CN110903311A - Polycyclic organoboron derivatives and electronic devices - Google Patents
Polycyclic organoboron derivatives and electronic devices Download PDFInfo
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- CN110903311A CN110903311A CN201911141889.4A CN201911141889A CN110903311A CN 110903311 A CN110903311 A CN 110903311A CN 201911141889 A CN201911141889 A CN 201911141889A CN 110903311 A CN110903311 A CN 110903311A
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to polycyclic organoboron derivatives and electronic devices. The polycyclic organic boron derivative has excellent film forming property and thermal stability by introducing a cyclic rigid structure, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells. In addition, the polycyclic organoboron derivative of the present invention can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer, and can reduce a driving voltage, improve efficiency, luminance, lifetime, and the like. In addition, the preparation method of the polycyclic organic boron derivative is simple, raw materials are easy to obtain, and the industrial development requirement can be met.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and relates to a polycyclic organoboron derivative and an electronic device containing the polycyclic organoboron derivative. More particularly, the present invention relates to a polycyclic organoboron derivative suitable for use in electronic devices, particularly organic electroluminescent devices, organic field effect transistors, and organic solar cells, and an electronic device using the polycyclic organoboron derivative.
Background
The organic electroluminescent device has a series of advantages of self-luminescence, low-voltage driving, full curing, wide viewing angle, simple composition and process and the like, and compared with a liquid crystal display, the organic electroluminescent device does not need a backlight source. Therefore, the organic electroluminescent device has wide application prospect.
Organic electroluminescent devices generally comprise an anode, a metal cathode and an organic layer sandwiched therebetween. The organic layer mainly comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. In addition, a host-guest structure is often used for the light-emitting layer. That is, the light emitting material is doped in the host material at a certain concentration to avoid concentration quenching and triplet-triplet annihilation, improving the light emitting efficiency. Therefore, the host material is generally required to have a higher triplet energy level and, at the same time, a higher stability.
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, and a large number of organic electroluminescent materials with excellent performance have been developed. In view of the above, the future direction of organic electroluminescent devices is to develop high efficiency, long lifetime, low cost white light devices and full color display devices, but the industrialization of the technology still faces many key problems. Therefore, designing and searching a stable and efficient compound as a novel material of an organic electroluminescent device to overcome the defects of the organic electroluminescent device in the practical application process is a key point in the research work of the organic electroluminescent device material and the future research and development trend.
Disclosure of Invention
Problems to be solved by the invention
The invention aims to provide a polycyclic organic boron derivative. The polycyclic organic boron derivative has high thermal stability, good transmission performance, high triplet state and simple preparation method, and an organic light-emitting device prepared from the polycyclic organic boron derivative has the advantages of high luminous efficiency, long service life and low driving voltage, and is an organic electroluminescent material with excellent performance.
It is another object of the present invention to provide an electronic device using the polycyclic organoboron derivative, which has advantages of high efficiency, high durability and long life.
Means for solving the problems
The polycyclic organic boron derivative has a special ring structure, has higher thermal stability, chemical stability and carrier transmission property, and more importantly has proper singlet state, triplet state and molecular orbital energy level. Therefore, the organic electroluminescent material is introduced into molecules with electroluminescent characteristics, so that the stability and the luminous efficiency of a device are improved, and the driving voltage of the device is reduced.
Namely, the present invention is as follows.
[1] A polycyclic organoboron derivative represented by the following general formula (1) or general formula (2):
in the above general formula (1) or general formula (2),
L1、L2and L3Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms;
A1、A2and A3Each independently represents Ar1、Ar2、Ar3、
One or more of;
Ar1～Ar6each is independentRepresents a hydrogen atom, a cyano group, optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、-N(R2)2、-OR2、-SR2、-C(＝O)R2、-P(＝O)R2、-Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms;
m, n and p are each independently an integer of 0 to 4, and m, n and p are not simultaneously 0.
[2] The polycyclic organoboron derivative according to [1], which is represented by the following general formula (I), general formula (II), general formula (III) or general formula (IV):
in the above general formula (I), general formula (II), general formula (III) or general formula (IV), L1～L3、Ar1～Ar6And m, n and p have a structure according to [1] above]The meaning as defined.
[3]According to [1]The polycyclic organoboron derivative wherein Ar is1、Ar2、Ar3、Ar4、Ar5And Ar6Each independently of the otherIs selected from the following groups:
wherein the dotted line represents and L1、L2、L3Or a bond to an N atom;
R1having the structure according to [1] above]The meaning as defined.
[4]According to [1]～[3]A polycyclic organoboron derivative as described in any one of the above, wherein R is1And R2Each independently represents one or more of phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazole, benzofurocarbazole, benzofluorenocarbazole, benzanthracene, triphenylene, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron group, triphenyl phosphoxy, diphenyl phosphoxy, triphenyl silicon group, or tetraphenyl silicon group.
[5] The polycyclic organoboron derivative according to any one of [1] to [4], wherein the polycyclic organoboron derivative represented by the general formula (1) or the general formula (2) is selected from the following compounds:
[6] an electronic device comprising the polycyclic organoboron derivative according to any one of the above [1] to [5 ].
[7] The electronic device according to [6], wherein the electronic device is an organic electroluminescent device, an organic field effect transistor, or an organic solar cell;
wherein the organic electroluminescent device comprises: a first electrode, a second electrode provided so as to face the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the at least one organic layer contains the polycyclic organoboron derivative according to any one of the above [1] to [5 ].
[8] The electronic device according to [7], wherein the at least one organic layer is a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer.
[9] Use of the polycyclic organoboron derivative according to any one of [1] to [5] as a light emitting material, an electron transporting material, an electron blocking material, a hole injecting material, or a hole blocking material in an electronic device.
[10] The use according to [9], wherein the electronic device is an organic electroluminescent device, an organic field effect transistor, or an organic solar cell.
ADVANTAGEOUS EFFECTS OF INVENTION
The polycyclic organic boron derivative has good film forming property and thermal stability by introducing a ring-shaped rigid structure, can be used for preparing electronic devices such as organic electroluminescent devices, organic field effect transistors and organic solar cells, particularly used as a constituent material of a hole injection layer, a hole transmission layer, a luminescent layer, an electron blocking layer, a hole blocking layer or an electron transmission layer in the organic electroluminescent devices, can show the advantages of high luminous efficiency, long service life and low driving voltage, and is obviously superior to the existing organic electroluminescent devices.
In addition, the preparation method of the polycyclic organic boron derivative is simple, raw materials are easy to obtain, and the industrial development requirement can be met.
The polycyclic organic boron derivative has good application effect in electronic devices such as organic electroluminescent devices, organic field effect transistors, organic solar cells and the like, and has wide industrialization prospect.
The polycyclic organoboron derivatives of the present invention have high electron injection and mobility rates. Therefore, with the organic electroluminescent device having an electron injection layer and/or an electron transport layer prepared using the polycyclic organoboron derivative of the present invention, the electron transport efficiency from the electron transport layer to the light emitting layer is improved, thereby improving the light emitting efficiency. And, the driving voltage is also reduced, thereby enhancing durability of the resulting organic electroluminescent device.
The polycyclic organoboron derivative of the present invention has excellent hole blocking ability, excellent electron transporting property, and is stable in a thin film state. Therefore, the organic electroluminescent device having a hole blocking layer prepared using the polycyclic organoboron derivative of the present invention has high luminous efficiency, a reduced driving voltage, and improved current resistance, so that the maximum luminous brightness of the organic electroluminescent device is increased.
The polycyclic organoboron derivatives of the present invention have excellent electron transporting properties and have a wide band gap. Therefore, the polycyclic organoboron derivative of the present invention is used as a host material on which a fluorescence emitting substance, a phosphorescence emitting substance, or a delayed fluorescence emitting substance called a dopant is carried to form a light emitting layer. This makes it possible to realize an organic electroluminescent device that is driven at a reduced voltage and that is characterized by improved luminous efficiency.
The polycyclic organoboron derivative can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer or an electron transport layer of an organic electroluminescent device. With the organic electroluminescent device of the present invention, excitons generated in the light emitting layer can be confined, and the possibility of recombination of holes and electrons can be further increased to obtain high luminous efficiency. In addition, the driving voltage is so low that high durability can be achieved.
Drawings
FIG. 1 shows fluorescence spectra (PL) of compounds of examples 1 and 3 of the present invention (compounds 1 and 133) in a dichloromethane solution.
FIG. 2 is a fluorescence spectrum (PL) of the compounds of examples 1 and 3 of the present invention (compounds 1 and 133) under a solid state thin film.
FIG. 3 is a view showing the configurations of the organic electroluminescent devices of examples 5 to 8 and the organic electroluminescent devices of comparative examples 1 and 2.
Description of the reference numerals
1 substrate
2 anode
3 hole injection layer
4 hole transport layer
5 Electron blocking layer
6 light-emitting layer
7 hole blocking layer
8 electron transport layer
9 electron injection layer
10 cathode
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.
The polycyclic organoboron derivative of the present invention is a novel organoboron compound having a polycyclic structure and is represented by the following general formula (1) or general formula (2).
In the above general formula (1) or general formula (2),
L1、L2and L3Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms;
A1、A2and A3Each independently represents Ar1、Ar2、Ar3、
One or more of;
Ar1～Ar6each independently represents a hydrogen atom, a cyano group, optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)2、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 5 to 30 carbon atoms;
m, n and p are each independently an integer of 0 to 4, and m, n and p are not simultaneously 0.
Specifically, the polycyclic organoboron derivative of the present invention has a structure represented by the following general formula (I), general formula (II), general formula (III), or general formula (IV):
l in the general formula (I), the general formula (II), the general formula (III) or the general formula (IV)1～L3、Ar1～Ar6And m, n and p have the meanings as defined above.
The polycyclic organoboron derivative of the present invention is preferably represented by the following general formula (3) or general formula (4), more preferably represented by the following general formula (V), general formula (VI), general formula (VII), or general formula (VIII):
<L1to L3>
L1、L2And L3Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms.
In the present invention, the hetero atom in the aromatic heterocyclic group having 5 to 18 carbon atoms is preferably selected from N, O and/or S. In the present invention, the number of hetero atoms may be 1 to 5. An aromatic hydrocarbon group or aromatic heterocyclic group in the sense of the present invention means a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be interrupted by non-aromatic units (preferably less than 10% of non-hydrogen atoms), which may be, for example, carbon atoms, nitrogen atoms, oxygen atoms or carbonyl groups. For example, systems of 9,9' -spirobifluorenes, 9, 9-diarylfluorenes, triarylamines, diaryl ethers, etc., as well as systems in which two or more aryl groups are interrupted, for example by linear or cyclic alkyl groups or by silyl groups, are also intended to be considered aromatic hydrocarbon groups in the sense of the present invention. Furthermore, systems in which two or more aryl or heteroaryl groups are bonded directly to one another, such as biphenyl, terphenyl or quaterphenyl, are likewise intended to be regarded as aromatic hydrocarbon groups or aromatic heterocyclic groups.
From L1、L2And L3The aromatic hydrocarbon group having 6 to 18 carbon atoms or the aromatic heterocyclic group having 5 to 18 carbon atoms represented may be exemplified by: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, pentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, hydropyranyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, perylenyl, anthryl, benzopyrenyl, terphenylenyl, terphenylindenyl, etc, Phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinylimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazenanthrayl, 2, 7-diazapyranyl, 2, 3-diazapyranyl, 1, 6-diazapyranyl, 1, 8-diazapyranyl, 4, 5-diazepanyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorerynyl, naphthyridinyl, azacarbazolyl, naphthoyl, and the like,Benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, and the like.
In the present invention, preferably, L1、L2And L3Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 5 to 12 carbon atoms. More preferably, L1And L2Each independently represents one or more of a single bond, carbonyl, phenyl, triazinyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl or benzophenanthrenyl.
From L1、L2And L3The aromatic hydrocarbon group having 6 to 18 carbon atoms or the aromatic heterocyclic group having 5 to 18 carbon atoms represented may be unsubstituted, but may also have a substituent. The substituents may be exemplified by the following: a deuterium atom; a cyano group; a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; an alkyl group having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, or a n-hexyl group; alkoxy having 1 to 6 carbon atoms such as methoxy, ethoxy or propoxy; alkenyl, such as vinyl or allyl; aryloxy groups such as phenoxy or tolyloxy; arylalkoxy, such as benzyloxy or phenethyloxy; aromatic hydrocarbon radicals or condensed polycyclic aromatic radicals, e.g. phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthryl, benzo [9,10 ] benzo]Phenanthryl or spirobifluorenyl; aromatic heterocyclic radicals, e.g. pyridyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuryl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalyl, benzimidazoleA phenyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, an azafluorenyl group, a diazafluorenyl group, a carbolinyl group, an azaspirobifluorenyl group or a diazafluorafluorafluorenyl group; arylethenyl, such as styryl or naphthylethenyl; and acyl groups such as acetyl or benzoyl and the like.
The alkyl group having 1 to 6 carbon atoms and the alkoxy group having 1 to 6 carbon atoms may be linear or branched. Any of the above substituents may be further substituted with the above exemplary substituents. The above substituents may be present independently of each other, but may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.
<A1To A3>
A1、A2And A3Each independently represents Ar1、Ar2、Ar3、
One or more of the above.
(Ar1To Ar6)
Ar1～Ar6Each independently represents a hydrogen atom, a cyano group, optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms.
From Ar1～Ar6The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented may be exemplified by: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, pentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisoisoisoisoindenylTrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzothienocarbazolyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, bipyridyl, terpyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, benzoxadiazolyl, naphthoxazolyl, anthraoxazolyl, Phenanthrooxazolyl, isoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzothiadiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, quinazolinyl, azafluorenyl, diazahthranyl, diazapyranyl, pyrenyl, tetraazaperylenyl, naphthyridinyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescenzinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, triazolyl, benzotriazolyl, oxadiazolyl, thiadiazolyl, triazinyl, tetrazolyl, tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, pyridopyrrolyl, pyridotriazolyl, xanthenyl, benzofurocarbazolyl, benzofluorenocarbazolyl, N-phenylcarbazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boronyl, Triphenylphosphoxy, diphenylphosphinyloxy, triphenylsilyl, tetraphenylsilyl, and the like.
In the present invention, preferably, Ar1、Ar2、Ar3、Ar4、Ar5And Ar6Each independently selected from the following groups:
wherein the dotted line represents and L1、L2Or L3A bonded bond;
R1have the meaning according to the definition above.
From Ar1～Ar6The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented may be unsubstituted, but may also have a substituent. Preferably, from Ar1～Ar6The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented by1Substituted, aromatic hydrocarbon radicals having 5 to 30 carbon atoms or substituted by one or more R1A substituted aromatic heterocyclic group having 5 to 30 carbon atoms.
(R1)
R1Represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、-N(R2)、-OR2、-SR2、-C(＝O)R2、-P(＝O)R2、-Si(R2)3A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms.
From R1The alkyl group having 1 to 20 carbon atoms represented may be exemplified by: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, tert-butyl, tert-octyl, tert-decyl, octadecyl, dodecyl, tert-decyl, dodecyl,Cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like. The alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic.
From R1The alkyl group having 1 to 20 carbon atoms represented may be unsubstituted, but may also have a substituent. Preferably, from R1Alkyl having 1 to 20 carbon atoms represented by one or more of the following R2And (4) substitution. In addition, one or more non-adjacent CH in the alkyl group2The group may be represented by-R2C＝CR2-、-C≡C-、-Si(R2)3、-C＝O、-C＝NR2、-P(＝O)R2、-SO、-S(O)2、-NR2-O-, -S-or-CONR2And wherein one or more hydrogen atoms may be replaced with deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, nitro group.
From R1The alkenyl group having 2 to 20 carbon atoms represented may be exemplified by: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 2-ethylhexenyl, allyl, cyclohexenyl and the like. The alkenyl group having 2 to 20 carbon atoms may be linear, branched or cyclic.
From R1The alkenyl group having 2 to 20 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents.
From R1The alkynyl group having 2 to 20 carbon atoms represented may be exemplified by: ethynyl, isopropynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynylDecynyl, and the like.
From R1The alkynyl group having 2 to 20 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents.
From R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented by the formula are exemplified by the groups represented by the above formula Ar1～Ar6The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented by the above formula represent the same groups.
From R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents. In addition, two adjacent R1Substituents or two adjacent R2The substituents optionally may form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more R2Substitution; where two or more substituents R1May be connected to each other and may form a ring.
Preferably represented by R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented by (a) may be exemplified by: phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazolyl, benzofurocarbazolyl, benzofluorenocarbazolyl, benzanthracenyl, benzophenanthryl, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron, triphenylphosphoxy, diphenylphosphinophosphoxy, diphenylenecarbazolyl, benzofluorenocarbazolyl, benzofluorenylcarbazolyl, benzophenanthryl, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, indeOxy, triphenylsilyl, tetraphenylsilyl, and the like. The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms may be substituted with one or more R2And (4) substitution.
(R2)
R2Represents a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
From R2The alkyl group having 1 to 20 carbon atoms represented by R1The alkyl groups represented by the formulae having 1 to 20 carbon atoms represent the same groups.
From R2The aromatic hydrocarbon group having 6 to 30 carbon atoms or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms represented by1～Ar6The same groups as those shown for the aromatic hydrocarbon group having 6 to 30 carbon atoms or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
From R2The alkyl group having 1 to 20 carbon atoms, the aromatic hydrocarbon group having 6 to 30 carbon atoms, or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms represented may be unsubstituted, or may also have a substituent. The substituents may be exemplified by: a deuterium atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; cyano, and the like.
< m, n and p >
m, n and p each represent-L linked to a polycyclic organoboron skeleton structure1-A1Structural unit, -L2-A2Structural unit and-L3-A3The number of structural units. In the present invention, m, n and p are each independently an integer of 0 to 4, and m, n and p are not simultaneously 0. Preferably, m, n and p are each independently an integer of 0 to 2, more preferably 0,1 or 2, but not simultaneously 0.
< production method >
The polycyclic organoboron derivatives of the invention can be produced, for example, by the following method:
the obtained compound can be purified by, for example, purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, or the like, recrystallization or crystallization using a solvent, sublimation purification, or the like. Identification of compounds can be carried out by mass spectrometry, elemental analysis.
Specific examples of preferred compounds among the polycyclic organoboron derivatives of the present invention are shown below, but the present invention is by no means limited to these compounds.
< electronic device >
Various electronic devices containing the polycyclic organoboron derivatives of the present invention can be produced by using the polycyclic organoboron derivatives according to the present invention for producing organic materials which can be specifically configured in the form of layers. In particular, the polycyclic organoboron derivatives of the invention can be used in organic electroluminescent devices, organic solar cells, organic diodes, in particular organic field effect transistors. Particularly in the case of an organic electroluminescent device or a solar cell, the assembly may have a plug structure (the device has one or more p-doped hole transport layers and/or one or more n-doped electron transport layers) or an inverted structure (from the light emitting layer, the upper electrode and the hole transport layer are located on the same side while the substrate is on the opposite side), without being limited to these structures. The injection layer, transport layer, light-emitting layer, barrier layer, etc. can be made, for example, by forming a layer containing or consisting of the polycyclic organoboron derivative according to the invention between electrodes. However, the use of the polycyclic organoboron derivative according to the invention is not limited to the above exemplary embodiments.
< organic electroluminescent device >
The organic electroluminescent device of the present invention comprises: the organic electroluminescence device includes a first electrode, a second electrode provided so as to face the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the at least one organic layer includes the polycyclic organoboron derivative of the present invention.
Fig. 3 is a view showing the configuration of an organic electroluminescent device of the present invention. As shown in fig. 3, in the organic electroluminescent device of the present invention, for example, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially disposed on a substrate 1.
The organic electroluminescent device of the present invention is not limited to such a structure, and for example, some organic layers may be omitted in the multi-layer structure. For example, it may be a configuration in which the hole injection layer 3 between the anode 2 and the hole transport layer 4, the hole blocking layer 7 between the light emitting layer 6 and the electron transport layer 8, and the electron injection layer 9 between the electron transport layer 8 and the cathode 10 are omitted, and the anode 2, the hole transport layer 4, the light emitting layer 6, the electron transport layer 8, and the cathode 10 are sequentially provided on the substrate 1.
The organic electroluminescent device according to the present invention may be manufactured by materials and methods well known in the art, except that the above organic layer contains the compound represented by the above general formula (1) or general formula (2). In addition, in the case where the organic electroluminescent device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic electroluminescent device according to the present invention may be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, the following can be made: an anode is formed by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and a substance which can be used as a cathode is deposited on the organic layer. However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode of the organic electroluminescent device of the present invention may be made of a known electrode material. For example, an electrode material having a large work function, such as a metal of vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SNO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]And conductive polymers such as PEDOT, polypyrrole, and polyaniline. Among these, ITO is preferable.
As the hole injection layer of the organic electroluminescent device of the present invention, a known material having a hole injection property can be used. Examples thereof include: porphyrin compounds represented by copper phthalocyanine, naphthalenediamine derivatives, star-shaped triphenylamine derivatives, triphenylamine trimers such as arylamine compounds having a structure in which 3 or more triphenylamine structures are connected by a single bond or a divalent group containing no heteroatom in the molecule, tetramers, receptor-type heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, and an ink jet method.
As the hole transport layer of the organic electroluminescent device of the present invention, the polycyclic organoboron derivative of the present invention is preferably used. In addition, other known materials having a hole-transporting property can be used. Examples thereof include: a compound containing a m-carbazolylphenyl group; benzidine derivatives such as N, N ' -diphenyl-N, N ' -di (m-tolyl) benzidine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -tetrakisbiphenylylbenzidine, and the like; 1, 1-bis [ (di-4-tolylamino) phenyl ] cyclohexane (TAPC); various triphenylamine trimers and tetramers; 9,9',9 "-triphenyl-9H, 9' H, 9" H-3,3':6',3 "-tricarbazole (Tris-PCz), and the like. These may be used as a single layer formed by separately forming a film or by mixing them with other materials to form a film, or may be used as a laminated structure of layers formed by separately forming a film, a laminated structure of layers formed by mixing films, or a laminated structure of layers formed by separately forming a film and layers formed by mixing films. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, and an ink jet method.
In addition, in the hole injection layer or the hole transport layer, a material obtained by further P-doping tribromoaniline antimony hexachloride, an axial olefin derivative, or the like to a material generally used in the layer, a polymer compound having a structure of a benzidine derivative such as TPD in a partial structure thereof, or the like may be used.
As the electron blocking layer of the organic electroluminescent element of the present invention, the polycyclic organoboron derivative of the present invention is preferably used. In addition, other known compounds having an electron blocking effect may be used. For example, there may be mentioned: carbazole derivatives such as 4,4', 4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), 9-bis [4- (carbazol-9-yl) phenyl ] fluorene, 3' -bis (N-carbazolyl) -1,1' -biphenyl (mCBP), 1, 3-bis (carbazol-9-yl) benzene (mCP), and 2, 2-bis (4-carbazol-9-ylphenyl) adamantane (Ad-Cz); a compound having a triphenylsilyl and triarylamine structure represented by 9- [4- (carbazol-9-yl) phenyl ] -9- [4- (triphenylsilyl) phenyl ] -9H-fluorene; and compounds having an electron-blocking effect, such as monoamine compounds having a high electron-blocking property and various triphenylamine dimers. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers formed by mixing into a film, or a laminated structure of layers formed by film formation alone and layers formed by mixing into a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, and an ink jet method.
As the light-emitting layer of the organic electroluminescent element of the present invention, the polycyclic organoboron derivative of the present invention is preferably used. In addition to this, Alq can also be used3Various metal complexes such as metal complexes of a first hydroxyquinoline derivative, compounds having a pyrimidine ring structure, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, and the like.
The light emitting layer may be composed of a host material and a dopant material. As the host material, 9- (4- (1-naphthyl) -10- (2-naphthyl) anthracene (NNPA), mCBP, mCP, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, heterocyclic compounds having a partial structure in which an indole ring is a condensed ring, and the like can be used.
As doping materials, preference is given to using the polycyclic organoboron derivatives of the invention. In addition to these, aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like can be used. Examples thereof include pyrene derivatives, anthracene derivatives, quinacridones, coumarins, rubrenes, perylenes and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, spirobifluorene derivatives, and the like. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers formed by mixing into a film, or a laminated structure of layers formed by film formation alone and layers formed by mixing into a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, and an ink jet method.
As the hole blocking layer of the organic electroluminescent device of the present invention, the polycyclic organoboron derivative of the present invention is preferably used. In addition, the hole-blocking layer may be formed using another compound having a hole-blocking property. For example, a phenanthroline derivative such as 2,4, 6-tris (3-phenyl) -1,3, 5-triazine (T2T), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), Bathocuproine (BCP), a metal complex of a quinolyl derivative such as aluminum (III) bis (2-methyl-8-hydroxyquinoline) -4-phenylphenate (BAlq), and a compound having a hole-blocking effect such as various rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives can be used. These may be used as a single layer formed by separately forming a film or by mixing them with other materials to form a film, or may be used as a laminated structure of layers formed by separately forming a film, a laminated structure of layers formed by mixing films, or a laminated structure of layers formed by separately forming a film and layers formed by mixing films. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, and an ink jet method.
The above-described material having a hole-blocking property can also be used for formation of an electron transport layer described below. That is, by using the known material having a hole-blocking property, a layer which serves as both a hole-blocking layer and an electron-transporting layer can be formed.
As the electron transport layer of the organic electroluminescent element of the present invention, the polycyclic organoboron derivatives of the present invention are preferably used. In addition, the compound may be formed using other compounds having an electron-transporting property. For example, Alq can be used3Metal complexes of quinolinol derivatives including BAlq; various metal complexes; a triazole derivative; a triazine derivative; an oxadiazole derivative; a pyridine derivative; bis (10-hydroxybenzo [ H ]]Quinoline) beryllium (Be (bq)2) (ii) a Such as 2- [4- (9, 10-dinaphthalen-2-anthracen-2-yl) phenyl]-1-phenyl-1H-benzimidazole (Z)ADN), etc.; a thiadiazole derivative; an anthracene derivative; a carbodiimide derivative; quinoxaline derivatives; pyridoindole derivatives; phenanthroline derivatives; silole derivatives and the like. These may be used as a single layer formed by separately forming a film or by mixing them with other materials to form a film, or may be used as a laminated structure of layers formed by separately forming a film, a laminated structure of layers formed by mixing films, or a laminated structure of layers formed by separately forming a film and layers formed by mixing films. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, and an ink jet method.
As the electron injection layer of the organic electroluminescent device of the present invention, a material known per se can be used. For example, alkali metal salts such as lithium fluoride and cesium fluoride; alkaline earth metal salts such as magnesium fluoride; metal complexes of quinolinol derivatives such as lithium quinolinol; and metal oxides such as alumina.
In the electron injection layer or the electron transport layer, a material obtained by further N-doping a metal such as cesium, a triarylphosphine oxide derivative, or the like can be used as a material generally used for the layer.
As the cathode of the organic electroluminescent device of the present invention, an electrode material having a low work function such as aluminum, magnesium, or an alloy having a low work function such as magnesium-silver alloy, magnesium-indium alloy, aluminum-magnesium alloy is preferably used as the electrode material.
As the substrate of the present invention, a substrate in a conventional organic light emitting device, such as glass or plastic, can be used. In the present invention, a glass substrate is selected.
Examples
The production of the compound represented by the above general formula (1) or (2) and the organic electroluminescent device comprising the same is specifically described in the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
Example 1: synthesis of Compound 1
(Synthesis of intermediate 1-1)
To a three-necked flask equipped with a reflux condenser tube, 2, 6-difluoroiodobenzene (10g, 41.67mmol), dibenzofuran-1-ol (16.9g, 91.67mmol), potassium carbonate (23g, 166.68mmol), and 200ml of N-methylpyrrolidone (NMP) were sequentially added under nitrogen atmosphere, and heated under reflux for 6 hours. After the reaction was completed, the system was cooled to room temperature. Adding a large amount of water to generate white precipitate, and performing suction filtration and collection. The precipitate was washed successively with water and methanol (50% (V/V)). Finally, the obtained filter cake was dissolved in an appropriate amount of dichloromethane and further purified by column chromatography (mobile phase: petroleum ether: dichloromethane ═ 3: 1(V/V)) to obtain 20g of a white solid in 83% yield. Ms (ei): m/z: 568.28[ M ]+]。Anal.calcd for C30H17IO4(％)：C 63.40，H 3.01；found：C 63.38，H 3.04。
(Synthesis of Compound 1)
The synthetic route for compound 1 is shown below:
to a dry clean three-necked flask, intermediate 1-1(5.7g, 10.1mmol) and 100mL of m-xylene (m-xylene) were added sequentially under a nitrogen atmosphere, and the system was cooled at-40 ℃. N-butyllithium (5mL, 12.1mmol, 2.4M) was added dropwise to the system, and stirring was continued for 30 mm at this temperature after the addition was completed, followed by further stirring at room temperature for 12 hours. The reaction was cooled to-40 ℃ again and boron tribromide (3.8g, 15.1mmol) was added dropwise. After the addition was complete, the reaction was continued at 50 ℃ for 4 h. The system was then cooled to 0 deg.C, N-ethyldiisopropylamine (2.58g, 20.2mmol) was added, after which the temperature was gradually raised to 125 deg.C and the reaction continued at this temperature for 12 h. After the reaction was completed, the solvent was distilled off under reduced pressure, and the crude product was purified by column chromatography (mobile phase: petroleum ether: dichloromethane: 9: 1(V/V)) to obtain 2.3g of a yellow solid in a yield of 51%. Ms (ei): m/z: 450.24[ M ]+]。Anal.calcd for C30H15BO4(％)：C 80.03，H 3.36；found：C 80.01，H 3.38。
Example 2: synthesis of Compound 26
(Synthesis of intermediate 1-2)
The synthetic route of intermediate 1-2 is shown below:
under a nitrogen atmosphere, compound 1(1.9g, 4.2mmol) was dissolved in 200mL of chloroform and cooled to 0 ℃. To the above system was added dropwise a 10mL solution of N-bromosuccinimide (NBS) (822mg, 4.6mmol) in chloroform. After the dropwise addition, the cooling bath was removed, and the system was allowed to spontaneously warm to room temperature and the reaction was continued at room temperature overnight. After the reaction was completed, the reaction solution was poured into water, extracted with dichloromethane, and the organic phase was washed successively with water, 1N sodium hydroxide solution, and water. After the organic phase was dried, the solvent was removed under reduced pressure, and the obtained crude product was recrystallized from anhydrous ethanol to obtain 2.0g of a pale yellow solid with a yield of 90%. Ms (ei): m/z: 529.08[ M ]+]。Anal.calcd for C30H14BBrO4(％)：C 68.10，H 2.67；found：C 68.09，H 2.70。
(Synthesis of Compound 26)
The synthetic route for compound 26 is shown below:
under the protection of nitrogen, the intermediates 1-2(2.2g, 4.2mmol) and N- ([1,1' -biphenyl) were added in sequence into a 250mL Schlenk bottle]-4-yl) -9, 9-diphenyl-9H-fluoren-2-amine (2.4g, 5mmol), palladium acetate (18mg, 0.08mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (806mg, 8.4mmol) and 120mL of toluene were reacted with stirring under reflux for 12 hours. After completion of the reaction, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane and 50mL of water, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, the organic layers were combined, the solvent was distilled off, the residue was separated by column chromatography (petroleum ether: dichloromethane ═ 2: 1(V/V)), the solvent was distilled off, and after drying, 3.5g of a yellow solid was obtainedBulk, yield 90%. Ms (ei): m/z: 933.82[ M ]+]。Anal.calcd for C67H40BNO4(％)：C 86.17，H 4.32，N 1.50；found：C 86.15，H4.35，N 1.48。
Example 3: synthesis of Compound 133
(Synthesis of intermediate 133-1)
The synthetic route of intermediate 133-1 is shown below:
to a three-necked flask equipped with a reflux condenser tube, 2, 6-difluoroiodobenzene (10g, 41.67mmol), dibenzofuran-4-ol (16.9g, 91.67mmol), potassium carbonate (23g, 166.68mmol), and 200ml of N-methylpyrrolidone (NMP) were sequentially added under nitrogen atmosphere, and heated under reflux for 6 hours. After the reaction was completed, the system was cooled to room temperature. Adding a large amount of water to generate white precipitate, and performing suction filtration and collection. The precipitate was washed successively with water and methanol (50% (V/V)). Finally, the obtained filter cake was dissolved in an appropriate amount of dichloromethane and further purified by column chromatography (mobile phase: petroleum ether: dichloromethane ═ 3: 1(V/V)) to obtain 22g of a white solid in a yield of 93%. Ms (ei): m/z: 568.32[ M ]+]。Anal.calcd for C30H17IO4(％)：C 63.40，H 3.01；found：C 63.39，H 3.03。
(Synthesis of Compound 133)
The synthetic route for compound 133 is shown below:
to a dry clean three-necked flask, intermediate 133-1(5.7g, 10.1mmol) and 100mL of m-xylene (m-xylene) were added sequentially under a nitrogen atmosphere, and the system was cooled at-40 ℃. N-butyllithium (5mL, 12.1mmol, 2.4M) was added dropwise to the system, and stirring was continued for 30 mm at this temperature after the addition was completed, followed by further stirring at room temperature for 12 hours. The reaction was cooled to-40 ℃ again and boron tribromide (3.8g, 15.1mmol) was added dropwise. Dripping deviceAfter the addition was complete, the reaction was continued at 50 ℃ for 4 h. The system was then cooled to 0 deg.C, N-ethyldiisopropylamine (2.58g, 20.2mmol) was added, after which the temperature was gradually raised to 125 deg.C and the reaction continued at this temperature for 12 h. After the reaction was completed, the solvent was distilled off under reduced pressure, and the crude product was purified by column chromatography (mobile phase: petroleum ether: dichloromethane: 9: 1(V/V)) to obtain 2.0g of a yellow solid in 50% yield. Ms (ei): m/z: 450.28[ M ]+]。Anal.calcd for C30H15BO4(％)：C 80.03，H 3.36；found：C 80.02，H 3.39。
Example 4: synthesis of Compound 158
(Synthesis of intermediate 158-1)
The synthetic route of intermediate 158-1 is shown below:
under a nitrogen atmosphere, compound 133(1.9g, 4.2mmol) was dissolved in 200mL of chloroform and cooled to 0 ℃. To the above system was added dropwise a 10mL solution of N-bromosuccinimide (NBS) (822mg, 4.6mmol) in chloroform. After the dropwise addition, the cooling bath was removed, and the system was allowed to spontaneously warm to room temperature and the reaction was continued at room temperature overnight. After the reaction was completed, the reaction solution was poured into water, extracted with dichloromethane, and the organic phase was washed successively with water, 1N sodium hydroxide solution, and water. After the organic phase was dried, the solvent was removed under reduced pressure, and the obtained crude product was recrystallized from anhydrous ethanol to obtain 1.8g of a pale yellow solid with a yield of 81%. Ms (ei): m/z: 529.12[ M ]+]。Anal.calcd for C30H14BBrO4(％)：C 68.10，H 2.67；found：C 68.08，H 2.69。
(Synthesis of Compound 158)
The synthetic route for compound 158 is shown below:
under the protection of nitrogen, intermediate 158-1(2.2g, 4.2mmol) and N- ([1,1' -biphenyl) were added in sequence to a 250mL Schlenk flask]-4-yl) -9, 9-diphenyl-9H-fluoren-2-amine (2.4g, 5mmol), palladium acetate (18mg, 0.08mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (806mg, 8.4mmol) and 120mL of toluene were reacted with stirring under reflux for 12 hours. After the completion of the reaction, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane and 50mL of water, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, the organic layers were combined, the solvent was distilled off, and the residue was separated by column chromatography (petroleum ether: dichloromethane ═ 2: 1(V/V)), the solvent was distilled off, and after drying, 3.4g of a yellow solid was obtained in a yield of 87%. Ms (ei): m/z: 933.82[ M ]+]。Anal.calcd for C67H40BNO4(％)：C 86.17，H 4.32，N 1.50；found：C 86.16，H4.34，N 1.49。
Example 5: preparation of organic electroluminescent device 1 (organic EL device 1)
A hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode 10 were sequentially formed on a transparent anode 2 previously formed on a glass substrate 1 to prepare an organic electroluminescent device as shown in fig. 3.
Specifically, a glass substrate on which an ITO film having a film thickness of 100nm was formed was subjected to ultrasonic treatment in a Decon 90 alkaline cleaning solution, rinsed in deionized water, washed three times in acetone and ethanol, respectively, baked in a clean environment to completely remove moisture, washed with ultraviolet light and ozone, and bombarded on the surface with a low-energy cation beam. Placing the glass substrate with ITO electrode into a vacuum chamber, and vacuumizing to 4 × 10-4-2×10-5Pa. Then, 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN) was deposited on the ITO electrode-equipped glass substrate at a deposition rate of 0.2 nm/sec to form a layer having a film thickness of 10nm as a Hole Injection Layer (HIL). N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB) was vapor-deposited on the hole injection layer at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 40nm as a hole transport layer I (HTL I), and then 9,9' -triphenyl-9H, 9' H-3,3':6', 3' -tricarbazole (Tris-PCz) was vapor-deposited on the hole transport layer I at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 20nm as a hole transport layer I (HTL I)Hole transport layer ii (htl ii). 3,3 '-bis (N-carbazolyl) -1,1' -biphenyl (mCBP) was deposited on the hole transport layer II at a deposition rate of 0.2nm/s to form a layer having a thickness of 15nm as an Electron Blocking Layer (EBL). On the electron blocking layer, double-source co-evaporation was performed at a deposition rate of 0.2nm/s for 9- (4- (1-naphthyl) -10- (2-naphthyl) anthracene (NNPA) as a host material and 0.016nm/s for the compound of example 1 (compound 1) as a dopant material to form a layer with a thickness of 20nm as a light-emitting layer, the doping ratio of the compound 1 was 8 wt%, and the light-emitting layer was formed, 2,4, 6-tris (3-phenyl) -1,3, 5-triazine (T2T) was vapor-deposited at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 10nm as a Hole Blocking Layer (HBL) on the hole blocking layer, 2- [4- (9, 10-dinaphthalene-2-anthracene-2-yl) phenyl is evaporated at an evaporation rate of 0.2 nm/s.]-1-phenyl-1H-benzimidazole (ZADN) to form a layer with a film thickness of 40nm as an Electron Transport Layer (ETL). On the electron transport layer, 8-hydroxyquinoline-lithium (Liq) was vapor-deposited at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 2nm as an electron injection layer. Finally, aluminum was deposited at a deposition rate of 3.0nm/s or more to form a cathode having a film thickness of 100 nm.
Examples 6 to 8: preparation of organic EL devices 2 to 4
Organic EL devices were produced under the same conditions as the organic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of example 5, respectively.
Comparative examples 1 to 2: preparation of organic EL device comparative examples 1 to 2
Comparative examples of organic EL devices were prepared under the same conditions as the organic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of example 5, respectively.
The examples relate to compounds having the following structure:
TABLE 1
The light emission characteristics of the organic EL devices 1 to 4 produced in examples 5 to 8 and the organic EL devices produced in comparative examples 1 to 2 were measured at normal temperature under the application of a direct current voltage in the atmosphere. The measurement results are shown in table 2.
Testing the performance of the device: the current-luminance-voltage characteristics of the device were obtained from a Keithley source measuring system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with a calibrated silicon photodiode, the electroluminescence spectra were measured by a Photo research PR655 spectrometer, and the external quantum efficiency of the device was calculated by the method of the literature (adv. mater.,2003,15, 1043-. The device lifetime refers to the time for the luminance to decay to 9000 candelas per square meter (90%) starting at 10000 candelas per square meter. All devices were encapsulated in a nitrogen atmosphere.
The fluorescence spectra of the compounds of examples 1 and 3 were measured using a Hitachi F4600 spectrofluorometer with the amount of the substance in the solution at a concentration of 10-5M。
TABLE 2
As can be seen from Table 2, the luminous efficiency and the device lifetime of the green and blue organic electroluminescent devices prepared using the polycyclic organoboron derivatives of the present invention are significantly improved as compared with those of comparative examples 1 and 2. In addition, the color purity of the blue organic electroluminescent device is obviously better than that of the organic electroluminescent device prepared by adopting the sky blue material DPAVBi in the prior art.
Industrial applicability
The polycyclic organic boric acid derivative has excellent luminous efficiency, material color purity and life characteristics. Therefore, an organic electroluminescent device having an excellent lifetime can be prepared from the polycyclic organic boronic acid derivative of the present invention.
Claims (10)
1. A polycyclic organoboron derivative, characterized by being represented by the following general formula (1) or general formula (2):
in the above general formula (1) or general formula (2),
L1、L2and L3Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms;
A1、A2and A3Each independently represents Ar1、Ar2、Ar3、
One or more of;
Ar1～Ar6each independently represents a hydrogen atom, a cyano group, optionally substituted by one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、-N(R2)2、-OR2、-SR2、-C(＝O)R2、-P(＝O)R2、-Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atomsOne or more than one;
m, n and p are each independently an integer of 0 to 4, and m, n and p are not simultaneously 0.
2. A polycyclic organoboron derivative according to claim 1, which is represented by the following general formula (I), general formula (II), general formula (III) or general formula (IV):
in the above general formula (I), general formula (II), general formula (III) or general formula (IV), L1～L3、Ar1～Ar6And m, n and p have the meanings as defined in claim 1.
3. A polycyclic organoboron derivative according to claim 1, where Ar is Ar1、Ar2、Ar3、Ar4、Ar5And Ar6Each independently selected from the following groups:
wherein the dotted line represents and L1、L2、L3Or a bond to an N atom;
R1have the meaning as defined in claim 1.
4. A polycyclic organoboron derivative according to any of claims 1 to 3, where R is R1And R2Each independently represents a phenyl groupOne or more of biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazole, benzofurocarbazole, benzofluorenocarbazole, benzanthracene, triphenylene, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron group, triphenyl phosphoxy, diphenyl phosphoxy, triphenyl silyl, or tetraphenyl silyl.
5. A polycyclic organoboron derivative according to any of claims 1 to 4, wherein the polycyclic organoboron derivative represented by the general formula (1) or the general formula (2) is selected from the group consisting of:
6. an electronic device comprising the polycyclic organoboron derivative of any one of claims 1 to 5.
7. The electronic device according to claim 6, wherein the electronic device is an organic electroluminescent device, an organic field effect transistor, or an organic solar cell;
wherein the organic electroluminescent device comprises: a first electrode, a second electrode provided so as to face the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the at least one organic layer comprises the polycyclic organoboron derivative according to any one of claims 1 to 5.
8. The electronic device of claim 7, wherein the at least one organic layer is a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer.
9. Use of a polycyclic organoboron derivative according to any one of claims 1 to 5 as a light emitting material, an electron transporting material, an electron blocking material, a hole injecting material, or a hole blocking material in an electronic device.
10. Use according to claim 9, characterized in that the electronic device is an organic electroluminescent device, an organic field effect transistor or an organic solar cell.
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| CN114605455A (en) * | 2022-03-25 | 2022-06-10 | 中国科学院长春应用化学研究所 | Compound containing bridged trimeric indole and organic boron condensed ring structure and organic electroluminescent device |
| CN114685545A (en) * | 2020-12-29 | 2022-07-01 | 乐金显示有限公司 | Light-emitting compound and organic light-emitting device comprising same |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111647010A (en) * | 2020-06-02 | 2020-09-11 | 苏州久显新材料有限公司 | Polycyclic boron-containing compound and electronic device thereof |
| CN111647009A (en) * | 2020-06-02 | 2020-09-11 | 苏州久显新材料有限公司 | Boron-containing compound and electronic device thereof |
| CN111647009B (en) * | 2020-06-02 | 2023-04-07 | 苏州久显新材料有限公司 | Boron-containing compound and electronic device thereof |
| WO2022034916A1 (en) * | 2020-08-12 | 2022-02-17 | 学校法人関西学院 | Polycyclic aromatic compound |
| WO2022114407A1 (en) * | 2020-11-26 | 2022-06-02 | 경희대학교 산학협력단 | Delayed fluorescence compound, and organic light-emitting device comprising same |
| CN114685545A (en) * | 2020-12-29 | 2022-07-01 | 乐金显示有限公司 | Light-emitting compound and organic light-emitting device comprising same |
| EP4023653A1 (en) * | 2020-12-29 | 2022-07-06 | LG Display Co., Ltd. | Emitting compound and organic light emitting device including the same |
| WO2023113124A1 (en) * | 2021-12-16 | 2023-06-22 | 엘지디스플레이 주식회사 | Organic light-emitting diode and organic light-emitting device comprising same |
| CN114605455A (en) * | 2022-03-25 | 2022-06-10 | 中国科学院长春应用化学研究所 | Compound containing bridged trimeric indole and organic boron condensed ring structure and organic electroluminescent device |
| CN114605455B (en) * | 2022-03-25 | 2024-02-20 | 中国科学院长春应用化学研究所 | Compound containing bridged trimerization indole and organoboron condensed ring structure and organic electroluminescent device |
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