CN114702395A - Triarylamine compound and organic electroluminescent device comprising the same - Google Patents

Triarylamine compound and organic electroluminescent device comprising the same Download PDF

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CN114702395A
CN114702395A CN202210409935.XA CN202210409935A CN114702395A CN 114702395 A CN114702395 A CN 114702395A CN 202210409935 A CN202210409935 A CN 202210409935A CN 114702395 A CN114702395 A CN 114702395A
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何睦
王湘成
王鹏
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention discloses a triarylamine compound and an organic electroluminescent device containing the same, wherein the triarylamine compound has a structure shown in a formula (1), L1And L2Selected from the group consisting of single bonds, substituted or unsubstituted phenylene radicals, L11、L12、L21And L22Selected from the group consisting of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar)11、Ar12、Ar21And Ar22Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the group A is selected from the group shown as 2-a, 2-b or 2-c. The compound of the invention is used as a hole transport material for an organic electroluminescent device, can ensure that the device has higher hole mobility, can effectively prevent electrons and excitons from entering a hole transport layer, and greatly improves the luminous efficiency and the service life of the device.

Description

Triarylamine compound and organic electroluminescent device comprising the same
Technical Field
The invention belongs to the field of organic luminescent materials, and particularly relates to a triarylamine compound and an organic electroluminescent device containing the triarylamine compound.
Background
Organic electroluminescent devices (OLEDs) have advantages of high brightness, low power consumption, light weight, thin thickness, fast response speed, high contrast, wide viewing angle, and the like, and are receiving wide attention from both academic and industrial fields. At present, a common organic electroluminescent device mainly comprises an electrode, a carrier transport layer and a light-emitting layer, wherein a hole transport layer material is responsible for transferring holes at an anode to the light-emitting layer and occupies a very important position. At present, aromatic amine compounds are mainly adopted, and the molecules have good hole transport characteristics, and the front line orbital energy level is easy to adjust. For example, patent application CN113816863A discloses triarylamine compounds, which are centered on triarylamine, wherein aliphatic rings are incorporated on benzene or 9-phenyl of fluorenyl group, and the aliphatic rings have better electron donating ability than aryl groups, so that the compounds have good hole transport property and thermal stability, and can provide good service life for organic electroluminescent devices. Patent application CN113620818A discloses a triarylamine compound containing a condensed ring, wherein triarylamine is used as a center, a benzo aliphatic ring and a thick aryl group are simultaneously connected, and the aliphatic ring has electron pushing capacity relative to aryl, so that the compound has excellent hole transport performance, the thick aryl group increases the molecular weight of the compound, the glass transition temperature of the compound is increased, the stability is good, and the triarylamine compound is a good hole transport material. The application CN113773207A combines the benzo five-membered ring/six-membered ring into triarylamine to make the space configuration of the molecule more three-dimensional, improve the matching property between the hole transport layer and the luminescent layer, and is beneficial to the improvement of the triplet state energy level (T1), thereby effectively blocking the exciton diffusion and improving the efficiency of the device.
At present, research on organic light emitting materials has been widely conducted in academia and industry, and a large number of organic light emitting materials having excellent properties have been developed. In view of the above, the future direction of organic light emitting devices is to develop high efficiency, long lifetime, low cost white light devices and full color display devices, but the industrialization of this technology still faces many key issues. Therefore, designing and searching a stable and efficient organic compound as an organic light emitting device material to overcome the defects of the organic light emitting device material in the practical application process is a key point in organic light emitting device research and development trend in the future.
Disclosure of Invention
The invention provides a triarylamine compound, which has a structure shown in a formula (1):
Figure BDA0003603766130000021
in the formula (1), L1And L2Identical or different, each independently selected from the group consisting of single bonds, substituted or unsubstituted phenylene;
L11、L12、L21and L22The same or different, each independently selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
Ar11、Ar12、Ar21and Ar22The same or different, each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
the group A is selected from one of the groups shown as 2-a, 2-b or 2-c:
Figure BDA0003603766130000022
in formulae 2-a to 2-c, Z1、Z2、Z3、Z4And Z5Each independently selected from-CR1R2-, -NR-, O or S;
R1and R2Identical or different, are each independently selected from hydrogen, deuterium, deuterated or non-deuterated methyl, and in formula 2-a, when Z is1And Z3Are all O and Z2is-CR1R2When is, R1And R2Are not both hydrogen and deuterium (i.e. the group A is not
Figure BDA0003603766130000023
)；
R is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 heteroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl;
RAselected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C2-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;
n is selected from 0, 1,2 or 3, and represents a linking site.
Preferably, formula (1) is selected from the general structures shown in formulas 1-a and 1-b:
Figure BDA0003603766130000024
in the formulae 1-a and 1-b, each substituent is as described in the formula (1).
Preferably, in the formulae 2-a to 2-c, Z1、Z2、Z3、Z4And Z5Each independently selected from-NR-, O or S and in an amount greater than 1, such that there is at least a separation between any two substituents selected from-NR-, O or SOne is-CR1R2-。
Preferably, in formula 2-a, when Z1And Z3When both are O, satisfy Z2is-CR1R2-and at least one R1And R2Is deuterated or unsubstituted methyl.
Preferably, in formula 2-b, when Z is1、Z2、Z3And Z4Are all-CR1R2When at least one R is satisfied1And R2Is deuterated or unsubstituted methyl.
Preferably, in formula (1), "substituted" of "substituted or unsubstituted" means substituted with one or more substituents independently selected from deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C18 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl, C2-C30 heteroaryl, and L6-C30 heteroaryl1、L2、L11、L12、L21、L22、Ar11、Ar12、Ar21And Ar22The substituents in (1) may be the same or different from each other.
Preferably, in formula (1), the group a is selected from one of the following substituent groups:
Figure BDA0003603766130000031
Figure BDA0003603766130000041
wherein R is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 heteroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl;
RAselected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstitutedC2-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
n is selected from 0, 1,2 or 3, and represents a linking site.
Preferably, in the formula (1), L1And L2Identical or different, are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, wherein "substituted" of "substituted or unsubstituted" means substituted with one or more substituents independently selected from the group consisting of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, and L1、L2The number and kind of the substituents are the same or different.
Preferably, in formula (1), L11、L12、L21And L22The same or different, each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted dibenzofuranylene group, wherein "substituted" means substituted with one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl, and L is11、L12、L21And L22The number and kind of the substituents are the same or different.
Preferably, in formula (1), Ar21And Ar22The same or different, each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted selenophenyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzoselenophenylDibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzonaphthoselenophenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzocarbazolyl, and wherein "substituted" means substituted with one or more substituents independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, C1-C6 alkyl, C4-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C6-C14 aryl, C5-C14 heteroaryl, and Ar11、Ar12、Ar21And Ar22The number and kind of the substituents are the same or different.
Preferably, the compound represented by formula (1) is selected from any one of the following chemical structures:
Figure BDA0003603766130000051
Figure BDA0003603766130000061
Figure BDA0003603766130000071
Figure BDA0003603766130000081
Figure BDA0003603766130000091
Figure BDA0003603766130000101
Figure BDA0003603766130000111
Figure BDA0003603766130000121
the invention also provides an organic photoelectric material which contains any of the triarylamine compounds and can be used as a hole transport layer material of an organic electroluminescent device.
The invention also provides an organic electroluminescent device which comprises any of the triarylamine compounds or the organic photoelectric material.
The invention also provides a display or lighting device which comprises the organic electroluminescent device.
Compared with the prior art, the triarylamine compound has the advantages that the asymmetric structure of molecules is not easy to crystallize, the glass transition temperature is usually higher, the service life of a device is favorably prolonged, meanwhile, different aromatic groups are connected to nitrogen, the molecular energy level is easy to adjust, and the performance requirements of hole transport materials of red and green devices can be met. The compound is used as a hole transport material to be applied to an organic electroluminescent device, can improve the luminous efficiency and the service life of the device and reduce the driving voltage of the device, and can be applied to various display or lighting devices. In addition, the organic synthesis method of the triarylamine compound is simple and easy for industrial production.
Drawings
Fig. 1 is a schematic structural view of a bottom emission organic electroluminescent device in the example.
Fig. 2 is a schematic structural view of a top emission organic electroluminescent device in the example.
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. a hole blocking layer; (ii) a 108. An electron transport layer; 109. a second electrode (cathode); 110. and (4) a covering layer.
Detailed Description
The triarylamine compound shown in formula (1) provided by the invention can be prepared by conventional coupling reaction in the field, for example, the triarylamine compound can be prepared by the following synthetic route:
Figure BDA0003603766130000131
in compounds i and ii, W1And W0One is halogen atom I or Br, and the other is boric acid group or pinacolborate group; x1And X2Are all halogen atoms when Y1Or Y0When any one of them is selected as I, X1And X2Selected identically or differently as Br or Cl; when Y is1Or Y0When any one of them is Br, X1And X2Is Cl.
In the compound iii, when L1When not a single bond, Y1Can be selected from boric acid groups or pinacolato boroester groups; when L is1When it is a single bond, Y1Is hydrogen.
In compound iv, when L2When not a single bond, Y2Can be selected from boric acid groups or pinacolato boroester groups; when L is2When it is a single bond, Y2Is hydrogen.
The aromatic amine compound provided by the invention can be obtained by the common Suzuki coupling reaction and the Buhward coupling reaction in the field, namely, under the inert gas atmosphere, firstly, a polysubstituted benzene compound i and a derivative ii containing benzocycloalkane or benzo heterocycloalkane are subjected to Suzuki coupling reaction to obtain an intermediate compound MA; and then, reacting the compound MA with amine compounds iii and iv in sequence through two-step coupling reaction, reacting at corresponding catalyst, organic base, ligand, solution and corresponding temperature, and finally obtaining the target compound through an intermediate compound MB. Wherein, L in the amine compound iii or iv1Or L2When the single bond is adopted, a Buchwald coupling reaction is adopted; l in the amine compound iii or iv1Or L2When the group is not a single bond,suzuki coupling reaction is adopted.
The synthetic route of the object compound I of the present invention and the reactive group in the intermediate substance are not limited thereto. It is within the scope of the present invention to obtain the target compound by other synthetic means well known in the art. The synthesis method of triarylamine compounds in the present invention will be specifically described below with reference to synthetic examples, and compounds not mentioned in the present invention are commercially available.
(1) Synthesis of Compound HT-9:
Figure BDA0003603766130000132
(1-1) Synthesis of intermediate Compound MA-9:
to a three-necked flask, 2, 4-dichlorophenylboronic acid (1.9g,10.0mmol,1eq), 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (3.0g,11.2mmol,1.1eq), potassium carbonate (3.5g,25.3mmol,2.5eq), tetrakis (triphenylphosphine) palladium (57.8mg,0.05mmol, 0.5% eq), and degassed toluene (50mL), ethanol (30mL), and water (20mL) were added in this order under a nitrogen atmosphere. The above mixed system was refluxed for 13 hours under nitrogen atmosphere, cooled to room temperature and poured into 80mL of ethyl acetate, allowed to stand for layering, extracted with ethyl acetate (3X 80mL), the resulting organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized from a mixed solvent of ethanol/n-hexane to obtain compound MA-9(2.6g, yield 78.3%).
(1-2) Synthesis of Compound HT-9:
50mL of anhydrous toluene, the compound MA-9(2.5g, 7.5mmol,1eq), and N-phenyl-4-benzidine (4.6g, 18.8mmol,2.5eq) were added in this order to a three-necked flask under a nitrogen atmosphere, the mixture was stirred well, and sodium tert-butoxide (1.1g, 11.3mmol,1.5eq), palladium bis-dibenzylideneacetone (34mg, 0.05mmol, 0.7% eq), and tri-tert-butylphosphine (10% N-hexane solution, 0.26mL, 0.11mmol, 1.5% eq) were added, respectively. After heating under reflux for 12 hours, the heating was stopped by analyzing substantially no starting compound MA-9 remained by thin layer chromatography. When the temperature is reduced to below 45 ℃, the reaction system is fed5mL of concentrated HCl (37% H) was added2O) and 100mL of deionized water, separating with a separatory funnel, retaining the organic phase, extracting the aqueous phase with toluene (3 × 50mL), combining with the retained organic phase, distilling off the solvent, and subjecting the crude product to silica gel column chromatography separation (mobile phase is n-hexane/dichloromethane mixed solvent) and recrystallization with ethanol/n-hexane mixed solvent in this order to obtain compound HT-9(4.5g, yield 83.0%). The total yield of the two-step reaction is 65.0 percent, and the mass spectrum (M/z) is 751.40[ M + H ]]+。
Compounds HT-2, HT-14, HT-36, HT-48, HT-54, HT-76, HT-78, HT-82, HT-85, HT-87, HT-104, HT-114 were synthesized according to the preparation of compound HT-9, except that starting material ii-x was used in equivalent amount instead of 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene and starting material iii-x was used in equivalent amount instead of N-phenyl-4-benzidine, wherein the main starting materials used, the intermediates synthesized and the yields thereof are shown in Table 1.
TABLE 1
Figure BDA0003603766130000141
Figure BDA0003603766130000151
(2) Synthesis of Compound HT-66:
Figure BDA0003603766130000161
(2-1) Synthesis of intermediate Compound MA-66:
2-bromo-4-chloro-phenylboronic acid (2.3g, 9.8mmol, 1eq), 6-iodo-1, 4-dioxane (2.6g, 9.8mmol, 1eq), tetrakis (triphenylphosphine) palladium (113.2mg, 0.1mmol, 1% eq), potassium carbonate (3.0g, 21.6mmol,2.2eq), tetrabutylammonium bromide (632mg, 2.0mmol, 0.2eq), degassed toluene (40mL), ethanol (10mL), and deionized water (10mL) were added to a three-neck flask, in that order, under a nitrogen atmosphere. The temperature was raised to reflux under nitrogen atmosphere, and the heating was stopped after stirring for 12 hours. The reaction system was cooled to room temperature, ethyl acetate (3 × 70mL) was poured for extraction, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the obtained crude product was purified by recrystallization from an ethanol/n-heptane mixed solvent system to obtain compound MA-66(2.5g, yield 78.6%).
(2-2) Synthesis of intermediate Compound MB-66:
to a three-necked flask, the compound MA-66(2.4g,7.4mmol, 1eq), the amine compound iii-66(2.1g,7.4mmol,1eq), sodium tert-butoxide (840mg,8.8mmol,1.2eq), bis (tri-tert-butylphosphine) palladium (75.6mg, 0.15mmol, 2% mol), and anhydrous toluene (50mL) were added in this order under a nitrogen atmosphere, stirred and warmed to reflux. After 8 hours, the heating was stopped, the reaction was cooled to room temperature, extracted with dichloromethane (3 × 60mL), the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography (mobile phase was mixed solvent of n-hexane/dichloromethane) and recrystallization from an ethanol/n-hexane mixed solvent system in this order to obtain compound MB-66(2.9g, 74.2%).
(2-3) Synthesis of Compound HT-66:
to a three-necked flask, 40mL of anhydrous toluene, the compound MA-66(2.7g, 5.1mmol,1eq), and N-phenyl-4-benzidine (1.8g, 5.6mmol,1.1eq) were added in this order under a nitrogen atmosphere, the mixture was stirred well, and sodium tert-butoxide (733mg, 7.6mmol,1.5eq), palladium bis-dibenzylideneacetone (34mg, 0.05mmol, 1% eq), and tri-tert-butylphosphine (10% N-hexane solution, 0.18mL, 0.077mmol, 1.5% eq), respectively, were added. After heating under reflux for 12 hours, it was analyzed by thin layer chromatography that substantially no starting compound MB-66 remained, and the heating was stopped. When the temperature was reduced to 45 ℃ or below, 5mL of concentrated hydrochloric acid (37% H) was added to the reaction system2O) and 90mL of deionized water, separating with a separating funnel, retaining the organic phase, extracting the aqueous phase with toluene (3X 50mL), combining with the retained organic phase, distilling to remove the solvent, separating the crude product by silica gel column chromatography (the mobile phase is n-hexane/dichloromethane mixed solvent), and recrystallizing with ethanol/n-hexane mixed solvent to obtain compound HT-66(3.4g, yield 81)9%). The total yield of the three-step reaction is 47.8 percent, and the mass spectrum (M/z) is 815.36[ M + H ]]+
Compounds HT-16, HT-24, HT-29, HT-42, HT-50, HT-119 and HT-121 were synthesized with reference to the preparation of compound HT-66, except that the starting materials ii-x were used in equivalent amounts instead of 6-iodo-1, 4-dioxane, the starting materials iii-x were used in equivalent amounts instead of N-phenyl-2 (9, 9-dimethyl-9H-fluorene) amine, and the starting materials iv-x were used in equivalent amounts instead of bis (4-biphenylyl) amine, wherein the main starting materials used, the intermediates synthesized and the yields thereof are shown in Table 2.
TABLE 2
Figure BDA0003603766130000171
(3) Synthesis of Compound HT-164:
Figure BDA0003603766130000172
(3-1) Synthesis of intermediate Compound MA-164:
reference was made to the preparation of compound MA-9 for the synthesis of intermediate compound MA-164. Except that 3, 5-dichlorophenylboronic acid as a raw material was used in an equivalent amount in place of 2-bromo-4-chloro-phenylboronic acid, and 4-bromo-1, 2-methylenedioxybenzene (ii-164) as a raw material was used in an equivalent amount in place of 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (ii-9).
(3-2) Synthesis of intermediate Compound MB-164:
reference was made to the synthesis of intermediate compound MB-164 by a procedure for the preparation of compound HT-9 from intermediate compound MB-9. Except that intermediate compound MA-164 was used in equivalent amounts instead of compound MB-9; the amine compound iii-164 was used in place of N-phenyl-4-benzidine (iv-9), and the ratio of the amounts of the substances of iii-164 to MA-164 was 1: 1.
(3-3) Synthesis of Compound HT-164:
reference was made to the procedure for the preparation of compound HT-9 from intermediate compound MB-9 to synthesize compound HT-164. Except that an equivalent amount of the intermediate compound MB-164 was usedInstead of compound MB-9; the amine compound iv-164 was used instead of iv-9, and the mass ratio of iii-164 to MA-164 was 1:1, with a total yield of 45.4% in the three-step reaction, mass spectrum (M/z) ═ 855.35[ M + H ═ 855.35[]+
Compounds HT-132, HT-141, HT-152, HT-158, HT-159, HT-171, HT-176, HT-181, HT-184, HT-192, HT-194, HT-203, HT-207, HT-214, HT-215, HT-219, HT-220, HT-225, HT-230 were synthesized according to the method described for HT-164, with the difference that the starting materials ii-x were used in equivalent substitution of ii-164, the starting materials iii-x were used in equivalent substitution of iii-164, the starting materials iv-x were used in equivalent substitution of iv-164, wherein the main starting materials used, the intermediates synthesized and the yields thereof are shown in Table 3.
TABLE 3
Figure BDA0003603766130000181
Figure BDA0003603766130000191
Figure BDA0003603766130000201
(4) Synthesis of Compound HT-247:
Figure BDA0003603766130000202
(4-1) Synthesis of intermediate Compound MA-247:
reference was made to the preparation of compound MA-66 for the synthesis of intermediate compound MA-247. Except that the starting material, 4-bromo-2-chlorobenzeneboronic acid, was used in equivalent amounts in place of 2-bromo-4-chloro-phenylboronic acid and the starting material, 5-iodo-2, 3-dihydrobenzofuran (ii-247), was used in equivalent amounts in place of 6-iodo-1, 4-dioxane (ii-66).
(4-2) Synthesis of intermediate Compound MB-247:
to a three-necked flask, under a nitrogen atmosphere, were added in the order of compound MA-247(3.1g,10.0mmol,1eq), compound iii-247(3.8g,10.0mmol,1eq), potassium carbonate (3.5g,25.0mmol,2.5eq), tetrakis (triphenylphosphine) palladium (57.8mg,0.05mmol, 0.5% eq), and degassed toluene (50mL), ethanol (30mL), and water (20 mL). Stirring was started and the temperature was raised to reflux under nitrogen atmosphere, reacted for 15 hours, analyzed by thin layer chromatography that substantially no starting material remained and heating was stopped. After cooling to room temperature, the mixture was poured into 80mL of toluene, allowed to stand for layer separation, extracted with toluene (3X 80mL), and the resulting organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The crude product was subjected to silica gel column chromatography (mobile phase: n-hexane/dichloromethane mixed solvent) to obtain compound MB-247(4.2g, yield 74.3%).
(4-3) Synthesis of Compound HT-247:
compound HT-247 was synthesized according to the procedure for the preparation of compound HT-66, except that the starting compound MB-247 was used in an equivalent amount instead of compound HT-66 and the starting compound iv-247 was used in an equivalent amount instead of N-phenyl-4-benzidine (iv-66). The total yield of the three steps is 42.9 percent, and the mass spectrum (M/z) is 875.39[ M + H ]]+
Compounds HT-243, HT-244, HT-252, HT-254, HT-262, HT-264, HT-269, HT-270, HT-272, HT-276, HT-278, HT-283, HT-284, HT-285, HT-292, HT-297, HT-299, HT-305, HT-311, with the exception that compounds HT-243, HT-254, HT-270, HT-284, HT-311 use starting 2-bromo-4-chloro-phenylboronic acid in equivalent amounts instead of 4-bromo-2-chlorobenzeneboronic acid, and compounds HT-262, HT-264, HT-276, HT-283, HT-292, HT-297, in HT-299 and HT-305, 3, 5-dichlorophenylboronic acid as a raw material was used in place of 4-bromo-2-chlorobenzeneboronic acid in equivalent amounts. In the above compounds, all of the starting materials ii to x were used in the equivalent amount instead of ii to 247, the starting materials iii to x were used in the equivalent amount instead of iii to 247, and the starting materials iv to x were used in the equivalent amount instead of iv to 247, wherein the main raw materials used, the intermediates of the synthesis, and the yields thereof are shown in tables 4 to 6 (the starting material for the synthesis of the compounds in table 5 was 2-bromo-4-chloro-phenylboronic acid, and the starting material for the synthesis of the compounds in table 6 was 3, 5-dichlorophenylboronic acid).
TABLE 4
Figure BDA0003603766130000211
TABLE 5
Figure BDA0003603766130000212
Figure BDA0003603766130000221
TABLE 6
Figure BDA0003603766130000222
Figure BDA0003603766130000231
(5) Synthesis of Compound HT-258:
Figure BDA0003603766130000232
(5-1) Synthesis of intermediate Compound MA-258:
reference was made to the preparation of compound MA-66 for the synthesis of intermediate compound MA-258. Except that 3, 5-dibromophenylboronic acid was used in an equivalent amount as a starting material in place of 2-bromo-4-chloro-phenylboronic acid and 5-iodo-1-methyldihydroindole (ii-258) was used in an equivalent amount as a starting material in place of 6-iodo-1, 4-dioxane (ii-66).
(5-2) Synthesis of intermediate Compound MB-258:
reference compound MB-247 preparation method an intermediate compound MB-258 was synthesized. Except that the compound MA-247 was replaced by the equivalent of the starting compound MA-258 and the compound iii-247 was replaced by the equivalent of the starting boric acid compound iii-258.
(5-3) Synthesis of Compound HT-258:
referencingPreparation of Compound MB-247 Compound HT-258 was synthesized. Except that the compound MA-247 was replaced by an equivalent of the starting compound MB-258 and the compound iii-247 was replaced by an equivalent of the starting boronic acid compound iV-258, the total yield of the three steps was 48.1%, and the mass spectrum (M/z) was 892.33[ M + H ] 892.33]+
Compounds HT-251, HT-256, HT-271, HT-280, HT-282, HT-290, HT-295, HT-306, HT-308 were synthesized according to the method described for compound HT-258, except that for compounds HT-251, HT-280, HT-290, HT-295, HT-306, 2, 4-dibromophenylboronic acid equivalent as starting material was used instead of 3, 5-dibromophenylboronic acid, ii-x equivalent as starting material was used instead of ii-247, iii-247 equivalent as starting material was used instead of iii-247, iv-x equivalent as starting material was used instead of iv-247, the main raw materials used, the intermediates synthesized, and the yields thereof are shown in tables 7 to 8 (the starting raw material for the synthesis of the compounds in table 8 is 2, 4-dibromophenylboronic acid).
TABLE 7
Figure BDA0003603766130000233
Figure BDA0003603766130000241
TABLE 8
Figure BDA0003603766130000242
Blue device example 1: preparation of blue organic electroluminescent device
The blue top-emitting organic electroluminescent device is manufactured according to the structure shown in FIG. 2, and the preparation process comprises the following steps: a transparent anode ITO film layer is formed on a substrate 101 made of glass, the thickness of the film is 150nm, a first electrode 102 is obtained as an anode, then a mixed material of a compound 1 and a compound HT-2 of the invention is evaporated as a hole injection layer 103, the mixing ratio is 3:97 (mass ratio), the thickness is 10nm, then a compound HT-2 with the thickness of 100nm is evaporated, a first hole transmission layer 104 is obtained, then evaporating a compound 1-2 with the thickness of 20nm to obtain a second hole transport layer 105, then, compounds 1-3 and compounds 1-4 (thickness 30nm) were vapor deposited at a vapor deposition rate of 95:5 to produce a blue light emitting unit 106, then, compound 5 was sequentially evaporated to a thickness of 10nm to form a hole blocking layer 107, and compound 6 and LiQ were mixed at a ratio of 4:6 (mass ratio) to form an electron transporting layer 108 (thickness 30 nm). Then, ytterbium (Yb) with the thickness of 3nm, magnesium (Mg) and silver (Ag) with the thickness of 10nm are sequentially evaporated on the electron injection layer in vacuum at the evaporation rate of 1: 9 to serve as a second electrode 109, and then a compound 7 with the thickness of 70nm is evaporated to serve as a covering layer material, so that the device manufacturing is completed.
TABLE 9
Figure BDA0003603766130000251
Blue device examples 2-24
An organic electroluminescent device was fabricated in the same manner as in example 1 of the blue device, except that the compounds in table 10 were used instead of compound HT-2, respectively, in forming the hole injection layer and the hole transport layer.
Comparative examples 1 to 2
An organic electroluminescent device was fabricated in the same manner as in mutexample 1 of the blue device, mutexcept that in the formation of the hole injection layer and the hole transport layer, the compound HT-a and the compound HT-B were used instead of the compound HT-2, respectively.
For the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience Co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each set of the devices of the blue device examples and comparative example 2 was produced and tested in the same batch as the device of comparative example 1, the device operating voltage, efficiency and lifetime of comparative example 1 were each noted as 1, and the ratios of the respective indices of the devices of blue device examples 1-24, comparative example 1 and comparative example 2 were calculated, respectively, as shown in table 10.
Watch 10
Hole transport layer Relative operating voltage Relative efficiency Relative life time
Comparative example 1 HT-A 1 1 1
Comparative example 2 HT-B 0.965 0.980 0.922
Blue light device example 1 HT-2 0.875 1.185 1.279
Blue light device example 2 HT-16 0.894 1.126 1.321
Blue light device example 3 HT-42 0.871 1.089 1.396
Blue device example 4 HT-48 0.900 1.194 1.379
Blue light device example 5 HT-82 0.856 1.083 1.135
Blue light device example 6 HT-85 0.862 1.108 1.337
Blue light device example 7 HT-104 0.950 1.086 1.286
Blue light device example 8 HT-119 0.879 1.199 1.139
Blue light device example 9 HT-141 0.840 1.128 1.152
Blue device example 10 HT-171 0.926 1.153 1.129
Blue light device example 11 HT-176 0.884 1.100 1.150
Blue light device example 12 HT-214 0.943 1.116 1.273
Blue light device example 13 HT-225 0.833 1.090 1.147
Blue light device example 14 HT-243 0.845 1.195 1.293
Blue light device example 15 HT-247 0.905 1.168 1.356
Blue light device example 16 HT-250 0.921 1.191 1.364
Blue light device example 17 HT-256 0.927 1.113 1.352
Blue light device example 18 HT-270 0.853 1.176 1.340
Blue light device example 19 HT-272 0.862 1.140 1.200
Blue light device example 20 HT-276 0.947 1.102 1.218
Blue light device example 21 HT-280 0.941 1.119 1.178
Blue light device example 22 HT-282 0.936 1.133 1.189
Blue light device example 23 HT-283 0.929 1.182 1.125
Blue light device example 24 HT-292 0.881 1.170 1.239
From the results of table 10, it is understood that the organic compounds used in examples 1 to 24, when used as a hole transport layer of a blue device, have a voltage drop of at least 5%, a luminous efficiency increase of at least 8%, and a lifetime increase of at least 12.5% as compared with the devices formed of the organic compounds used in comparative examples 1 to 2.
Red device example 1: preparation of red organic electroluminescent device
The red bottom light-emitting organic electroluminescent device is manufactured according to the structure shown in figure 1, and the preparation process comprises the following steps: a transparent anode ITO film (thickness 150nm) was formed on a glass substrate 101 to obtain a first electrode 102 as an anode. Subsequently, a mixed material of compound 1 in Table 9 and compound 2-2 in Table 11 was evaporated as a hole injection layer 103 on the surface of the anode by a vacuum evaporation method at a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm. Then, compound 2-2 was vapor-deposited on the hole injection layer to a thickness of 100nm to obtain a first hole transport layer 104. Subsequently, a compound HT-9 of the present invention was evaporated on the first hole transport layer to a thickness of 10nm to obtain a second hole transport layer 105. On the second hole transport layer, the compound 2-3 and the compound 2-4 were co-evaporated at a mass ratio of 95:5 to form an organic light emitting layer 106 having a thickness of 40 nm. Then, on the organic light-emitting layer, a compound 5 was sequentially vapor-deposited to form a hole-blocking layer 107 (thickness 10nm), and a compound 6 and LiQ at a mixing ratio of 4:6 (mass ratio) were mixed to form an electron-transporting layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed at an evaporation rate of 1: 9, and vacuum evaporated on the electron injection layer to form a second electrode 109, thereby completing the fabrication of the organic electroluminescent device.
Red light device examples 2-22
An organic electroluminescent device was fabricated in the same manner as in example 1 of the red light device, except that the compounds in table 12 were each used instead of compound HT-9 in forming the second hole transport layer.
Comparative examples 1 to 2
An organic electroluminescent device was fabricated in the same manner as in red device mutexample 1, mutexcept that the compound HT-13 was replaced with the compound HT-a and the compound HT-B, respectively, in forming the second hole transport layer.
TABLE 11
Figure BDA0003603766130000271
For the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience Co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each set of the devices of the red device examples and comparative example 4 was produced and tested in the same batch as the device of comparative example 3, the operating voltage, efficiency and lifetime of the device of comparative example 3 were each designated as 1, and the ratios of the respective indices of the devices of red device examples 1 to 22, comparative example 4 and comparative example 3 were calculated, respectively, as shown in table 12.
TABLE 12
Figure BDA0003603766130000272
Figure BDA0003603766130000281
As can be seen from the results in table 12, when used as the second hole transport layer of the red light device, the organic compounds used in examples 1 to 22 of the red light device all showed a decrease in voltage, an increase in luminous efficiency (up to 20%), and an increase in lifetime of 42% to 99%, as compared with the devices formed of the organic compounds used in comparative examples 1 to 2.
Green device example 1: preparation of green organic electroluminescent device
The green bottom light-emitting organic electroluminescent device is manufactured according to the structure shown in figure 1, and the preparation process comprises the following steps: a transparent anode ITO film (150 nm in thickness) is formed on a glass substrate 101 to obtain a first electrode 102 as an anode. Subsequently, a mixed material of compound 1 shown in Table 9 and compound 2-2 shown in Table 11 was evaporated as a hole injection layer 103 on the surface of the anode by a vacuum evaporation method at a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm. Then, compound 2-2 was vapor-deposited on the hole injection layer to a thickness of 100nm to obtain a first hole transport layer 104. Subsequently, a compound HT-16 of the present invention was evaporated to a thickness of 40nm on the first hole transporting layer to obtain a second hole transporting layer 105. On the second hole transport layer, the compound 2-3 and the compound 2-4 were co-evaporated at a mass ratio of 90:10 to form an organic light emitting layer 106 having a thickness of 40 nm. Then, on the organic light-emitting layer, a compound 5 was sequentially vapor-deposited to form a hole-blocking layer 107 (thickness 10nm), and a compound 6 and LiQ at a mixing ratio of 5:5 (mass ratio) were mixed to form an electron-transporting layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed at an evaporation rate of 1: 9, and vacuum evaporated on the electron injection layer as the second electrode 109, thereby completing the fabrication of the organic electroluminescent device.
Green device examples 2-22
Organic electroluminescent devices were fabricated in the same manner as in example 1 of the green device, except that compounds in the following table 10 were respectively substituted for the compound HT-16 in forming the second hole transport layer.
Comparative example 1
An organic electroluminescent device was fabricated in the same manner as in example 1 of the green device, except that the compound HT-16 was replaced with the compound HT-E in forming the second hole transport layer.
Watch 13
Figure BDA0003603766130000291
For the organic electroluminescent device prepared as above, the operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 testing system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience Co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Each set of green device examples was produced and tested in the same batch as the device of comparative example 5, the operating voltage, efficiency and lifetime of the device of comparative example 5 were each designated as 1, and the ratios of the respective indices of the green device examples 1-22 to the device of comparative example 5 were calculated as shown in table 14.
TABLE 14
Second hole transport layer Relative operating voltage Relative efficiency Relative life time
Comparative example 5 HT-E 1 1 1
Green device example 1 HT-14 0.920 1.090 1.288
Green device embodiment 2 HT-24 0.971 1.132 1.372
Green device example 3 HT-54 0.933 1.126 1.361
Green device example 4 HT-76 0.979 1.145 1.478
Green device example 5 HT-78 0.966 1.080 1.465
Green device example 6 HT-121 0.918 1.105 1.267
Green device example 7 HT-152 0.927 1.143 1.271
Green light device example 8 HT-159 0.979 1.166 1.373
Green device example 9 HT-181 0.950 1.195 1.287
Green light deviceExample 10 HT-192 0.938 1.108 1.418
Green device example 11 HT-203 0.906 1.063 1.307
Green device example 12 HT-219 0.968 1.802 1.236
Green device example 13 HT-230 0.944 1.051 1.280
Green device example 14 HT-254 0.929 1.156 1.490
Green device example 15 HT-258 0.915 1.136 1.387
Green device example 16 HT-264 0.973 1.164 1.455
Green device example 17 HT-269 0.924 1.192 1.315
Green device example 18 HT-271 0.931 1.144 1.398
Green device example 19 HT-290 0.903 1.097 1.404
Green device embodiment 20 HT-295 0.913 1.112 1.352
Green device example 21 HT-305 0.965 1.188 1.343
Green device example 22 HT-308 0.923 1.175 1.302
As can be seen from the results in table 14, the organic compounds used in examples 1 to 22 as the second hole transport layer of the green device all showed a lower voltage, an improved luminous efficiency, and an improved lifetime of 20% to 49%, as compared with the devices formed of the organic compound used in comparative example 5.
In conclusion, the triarylamine compound can ensure that the organic electroluminescent devices of blue light, red light and green light have higher hole mobility, and can effectively prevent electrons and excitons from entering a hole transport layer, so that the efficiency of the device is improved, the stability of molecules is high, the luminous efficiency of the device is further improved, and the service life of the device is further prolonged.
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 (14)

1. A triarylamine compound having a structure according to formula (1):
Figure FDA0003603766120000011
in the formula (1), L1And L2Identical or different, each independently selected from the group consisting of single bonds, substituted or unsubstituted phenylene;
L11、L12、L21and L22The same or different, each independently selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
Ar11、Ar12、Ar21and Ar22The same or different, each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
the group A is selected from one of the groups shown as 2-a, 2-b and 2-c:
Figure FDA0003603766120000012
in formulae 2-a to 2-c, Z1、Z2、Z3、Z4And Z5Each independently selected from-CR1R2-, -NR-, O or S;
R1and R2Identical or different, each independently selected from hydrogen, deuterium, deuterated or non-deuterated methyl, satisfies Z in formula 2-a1And Z3Are both O and Z2is-CR1R2When is, R1And R2Neither hydrogen nor deuterium;
r is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 heteroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl;
RAselected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C2-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;
n is selected from 0, 1,2 or 3, and represents a linking site.
2. Triarylamine compound according to claim 1, characterised in thatIn the formula (1), Z1、Z2、Z3、Z4And Z5Each independently selected from-NR-, O or S and in an amount greater than 1, such that there is at least one-CR separation between any two substituents selected from-NR-, O or S1R2-。
3. A triarylamine compound according to claim 1 wherein in formula 2-a, when Z is1And Z3When both are O, satisfy Z2is-CR1R2-and at least one R1And R2Is deuterated or unsubstituted methyl.
4. A triarylamine compound according to claim 1 wherein in formula 2-b, when Z is1、Z2、Z3And Z4Are all-CR1R2When at least one R is satisfied1And R2Is deuterated or unsubstituted methyl.
5. A triarylamine compound according to any one of claims 1 to 4 wherein in formula (1), "substituted" optionally substituted "means substituted with one or more substituents independently selected from deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C18 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl, C2-C30 heteroaryl, and L1-C30 heteroaryl, and L1、L2、L11、L12、L21、L22、Ar11、Ar12、Ar21And Ar22The substituents in (A) may be the same or different from each other.
6. A triarylamine compound according to claim 1 wherein in formula (1), group a is selected from one of the following substituents:
Figure FDA0003603766120000021
Figure FDA0003603766120000031
wherein R is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 heteroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl;
RAselected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C2-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;
n is selected from 0, 1,2 or 3, and represents a linking site.
7. A triarylamine compound according to claim 1 wherein in formula (1), L is1And L2Identical or different, are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, wherein "substituted" of "substituted or unsubstituted" means substituted with one or more substituents independently selected from the group consisting of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, and L1、L2The number and kind of the substituents are the same or different.
8. A triarylamine compound according to claim 1 wherein in formula (1), L is11、L12、L21And L22The same or different, each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted dibenzofuranyl group, wherein"substituted" means substituted with one or more substituents independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and L11、L12、L21And L22The number and kind of the substituents are the same or different.
9. The triarylamine compound according to claim 1, wherein in formula (1), Ar is21And Ar22The same or different, each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted selenophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzoselenophenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthothienyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthoselenophenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzocarbazolyl, and wherein "substituted or unsubstituted" means being independently selected from deuterium, Fluorine, cyano, trimethylsilyl, trifluoromethyl, C1-C6 alkyl, C4-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C6-C14 aryl, C5-C14 heteroaryl, and Ar11、Ar12、Ar21And Ar22The number and kind of the substituents are the same or different.
10. A triarylamine compound according to claim 1 wherein the compound of formula (1) is selected from any of the following chemical structures:
Figure FDA0003603766120000041
Figure FDA0003603766120000051
Figure FDA0003603766120000061
Figure FDA0003603766120000071
Figure FDA0003603766120000081
Figure FDA0003603766120000091
Figure FDA0003603766120000101
Figure FDA0003603766120000111
11. an organic optoelectronic material comprising one or more of the triarylamine compounds defined in any one of claims 1 to 10.
12. An organic electroluminescent device comprising one or more of the triarylamine compounds defined in any one of claims 1 to 10 or the organic photovoltaic material defined in claim 11.
13. The organic electroluminescent device according to claim 12,
a second electrode element including a substrate, a first electrode, one or more organic layers including a light-emitting layer and a hole-transporting layer;
the hole transport layer material contains one or more of the organic compounds described in any one of claims 1 to 10, or the organic photoelectric material described in claim 14.
14. A display or illumination apparatus, characterized in that it comprises the organic electroluminescent device according to claim 12 or 13.
CN202210409935.XA 2022-04-19 2022-04-19 Triarylamine compound and organic electroluminescent device comprising the same Pending CN114702395A (en)

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