CN106608828A - Benzoperylene derivative for organic light-emitting material - Google Patents
Benzoperylene derivative for organic light-emitting material Download PDFInfo
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- CN106608828A CN106608828A CN201510695392.2A CN201510695392A CN106608828A CN 106608828 A CN106608828 A CN 106608828A CN 201510695392 A CN201510695392 A CN 201510695392A CN 106608828 A CN106608828 A CN 106608828A
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- JDPBLCQVGZLACA-UHFFFAOYSA-N benzo[a]perylene Chemical group C1=CC(C=2C3=CC=CC=C3C=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 JDPBLCQVGZLACA-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 239000000463 material Substances 0.000 title claims abstract description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- -1 acryloyloxy Chemical group 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 230000000903 blocking effect Effects 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 239000002019 doping agent Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a benzoperylene derivative for an organic light-emitting material. The structure of the benzoperylene derivative is shown in the general formula 1 (as shown in the description), wherein two positions in R1-R12 are substituted for amino, and other positions are independently selected from hydrogen atom, halogen atom, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted aromatic base, substituted or unsubstituted aromatic condensed ring, substituted or unsubstituted aralkyl and substituted or unsubstituted acryloyloxy. The benzoperylene derivative is used in an organic light-emitting device (OLED), and particularly as an organic light-emitting material, used in an OLED luminous layer, an OLED electronic transmission layer or an OLED hole blocking layer, and has excellent performance mainly manifested in such aspects as solubility and heat stability.
Description
Technical Field
The invention relates to the field of materials, in particular to a benzoperylene derivative for an organic electroluminescent material.
Background
The organic electroluminescence refers to a phenomenon that a thin film device prepared from an organic photoelectric functional material emits light under the excitation action of an electric field, is known as the most potential next-generation flat panel display technology by the industry and academia, and has the advantages of low power consumption, wide viewing angle, fast response, lightness, thinness, flexible display and the like.
The organic electroluminescent device, also called an Organic Light Emitting Diode (OLED), is composed of a transparent anode ITO, a metal cathode, and an organic thin film layer. Under the drive of direct current voltage, electrons injected from the cathode and holes injected from the anode move to the organic light-emitting layer, and finally meet in the light-emitting layer and are recombined to emit light. Organic semiconductor diodes have more complicated physical processes of carriers due to disorder of their structures and diversity of materials than inorganic semiconductor diodes, and organic materials for electron transport layers and hole blocking layers are important.
The organic electroluminescent material is used as a core component of an organic electroluminescent device, and the thermal stability, photochemical stability, quantum efficiency, film forming property, crystallinity and the like of the organic electroluminescent material have great influence on the manufacture of the device. CN104650040A discloses an organic electroluminescent compound of phenazine derivatives, the structural formula of which is:wherein the organic electroluminescent compound is used in at least one or more of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer or an electron transport layer, and has the advantages of good electroluminescent efficiency, excellent color purity and long service life; CN104744369A discloses an organic electroluminescent material, which contains a compound with a structural formulaA derivative of (a); the derivative forms a substance of a spiro-like compound due to the introduction of 2 benzene rings, increases the plane conjugation of a molecular structure, improves the solubility of the organic electroluminescent material, and enables the organic electroluminescent material to be easier to prepare.
Disclosure of Invention
The inventor of the application finds that the benzoperylene derivative used for the organic electroluminescent material can be used as an organic electroluminescent blue material, can also be used in a luminescent layer host material or a dopant, an electron transport layer and a hole blocking layer, and has good solubility and thermal stability.
The technical scheme of the invention comprises a benzoperylene derivative used for an organic electroluminescent material, which is characterized in that the structure of the benzoperylene derivative is shown in a general formula 1:
wherein two positions of R1-R12 are substituted by amino groups, and the other positions are independently selected from hydrogen atoms, halogen atoms, cyano groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic condensed ring groups, substituted or unsubstituted aralkyl groups, and substituted or unsubstituted propyleneoxy groups;
A1-A4 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, and a substituted or unsubstituted propyleneoxy group.
In one embodiment of the present invention, the other positions of R1-R12 are independently selected from hydrogen atom, halogen atom, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C6-C30 aromatic hydrocarbon, substituted or unsubstituted C6-C30 aromatic condensed ring, substituted or unsubstituted C6-C30 aralkyl, and substituted or unsubstituted C1-C10 propenyloxy.
Preferably, the A1-A4 are respectively and independently selected from a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C6-C30 aromatic heterocyclic group, a substituted or unsubstituted C6-C30 aralkyl group, and a substituted or unsubstituted C1-C10 propenyloxy group.
In one embodiment of the invention, R5 and R10 are substituted with amino.
In another embodiment of the invention, the other positions in R1-R12 are all replaced by hydrogen atoms.
In another embodiment of the present invention, each of A1-A4 is independently selected from substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, and substituted or unsubstituted aralkyl groups.
The benzo perylene derivative of the present invention preferably has the following structure:
the technical scheme of the invention also comprises an OLED light-emitting layer containing the benzo perylene derivative.
Furthermore, the host material or the dopant in the OLED light-emitting layer contains the benzo perylene derivative.
The technical scheme of the invention also comprises an OLED electronic transmission layer containing the benzo perylene derivative.
The technical scheme of the invention also comprises an OLED hole blocking layer containing the benzoperylene derivative.
The technical scheme of the invention also comprises an organic electroluminescent device containing the benzoperylene derivative.
The structure shown in the general formula 1 limits that two positions in R1-R12 are substituted by amino groups, and further specifies the category of other substituent groups, and the finally obtained benzoperylene derivative is used in an organic electroluminescent device, particularly as an organic electroluminescent material, is used in an OLED light-emitting layer, an OLED electron transport layer or an OLED hole blocking layer, has good performance, and is mainly shown in the aspects of hole transport property, solubility, thermal stability and the like.
Detailed Description
The invention provides a benzoperylene derivative for an organic electroluminescent material, which is characterized in that the structure of the benzoperylene derivative is shown as a general formula 1:
wherein two positions of R1-R12 are substituted by amino groups, and the other positions are independently selected from hydrogen atoms, halogen atoms, cyano groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic condensed ring groups, substituted or unsubstituted aralkyl groups, and substituted or unsubstituted propyleneoxy groups;
A1-A4 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, and a substituted or unsubstituted propyleneoxy group.
In one embodiment of the present invention, the other positions of R1-R12 are independently selected from hydrogen atom, halogen atom, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C6-C30 aromatic hydrocarbon, substituted or unsubstituted C6-C30 aromatic condensed ring, substituted or unsubstituted C6-C30 aralkyl, and substituted or unsubstituted C1-C10 propenyloxy.
Preferably, the A1-A4 are respectively and independently selected from a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C1-C10 alkenyl group, a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a substituted or unsubstituted C6-C30 aromatic heterocyclic group, a substituted or unsubstituted C6-C30 aralkyl group, and a substituted or unsubstituted C1-C10 propenyloxy group.
In one embodiment of the invention, R5 and R10 are substituted with amino.
In another embodiment of the invention, the other positions in R1-R12 are all replaced by hydrogen atoms.
In another embodiment of the present invention, each of A1-A4 is independently selected from substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, and substituted or unsubstituted aralkyl groups. The benzo perylene derivative of the present invention preferably has the following structure:
the invention also provides an OLED light-emitting layer containing the benzo perylene derivative. Furthermore, the host material or the dopant in the OLED light-emitting layer contains the benzo perylene derivative.
The invention also provides an OLED electronic transmission layer containing the benzo perylene derivative.
The invention also provides an OLED hole blocking layer containing the benzo perylene derivative.
The invention also provides an organic electroluminescent device containing the benzo perylene derivative.
Example 1
1. A benzoperylene derivative for organic electroluminescent materials has a structure shown in a general formula 1-1:
2. the preparation method of the benzoperylene derivative (1-1) comprises the following steps:
under the protection of nitrogen, 2, 7-dibromo- (1,12) benzoperylene (1mol), 7-quinazolinoaniline (2.2mol), 1, 2-cyclohexanediamine (4mol) and cuprous iodide (0.1mol) are dissolved in 1, 4-dioxane, stirred at 100 ℃ for 6 hours until the reaction is completed, and then LC-MS shows that the reaction is completed, C50H30N6(M +1 ═ 715.4) is cooled to room temperature, slowly dropped into stirred water (10 volume ratio), extracted with ethyl acetate (3 volume) for 3 times, the organic phases are combined, dried and concentrated, and then passed through a silica gel column (ethyl acetate/petroleum ether ═ 1: 10) to obtain the benzoperylene derivative (1-1) as a white solid (70% yield).
3. Structural characterization:
1HNMR(400MHz,DMSO)9.30(s,2H),9.23(s,2H),8.1-7.8(m,3H),7.4-7.6(m,6H),7.2(d,3H),7.0-6.9(m,6H),6.6-6.5(m,8H)。
example 2
1. A benzoperylene derivative for organic electroluminescent materials has a structure shown in general formula 1-2:
2. the preparation method of the benzoperylene derivative (1-2) comprises the following steps:
will be provided withIs replaced byLC-MS showed C54H34N2(M +1 ═ 711.4), and the other starting materials and procedure were the same as in example 1 to give the benzo perylene derivative (1-2) as a white solid (65% yield).
3. Structural characterization:
1HNMR(400MHz,DMSO)8.1-7.9(m,3H),7.6-7.4(m,11H),7.1-6.9(m,12H),6.6-6.4(m,8H)。
example 3
1. A benzoperylene derivative for organic electroluminescent materials has a structure shown in general formulas 1-3:
2. the preparation method of the benzoperylene derivative (1-3) comprises the following steps:
will be provided withIs replaced byLC-MS showed C50H38N2(M +1 ═ 667.4), and the other starting materials and procedure were the same as in example 1 to give the benzo perylene derivative (1-3) as a white solid (73% yield).
3. Structural characterization:
1HNMR(400MHz,DMSO)8.1-7.9(m,3H),7.4(dd,4H),7.2(d,1H),6.8-6.6(m,10H),6.4(d,8H),2.4(s,12H)。
application examples
The device structure is as follows:
ITO(50nm)/HIL(40nm)/HTL(45nm)/BH:BD(5％)(25nm)/TB(5nm)/ET(20nm)/LiF(1nm)/Al(100nm)；
wherein,
the benzo perylene derivatives (1-1), (1-2) and (1-3) obtained in examples 1 to 3 were used as blue light dopants in the preparation of blue light devices, respectively, and the characteristic values of the obtained devices are shown in the following table:
from the table, one can see: the benzo perylene derivatives (1-1), (1-2) and (1-3) show good blue light characteristics on light emitting wavelength and color scale, have good blue light service life, and are likely to be matched with a main body material to be further improved. At present, the benzoperylene derivatives (1-1), (1-2) and (1-3) are all promising blue dopant materials, which is demonstrated from the existing data.
Further, the physical properties of the benzoperylene derivatives (1-1), (1-2) and (1-3) are shown in the following table:
from the table, one can see: the benzopyrene derivatives (1-1), (1-2) and (1-3) have high glass transition temperature and good mobility, especially (1-1), and may be related to the electron deficiency of the branched chain.
The embodiments of the present invention have been described in detail, but the embodiments are merely examples, and the present invention is not limited to the embodiments described above. Any equivalent modifications and substitutions to those skilled in the art are also within the scope of the present invention. Accordingly, equivalent changes and modifications made without departing from the spirit and scope of the present invention should be covered by the present invention.
Claims (10)
1. A benzoperylene derivative used for an organic electroluminescent material is characterized in that the structure of the benzoperylene derivative is shown as a general formula 1:
wherein two positions of R1-R12 are substituted by amino groups, and the other positions are independently selected from hydrogen atoms, halogen atoms, cyano groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic condensed ring groups, substituted or unsubstituted aralkyl groups, and substituted or unsubstituted propyleneoxy groups;
A1-A4 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, and a substituted or unsubstituted propyleneoxy group.
2. The benzoperylene derivative of claim 1, wherein R5 and R10 are substituted with amino groups.
3. The benzoperylene derivative of claim 1, wherein the other positions of R1-R12 are substituted with hydrogen atoms.
4. The benzoperylene derivative of claim 1, wherein each of a1-a4 is independently selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, and a substituted or unsubstituted aralkyl group.
5. The benzoperylene derivative of claim 1, wherein the benzoperylene derivative is preferably of the structure as follows:
6. an OLED light emitting layer comprising the benzoperylene derivative according to any one of claims 1 to 5.
7. The OLED light-emitting layer of claim 6 wherein the host material or dopant in the OLED light-emitting layer comprises the benzoperylene derivative.
8. An OLED electron transport layer comprising the benzoperylene derivative according to any one of claims 1 to 5.
9. An OLED hole blocking layer comprising the benzoperylene derivative according to any one of claims 1 to 5.
10. An organic electroluminescent device comprising the benzoperylene derivative according to any one of claims 1 to 5.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111153810A (en) * | 2020-01-15 | 2020-05-15 | 合肥鼎材科技有限公司 | Compound, application thereof and organic electroluminescent device containing compound |
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Application publication date: 20170503 |
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