CN111187265A - Organic main body material, preparation method thereof and organic electroluminescent device - Google Patents

Organic main body material, preparation method thereof and organic electroluminescent device Download PDF

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CN111187265A
CN111187265A CN202010025267.1A CN202010025267A CN111187265A CN 111187265 A CN111187265 A CN 111187265A CN 202010025267 A CN202010025267 A CN 202010025267A CN 111187265 A CN111187265 A CN 111187265A
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CN111187265B (en
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王士凯
马晓宇
汪康
王铁
姚明明
邱镇
王永光
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Jilin Optical and Electronic Materials Co Ltd
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    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract

The invention discloses an organic main material, a preparation method thereof and an organic electroluminescent device, belonging to the field of chemical synthesis and photoelectric materials, and the structural general formula is as follows:

Description

Organic main body material, preparation method thereof and organic electroluminescent device
Technical Field
The invention relates to the field of chemical synthesis and photoelectric materials, in particular to an organic main body material, a preparation method thereof and an organic electroluminescent device.
Background
Organic Electroluminescence (EL) has characteristics of self-luminescence, bright and bright color, thin thickness, light weight, etc., and has gradually developed into the most advantageous technology in the field of new generation flat panel display. However, the development of the organic electroluminescent device is restricted by factors such as efficiency and life span. The most important factor determining the luminous efficiency of an organic EL device is a light emitting material. The light emitting material is required to have higher quantum efficiency, higher electron mobility, and higher hole mobility. In addition, a light-emitting layer formed of a light-emitting material needs to be uniform and stable.
Currently, a light emitting material can be prepared by combining a host material with a dopant material to improve color purity, light emitting efficiency, and stability. Among them, 4,4'-N, N' -dicarbazole-biphenyl (CBP) is a relatively wide host material currently used for phosphorescent materials.
However, when CBP is used as a host material of a phosphorescent light-emitting material represented by an iridium complex, CBP has characteristics of easily transporting holes and hardly transporting electrons, so that charge injection balance is disrupted, and excessive holes flow out to the electron transport layer side, which leads to a decrease in light-emitting efficiency of a finally produced organic electroluminescent device.
Disclosure of Invention
An object of an embodiment of the present invention is to provide an organic host material to solve the problems mentioned in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
an organic host material having a general structural formula of formula I:
Figure BDA0002360356210000021
in the formula I, Ar is one of substituted or unsubstituted C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy, monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 10-membered aromatic ring formed by connecting adjacent substituents;
l is one of a chemical bond, substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl, C3-C60 cycloalkynyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl or 3-to 10-membered heterocyclic group, substituted or unsubstituted single-or polycyclic C3-C30 aliphatic ring or 3-to 10-membered aromatic ring connected with adjacent substituent;
R1、R2、R5、R6、R7each independently is one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C7 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, a monocyclic or polycyclic C3-C30 aliphatic ring or a 3-to 10-membered aromatic ring connected with adjacent substituents;
R3、R4each independently is one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 alkylamino, substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, monocyclic or polycyclic C3-C30 aliphatic ring connected with adjacent substituents, or substituted or unsubstituted 3-to 30-membered aromatic ring.
Preferably, at least one carbon atom in the monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 10-membered aromatic ring connected to the adjacent substituent(s) is replaced or not replaced by a heteroatom; at least one carbon atom in the substituted or unsubstituted, mono-or polycyclic, C3-C30 aliphatic ring or 3-to 10-membered aromatic ring, which is linked to an adjacent substituent, is replaced or not replaced with a heteroatom; at least one carbon atom in the monocyclic or polycyclic C3-C30 aliphatic ring or the substituted or unsubstituted 3-to 30-membered aromatic ring connected to the adjacent substituent(s) is replaced or not replaced with a heteroatom.
Wherein the above-mentioned occurrence of "substituted or unsubstituted" means being substituted by one, two or more substituents selected from: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted alkylamino; substituted or unsubstituted heterocyclylamino; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclyl. Wherein "substituted or unsubstituted" appearing above may mean substituted with a substituent in which two or more substituents among the substituents shown above are linked, or having no substituent. For example, "a substituent in which two or more substituents are linked" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
Preferably, the heteroatom is independently one of O, S, N and Si.
Preferably, the chemical structural formula of the organic host material is one of formula 1 to formula 80:
Figure BDA0002360356210000041
Figure BDA0002360356210000051
Figure BDA0002360356210000061
another objective of an embodiment of the present invention is to provide a method for preparing the organic host material, which includes the following steps:
Figure BDA0002360356210000071
mixing a compound A with a general formula II, a compound B with a general formula III and toluene, placing the mixture in a protective atmosphere, and adding a palladium catalyst and tri-tert-butylphosphine (P (t-Bu)3) Reacting with sodium tert-butoxide (t-BuO Na) to obtain an intermediate C;
mixing the intermediate C with dimethylacetamide, placing the mixture in a protective atmosphere, and adding tricyclohexylphosphine and palladium acetate to react to obtain an intermediate D;
mixing the intermediate D with a compound E with a general formula IV, placing the mixture in a protective atmosphere, and adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide to react to obtain an intermediate F;
mixing the intermediate F and Tetrahydrofuran (THF), placing the mixture in a protective atmosphere, and adding a Grignard reagent to react to obtain an intermediate G;
dissolving the intermediate G in a mixed solvent, and reacting with Methanesulfonic acid (MSA) to obtain an intermediate H;
and mixing the intermediate H, the compound I with the general formula V and toluene, placing the mixture in a protective atmosphere, and adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide for reaction to obtain the organic main body material.
Wherein, the chemical synthesis route of the preparation method is as follows:
Figure BDA0002360356210000081
preferably, the mixed solvent is a mixture of tetrahydrofuran and toluene.
Preferably, the Grignard reagent is methyl magnesium bromide.
Another object of an embodiment of the present invention is to provide an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer partially or completely includes the organic host material.
Preferably, the organic layer includes a light-emitting layer including the organic host material and a dopant material.
Preferably, the doping material is an iridium-containing compound.
Preferably, the organic electroluminescent device is one of a top emission type organic electroluminescent device, a bottom emission type organic electroluminescent device, and a dual emission type organic electroluminescent device.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
compared with the existing CBP used as the main material, the organic main material provided by the embodiment of the invention can obviously reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and prolong the service life of the organic electroluminescent device, thereby improving the practicability of the organic electroluminescent device.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1
This example provides an organic host material, whose chemical structural formula is formula 1 in the summary of the invention, and the reaction route of the preparation method of the organic host material is as follows:
Figure BDA0002360356210000091
the specific preparation method comprises the following steps:
step 1: after Compound A-1(150mmol), Compound B-1(150mmol) and toluene (500mL) were charged into a reaction vessel, Pd was further added under a nitrogen atmosphere2(dba)3(1.50mmol)、P(t-Bu)3(7.5mmol), t-BuONa (450 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to obtain intermediate C-1(35.2g, 77% yield).
Step 2: after the intermediate C-1(110mmol) and dimethylacetamide were charged into a reaction vessel, tricyclohexylphosphine and palladium acetate were added under nitrogen atmosphere, and the temperature was raised to 140 ℃ to react for 10 hours, whereby a solid was precipitated to obtain an intermediate D-1(24.0g, yield 81%).
And step 3: the intermediate D-1(77mmol), the compound E-1(85mmol) and 300ml of toluene were added to a reaction vessel, and Pd was added under nitrogen atmosphere2(dba)3(0.77mmol)、P(t-Bu)3(3.85mmol), t-BuONa (231 mmol). After the addition, the reaction temperature was slowly raisedThe temperature was raised to 110 ℃ and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate F-1(21.8g, 73% yield).
And 4, step 4: intermediate F-1(54mmol) and THF (300mL) were added to the reaction vessel, the temperature was reduced to 0 deg.C and methylmagnesium bromide was added under nitrogen. The mixture was stirred for 5 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to obtain intermediate G-1(19.1G, 76% yield).
And 5: intermediate G-1(40mmol), THF (150mL) and toluene (150mL) were added to a reaction vessel and MSA (400mmol) was added to the reaction. After stirring the mixture at room temperature for 8 hours, the mixture was extracted with distilled water and with dichloromethane. The extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate H-1(14.7g, 82% yield).
Step 6: adding intermediate H-1(30mmol), compound I-1(33mmol) and 150ml toluene into a reaction vessel, and adding Pd under nitrogen atmosphere2(dba)3(0.30mmol)、P(t-Bu)3(1.5mmol) and t-BuONa (90 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to obtain the final product 1(13.2g, 84% yield).
The mass spectrum theoretical value of the organic host material is 523.20; mass spectrometry test value 523.71; the elemental analysis of the organic host material is as follows: theoretical value C: 87.16, respectively; h: 4.81; n: 8.02; test value C: 87.14, respectively; h: 4.80; n: 8.03.
example 2
This example provides an organic host material, whose chemical structural formula is formula 38 in the summary of the invention, and the reaction route of the preparation method of the organic host material is as follows:
Figure BDA0002360356210000111
the specific preparation method comprises the following steps:
step 1: after Compound A-38(150mmol), Compound B-38(150mmol) and toluene (500mL) were charged into a reaction vessel, Pd was further added under a nitrogen atmosphere2(dba)3(1.50mmol)、P(t-Bu)3(7.5mmol), t-BuONa (450 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate C-38(50.8g, 74% yield).
Step 2: after the intermediate C-38(110mmol) and dimethylacetamide were charged into a reaction vessel, tricyclohexylphosphine and palladium acetate were added under nitrogen atmosphere, and the temperature was raised to 140 ℃ to react for 10 hours, whereby a solid was precipitated to obtain an intermediate D-38(35.3g, yield 76%).
And step 3: adding intermediate D-38(80mmol), compound E-38(88mmol) and 300ml toluene into a reaction vessel, and adding Pd under nitrogen atmosphere2(dba)3(0.8mmol)、P(t-Bu)3(4mmol) and t-BuONa (240 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate F-38(34.4g, 80% yield).
And 4, step 4: intermediate F-38(60mmol) and THF (300mL) were added to the reaction vessel, the temperature was reduced to 0 deg.C and methylmagnesium bromide was added under nitrogen. The mixture was stirred for 5 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate G-38(25.3G, 76% yield).
And 5: intermediate G-38(45mmol) and THF (150mL) and toluene (150mL) were added to a reaction vessel and MSA (450mmol) was added to the reaction. After stirring the mixture at room temperature for 8 hours, the mixture was extracted with distilled water and with dichloromethane. The extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate H-38(19.8g, 82% yield).
Step 6: adding intermediate H-38(35mmol), compound I-38(38mmol) and 150ml toluene into a reaction vessel, and adding Pd under nitrogen atmosphere2(dba)3(0.35mmol)、P(t-Bu)3(1.8mmol), t-BuONa (105 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to obtain the final product 38(19.3g, 80% yield).
The mass spectrum theoretical value of the organic host material is 690.28; mass spectrometry test value 690.52; the elemental analysis of the organic host material is as follows: theoretical value C: 86.93, respectively; h: 4.96; n: 8.11; test value C: 86.92, respectively; h: 4.97; n: 8.12.
example 3
This example provides an organic host material, whose chemical structural formula is formula 41 in the summary of the invention, and the reaction route of the preparation method of the organic host material is as follows:
Figure BDA0002360356210000131
the specific preparation method comprises the following steps:
step 1: after adding Compound A-41(150mmol), Compound B-41(150mmol) and toluene (500mL) to a reaction vessel, Pd was further added under a nitrogen atmosphere2(dba)3(1.50mmol)、P(t-Bu)3(7.5mmol), t-BuONa (450 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate C-41(35.2g, 77% yield).
Step 2: after the intermediate C-41(110mmol) and dimethylacetamide were charged into a reaction vessel, tricyclohexylphosphine and palladium acetate were added under nitrogen atmosphere, and the temperature was raised to 140 ℃ to react for 10 hours, whereby a solid was precipitated to obtain an intermediate D-41(24.0g, yield 81%).
And step 3: the intermediate D-41(77mmol), the compound E-41(85mmol) and 300ml of toluene were charged into a reaction vessel, and Pd was added under nitrogen atmosphere2(dba)3(0.77mmol)、P(t-Bu)3(3.85mmol), t-BuONa (231 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate F-41(18.7g, 75% yield).
And 4, step 4: intermediate F-41(54mmol) and THF (300mL) were added to the reaction vessel, the temperature was reduced to 0 deg.C and methylmagnesium bromide was added under nitrogen. The mixture was stirred for 5 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate G-41(13.4G, 73% yield).
And 5: intermediate G-41(37mmol) and THF (150mL) and toluene (150mL) were added to a reaction vessel and MSA (370mmol) was added to the reaction. After stirring the mixture at room temperature for 8 hours, the mixture was extracted with distilled water and with dichloromethane. The extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate H-41(10.1g, 85% yield).
Step 6: adding intermediate H-41(30mmol), compound I-41(33mmol) and 150ml toluene into a reaction vessel, and adding Pd under nitrogen atmosphere2(dba)3(0.30mmol)、P(t-Bu)3(1.5mmol) and t-BuONa (90 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to obtain final product 41(9.8g, 82% yield).
The mass spectrum theoretical value of the organic host material is 398.18; mass spectrometry test value 398.27; the elemental analysis of the organic host material is as follows: theoretical value C: 87.41; h: 5.56; n: 7.03; test value C: 87.40, respectively; h: 5.57; n: 7.05.
example 4
This example provides an organic host material, whose chemical structural formula is formula 63 in the summary of the invention, and the reaction route of the preparation method of the organic host material is as follows:
Figure BDA0002360356210000151
the specific preparation method comprises the following steps:
step 1: after adding Compound A-63(150mmol), Compound B-63(150mmol) and toluene (500mL) to a reaction vessel, Pd was further added under a nitrogen atmosphere2(dba)3(1.50mmol)、P(t-Bu)3(7.5mmol), t-BuONa (450 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. Followed by drying extraction with magnesium sulfateOrganic layer, and solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate C-63(35.2g, 77% yield).
Step 2: after the intermediate C-63(110mmol) and dimethylacetamide were charged into a reaction vessel, tricyclohexylphosphine and palladium acetate were added under nitrogen atmosphere, and the temperature was raised to 140 ℃ to react for 10 hours, whereby a solid was precipitated to obtain intermediate D-63(24.0g, yield 81%).
And step 3: the intermediate D-63(77mmol), the compound E-63(85mmol) and 300ml of toluene were charged into a reaction vessel, and Pd was added under nitrogen atmosphere2(dba)3(0.77mmol)、P(t-Bu)3(3.85mmol), t-BuONa (231 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate F-63(18.7g, 75% yield).
And 4, step 4: intermediate F-63(54mmol) and THF (300mL) were added to the reaction vessel, the temperature was reduced to 0 deg.C and methylmagnesium bromide was added under nitrogen. The mixture was stirred for 5 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate G-63(13.4G, 73% yield).
And 5: intermediate G-63(37mmol), THF (150mL) and toluene (150mL) were added to a reaction vessel and MSA (370mmol) was added to the reaction. After stirring the mixture at room temperature for 8 hours, the mixture was extracted with distilled water and with dichloromethane. The extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give intermediate H-63(10.1g, 85% yield).
Step 6: adding intermediate H-63(30mmol), compound I-63(33mmol) and 150ml toluene into a reaction vessel, and adding Pd under nitrogen atmosphere2(dba)3(0.30mmol)、P(t-Bu)3(1.5mmol) and t-BuONa (90 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃, and the mixture was stirred for 10 hours. Distilled water was then added to the reaction solution and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining material was purified by column chromatography to give final product 63(14.9g, 79% yield).
The mass spectrum theoretical value of the organic host material is 627.27; mass spectrometry test value 627.64; the elemental analysis of the organic host material is as follows: theoretical value C: 88.01; h: 5.30 of; n: 6.69; test value C: 88.11, respectively; h: 5.33; n: 6.67.
the synthetic routes and principles of the preparation methods of other compounds with the general structural formulas of formula I in the summary of the invention are the same as those of the above-listed examples 1 to 4, so that the description is not exhaustive, and 15 compounds (formulas 2, 3, 6, 10, 15, 35, 36, 39, 42, 43, 58, 62, 67, 72 and 80 in the summary of the invention) are selected as examples in the invention, and the corresponding mass spectrum test values and molecular formulas are shown in table 1 below.
TABLE 1
Structural formula of compound Molecular formula Theoretical value of mass spectrum Mass spectrometric test values
2 C50H32N4 688.26 688.45
3 C53H34N6 754.28 754.61
6 C42H27N3 573.22 573.34
10 C42H27N3 573.22 573.53
15 C45H30N2 598.24 598.41
35 C48H32N4 664.26 664.32
36 C52H34N4 714.28 714.23
39 C50H34N4 690.28 690.55
42 C41H29N3 563.24 563.41
43 C44H31N5 629.26 629.74
58 C33H24N4 476.20 476.52
62 C44H31N5 629.26 629.84
67 C36H29N3 503.24 503.71
72 C43H34N2 578.27 578.48
80 C53H38N2 702.30 702.42
The embodiment of the invention also provides an organic electroluminescent device prepared by adopting the organic host material provided by the embodiment, wherein the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode.
The organic layer may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, and a light-emitting layer, and may also include an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and the like; the organic host materials provided in the above embodiments may be used as the host material in the light-emitting layer, and the dopant material of the light-emitting layer may be selected from compounds containing iridium, such as tris (2-phenylpyridine) iridium (ir (ppy)3)。
Specifically, the method for manufacturing the organic electroluminescent element described above can be referred to example 5.
Example 5
The embodiment provides a method for manufacturing an organic electroluminescent device, which includes the steps of:
(1) coating thickness of Fisher company of
Figure BDA0002360356210000181
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30min, the ITO glass substrate is repeatedly cleaned for 2 times by distilled water and is ultrasonically cleaned for 10min, after the cleaning by distilled water is finished, the ITO glass substrate is sequentially ultrasonically cleaned by solvents such as isopropanol, acetone, methanol and the like, then dried, transferred into a plasma cleaning machine, and cleaned for 5min to obtain an ITO transparent electrode which is used as an anode and sent into an evaporation machine.
(2) Sequentially evaporating CuPc on the prepared ITO transparent electrode
Figure BDA0002360356210000182
N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB,
Figure BDA0002360356210000183
) The organic main body material and the doped material Ir (ppy) with the chemical structural formula 13Mixture mixed according to the weight ratio of 95:5
Figure BDA0002360356210000184
Tris (8-hydroxyquinoline) aluminum electron transport layer (Alq3,
Figure BDA0002360356210000185
)、LiF
Figure BDA0002360356210000186
cathode Al
Figure BDA0002360356210000187
And obtaining the organic electroluminescent device.
Referring to the method provided in example 5, instead of the organic host material of formula 1, the organic host material of formula 2, 3, 6, 10, 15, 35, 36, 39, 42, 43, 58, 62, 67, 72, 80 is selected as the host material and the dopant material Ir (ppy)3And carrying out mixed evaporation according to the weight ratio of 95:5, and preparing the corresponding organic electroluminescent device.
Comparative example 1
The comparative example provides an organic electroluminescent device, and the only difference between the preparation method of the organic electroluminescent device and the embodiment 5 is that the organic electroluminescent device adopts CBP to replace the organic host material with the chemical structural formula of formula 1 as the host material and the doping material Ir (ppy)3Mixed evaporation is carried out according to the weight ratio of 95: 5. Wherein, the structural formula of CBP is:
Figure BDA0002360356210000188
the organic electroluminescent devices obtained in example 5 and comparative example 1 were tested for driving voltage, luminous efficiency, and T95 lifetime using a KEITHLEY model 2400 source measuring unit and a CS-2000 spectroradiometer, respectively, and the test results are shown in table 2 below.
TABLE 2
Figure BDA0002360356210000191
Figure BDA0002360356210000201
As can be seen from table 2 above, compared with the organic electroluminescent device prepared by using the existing CBP as the host material of the light-emitting layer, the organic electroluminescent device prepared by using the organic host material provided by the embodiment of the present invention as the host material of the light-emitting layer has significantly reduced driving voltage, and significantly improved light-emitting efficiency and lifetime.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (10)

1. An organic host material, wherein the structural general formula of the organic host material is formula I:
Figure FDA0002360356180000011
in the formula I, Ar is one of substituted or unsubstituted C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy, monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 10-membered aromatic ring formed by connecting adjacent substituents;
l is one of a chemical bond, substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl, C3-C60 cycloalkynyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl or 3-to 10-membered heterocyclic group, substituted or unsubstituted single-or polycyclic C3-C30 aliphatic ring or 3-to 10-membered aromatic ring connected with adjacent substituent;
R1、R2、R5、R6、R7each independently is one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C7 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, a monocyclic or polycyclic C3-C30 aliphatic ring or a 3-to 10-membered aromatic ring connected with adjacent substituents;
R3、R4respectively and independently represent substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 alkylamino, substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, monocyclic or polycyclic C3-C30 aliphatic ring formed by connecting adjacent substituents or substituted or unsubstituted C3-C30 aliphatic ringOr an unsubstituted 3-to 30-membered aromatic ring.
2. The organic host material of claim 1, wherein at least one of the carbon atoms in the monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 10-membered aromatic ring linked to an adjacent substituent is replaced or not replaced by a heteroatom; at least one carbon atom in the substituted or unsubstituted, mono-or polycyclic, C3-C30 aliphatic ring or 3-to 10-membered aromatic ring, which is linked to an adjacent substituent, is replaced or not replaced with a heteroatom; at least one carbon atom in the monocyclic or polycyclic C3-C30 aliphatic ring or the substituted or unsubstituted 3-to 30-membered aromatic ring connected to the adjacent substituent(s) is replaced or not replaced with a heteroatom.
3. An organic host material according to claim 2, wherein the heteroatom is independently one of O, S, N and Si.
4. The organic host material of claim 1, wherein the chemical structure of the organic host material is one of formula 1 to formula 80:
Figure FDA0002360356180000021
Figure FDA0002360356180000031
Figure FDA0002360356180000041
Figure FDA0002360356180000051
5. a method for preparing an organic host material according to any one of claims 1 to 4, comprising the steps of:
Figure FDA0002360356180000052
mixing a compound A with a general formula II, a compound B with a general formula III and toluene, placing the mixture in a protective atmosphere, and adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide to react to obtain an intermediate C;
mixing the intermediate C with dimethylacetamide, placing the mixture in a protective atmosphere, and adding tricyclohexylphosphine and palladium acetate to react to obtain an intermediate D;
mixing the intermediate D with a compound E with a general formula IV, placing the mixture in a protective atmosphere, and adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide to react to obtain an intermediate F;
mixing the intermediate F and tetrahydrofuran, placing the mixture in a protective atmosphere, and adding a Grignard reagent to react to obtain an intermediate G;
dissolving the intermediate G in a mixed solvent, and reacting with methanesulfonic acid to obtain an intermediate H;
and mixing the intermediate H, the compound I with the general formula V and toluene, placing the mixture in a protective atmosphere, and adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide for reaction to obtain the organic main body material.
6. The method according to claim 5, wherein the mixed solvent is a mixture of tetrahydrofuran and toluene.
7. The method according to claim 5, wherein the Grignard reagent is methyl magnesium bromide.
8. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer partially or wholly comprises the organic host material as claimed in any one of claims 1 to 4.
9. The device of claim 8, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic host material and a dopant material.
10. An organic electroluminescent device according to claim 9, wherein the dopant material is an iridium-containing compound.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014104585A1 (en) * 2012-12-24 2014-07-03 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using same, and electronic device thereof
CN108623480A (en) * 2017-03-17 2018-10-09 吉林奥来德光电材料股份有限公司 New organic luminescent compounds and use its organic electroluminescence device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014104585A1 (en) * 2012-12-24 2014-07-03 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using same, and electronic device thereof
CN108623480A (en) * 2017-03-17 2018-10-09 吉林奥来德光电材料股份有限公司 New organic luminescent compounds and use its organic electroluminescence device

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