CN107098818B - Aromatic compound and organic light emitting diode comprising same - Google Patents

Aromatic compound and organic light emitting diode comprising same Download PDF

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CN107098818B
CN107098818B CN201610093779.5A CN201610093779A CN107098818B CN 107098818 B CN107098818 B CN 107098818B CN 201610093779 A CN201610093779 A CN 201610093779A CN 107098818 B CN107098818 B CN 107098818B
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CN107098818A (en
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郑建鸿
陈奕翔
吴奕靓
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Abstract

An aromatic compound represented by chemical formula 1 and an organic light emitting diode including the same. In chemical formula 1, A, Ar2, R1, R2 and m are the same as those described in the embodiments. The aromatic compound of the present invention has blue light emission, high quantum efficiency and excellent thermal stabilityQualitative characteristics. In addition, the aromatic compound of the present invention can be applied to a light emitting layer or a hole transport layer of an organic light emitting diode to improve external quantum efficiency, maximum brightness, current efficiency, power efficiency and lifetime of the organic light emitting diode.
Figure DDA0000926430500000011

Description

Aromatic compound and organic light emitting diode comprising same
Technical Field
The present invention relates to a compound and an organic light emitting diode including the same, and more particularly, to an aromatic compound and an organic light emitting diode including the same.
Background
Organic Light Emitting Diode (OLED) flat panel displays have advantages of wider viewing angle, faster response time, thinner and lighter size, and are currently used for large-area, high-brightness, full-color displays.
In order to develop full-color flat panel displays, the development of stable and high-efficiency light-emitting materials (red, green, and blue) is a major objective of the present research on OLEDs. However, development of a blue light emitting material is slow in luminous efficiency and emission lifetime compared to a red light emitting material and a green light emitting material, and thus development of a novel blue light emitting material having high luminous efficiency and long lifetime is an object of great efforts.
Disclosure of Invention
The present invention provides an aromatic compound which can realize an organic light emitting diode having high light emitting efficiency and long life.
The present invention provides an aromatic compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure BDA0000926430480000011
In chemical formula 1, R1And R2Each independently of the other being hydrogen, halogen, C1-C6Alkyl or aryl, m is 0 or1, A is a substituted or unsubstituted carbazolyl Ar1Or is an organic amino group, and Ar2Is a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted triazinyl group or a substituted or unsubstituted
Figure BDA0000926430480000012
In an embodiment of the present invention, the aromatic compound is represented by the following chemical formula 2:
[ chemical formula 2]
Figure BDA0000926430480000021
In chemical formula 2, Ar3Is selected from the following structural formulas,
Figure BDA0000926430480000022
the remaining substituents are the same as defined in chemical formula 1.
In an embodiment of the present invention, the aromatic compound is represented by the following chemical formula 3:
[ chemical formula 3]
Figure BDA0000926430480000023
In chemical formula 3, Ar4Is selected from the following structural formulas,
Figure BDA0000926430480000024
the remaining substituents are the same as defined in chemical formula 1.
In an embodiment of the invention, Ar is as described above2Is selected from the following structural formulas,
Figure BDA0000926430480000025
the invention provides an organic light emitting diode, which comprises a cathode, an anode and a light emitting layer. A light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer contains the aromatic compound
In an embodiment of the invention, the organic light emitting diode is, for example, a blue light emitting diode.
In an embodiment of the invention, the light emitting layer includes a host light emitting material and a guest light emitting material.
In an embodiment of the invention, the host light emitting material includes the aromatic compound.
In an embodiment of the invention, the guest light emitting material includes the aromatic compound.
In an embodiment of the invention, the host light emitting material is, for example, 1- (2,5-dimethyl-4- (1-pyrenyl) phenyl) pyrene (1- (2,5-dimethyl-4- (1-pyrenyl) phenyl) pyrene; DMPPP), 4'-N, N' -dicarbazole-biphenyl (4,4'-N, N' -dicarbazole-biphenyl; CBP) or 2- (3- (pyrene-1-yl) phenyl) terphenyl (2- (3- (pyren-1-yl) phenyl) triphenylene; m-PPT).
In an embodiment of the invention, the organic light emitting diode further includes at least one auxiliary layer, and the auxiliary layer is selected from a group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron blocking layer.
In an embodiment of the invention, the at least one auxiliary layer includes the aromatic compound.
Based on the above, the aromatic compound of the present invention has characteristics of blue light emission, high quantum efficiency, and excellent thermal stability. In addition, the aromatic compound of the present invention can be applied to a light emitting layer or a hole transport layer of an organic light emitting diode to improve external quantum efficiency, maximum brightness, current efficiency, power efficiency and lifetime of the organic light emitting diode.
In order to make the aforementioned and other features and advantages of the invention more comprehensible, embodiments accompanied with figures are described in detail below.
Drawings
FIG. 1 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention;
FIG. 2 is a schematic cross-sectional view of an OLED according to another embodiment of the present invention;
FIGS. 3A and 3B are transient light-excited fluorescence curves of a toluene solution containing the compound CZSSO under the condition of respectively introducing air and nitrogen;
FIGS. 4A and 4B are transient light-excited fluorescence curves of a toluene solution containing the compound TCZSSO under the condition of respectively introducing air and nitrogen;
FIGS. 5A and 5B are transient light-excited fluorescence curves of a toluene solution containing the compound OCZSSO under the condition of respectively introducing air and nitrogen;
FIGS. 6A and 6B are transient light-excited fluorescence curves of a toluene solution containing the compound CZSDCN under the respective introduction of air and nitrogen;
FIGS. 7A and 7B are transient light-excited fluorescence curves of a toluene solution containing the compound CZSDPT under air and nitrogen respectively;
fig. 8 is a transient electroluminescence (oel) fluorescence curve of the organic light emitting diodes of experimental examples 1 to 4;
FIG. 9 is a graph showing transient electroluminescence (EEL) curves of the organic light emitting diodes of Experimental examples 5 to 7 and comparative examples;
fig. 10 is a graph of transient electroluminescence fluorescence of the organic light emitting diodes of experimental examples 8 to 10;
FIG. 11 is a transient electroluminescence curve of an organic light emitting diode of experimental example 18;
fig. 12 is a luminance-external quantum efficiency curve of the organic light emitting diodes of experimental examples 11 to 15.
Reference numerals:
10. 20: organic light emitting diode
102: anode
103: hole transport layer
104: cathode electrode
105: electron transport layer
106: luminescent layer
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are illustrative, and the present invention is not limited thereto.
An aromatic compound according to an embodiment of the present invention is represented by the following chemical formula 1:
[ chemical formula 1]
Figure BDA0000926430480000041
In chemical formula 1, R1And R2Each independently of the other being hydrogen, halogen, C1-C6Alkyl or aryl. m is an integer of 0 or 1. A is substituted or unsubstituted carbazolyl Ar1Or an organic amine group. Ar (Ar)2Is a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted triazinyl group or a substituted or unsubstituted
Figure BDA0000926430480000042
In one embodiment of the present invention, the aromatic compound is represented by the following chemical formula 2:
[ chemical formula 2]
Figure BDA0000926430480000043
In chemical formula 2, R1、R2And Ar2Ar is the same as defined in chemical formula 13For example, selected from the following structural formulae:
Figure BDA0000926430480000044
in another embodiment of the present invention, the aromatic compound is represented by the following chemical formula 2:
[ chemical formula 3]
Figure BDA0000926430480000045
In chemical formula 3, R1、R2And Ar2Ar is the same as defined in chemical formula 14Is selected from the following structural formulas:
Figure BDA0000926430480000051
in the present specification, the term "substituted" means substituted by the following groups, if not otherwise defined: halogen, aryl, hydroxy, alkenyl, C1-C20Alkyl, alkynyl, cyano, trifluoromethyl, alkylamino, amino, C1-C20Alkoxy, heteroaryl, aryl with halogen substituent, aralkyl with halogen substituent, aryl with haloalkyl substituent, aralkyl with haloalkyl substituent, C with aryl substituent1-C20Alkyl, cycloalkyl, having C1-C20An amino group having an alkyl substituent, an amino group having a haloalkyl substituent, an amino group having an aryl substituent, an amino group having a heteroaryl substituent, a phosphonooxy group having an aryl substituent, a phosphonooxy group having C1-C20Alkyl-substituted phosphonoxy, phosphonooxy with haloalkyl substituent, phosphonooxy with halogen substituent, phosphonooxy with heteroaryl substituent, nitro, carbonyl, arylcarbonyl, heteroarylcarbonyl or C with halogen substituent1-C20An alkyl group.
In the present specification, the term "aryl" is meant to include substituents having rings that form a conjugated p-orbital, and which may be monocyclic, polycyclic or fused polycyclic (fused ring) functional groups.
Specifically, examples of the aryl group include, but are not limited to, phenyl, phenylene, naphthyl, naphthylene, pyrenyl, anthracenyl, and phenanthrenyl.
In the present specification, the term "heteroaryl" refers to an aryl group comprising 1 to 3 heteroatoms selected from N, O, S, P and Si, and the remaining carbons in a functional group. Heteroaryl groups can be fused rings, wherein each ring can include 1 to 3 heteroatoms.
Specifically, examples of the heteroaryl group include furyl (furyl), furanylene (furylene), fluorenyl (fluoronyl), pyrrolyl (pyrrolyl), thienyl (thienyl), oxazolyl (oxazoyl), imidazolyl (imidazoyl), thiazolyl (thiazoyl), pyridyl (pyridyl), pyrimidinyl (pyridimidyl), quinazolinyl (quinazolinyl), quinolyl (quinolyl), isoquinolyl (isoquinolyl), and indolyl (indolyl), but are not limited thereto.
Hereinafter, an organic light emitting diode according to an embodiment of the present invention will be described with reference to the drawings.
Fig. 1 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the invention.
Referring to fig. 1, the organic light emitting diode 10 of the present embodiment includes an anode 102, a cathode 104, and a light emitting layer 106. The light emitting layer 106 is disposed between the anode 102 and the cathode 104. The anode 102 may be made of a conductor having a high work function to assist hole injection into the light emitting layer 106. The material of the anode 102 is, for example, a metal oxide, a conductive polymer, or a combination thereof. Specifically, the metal is, for example, nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; the metal oxide is, for example, zinc oxide, Indium Tin Oxide (ITO), or Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO and Al or SnO2In combination with Sb; the conductive polymer is, for example, poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene (poly (3,4- (ethylene-1,2-dioxy) thiophene, PEDT), polypyrrole (polypyrole), or polyaniline (polyailine), but the present invention is not limited thereto.
The cathode 104 may be made of a conductor having a low work function to assist electron injection into the light emitting layer 106. The material of the cathode 104 is, for example, a metal or a material of a multilayer structure. Specifically, the metal is, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium (gadolinium), aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; the material of the multilayer structure is, for example, LiF/Al, LiO2Al, LiF/Ca, LiF/Al or BaF2The present invention is not limited thereto.
In the present embodiment, the light-emitting layer 106 includes the aromatic compound of the above-described embodiment. Specifically, the light-emitting layer 106 includes one aromatic compound of the above embodiment, at least two aromatic compounds of the above embodiment, or a mixture of at least one of the aromatic compounds of the above embodiment and another compound.
The light-emitting layer 106 typically includes a host light-emitting material and a guest light-emitting material. The aromatic compound of the above embodiments may be mixed with a host light-emitting material as a guest light-emitting material, or may be mixed with a guest light-emitting material as a host light-emitting material.
Other host luminescent materials are, for example, fused aromatic ring derivatives (condensed), heterocyclic-containing compounds (heterocyclic-containing compounds) or the like. The fused aromatic ring derivative is, for example, an anthracene (anthrene) derivative, a pyrene (pyrene) derivative, a naphthalene (naphthalene) derivative, a pentacene (pentacene) derivative, a phenanthrene (phenanthrene) derivative, a fluoranthene (fluoranthene) compound, or the like. The heterocyclic ring-containing compound is, for example, a carbazole derivative, a dibenzofuran (dibenzofuran) derivative, a ladder-type furan (ladder-type furan) compound, a pyrimidine (pyrimidine) derivative or an analog thereof. Specifically, the host luminescent material is, for example, 1- (2,5-dimethyl-4- (1-pyrene) phenyl) pyrene (1- (2,5-dimethyl-4- (1-pyrenyl) pyrene; DMPPP), 4'-N, N' -dicarbazole-biphenyl (4,4'-N, N' -dicarbazole-biphenol; CBP) or 2- (3- (pyrene-1-yl) phenyl) terphenyl (2- (3- (pyren-1-yl) phenyl) terphenyl; m-phenylene), but the present invention is not limited thereto.
The guest light emitting material other than the aromatic compound of the above embodiment is, for example, an arylamine derivative, a styrylamine compound, a boron complex (boron complex), a fluoranthene compound, a metal complex, or the like. Specifically, the aromatic amine derivative is, for example, a fused aromatic ring derivative substituted with an aromatic amine group, and examples thereof include pyrene, anthracene, chrysene, diindenopyrene (periflanthene), and the like having an aromatic amine group; specific examples of the styrene amine compound include styrene amine (styryl amine), styrene diamine (styryl diamine), styrene triamine (styryl triamine), and styrene tetramine (styryl tetramine). Examples of the metal complex include iridium complex (iridium complex) and platinum complex (platinum complex), but are not limited thereto.
In one embodiment, the organic light emitting diode 10 further comprises at least one auxiliary layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron blocking layer.
In one embodiment, at least one of the auxiliary layers comprises the aromatic compound of the above embodiments.
Fig. 2 is a schematic cross-sectional view of an organic light emitting diode according to another embodiment of the invention. In fig. 2, the same components as those in fig. 1 will be denoted by the same reference numerals, and the description of the same technical contents will be omitted. The organic light emitting diode 20 includes an anode 102, a hole transport layer 103, a light emitting layer 106, an electron transport layer 105, and a cathode 104.
In the present embodiment, the light-emitting layer 106 includes the aromatic compound of the above-described embodiment. In another embodiment, in addition to the light emitting layer 106 comprising the aromatic compound of the above embodiment, at least one of the hole transporting layer 103 and the electron transporting layer 105 also comprises the aromatic compound of the above embodiment.
Hereinafter, the above embodiments are described in more detail with reference to examples. However, these examples are not to be construed in any way as limiting the scope of the invention.
Synthesis of organic compounds
[ intermediate Synthesis ]
Synthesis example 1: synthesis of intermediate I-1
[ reaction scheme 1]
Figure BDA0000926430480000071
4- (diphenylamino) benzaldehyde (4- (diphenylamino) benzidehydes) (2.73g,10.0mmol) and diethyl 4-bromobenzylphosphate (3.53g,11.5mmol) were placed in a two-necked flask, and after evacuation and introduction of nitrogen gas, anhydrous Tetrahydrofuran (THF) of 20m L was added; potassium tert-butoxide (t-BuOK) (3.36g,30mmole) dissolved in THF (30mL) was slowly added thereto and mixed while cooling on ice, followed by reaction at 0 ℃ for 15 minutes. The solvent was removed by concentration under reduced pressure, and the residue was purified by column chromatography (N-hexane: dichloromethane ═ 9:1) to give I-1((E) -4- (4-bromosylyl) -N, N-diphenylaniline) (3.71g, yield 87%) as a yellow intermediate.
1H NMR(400MHz,CDCl3,δ):7.45(d,J＝8.4Hz,2H),7.36(d,J＝8.8Hz,2H),7.34(d,J＝8.8Hz,2H),7.28-7.24(m,4H),7.11(d,J＝7.6Hz,4H),7.05-7.01(m,5H),6.90(d,J＝16Hz,1H).
13C NMR(100MHz,CDCl3,δ):147.53,147.38,136.50,131.65,130.89,129.68,129.26,127.69,127.37,125.55,124.52,123.30,123.09,120.80.
HRMS(m/z):[M]+calcd for C26H20BrN,425.0779；found,425.0772.
Synthesis example 2: synthesis of intermediate I-2
[ reaction scheme 2]
Figure BDA0000926430480000072
4- (bis (4-fluorophenyl) amine) benzaldehyde (4- (bis (4-fluorophenyl) amino) benzadhehyde) (4.64g,15mmol) and diethyl 4-bromobenzylphosphate (5.07g,16.5mmol) were placed in a two-necked flask, and after evacuation and introduction of nitrogen gas, anhydrous Tetrahydrofuran (THF) of 20m L was added; potassium tert-butoxide (t-BuOK) (5.0g,45mmol) dissolved in THF (30mL) was slowly added to mix under ice bath and reacted at 0 ℃ for 15 minutes. The solvent was removed by concentration under reduced pressure, and the residue was purified by column chromatography (N-hexane: dichloromethane ═ 9:1) to give I-2((E) -4- (4-bromostyryl) -N, N-bis (4-fluorophenyl) aniline) as a yellow intermediate (6.17g, yield 89%).
1H NMR(400MHz,CDCl3,δ):7.44(d,J＝8.4Hz,2H),7.33(d,J＝8.8Hz,2H),7.32(d,J＝8.8Hz,2H),7.06-6.92(m,11H),6.88(d,J＝16Hz,1H).
13C NMR(100MHz,CDCl3,δ):158.00ppm(d,13C-19F coupling J＝242Hz,C),147.62(C),143.42(d,13C-19F coupling J＝3Hz,C),136.47(C),131.69(CH),130.69(C),128.70(CH),127.71(CH),127.47(CH),126.23(d,13C-19F coupling J＝7.6Hz,CH),125.62(CH),122.10(CH),120.86(C),116.15(d,13C-19F coupling J＝22.8Hz,CH)
HRMS(m/z):[M]+calcd.for C26H18BrF2N,461.0591；found,461.0594.
Synthesis example 3: synthesis of intermediate I-3
[ reaction scheme 3]
Figure BDA0000926430480000081
4- (1-naphthyl (phenyl) amine) carboxaldehyde (4- (naphthalene-1-yl (phenyl) amino) benzodiazepine) (2.87g,8.9 mmol) and diethyl 4-bromobenzylphosphate (3.0g,9.76mmol) were placed in a two-neck flask, and after evacuation and introduction of nitrogen gas, anhydrous Tetrahydrofuran (THF) of 20m L was added; potassium tert-butoxide (t-BuOK) (2.24g,20mmol) dissolved in THF (30mL) was slowly added to mix under ice bath and reacted at 0 ℃ for 15 minutes. The solvent was removed by concentration under reduced pressure, and the residue was purified by column chromatography (N-hexane: dichloromethane ═ 9:1) to give I-3((E) -N- (4- (4-bromostyryl) phenyl) -N-phenylnaphthalene-1-amine) (2.67g, yield 63%) as a yellow intermediate.
1H NMR(400MHz,CDCl3,δ):7.91-7.86(m,2H),7.77(d,J＝8.0Hz,1H),7.48-7.29(m,10H),7.22-6.94(m,8H),6.85(d,J＝16Hz,1H).
13C NMR(100MHz,CDCl3,δ):148.22,147.89,143.11,136.63,135.24,131.67,131.11,129.95,129.17,128.93,128.41,127.66,127.37,127.24,126.66,126.48,126.34,126.18,125.13,124.11,122.48,122.26,121.11,120.69.
HRMS(m/z):[M]+calcd.for C30H22BrN,475.0936；found,475.0937.
Synthesis example 4: synthesis of intermediate I-4
[ reaction scheme 4]
Figure BDA0000926430480000082
Placing 9-phenyl-9H-carbazole-3-carbaldehyde (3.52g,13mmol) and diethyl 4-bromobenzyl phosphate (4.42g,14.4mmol) in a two-neck flask, evacuating and introducing nitrogen, adding 20m L of anhydrous Tetrahydrofuran (THF); potassium tert-butoxide (t-BuOK) (3.36g,30mmol) dissolved in THF (30mL) was slowly added to mix under ice bath and reacted at 0 ℃ for 15 minutes. The solvent was removed by concentration under reduced pressure, and the residue was purified by column chromatography (n-hexane: dichloromethane ═ 5:1) to give I-4((E) -3- (4-bromostyryl) -9-phenyl-9H-carbazole) (4.52g, yield 82%) as a white intermediate.
1H NMR(400MHz,CDCl3,δ):8.26(s,1H),8.15(d,J＝7.6Hz,1H),7.60-7.35(m,13H),7.31-7.27(m,2H),7.07(d,J＝16.4Hz,1H).
13C NMR(100MHz,CDCl3,δ):141.26,140.64,137.41,136.76,131.68,130.11,129.88,129.18,127.68,127.53,126.96,126.18,125.04,124.68,123.72,123.24,120.61,120.33,120.17, 118.64,110.00,109.95.
HRMS m/z:[M]+calcd forC26H18BrN,423.0623；found,423.0621.
Synthesis example 5: synthesis of intermediate I-5
[ reaction scheme 5]
Figure BDA0000926430480000091
Potassium tert-butoxide (t-BuOK) (0.22g,2mmol) was placed in a two-necked flask and, after evacuation and introduction of nitrogen, 3mL of anhydrous Tetrahydrofuran (THF) were added. 4- (9H-carbazol-9-yl) benzaldehyde (4- (9H-carbazol-9-yl) benzadheide) (0.27g,1mmol) and diethyl (4-bromobenzyl) phosphate (0.34g,1.1mmol) were mixed together
Put into a single-neck flask, and 3mL of anhydrous tetrahydrofuran is added under nitrogen atmosphere. The solution in the single-necked flask was slowly added to the double-necked flask under ice bath and mixed, and reacted at 0 ℃ for 1 day. The reaction solution was poured into water to precipitate a yellow solid. The precipitated yellow solid was filtered under suction and washed repeatedly with methanol to obtain intermediate product I-5((E) -9- (4- (4-bromostyryl) phenyl) -9H-carbozole) (0.39g, yield 93%) as a pale yellow powder.
1H NMR(400MHz,CDCl3)：δ8.13(d,J＝7.6Hz,2H),7.71(d,J＝8.4Hz,2H),7.55(d,J＝8.4Hz,2H),7.50(d,J＝8.8Hz,2H),7.44-7.38(m,6H),7.30-7.26(m,2H),7.19(d,J＝16Hz,1H),7.11(d,J＝16Hz,1H)
13C NMR(100MHz,CDCl3)：δ140.69,137.09,136.05,13.01,131.86,128.34,128.21,128.04,127.84,127.19,125.95,123.42,121.60,120.32,120.02,109.77
Synthesis example 6: synthesis of intermediate I-6
[ reaction scheme 6]
Figure BDA0000926430480000092
Intermediate I-5(0.42g,1mmol) and bis (4,4, 4', 4', 5,5,5 ', 5 ' -octamethyl-2,2 ' -bi (1,3,2-dioxaborolane)) (0.31g,1.2mmol) were placed in a high pressure tube. Potassium acetate (0.29g,2.93mmol) and bis (triphenylphosphine) palladium dichloride (Pd (PPh) were added to the autoclave tube3)2Cl2) (0.04g,0.05 mmol). 4mL of anhydrous tetrahydrofuran was added under nitrogen and the above compounds were mixed. The mixture was heated and reacted at 80 ℃ for 1 day, and the reaction solution was filtered using celite and silica gel. After removing the solvent by rotary concentration, the product was purified by column chromatography (ethyl acetate: n-hexane ═ 1:5) to obtain white intermediate I-6((E) -9- (4- (4- (3,3,4, 4-tetramethylvaleran-1-yl) styryl) phenyl) -9H-carbozole) (0.20g, yield 43%).
1H NMR(400MHz,CDCl3)：δ8.14-8.12(m,2H),7.82(d,J＝8.4Hz,2H),7.73(d,J＝8.4Hz, 2H),7.55(d,J＝7.6Hz,4H),7.44-7.38(m,4H),7.30-7.25(m,3H),7.19(d,J＝16.4Hz,1H),1.35(s,12H)
13C NMR(100MHz,CDCl3)：δ140.72,139.73,136.98,136.31,135.21,134.71,129.45,128.56,127.89,127.17,125.95,125.89,123.40,120.30,119.98,109.81,83.82,24.87
Synthesis example 7: synthesis of intermediate I-7
[ reaction scheme 7]
Figure BDA0000926430480000101
Intermediate I-7((E) -9- (4- (4-bromostyryl) phenyl) -3, 6-di-tert-butyl-9H-carboxylate) was prepared using a method similar to that of synthesis example 5, except that 4- (9H-carbazol-9-yl) benzaldehyde in synthesis example 5 was replaced with 4- (3,6-di-tert-butyl-9H-carbazol-9-yl) benzaldehyde (4- (3,6-di-tert-butyl-9H-carbazol-9-yl) benzylaldehyde) (0.38g,1 mmol). Intermediate I-7(0.49g, 91% yield) was obtained as a pale yellow powder according to the above-mentioned method.
1H NMR(400MHz,CDCl3)：δ8.12(d,J＝1.2Hz,2H),7.69(d,J＝8.4Hz,2H),7.55-7.35(m,10H),7.17(d,J＝16.4Hz,1H),7.17(d,J＝16.4Hz,1H),1.45(s,18H)
13C NMR(100MHz,CDCl3)：δ142.96,139.03,137.65,136.10,135.52,131.85,128.47,128.02,127.93,127.77,126.77,123.62,123.42,121.52,116.25,109.21
Synthesis example 8: synthesis of intermediate I-8
[ reaction scheme 8]
Figure BDA0000926430480000102
Intermediate I-8((E) -9- (4- (4-bromostyryl) phenyl) -3, 6-dimethoxy-9H-carbozole) was prepared using a method similar to that of synthesis example 5, except that 4- (9H-carbazol-9-yl) benzaldehyde in synthesis example 5 was replaced with 4- (3,6-dimethoxy-9H-carbazol-9-yl) benzaldehyde (4- (3, 6-dimethoxy-9H-carbozol-9-yl) benzyle) (0.33g,1 mmol). Intermediate I-7(0.45g, 93% yield) was obtained as a pale yellow powder according to the above-mentioned method.
1H NMR(400MHz,CDCl3)：δ7.68(d,J＝8.0Hz,2H),7.53-7.48(m,6H),7.41-7.39(m,2H),7.35(d,J＝8.8Hz,2H),7.16(d,J＝16.4Hz,1H),7.08(d,J＝16.4Hz,1H),7.03(dd,J＝2.8,9.2Hz,2H),3.93(s,6H)
13C NMR(100MHz,CDCl3)：δ154.06,137.55,136.03,136.01,135.44,131.80,128.35,127.99,127.90,127.76,126.60,123.70,121.49,115.16,110.71,102.87
[ Synthesis of Final Compound ]
Synthesis example 9: synthesis of the Compound DPASP
[ reaction scheme 9]
Figure BDA0000926430480000111
Intermediate I-1(0.85g,2mmol), 1-pyreneboronic acid (0.59g,2.4mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) (10mg,0.01mmol), aqueous potassium carbonate (2.0M,3.5mL), ethanol (3.5mL) and toluene (10.5mL) were placed in a two-necked flask. Oxygen was removed and nitrogen was added and the reaction was warmed to 110 ℃ and stirred for 24 hours. The metal was removed by filtration, extracted with Ethyl Acetate (EA), THF, and the organic layer was collected and washed with magnesium sulfate (MgSO)4) Water was removed, the solvent was removed by filtration and concentration under reduced pressure, and the residue was purified by column chromatography (dichloromethane: hexane ═ 1:5) to collect a solid. Sublimation was carried out at 265 ℃ to obtain DPASP ((E) -4- (4- (4,6-dihydropyren-1-yl) styryl) -N, N-diphenylaniline) as a yellow compound (0.82g, yield 75%).
1H NMR(400MHz,CDCl3,δ):8.25-7.95(m,9H),7.67(d,J＝8Hz,2H),7.61(d,J＝8Hz,2H),7.43(d,J＝8.4Hz,2H),7.26(dd,J＝8.4Hz,J＝7.6Hz,4H),7.18(d,J＝16.4Hz,1H),7.12(d,J＝8.4Hz,2H),7.11(d,J＝16.4Hz,1H),7.07(d,J＝8.4Hz,4H),7.01(t,J＝7.6Hz,2H).
13C NMR(100MHz,CDCl3,δ):147.53,147.46,140.13,137.40,136.66,131.49,130.93,130.58,129.39,128.49,127.43,126.60,126.30,126.01,125.27,125.10,125.02,124.93,124.81,124.68,124.53,123.57,123.07.
HRMS m/z:[M]+calcd for C42H29N,547.2300；found,547.2305.
Anal.calcd for C42H29N:C92.11,H5.34,N 2.56；found:C 91.89,H5.32,N 2.47.
Synthesis example 10: synthesis of compound DFASP
[ reaction scheme 10]
Figure BDA0000926430480000112
Intermediate I-2(0.92g,2mmol), 1-pyreneboronic acid (0.59g,2.4mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) (10mg,0.01mmol), aqueous potassium carbonate (2.0M,3.5mL), ethanol (3.5mL) and toluene (10.5mL) were placed in a two-necked flask. Oxygen was removed and nitrogen was added and the reaction was warmed to 110 ℃ and stirred for 24 hours. The metal was removed by filtration, extracted with Ethyl Acetate (EA), THF, and the organic layer was collected and washed with magnesium sulfate (MgSO)4) Water was removed, the solvent was removed by filtration and concentration under reduced pressure, and the residue was purified by column chromatography (dichloromethane: hexane ═ 1:5) to collect a solid. Sublimation was carried out at 250 ℃ to obtain DFASP ((E) -4- (4- (4,6-dihydropyren-1-yl) styryl) -N, N-bis (4-fluorophenyl) aniline) as a yellow compound (0.89g, yield 77%).
1H NMR(400MHz,CDCl3,δ):8.23-7.98(m,9H),7.67(d,J＝8.4Hz,2H),7.62(d,J＝8.4Hz,2H),7.42(d,J＝8.8Hz,2H),7.17(d,J＝16Hz,1H),7.12-7.04(m,5H),7.00-6.90(m,6H).
13C NMR(100MHz,CDCl3,δ):158.00ppm(d,13C-19F coupling J＝242Hz,C),147.44(C),143.50(d,13C-19F coupling J＝2.3Hz,C),140.12(C),137.30(C),136.51(C),131.43(C),131.18(C),130.91(CH),130.53(C),128.39(C),128.28(CH),127.46(CH),127.38(CH),126.56(CH),126.27(CH),126.19(CH),126.11(CH),125.97(CH),125.19(CH),125.08(CH),124.97(C),124.87(C),124.79(CH),124.67(CH),122.27(CH),116.10(d,13C-19Fcoupling J＝22.7Hz,CH)
HRMS m/z:[M]+calcd for C42H27F2N,583.2112；found,583.2109.
Anal.calcd for C42H27F2N:C86.43,H 4.66,N 2.40；found:C 86.31,H 4.70,N2.37.
Synthesis example 11: synthesis of Compound NASP
[ reaction scheme 11]
Figure BDA0000926430480000121
Intermediate I-3(0.95g,2mmol), 1-pyreneboronic acid (0.59g,2.4mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) (10mg,0.01mmol), aqueous potassium carbonate (2.0M,3.5mL), ethanol (3.5mL) and toluene (10.5mL) were placed in a two-necked flask. Oxygen was removed and nitrogen was added and the reaction was warmed to 110 ℃ and stirred for 24 hours. The metal was removed by filtration, extracted with Ethyl Acetate (EA), and the organic layer was collected and washed with magnesium sulfate (MgSO)4) Water was removed, the solvent was removed by filtration and concentration under reduced pressure, and the residue was purified by column chromatography (dichloromethane: hexane ═ 1:5) to collect a solid. Sublimation was carried out at 295 ℃ to obtain the yellow compound NASP ((E) -N-phenyl-N- (4- (4- (pyren-1-yl) styryl) phenyl) naphthalen-1-amine) (0.85g, yield 71%).
1H NMR(400MHz,CDCl3,δ):8.26-7.98(m,10H),7.91(d,J＝8.0Hz,1H),7.80(d,J＝8.0Hz,1H),7.66-7.60(m,4H),7.51-7.46(m,2H),7.40-7.37(m,4H),7.26-6.98(m,9H).
13C NMR(100MHz,CDCl3,δ):141.23,140.54,139.83,137.44,137.37,136.78,131.40,130.90,130.46,129.81,129.69,129.59,128.36,127.48,127.41,127.36,127.31,126.89,126.21,126.11,125.93,125.91,125.23,125.01,124.95,124.86,124.74,124.65,123.74,123.33,120.37,120.14,118.61,109.96,109.91.
HRMSm/z:[M]+calcd for C46H31N:597.2457；found,547.2456.
Anal.calcd for C46H31N:C 92.43,H5.23,N2.34；found:C 92.31,H 5.20,N2.29.
Synthesis example 12: synthesis of compound PCzSP
[ reaction scheme 12]
Figure BDA0000926430480000131
Intermediate I-4(0.85g,2mmol), 1-pyreneboronic acid (0.59g,2.4mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) (10mg,0.01mmol), aqueous potassium carbonate (2.0M,3.5mL), ethanol (3.5mL) and toluene (10.5mL) were placed in a two-necked flask. Oxygen was removed and nitrogen was added and the reaction was warmed to 110 ℃ and stirred for 24 hours. The metal was removed by filtration, extracted with Ethyl Acetate (EA), and the organic layer was collected and washed with magnesium sulfate (MgSO)4) Water was removed, the solvent was removed by filtration and concentration under reduced pressure, and the residue was purified by column chromatography (dichloromethane: hexane ═ 1:5) to collect a solid. Sublimation was carried out at 275 ℃ to obtain PCzSP ((E) -9-phenyl-3- (4- (pyren-1-yl) styryl) -9H-carbozole) as a yellow compound (0.73g, 67% yield).
1H NMR(400MHz,CDCl3,δ):8.33-7.99(m,11H),7.75(d,J＝8.0Hz,2H),7.68-7.57(m,7H),7.50-7.40(m,5H),7.36-7.27(m,2H).
13C NMR(100MHz,CDCl3,δ):141.27,140.58,139.87,137.47,137.41,136.81,131.43,130.91,129.84,129.71,129.62,128.40,127.49,127.46,127.42,127.37,127.33,126.94,126.22,126.12,125.94,125.25,125.03,124.97,124.89,124.75,124.66,123.76,123.33,120.38,120.14,118.61,109.98,109.92.
HRMS m/z:[M]+calcd forC42H27N,545.2143；found,545.2138.
Anal.calcd for C42H27N:C 92.45,H 4.99,N2.57；found:C 92.31,H 5.04,N2.53.
Synthesis example 13: synthesis of compound CZSSO
[ reaction scheme 13]
Figure BDA0000926430480000132
Intermediate I-5(0.42g,1mmol) and 4,4,5,5-tetramethyl-2- (4-phenylsulfonylphenyl) -1,3,2-dioxaborolan (4,4,5,5-tetramethyl-2- (4- (phenylsulfonyl) phenyl) -1,3, 2-dioxaborolan) (0.34g,1mmol) were placed in a high pressure tube, and potassium carbonate (0.49g,3.5mmol) and tetrakis (triphenylphosphine) palladium (Pd (PPh) were added to the high pressure tube3)4) (0.12g,0.1 mmol). Toluene (3mL), water (1mL) and ethanol (1mL) were added to the autoclave tube under nitrogen and the above compounds were mixed. The mixture was heated and reacted at 80 ℃ for 1 day, and the reaction solution was filtered with celite and silica gel. After removing the solvent by rotary concentration, the residue was purified by column chromatography (dichloromethane: n-hexane: 1) to obtain 0.49g of a yellow solid (yield: 87%). At a temperature of 305 ℃ and a pressure of 9X 10-6the resulting mixture was sublimed below torr to give a yellow compound CZSSO ((E) -9- (4- (2- (4'- (phenylsulfonyl) - [1,1' -biphenyl) - ]]-4-yl) vinyl) phenyl) -9H-carbazole) (82% yield).
1H NMR(400MHz,CDCl3)：δ8.16(d,J＝7.6Hz,2H),8.02-7.97(m,4H),7.81-7.78(m,4H),7.70-7.64(m,4H),7.61-7.53(m,5H),7.48-7.41(m,4H),7.35-7.25(m,4H)
HRMS(m/z)：[M+]calcd.for C38H27NO2S,561.1762；found,561.1769
Anal.calcd for C38H27NO2S：C,81.26；H,4.85；N,2.49；found：C,81.34；H,4.71；N,2.55
Synthesis example 14: synthesis of compound TCZSSO
[ reaction scheme 14]
Figure BDA0000926430480000141
Intermediate I-7(0.54g,1mmol) was placed in a high pressure tube with 4,4,5,5-tetramethyl-2- (4-phenylsulfonylphenyl) -1,3,2-dioxaborolan (0.34g,1mmol) and potassium carbonate (0.49g,3.5mmol) and tetrakis (triphenylphosphine) palladium (0.12g,0.1mmol) were added to the high pressure tube. Under high pressure in a nitrogen atmosphereToluene (3mL), water (1mL) and ethanol (1mL) were added to the tube and the above compounds were mixed. The mixture was heated and reacted at 80 ℃ for 1 day, and the reaction solution was filtered with celite and silica gel. After removing the solvent by rotary concentration, the residue was purified by column chromatography (dichloromethane: n-hexane: 1) to obtain 0.56g of a yellow solid (yield: 83%). At a temperature of 330 ℃ and a pressure of 9X 10-6the resulting mixture was sublimed below torr to give TCZSSO ((E) -3,6-di-tert-butyl-9- (4- (2 '- (phenylsulfonyl) - [1,1' -biphenyl) - [ as-received ] as a green glass]-4-yl) vinyl) phenyl) -9H-carbazole) (84% yield).
1H NMR(400MHz,CDCl3)：δ8.16(d,J＝1.6Hz,2H),8.02-7.97(m,4H),7.80-7.77(m,4H),7.70-7.64(m,4H),7.61-7.53(m,5H),7.49(dd,J＝2,8.8Hz,2H),7.42-7.39(m,2H),7.32(d,J＝16.4Hz,1H),7.25(d,J＝16.4Hz,1H),1.46(s,18H)
13C NMR(100MHz,CDCl3)：δ145.50,142.97,141.71,140.07,139.02,138.20,137.65,137.56,135.59,133.17,129.30,128.70,128.24,128.21,127.82,127.64,127.61,127.19,126.75,123.61,123.43,116.24,109.22,34.71,31.98
HRMS(m/z)：[M+]calcd.for C46H43NO2S,673.3015；found,673.3010
Anal.calcd for C46H43NO2S：C,81.98；H,6.43；N,2.08；found：C,81.87；H,6.41；N,2.13
Synthesis example 15: synthesis of compound OCZSSO
[ reaction scheme 15]
Figure BDA0000926430480000142
Intermediate I-8(0.48g,1mmol) was placed in a high pressure tube with 4,4,5,5-tetramethyl-2- (4-phenylsulfonylphenyl) -1,3,2-dioxaborolan (0.34g,1mmol) and potassium carbonate (0.49g,3.5mmol) and tetrakis (triphenylphosphine) palladium (0.12g,0.1mmol) were added to the high pressure tube. Toluene (3mL), water (1mL) and ethanol (1mL) were added to a high pressure tube under nitrogen, and the above compounds were mixed. The mixture was heated and reacted at 80 ℃ for 1 day, and the reaction solution was filtered with celite and silica gel. After removing the solvent by rotary concentration, the residue was purified by column chromatography (dichloromethane: n-hexane: 1) to obtain 0.52g of a yellow solid (yield: 84%). At a temperature of 310 ℃ and a pressure of 9X 10-6the resulting mixture was sublimed below torr to give OCZSSO ((E) -3,6-dimethoxy-9- (4- (2- (4'- (phenylsulfonyl) - [1,1' -biphenyl) as a yellow glass compound]-4-yl) vinyl) phenyl) -9H-carbazole) (76% yield).
1H NMR(400MHz,CDCl3)：δ8.02-7.97(m,4H),7.79-7.76(m,4H),7.69-7.63(m,4H),7.62-7.53(m,7H),7.40-7.38(m,2H),7.31(d,J＝16.4Hz,1H),7.24(d,J＝16.4Hz,1H),7.04(dd,J＝2.8,9.2Hz,2H)
HRMS(m/z)：[M+]calcd.for C40H31NO4S,621.1974；found,621.1970
Anal.calcd for C40H31NO4S：C,77.27；H,5.03；N,2.25；found：C,77.11；H,4.95；N,2.31
Synthesis example 16: synthesis of compound CZSDCN
[ reaction scheme 16]
Figure BDA0000926430480000151
Intermediate I-5(0.42g,1mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) isophthalonitrile (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) isophthalonitrile) (0.25g,1mmol) were placed in a high pressure tube and potassium carbonate (0.49g,3.5mmol) and tetrakis (triphenylphosphine) palladium (0.12g,0.1mmol) were added to the high pressure tube. Toluene (3mL), water (1mL) and ethanol (1mL) were added to the autoclave tube under nitrogen and the above compounds were mixed. The mixture was heated and reacted at 80 ℃ for 1 day, and the reaction solution was filtered with celite and silica gel. After removing the solvent by rotary concentration, the residue was purified by column chromatography (dichloromethane: n-hexane ═ 2:1) to obtain 0.42g of a yellow solid (yield: 89%). At a temperature of 290 ℃ and a pressure of 9X 10- 6torr toThen sublimed to obtain a yellow compound CZSDCN ((E) -4'- (4- (9H-carbazol-9-yl) styryl) - [1,1' -biphenyl)]3,5-dicarbonitrile) (83% yield).
1H NMR(400MHz,CDCl3)：δ8.17-8.15(m,4H),7.92(t,J＝1.4Hz,1H),7.82(d,J＝8.4Hz,2H),7.74(d,J＝8.4Hz,2H),7.64-7.61(m,4H),7.49-7.42(m,4H),7.38-7.26(m,4H)
13C NMR(100MHz,CDCl3)：δ143.42,140.66,138.51,137.36,135.86,135.52,134.07,133.32,129.40,128.02,128.01,127.61,127.37,127.22,125.98,123.46,120.36,120.09,116.71,114.65,109.76
HRMS(m/z)：[M+]calcd.for C34H21N3,471.1735；found,471.1745
Anal.calcd for C34H21N3：C,86.60；H,4.49；N,8.91；found：C,86.39；H,4.23；N,9.21
Synthesis example 17: synthesis of compound CZSDPT
[ reaction scheme 17]
Figure BDA0000926430480000152
Intermediate I-6(0.47g,1mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) (0.27g,1mmol) were placed in a high pressure tube and potassium carbonate (0.49g,3.5mmol) and tetrakis (triphenylphosphine) palladium (0.12g,0.1mmol) were added to the high pressure tube. Toluene (3mL), water (1mL) and ethanol (1mL) were added to the autoclave tube under nitrogen and the above compounds were mixed. The mixture was heated and reacted at 80 ℃ for 1 day, and the reaction solution was filtered with celite and silica gel. After removing the solvent by rotary concentration, the mixture was purified by column chromatography (dichloromethane: n-hexane: 1) to obtain 0.44g of a yellow solid (yield 76%). At a temperature of 310 ℃ and a pressure of 9X 10-6the resulting mixture was sublimed below torr to obtain a yellow compound CZSDPT ((E) -9- (4- (4- (4,6-diphenyl-1,3,5-triazin-2-yl) styryl) phenyl) -9H-carbazole) (yield 70%).
1H NMR(400MHz,CDCl3)：δ8.84-8.80(m,5H),8.17(d,J＝8.4Hz,2H),7.83(dd,J＝8.4,14.8Hz,4H),7.68-7.60(m,8H),7.51-7.42(m,6H),7.38-7.29(m,3H)
13C NMR(100MHz,CDCl3)：δ171.58,171.15,141.14,140.70,137.28,136.25,136.06,135.53,132.49,129.57,129.43,128.96,128.84,128.63,128.67,127.19,126.76,125.98,123.46,120.34,120.05,109.81
HRMS(m/z)：[M+]calcd.for C41H28N4,576.2314；found,576.2305
Anal.calcd for C41H28N4：C,85.39；H,4.89；N,9.72；found：C,85.07；H,5.03；N,9.60
[ evaluation of Properties of Compounds ]
[ photophysical Properties ]
Table 1 shows the luminescent properties of the aromatic compounds of the above examples.
[ Table 1]
Figure BDA0000926430480000161
As can be seen from the results in table 1, the wavelength of fluorescence emission of the aromatic compounds of the above embodiments is distributed between 420nm and 497nm, that is, the aromatic compounds of the above embodiments can emit blue light, and thus are suitable for use as blue light emitting materials. In addition, the aromatic compounds of the above examples also have high quantum efficiency.
FIGS. 3A and 3B are transient light-excited fluorescence curves of toluene solutions containing the compound CZSSO under air and nitrogen respectively. FIGS. 4A and 4B are transient light-excited fluorescence curves of a toluene solution containing the compound TCZSSO under air and nitrogen respectively. FIGS. 5A and 5B are transient light-excited fluorescence curves of toluene solutions containing the compound OCZSSO under air and nitrogen respectively. FIGS. 6A and 6B are transient light-excited fluorescence curves of toluene solutions containing the compound CZSDCN under air and nitrogen respectively. Fig. 7A and 7B are transient light-excited fluorescence curves of a toluene solution containing the compound CZSDPT under air and nitrogen respectively.
In general, an organic light emitting diode emits light by injecting charges into a light emitting substance from an anode and a cathode and generating excitons in an excited state. Among the generated excitons, 25% of those excited into a singlet excited state and the remaining 75% are excited into a triplet excited state, wherein only the excitons in the singlet excited state can emit fluorescence. However, a specific light emitting material has a property of delayed fluorescence (delayed fluorescence) whose fluorescence emission is mainly derived from radiative transition of excitons from a triplet excited state to a singlet excited state. Delayed fluorescence can be divided into Triplet-Triplet excited (TTA) delayed fluorescence and Thermally Activated Delayed Fluorescence (TADF), in which TTA delayed fluorescence is the conversion of two Triplet excited excitons into one radiation-transmissive singlet excited exciton by a collision quenching process, so that the Triplet excitons are partially reused; whereas excitons whose TADF delayed fluorescence is a triplet excited state emit fluorescence by absorption of thermal energy and crossing between the opposite directions to a singlet excited state.
It is known that a light-emitting material having TADF characteristics exhibits delayed fluorescence in an aqueous solution for more than 500 ns. As can be seen from the results of fig. 3 to 7, no delayed fluorescence occurred in the case where the film comprising the aromatic compound (CZSSO, TCZSSO, OCZSSO, CZSDCN, CZSDPT) of the present invention was optically excited in an aqueous solution under the condition of air or nitrogen gas. That is, the aromatic compounds CZSSO, TCZSSO, OCZSSO, CZSDCN, CZSDPT of the present invention do not belong to the light emitting materials having TADF characteristics.
[ Heat stability Properties ]
In the thermal stability test, a thermal gravimetric thermal differential analyzer is used for carrying out the thermal stability test at the heating rate of 10 ℃/min-20 ℃/min.
Table 2 shows the results of the thermal stability test of the aromatic compounds.
[ Table 2]
Compound (I) Tg(℃) Tc(℃) Tm(℃) Td(℃)
DPASP 96 N.D. 270 439
DFASP N.D. N.D. 246 410
NASP 106 N.D. 226 452
PCzSP N.D. N.D. 204 431
CZSSO N.D. N.D. 285 407
TCZSSO 148 226 260 424
OCZSSO 111 N.D. 246 436
CZSDCN 147 N.D. 288 405
CZSDPT 76 N.D. 298 437
Tg: a glass transition temperature; t isc: a crystallization temperature; t ism: melting point temperature; t isd: the thermal decomposition temperature; N.D.: no detection was detected.
As is clear from the results shown in Table 2, the aromatic compounds of the present invention all had thermal decomposition temperatures higher than 400 ℃ and excellent thermal stability.
[ production of organic light-emitting diode ]
Experimental example 1
An organic light emitting diode was fabricated using DMPPP as a host light emitting material and using DPASP, a compound obtained in synthesis example 9, as a guest light emitting material (i.e., dopant).
Specifically, the manufacturing process of the organic light emitting diode is as follows: first, N '-di- (1-naphthyl) -N, N' -diphenyl-biphenyl-4, 4 '-ethylenediamine (N, N' -di (naphthalene-1-yl) -N, N '-diphenylbiphenol-4, 4' -diamine, NPB) (60nm) and 3% compound DPASP-doped NPB (10nm) were sequentially deposited on an ITO glass substrate (150nm) as an anode to form a hole transport layer. Then, a host light emitting material DMPPP (15nm) doped with 5% of the compound DPASP was deposited on the hole transport layer to form a light emitting layer. Then, bis (2-methyl-8-quinolinolato) -4- (phenylphenolate) aluminum (bis (2-methyl-8-quinolinolato) -4- (phenylphenolato) aluminum, BAlq) (20nm) was deposited on the light emitting layer to form an electron transporting layer. Then, LiF (1nm) and Al (100nm) are sequentially deposited on the electron transport layer to form a cathode. Thus, the organic light emitting diode of the present experimental example was manufactured. The organic light emitting diode has the following structure: ITO/NPB (60nm)/NPB 3% DPASP (10nm)/DMPPP 3% DPASP (15nm)/BALq (20nm)/LiF (1nm)/Al (100 nm).
Experimental example 2
An organic light emitting diode was formed using a method similar to that of experimental example 1, except that DFASP, a compound obtained in synthesis example 10, was used as a dopant for a hole transport layer and a light emitting layer.
Experimental example 3
An organic light emitting diode was formed using a method similar to that of experimental example 1, except that the compound NASP obtained in synthesis example 11 was used as a dopant for the hole transport layer and the light emitting layer.
Experimental example 4
An organic light emitting diode was formed using a method similar to that of experimental example 1, except that the compound PCzSP obtained in synthesis example 12 was used as a dopant for the hole transport layer and the light emitting layer.
Experimental example 5
An organic light emitting diode was fabricated using CBP as a host light emitting material and using DPASP, a compound obtained in synthesis example 9, as a guest light emitting material (i.e., dopant).
Specifically, the manufacturing process of the organic light emitting diode is as follows: first, NPB (30nm) and N, N ', N ″ -tris (N-carbazolyl) triphenylamine (4,4',4 ″ -tri (N-carbazolyl) triphenylamine, TCTA) (20nm) were sequentially deposited on an ITO glass substrate (150nm) as an anode to form a hole transport layer. Next, a host light emitting material CBP (30nm) doped with 3% of the compound DPASP was deposited on the hole transport layer to form a light emitting layer. Then, 1,3,5-tris [ (3-pyridyl) -3-phenyl ] benzene (1,3,5-tris [ (3-pyridyl) -3-phenyl ] bezene, TmPyPb) (30nm) was deposited on the light-emitting layer to form an electron transport layer. Then, LiF (1nm) and Al (100nm) are sequentially deposited on the electron transport layer to form a cathode. Thus, the organic light emitting diode of the present experimental example was manufactured. The organic light emitting diode has the following structure: ITO/NPB (30nm)/TCTA (20nm)/CBP 3% DPASP (30nm)/TmPyPb (30nm)/LiF (1nm)/Al (100 nm).
Experimental example 6
An organic light emitting diode was formed using a method similar to that of experimental example 5 except that the concentration of the doping compound DPASP was 5%.
Experimental example 7
An organic light emitting diode was formed using a method similar to that of experimental example 5, except that the concentration of the doping compound DPASP was 10%.
Experimental example 8
An organic light emitting diode was formed using a method similar to that of experimental example 5 except that the compound DFASP obtained in synthesis example 10 was used as a dopant of the light emitting layer and the concentration of the compound DFASP was 5%.
Experimental example 9
An organic light emitting diode was formed using a method similar to that of experimental example 5, except that the compound NASP obtained in synthesis example 11 was used as a dopant of the light emitting layer, and the concentration of the compound NASP was 5%.
Experimental example 10
An organic light emitting diode was formed using a method similar to that of experimental example 5, except that the compound PCzSP obtained in synthesis example 12 was used as a dopant of the light emitting layer, and the concentration of the compound PCzSP was 5%.
Experimental example 11
An organic light emitting diode was fabricated using DMPPP as a host light emitting material and CZSSO, the compound obtained in synthesis example 13, as a guest light emitting material (i.e., dopant).
Specifically, the manufacturing process of the organic light emitting diode is as follows: first, NPB (10nm) and TCTA (40nm) were sequentially deposited on an ITO glass substrate (150nm) as an anode to form a hole transport layer. Then, a host light emitting material DMPPP (30nm) doped with 10% of the compound CZSSO is deposited on the hole transport layer to form a light emitting layer. Then, TmPyPb (40nm) was deposited on the light-emitting layer to form an electron transport layer. Then, LiF (1nm) and Al (100nm) are sequentially deposited on the electron transport layer to form a cathode. Thus, the organic light emitting diode of the present experimental example was manufactured. The organic light emitting diode has the following structure: ITO/NPB (10nm)/TCTA (40nm)/DMPPP 10% CZSSO (30nm)/TmPyPb (40nm)/LiF (1nm)/Al (100 nm).
Experimental example 12
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that the compound TCZSSO obtained in synthesis example 14 was used as a dopant of the light emitting layer.
Experimental example 13
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that the compound OCZSSO obtained in synthesis example 15 was used as a dopant of the light emitting layer.
Experimental example 14
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that the compound CZSDCN obtained in synthesis example 16 was used as a dopant of the light emitting layer.
Experimental example 15
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that the compound CZSDPT obtained in synthesis example 17 was used as a dopant of the light emitting layer.
Experimental example 16
An organic light emitting diode was formed using a method similar to that of experimental example 11 except that CBP was used as a host light emitting material and the concentration of the compound CZSSO was 7%.
Experimental example 17
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that CBP was used as a host light emitting material, and the compound TCZSSO obtained in synthesis example 14 was used as a dopant of a light emitting layer, wherein the concentration of the compound TCZSSO was 7%.
Experimental example 18
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that CBP was used as a host light emitting material, and the compound OCZSSO obtained in synthesis example 15 was used as a dopant of a light emitting layer, wherein the concentration of the compound OCZSSO was 7%.
Experimental example 19
An organic light emitting diode was formed using a method similar to that of experimental example 11, except that CBP was used as a host light emitting material, and the compound CZSDCN obtained in synthesis example 16 was used as a dopant of a light emitting layer, wherein the concentration of the compound CZSDCN was 7%.
Experimental example 20
An organic light emitting diode was formed using a method similar to that of experimental example 11 except that CBP was used as a host light emitting material and the compound CZSDPT obtained in synthesis example 17 was used as a dopant of a light emitting layer, wherein the concentration of the compound CZSDPT was 7%.
Comparative example
An organic light emitting diode was formed using a method similar to that of experimental example 5, except that the light emitting layer had no dopant.
[ evaluation of efficacy of organic light emitting diode ]
Fig. 8 is a transient electroluminescence curve of the organic light emitting diodes of experimental examples 1 to 4. Fig. 9 is a transient electroluminescence curve of the organic light emitting diodes of experimental examples 5 to 7 and comparative example. Fig. 10 is a transient electroluminescence curve of the organic light emitting diodes of experimental examples 8 to 10. Fig. 11 is a transient electroluminescence curve of the organic light emitting diode of experimental example 18.
As can be seen from the results of fig. 8 to 11, the light emitting diodes of the experimental examples 1 to 10 and 18 have delayed fluorescence, compared to the light emitting diodes of the comparative examples, which do not have delayed fluorescence.
It is to be particularly noted that, as it is known from the results of fig. 5A and 5B that the aromatic compound OCZSSO is not a light-emitting material having TADF characteristics, it is known that the delayed fluorescence exhibited by the organic light-emitting diode of experimental example 18 is derived from TTA delayed fluorescence.
Fig. 12 is a luminance-external quantum efficiency curve of the organic light emitting diodes of experimental examples 11 to 15.
As is apparent from the results of fig. 12, the external quantum efficiency of the organic light emitting diodes of experimental examples 11 to 15 does not decrease with an increase in luminance, indicating that the organic light emitting diodes of experimental examples 11 to 15 have a long life span characteristic.
Table 3 shows the results of testing the performance of the organic light emitting diodes of experimental examples 1 to 20 and comparative example.
[ Table 3]
Figure BDA0000926430480000201
Figure BDA0000926430480000211
Vd: a drive voltage; e.q.e.: an external quantum efficiency; l ismax: a maximum brightness; C.E.: current efficiency; P.E.: power efficiency; CIE: chromaticity coordinate
As can be seen from the results of table 3, the organic light emitting diodes of experimental examples 1 to 20 have a maximum emission wavelength in the range of 440nm to 476nm, and thus have blue light emission characteristics.
In addition, the organic light emitting diodes of experimental examples 1 to 20 have significantly higher external quantum efficiency, maximum luminance, current efficiency, and power efficiency due to the aromatic compound of the present invention in the light emitting layer, compared to the organic light emitting diode of the comparative example having no dopant in the light emitting layer.
As described above, the aromatic compound of the present invention has characteristics of blue light emission, high quantum efficiency, and excellent thermal stability. In addition, the aromatic compound of the present invention can be doped in a light emitting layer or a hole transport layer of the organic light emitting diode to improve external quantum efficiency, maximum brightness, current efficiency, power efficiency and lifetime of the organic light emitting diode.
Although the present invention has been described with reference to the above embodiments, it should be understood that the invention is not limited to the embodiments, and various changes and modifications can be made by one skilled in the art without departing from the spirit and scope of the invention.

Claims (10)

1. An aromatic compound represented by the following chemical formula 1 or chemical formula 3:
[ chemical formula 1]
Figure FDA0002377949360000011
In the chemical formula 1, the first and second,
R1and R2Each independently of the other being hydrogen, halogen, C1-C6An alkyl or aryl group;
m is an integer of 1;
a is substituted or unsubstituted
Figure FDA0002377949360000012
Figure FDA0002377949360000013
And
Ar2is a substituted or unsubstituted triazinyl group or
Figure FDA0002377949360000014
[ chemical formula 3]
Figure FDA0002377949360000015
In the chemical formula 3, the first and second,
R1and R2Each independently of the other being hydrogen, halogen, C1-C6An alkyl group or an aryl group, or a salt thereof,
Ar2is substituted or unsubstituted pyrenyl,
Ar4is selected from the following structural formulas,
Figure FDA0002377949360000016
2. the aromatic compound according to claim 1, wherein Ar is represented by formula 12Is selected from the following structural formulas,
Figure FDA0002377949360000021
3. an organic light emitting diode, comprising:
a cathode;
an anode; and
a light-emitting layer disposed between the cathode and the anode, the light-emitting layer comprising the aromatic compound according to any one of claims 1 to 2.
4. The OLED of claim 3, wherein the OLED is a blue LED.
5. The OLED of claim 3, wherein the light-emitting layer comprises a host light-emitting material and a guest light-emitting material.
6. The OLED of claim 5, wherein the host light emitting material comprises the aromatic compound.
7. The organic light-emitting diode of claim 5, wherein the guest light-emitting material comprises the aromatic compound.
8. The organic light-emitting diode of claim 5, wherein the host light-emitting material comprises 1- (2,5-dimethyl-4- (1-pyrenyl) phenyl) pyrene, 4'-N, N' -dicarbazole-biphenyl or 2- (3- (pyrene-1-yl) phenyl) terphenyl.
9. The OLED of claim 3, further comprising at least one auxiliary layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron blocking layer.
10. The oled according to claim 9, wherein the at least one auxiliary layer comprises the aromatic compound according to any one of claims 1 to 2.
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