (1-2) and (1-3), x represents the same as above;
L 1 one or more than two of the following groups are selected from single bond:
Figure BDA0003779452990000042
Y 1 –Y 5 、R 1 、R 2 each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro or one or more of the following groups:
Figure BDA0003779452990000043
Figure BDA0003779452990000051
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
A 1 and A 2 Each independently selected from hydrogen, deuterium, fluoro, -CF 3 、-CN、-NO 2 Substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C5-C20 heteroaryl;
x is selected from O, S or-NR f -，R f Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
X 1 –X 7 each independently selected from O, S or-CR f R g ，R f And R g Each independently selected from hydrogen, deuterium, fluoro, -CF 3 、-CN、-NO 2 Substituted or unsubstituted C1-C10 straight or branched alkyl, or substituted or unsubstituted C3-C20 cycloalkyl;
Z 1 –Z 8 each independently selected from C or N, and m is an integer of 0 to 7.
In some embodiments, the non-aromatic ring in formula (1) is selected from substituted or unsubstituted C5-C12 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, or one of the following:
Figure BDA0003779452990000052
any two adjacent carbon atom positions are coincident with any two adjacent carbon atom positions in the formula (1).
In some embodiments, the fluoranthene-based compound represented by formula (1) is selected from one or more of the following chemical structures:
Figure BDA0003779452990000053
Figure BDA0003779452990000061
Figure BDA0003779452990000071
Figure BDA0003779452990000081
Figure BDA0003779452990000091
synthetic examples
(a) Fluoranthene intermediates are prepared by the following reaction formula 1, wherein the technical route of the reaction formula 1 is as follows:
Figure BDA0003779452990000092
(b) Preparation of Compounds by reaction of general formula 2
Figure BDA0003779452990000093
The technical route of the reaction formula 2 is as follows:
Figure BDA0003779452990000094
(c) Preparation of compounds by reaction of general formula 3
Figure BDA0003779452990000095
The technical route of reaction formula 3 is as follows:
Figure BDA0003779452990000096
(d) Preparation of Compounds by reaction of general formulae 4 and 5
Figure BDA0003779452990000097
The technical route of the reaction formulae 4 and 5 is as follows:
(d-1) reaction general formula 4:
Figure BDA0003779452990000101
(d-2) reaction formula 5:
Figure BDA0003779452990000102
synthesis example 1
Figure BDA0003779452990000103
Synthesis of M1-3: in a three-necked flask, M1-1 (30g, 145mmol), M1-2 (37.8g, 145mmol) and K were sequentially added 2 CO 3 (60g, 436 mmol), pd palladium acetate (OAc) 2 (0.33g, 1.45mmol), triphenylphosphine pph 3 (3.7g, 14.5 mmol) was added to 200mL of toluene, the reaction mixture was heated to 110 ℃ and stirred for 6 hours. After the reaction solution was cooled, 100mL of brine was added for extraction, the organic phase was dried over anhydrous sodium sulfate and then concentrated in vacuo, and the resulting solid was subjected to column chromatography 2 times using toluene and petroleum ether as a washing solution. Then toluene recrystallization was performed again for 2 times to obtain a solid, which was dried to obtain 29g of M1-3 intermediate compound in 68% yield, M/Z by LCMS (ESI ion source): 295.0.
synthesis of M1-4: in a three-necked flask, M1-3 (20g, 67.8mmol) was dissolved in 200mL of acetonitrile, and triethylamine Et was added thereto at room temperature 3 N (27g, 271.2mmol), the solution was cooled to 0 ℃ and perfluorobutanesulfonyl fluoride N was added dropwise f And F, heating to room temperature, stirring for 20 hours, neutralizing with 1mol/L hydrochloric acid to be neutral, extracting twice with ethyl acetate, drying with anhydrous sodium sulfate, performing column chromatography separation by using toluene and petroleum ether as washing liquid, and drying to obtain 28g of a solid M1-4 intermediate compound with the yield of 72%.
Synthesis of M1: in a three-necked flask, 200mL of a DMA solvent, M1-3 (20g, 34.6mmol) and tris (dibenzylideneacetone) dipalladium (Pd) were sequentially added 2 (dba) 3 (1.6 g,1.7 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxy-1, 1' -bigeminyBenzene Sphos (2.8g, 6.9mmol), K 3 PO 4 (29.4g, 138mmol) was heated to 110 ℃ and reacted with stirring for 20 hours. After the reaction solution was cooled, it was neutralized to neutrality with 1mol/L hydrochloric acid, extracted three times with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, and then concentrated in vacuo to obtain a solid. Separating the solid by column chromatography with ethyl acetate and petroleum ether as washing liquid for 2 times, and vacuum evaporating to remove solvent. After drying the solid, intermediate compound M1.1 g was obtained in 85% yield, M/Z by LCMS (ESI ion source): 277.0.
other fluoranthene intermediates were synthesized in the above manner, except that the starting materials used were different, and the starting materials for synthesis examples 2 to 8 are shown in Table 1.
TABLE 1
Figure BDA0003779452990000111
Synthesis example 9
Synthesis of Compound A2
Figure BDA0003779452990000112
A2-1 (10g, 22.5mmol), A2-2 (6.2g, 222.5mmol), and tris (dibenzylideneacetone) dipalladium (Pd) were added to a three-necked flask 2 (dba) 3 (0.4g, 0.45mmol), tri-tert-butylphosphine t-Bu 3 P (0.5g, 2.25mmol), sodium tert-butoxide NaOBu-t, (6.5g, 67.6 mmol) were stirred in 100mL of a toluene solvent (toluene) under a nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for reaction for 3 hours. Cooling the reaction liquid to room temperature, adding 50mL of water for extraction and phase separation, evaporating a toluene phase to dryness, separating and purifying a solid by using toluene-petroleum ether column chromatography, then concentrating in vacuum, recrystallizing and purifying a concentrated solution by using toluene to obtain 11g of a compound A, wherein the yield is 72%, and M/Z is measured by LCMS (ESI ion source): 684.3, 1 HNMR(DMSO-d 6 ):δ,8.02–7.87(m,1H),7.80–7.68(m,4H),7.63–7.52(m,4H),7.51–7.43(m,3H),7.43–7.20(m,7H),7.19–7.12(m,2H),7.05–6.90(m,1H),2.84(t,2H),2.70(m,3H),2.17(m,2H),2.07–1.87(m,2H),1.73–1.25(m,14H)。
the procedures of the examples using the reaction formula 3 were exactly the same as those of the compound A2 except that the starting materials were replaced, and the starting materials, yields and the like of the compounds synthesized in Synthesis examples 10 to 21 are shown in Table 2.
TABLE 2
Figure BDA0003779452990000121
Compounds prepared in the above Synthesis examples 1 H NMR is shown in Table 3.
TABLE 3
Figure BDA0003779452990000122
Figure BDA0003779452990000131
Synthesis example 22
Synthesis of compound B43:
Figure BDA0003779452990000132
a three-necked flask was charged with B43-1 (10g, 38mmol), B43-2 (9g, 38mmol) and K in this order 2 CO 3 (13g, 114mmol), tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 (0.87g, 0.76mmol) was added to a mixed solvent of 80mL of toluene, 10mL of water and 10mL of ethanol, and the reaction mixture was heated to reflux and stirred for 6 hours. After the reaction solution was cooled, 100mL of brine was added for extraction, the organic phase was dried over anhydrous sodium sulfate and then concentrated in vacuo, and the resulting solid was subjected to column chromatography using toluene and petroleum ether as a washing solution. Then carrying out toluene recrystallization for 2 times to obtain a solid, and drying the solid to obtain a compound B43 g with a yield of 72%; LCMS (ESI ion source) M/Z:421.1; 1 H NMR(DMSO-d 6 ):δ8.68–8.32(m,1H),8.07(d,2H),7.71–7.63(m,3H),7.63–7.58(m,2H),7.58–7.53(m,1H),7.52–7.37(m,4H),7.23(m,2H),3.46(s,4H).
other examples using the reaction formula 2 are exactly the same as the compound B43 except that the starting materials were replaced, and the starting materials and yields of the synthesized compounds of synthesis examples 23 to 35 are shown in table 4.
TABLE 4
Figure BDA0003779452990000141
Compounds prepared in the above synthetic examples 1 H NMR is shown in Table 5.
TABLE 5
Figure BDA0003779452990000151
Synthesis example 36
Synthesis of Compound D39
Figure BDA0003779452990000152
Synthesis of intermediate D39-3: d39-1 (20g, 76.3mmol), D39-2 (38g, 76.3mmol) and K were added in this order to a three-necked flask 2 CO 3 (31.5g, 229mmol), pd palladium acetate (OAc) 2 (0.17g, 0.76mmol), triphenylphosphine pph 3 (60g, 228.9 mmol) was added to 400mL of dichlorobenzene, and the reaction mixture was heated to reflux (180 ℃ C.), and stirred for 24 hours. After the reaction solution was cooled, it was concentrated in vacuo, and the remaining solution was subjected to column chromatography 2 times using toluene and petroleum ether as a washing solution. After the collected liquid was evaporated to dryness in vacuo, toluene was recrystallized 2 times to obtain a solid, which was dried to obtain intermediate compound D39-3 25g in 51% yield, M/Z by LCMS (ESI ion source): 649.2.
synthesis of compound D39: into a three-necked flask, D39-3 (10g, 15.4mmol), D39-4 (1.7g, 15.4mmol) and tris (dibenzylideneacetone) dipalladium (Pd) were charged 2 (dba) 3 ，(0.13g，0.15mmol), tri-tert-butylphosphine t-Bu 3 P (0.33g, 1.54mmol), sodium t-butoxide NaOBu-t, (4.4g, 46.2mmol) were stirred in toluene solvent (toluene) under nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for 3 hours. Cooling the reaction liquid to room temperature, extracting with toluene and water, evaporating the toluene phase to dryness, separating and purifying the solid by column chromatography with toluene-petroleum ether, then carrying out vacuum concentration, and recrystallizing and purifying the concentrated solution with toluene to obtain a compound D397.8g with the yield of 70%; LCMS (ESI ion source) M/Z:725.2 and the balance of the total weight of the mixture; 1HNMR (DMSO-d 6) < delta > 9.02 (s, 1H), 8.14-8.08 (m, 1H), 8.04-7.97 (m, 2H), 7.74 (m, 1H), 7.65 (s, 1H), 7.63-7.30 (m, 18H), 7.30-7.25 (m, 2H), 7.21 (m, 2H), 3.45 (s, 4H).
Other examples using the reaction scheme 4 are the same as those in Synthesis example 36 except for the difference in the starting materials, and the starting materials and yields in Synthesis examples 37 to 40 are shown in Table 6.
TABLE 6
Figure BDA0003779452990000161
Compounds prepared in the above Synthesis examples 1 H NMR is shown in Table 7.
TABLE 7
Figure BDA0003779452990000162
Figure BDA0003779452990000171
Synthesis example 41
Synthesis of Compound D12
Figure BDA0003779452990000172
Synthesis of Compound D12-3: d12-1 (20g, 47.7mmol), D12-2 (15.5g, 47.7mmol) and tris (dibenzylideneacetone) dipalladium (Pd) were added to a three-necked flask 2 (dba) 3 (0.4g, 0.95mmol), tri-tert-butylphosphine t-Bu 3 P (1.04g, 4.8 mmol), sodium t-butoxide NaOBu-t (13.7g, 143.2mmol) and 200mL of a toluene solvent (toluene) were stirred under a nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for reaction for 3 hours. Cooling the reaction liquid to room temperature, extracting with toluene and water, evaporating the toluene phase to dryness, separating and purifying the solid by column chromatography with toluene-petroleum ether, then carrying out vacuum concentration, and recrystallizing and purifying the concentrated solution by using a toluene-n-hexane mixed solvent to obtain 23.1g of the D12-3 compound with the yield of 73%. LCMS (ESI ion source) M/Z:662.1.
synthesis of Compound D12-4: d12-3 (20g, 30.1mmol) and K were added in this order to a three-necked flask 2 CO 3 (12.4g, 90.5mmol), pd palladium acetate (OAc) 2 (0.06g, 0.30mmol) and tricyclohexylphosphine tetrafluoroborate pcy3-HBF4 (0.11g, 3mmol), adding into 200mLN, N-Dimethylacetamide (DMA), heating the reaction solution to 130 ℃, and stirring for 8 hours. After the reaction is finished, cooling, concentrating in vacuum, and performing column chromatography separation and purification on the residual solution by using toluene and petroleum ether as flushing liquid. The collected liquid is evaporated to dryness in vacuum, and then is recrystallized by toluene to obtain a solid, and the solid is dried to obtain an intermediate compound D12-4.5 g with the yield of 72%. LCMS (ESI ion source) M/Z:627.2.
synthesis of compound D12: in a three-necked flask, D12-4 (10g, 15.9mmol), D12-5 (2.5g, 15.9mmol) and tris (dibenzylideneacetone) dipalladium (Pd) 2 (dba) 3 (0.27g, 0.32mmol), tri-tert-butylphosphine t-Bu 3 P (0.34g, 1.59mmol), sodium t-butoxide NaOBu-t, (4.6g, 47.9 mmol) were stirred in toluene solvent (tolumen) under nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for 3 hours. Cooling the reaction liquid to room temperature, extracting with toluene and water, evaporating the toluene phase to dryness, separating and purifying the solid by column chromatography with toluene-petroleum ether, then carrying out vacuum concentration, and recrystallizing and purifying the concentrated solution with toluene to obtain a compound D12.4 g with a yield of 75%; LCMS (ESI ion source) M/Z:703.2, preparing a mixture; 1 H NMR(DMSO-d 6 ):δ9.21–9.04(m,2H),8.53(m,1H),8.09–8.01(m,2H),7.96–7.86(m,2H),7.84–7.79(m,2H),7.76–7.66(m,3H),7.64–7.58(m,1H),7.57–7.38(m,13H),7.06(d,2H),6.07(s,2H).
other examples using the reaction scheme 5 are the same as those in Synthesis example 41 except for the difference in the starting materials, and the starting materials and yields in Synthesis examples 42 to 44 are shown in Table 8.
TABLE 8
Figure BDA0003779452990000181
Of the compounds of the above examples 1 H NMR is shown in FIG. 9.
TABLE 9
Figure BDA0003779452990000182
The bottom emission device shown in fig. 1 refers to light emitted from the TFT substrate side, the top emission device shown in fig. 2 refers to light emitted from the TFT substrate side, and the top emission device has a cap layer on the cathode as compared with the bottom emission device, and the emission colors of the device may be various colors such as red, green, blue, white, and yellow.
In some embodiments, the bottom emission device can be configured in any of the following configurations:
(1) anode/hole injection layer/hole transport layer 1/light emitting layer/electron transport layer 1/cathode;
(2) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer/electron transport layer 1/cathode;
(3) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer/electron transport layer 1/electron transport layer 2/cathode;
(4) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer/electron transport layer 1/electron transport layer 2/electron injection layer/cathode;
(5) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer/electron transport layer 1/electron transport layer 2/multilayer cathode;
(6) anode/hole injection layer/hole transport layer 1/luminescent layer 1/carrier generation layer/hole transport layer 2/luminescent layer 2/electron transport layer 1/cathode;
(7) anode/hole injection layer/hole transport layer 1/luminescent layer 1/carrier generation layer/hole transport layer 2/luminescent layer 2/electron transport layer 1/electron transport layer 2/cathode;
(8) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer 1/carrier generation layer/hole transport layer 3/luminescent layer 2/electron transport layer 1/cathode;
(9) anode/hole injection layer/hole transport layer 1/hole transport layer 2/light-emitting layer 1/carrier generation layer/hole transport layer 3/light-emitting layer 2/electron transport layer 1/electron transport layer 2/cathode.
In some embodiments, the top-emitting device may be configured in any of the following configurations:
(1) anode/hole injection layer/hole transport layer 1/light emitting layer/electron transport layer 1/cathode/capping layer;
(2) anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer/electron transport layer 1/cathode/capping layer;
(3) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer/electron transport layer 1/electron transport layer 2/cathode/capping layer;
(4) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer/electron transport layer 1/electron transport layer 2/electron injection layer/cathode/capping layer;
(5) anode/hole injection layer/hole transport layer 1/luminescent layer/electron transport layer 1/electron transport layer 2/multilayer cathode/cover layer;
(6) anode/hole injection layer/hole transport layer 1/luminescent layer 1/carrier generation layer/hole transport layer 2/luminescent layer 2/electron transport layer 1/cathode/capping layer;
(7) anode/hole injection layer/hole transport layer 1/luminescent layer 1/carrier generation layer/hole transport layer 2/luminescent layer 2/electron transport layer 1/electron transport layer 2/cathode/capping layer;
(8) anode/hole injection layer/hole transport layer 1/hole transport layer 2/luminescent layer 1/electron transport layer 2/carrier generation layer/hole transport layer 3/luminescent layer 2/electron transport layer 1/cathode/capping layer;
(9) anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer 1/electron transport layer 3/carrier generation layer/hole transport layer 3/light emitting layer 2/electron transport layer 1/electron transport layer 2/cathode/capping layer.
In any of the above device structures, the thickness of the hole transport layer 1 is generally 40-150nm, an arylamine-containing compound is usually adopted, an arylamine can be adopted, an aromatic polyamine can also be adopted, high hole mobility is required, the driving voltage can be reduced, the glass transition temperature exceeds 100 ℃, and crystallization at high temperature is avoided. The hole transport layer a may be selected from the following molecular structures: the hole transport layer 2 and the hole transport layer 3 are generally 3 to 150nm thick.
The content of the host material (host) in the luminescent material layer is larger than that of the luminescent object doping material (dopant), and the mass percentage of the object doping material in the optional luminescent material layer is 1-20%. The guest doping material may include a phosphorescent material, or a fluorescent material, or a thermally activated delayed fluorescence material, and the red, green, and blue light may be selected from the above three guest doping materials.
The light emitting body may select one light emitting body or two light emitting bodies.
The electron transport layer is used for transporting electrons of the cathode to the light-emitting layer, and generally adopts a material with hole transport capability, and the thickness is 10-50nm.
The cover layer is formed on the side of the semitransparent cathode of the device far from the substrate, and can improve the light output efficiency, the thickness is generally 50-90nm, such as 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm and the like, and the light transmittance between 450-650nm is not less than 65%, such as 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93% and the like.
The fluoranthene compound can be used in a hole transport layer, a light emitting layer, an electron transport layer and a top light emitting covering layer of OLED bottom light emitting and top light emitting devices, and device embodiments are given for different functional layers, which are specifically described below.
Device example 1
In this embodiment, a fluoranthene compound A2 is used as a material of the hole transport layer 1 104, and a blue light device (bottom emission) manufacturing method is taken as an example, and the preparation process is as follows:
a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003779452990000201
And hole transport material
Figure BDA0003779452990000202
The mixed material of (3) as the hole injection layer 103 was mixed at a ratio of 3 to 97 (mass ratio), and then the compound of the present invention was evaporated to a thickness of 100nm
Figure BDA0003779452990000203
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003779452990000204
A second hole transport layer 105 was obtained, and then a light emitting host material was vapor-deposited at a vapor deposition rate of 95
Figure BDA0003779452990000205
And a light-emitting material
Figure BDA0003779452990000206
30nm, fabricating a blue light emitting unit 106, and evaporating to deposit 10nm
Figure BDA0003779452990000207
The hole blocking layer 107 was formed, and then evaporation was performed at an evaporation rate of 4
Figure BDA0003779452990000211
And
Figure BDA0003779452990000212
an electron transport layer 108 having a thickness of 30nm was formed, and then magnesium silver (mass ratio 1.
Device examples 2 to 8 were each A2 of device example 1 replaced with the above-mentioned fluoranthene-based compounds A6, a17, a26, a42, a50, a59, and a67, and comparative example 1 used the compounds
Figure BDA0003779452990000213
(E1) Instead of A2 of device example 1, the other materials remained unchanged. The device test adopts a Keithley power supply and a combined test device of an MS-75 spectral radiometer, and the voltage and the efficiency adopt 10mA/cm 2 Voltage (V) and current efficiency (in Cd/A) at time, and a lifetime of 10mA/cm 2 The time required for the luminance to decay to 95% of the initial luminance at the time of current is specifically shown in table 10.
Watch 10
Figure BDA0003779452990000214
Device example 9
In this embodiment, a fluoranthene compound C1 is used as an electron transport layer 108 material, and a blue light device (bottom emission) manufacturing method is taken as an example, and the preparation process is as follows:
a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003779452990000215
And hole transport material
Figure BDA0003779452990000216
The mixed material of (3) was mixed as the hole injection layer 103 at a mixing ratio of 3
Figure BDA0003779452990000221
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003779452990000222
The second hole transport layer 105 was obtained, and then evaporated at an evaporation rate of 95Plated luminescent host materials
Figure BDA0003779452990000223
And a light-emitting material
Figure BDA0003779452990000224
30nm, fabricating a blue light emitting unit 106, and then evaporating to deposit 10nm
Figure BDA0003779452990000225
The hole-blocking layer 107 was formed, and then the compound C1 of the present invention was evaporated at an evaporation rate of 4
Figure BDA0003779452990000226
And
Figure BDA0003779452990000227
an electron transport layer 108 having a thickness of 30nm was formed, and then magnesium silver (mass ratio 1.
Device examples 10 to 14 replaced C1 of device example 9 with inventive compounds C11, C27, C36, C38, C39, respectively, and comparative example 2 with the compound
Figure BDA0003779452990000228
(E2) Instead of C1 of device example 1, the other materials remained unchanged. The device test adopts a Keithley power supply and a combined test device of an MS-75 spectral radiometer, and the voltage and the efficiency adopt 10mA/cm 2 Voltage (V) and current efficiency (in Cd/A) at time, lifetime of 10mA/cm 2 The time required for the luminance to decay to 95% of the initial luminance at the time of current is specifically shown in table 11.
TABLE 11
Figure BDA0003779452990000229
Figure BDA0003779452990000231
Device example 15
In this embodiment, a fluoranthene compound B1 is used as a material of the cover layer 110 of the top emission device, and the preparation process is as follows, taking the blue light device manufacturing method as an example:
a light-impermeable reflective anode Ag/ITO film layer with a thickness of 100nm/15nm was formed on a glass substrate 101 to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003779452990000232
And hole transport material
Figure BDA0003779452990000233
The mixed material of (3) was mixed as the hole injection layer 103 at a mixing ratio of 3
Figure BDA0003779452990000234
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003779452990000235
A second hole transport layer 105 was obtained, and then a light emitting host material was vapor-deposited at a vapor deposition rate of 95
Figure BDA0003779452990000236
And a luminescent material
Figure BDA0003779452990000237
30nm, fabricating a blue light emitting unit 106, and then evaporating to deposit 10nm
Figure BDA0003779452990000238
The hole-blocking layer 107 was formed, and then a compound was evaporated at an evaporation rate of 4
Figure BDA0003779452990000239
And
Figure BDA00037794529900002310
forming electrons with a thickness of 30nmAfter the transfer layer 108, magnesium silver (mass ratio 1
Figure BDA00037794529900002311
A capping layer 110 is formed.
Device examples 16 to 21 replace B1 of device example 15 with inventive compounds B3, B9, B17, B31, B43, B47, respectively, comparative example 3 with a compound
Figure BDA0003779452990000241
(E3) Instead of B1 of device example 1, the other materials remained unchanged. The device test adopts a Keithley power supply and a combined test device of an MS-75 spectral radiometer, and the voltage and the efficiency adopt 10mA/cm 2 The voltage (V) and current efficiency at that time to the color coordinate CIEy are expressed in Cd/a/CIEy, and the refractive index is obtained by testing a single-layer film of the material with a film thickness of 70nm using an ellipsometer at a set test wavelength of 460nm, as shown in table 12.
TABLE 12
Figure BDA0003779452990000242
In some embodiments, the luminescent host material is made of a mixture of multiple materials, wherein the luminescent dopant material is made of a metal iridium compound selected from, but not limited to, the following compounds:
Figure BDA0003779452990000243
Figure BDA0003779452990000251
device example 22
In this embodiment, fluoranthene compound C7 is used as the host material of the red phosphorescent light emitting layer, and the manufacturing method of the bottom emission device is taken as an example, in which the red light emitting layer emits lightA host material and a phosphorescent material, and is composed of a metal iridium compound Ir1
Figure BDA0003779452990000252
The preparation process of the luminescent doped material comprises the following steps: a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003779452990000253
And hole transport material
Figure BDA0003779452990000254
The mixed material of (3) was mixed as the hole injection layer 103 at a mixing ratio of 3
Figure BDA0003779452990000255
A first hole transport layer 104 was obtained, and then a compound having a thickness of 100nm was evaporated
Figure BDA0003779452990000256
A second hole transport layer 105 was obtained, and then a 40nm compound C7 of the present invention was evaporated at an evaporation rate of 48
Figure BDA0003779452990000257
D1
Figure BDA0003779452990000258
And Ir1
Figure BDA0003779452990000259
The red light emitting unit 106 is manufactured, and then 10nm is evaporated
Figure BDA0003779452990000261
Forming a hole blocking layer 107, and then evaporating
Figure BDA0003779452990000262
And
Figure BDA0003779452990000263
the electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4.
Device examples 23 to 34 were each prepared using a mixture of the compound of the present invention C7: D5 (content ratio 38: comparative compound 5 (content ratio 48), comparative compound 6 as the light-emitting layer 105 in place of C7: D1 (content ratio 48:
Figure BDA0003779452990000264
the device test adopts a Keithley power supply and a combined test device of an MS-75 spectral radiometer, and adopts the voltage and the efficiency of 10mA/cm 2 Voltage (V) and current efficiency (in Cd/A) at time, and a lifetime of 10mA/cm 2 The time required for the luminance to decay to 95% of the initial luminance at the time of current is shown in table 13.
Watch 13
Figure BDA0003779452990000265
Figure BDA0003779452990000271
Thermal stability test
In a chamber simulating production evaporation, the chamber is provided with a vacuum system, a heating system and a speed detection system, and the chamber is vacuumized to 10-7torr
Figure BDA0003779452990000272
Heating the material at a deposition rate for 200 hoursThereafter, the chamber was opened and the material in the material-containing vessel was removed and the purity of the remaining material was tested by HPLC, wherein the chemical structures of comparative compounds 7, 8 and 9 were respectively
Figure BDA0003779452990000273
The initial material purity before heating and the material purity after heating for 200 hours were compared to confirm that the materials were resistant to high temperatures, as shown in table 14.
TABLE 14
Name of Material Initial purity of the Material (HPLC) Purity after 200 Hours (HPLC)
A2 99.992％ 99.981％
Comparative Compound 7 99.994％ 99.963％
C1 99.993％ 99.962％
Comparative Compound 8 99.992％ 99.944％
D25 99.992％ 99.992％
Comparative Compound 9 99.994％ 99.981％
As can be seen from Table 14, the compounds of the present invention have better heat stability than the compounds without alkyl group.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (10)

1. The fluoranthene compound has a chemical structure shown as a formula (1):
Figure FDA0003779452980000011
in formula (1), a carbon atom of a fluoranthene group is represented, and at least two adjacent carbon atoms are superposed with a carbon atom represented by formula (2) or formula (3) to form a non-aromatic ring;
in formulae (2) and (3), B 1 –B 7 Each independently selected from O, S and-CR 3 R 4 -or-NR 5 -，B 1 –B 4 Or B 5 –B 7 Any two groups in between can be connected to form a ring, R 3 –R 5 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl or heteroatom-containing alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine;
a is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl;
or A is selected from-R a N(R b R c )，R a And is linked to a member selected from the group consisting of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene, R b And R c Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R a 、R b And R c Any two are connected into a ring;
or A is selected from-N (R) d R e ) N is connected to R d And R e Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R d And R e Linked to form a ring, or R d Or R e To which carbon atom(s) is attached;
the heteroatom of A is selected from O, N, S, P, si, se or B;
R 1 each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or two or more adjacent groups are linked to each other to form a ring; m is an integer from 0 to 7.
2. The fluoranthene-based compound according to claim 1, characterized in that the compound represented by formula (1) is selected from one of the following chemical structures:
Figure FDA0003779452980000021
the compounds of the formulae (1-1), (1-2) and (1-3) as defined in claim 1;
L 1 one or more than two of the following groups are selected from single bond:
Figure FDA0003779452980000022
Y 1 –Y 5 、R 1 、R 2 each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro or one or more of the following groups:
Figure FDA0003779452980000023
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
A 1 and A 2 Each independently selected from hydrogen, deuterium, fluoro, -CF 3 、-CN、-NO 2 Substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C5-C20 heteroaryl;
x is selected from O, S or-NR f -，R f Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
X 1 –X 7 each independently selected from O, S or-CR f R g ，R f And R g Each independently selected from hydrogen, deuterium, fluoro, -CF 3 、-CN、-NO 2 Substituted or unsubstituted C1-C10 straight or branched alkyl, or substituted or unsubstituted C3-C20 cycloalkyl;
Z 1 –Z 8 each independently selected from C or N, and m is an integer of 0 to 7.
3. The fluoranthene-based compound according to claim 1, wherein the non-aromatic ring in formula (1) is selected from a substituted or unsubstituted C5-C12 cycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, or one of the following groups:
Figure FDA0003779452980000031
any two adjacent carbon atom positions are coincident with any two adjacent carbon atom positions in the formula (1).
4. The fluoranthene-based compound according to claim 1, characterized in that the fluoranthene-based compound represented by formula (1) is selected from one or more of the following chemical structures:
Figure FDA0003779452980000032
Figure FDA0003779452980000041
Figure FDA0003779452980000051
Figure FDA0003779452980000061
5. use of the fluoranthene-based compound of any one of claims 1 to 4 as an organic layer material or an optical coupling material of an organic electroluminescent device in an organic electroluminescent device.
6. Use according to claim 5, wherein the organic layer material comprises one or more of a hole transport material, a light emitting host material or an electron transport material.
7. An organic optoelectronic device comprising a first electrode, a second electrode, an organic layer and an optical coupling layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the organic layer comprises one or more fluoranthene-based compounds according to any one of claims 1 to 4.
8. The organic optoelectronic device according to claim 7, wherein the optical coupling layer comprises one or more of the fluoranthene-based compounds according to any one of claims 1 to 4.
9. The organic optoelectronic device according to claim 7 or 8, wherein the organic optoelectronic device is selected from an organic photovoltaic device, an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
10. A display or lighting device comprising the organic optoelectronic device according to any one of claims 7to 9.
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