CN115368343A - Compound with pyridine derivative as core and application thereof - Google Patents
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- CN115368343A CN115368343A CN202110538133.4A CN202110538133A CN115368343A CN 115368343 A CN115368343 A CN 115368343A CN 202110538133 A CN202110538133 A CN 202110538133A CN 115368343 A CN115368343 A CN 115368343A
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Abstract
The invention relates to a compound taking pyridine derivatives as a core and application thereof, belonging to the technical field of semiconductors, and the structure of the compound provided by the invention is shown as a general formula (1): the invention also discloses application of the compound. When the compound is used as a light-emitting layer material of an OLED light-emitting device, a TADF effect can be generated, the voltage of the device can be effectively reduced, the light-emitting efficiency of the device can be improved, and the service life of the device can be prolonged.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a compound taking a pyridine derivative as a core and application thereof.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED luminescent device is of a sandwich structure and comprises electrode material film layers and organic functional materials sandwiched between the different electrode material film layers, and the various organic functional materials are mutually superposed together according to purposes to form the OLED luminescent device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
The development and the use of the light-emitting layer material of the OLED are carried out in three main stages, wherein the first stage mainly adopts a fluorescence light-emitting mechanism, the second stage mainly adopts a phosphorescence light-emitting mechanism, and the third stage adopts a TADF material as the light-emitting layer material, so that triplet excitons are effectively utilized, and the light-emitting efficiency of the device is improved. The TADF material is developed to the present, has abundant application in a luminescent layer, has controllable structure, stable property and low price, does not need precious metal, and has wide application prospect in the field of OLEDs.
Theoretically, the TADF material can realize 100% exciton utilization rate through the reverse intersystem crossing from the triplet state to the singlet state, but in the process of actually using as a host or doping, the device effect is not good, and the following problems still exist: since the TADF material design requires a smaller S1-T1 band gap, a fast intersystem crossing rate (shorter delayed luminescence lifetime) and a high fluorescence quantum yield are difficult to achieve.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a compound taking a pyridine derivative as a core and application thereof, wherein the compound contains a specific cyano-group and carbazole substituted pyridine structure, so that the compound has shorter delayed luminescence life and higher fluorescence quantum yield, and the efficiency and the service life of an OLED device can be effectively improved.
The technical scheme of the invention is as follows:
a compound with a pyridine derivative as a core has a structure shown as a general formula (1):
in the general formula (1), ra, rb, rc, rd and Re are respectively expressed by H, CN, a structure shown in a general formula (2), a structure shown in a general formula (3) or a structure shown in a general formula (4) which are the same or different;
one and only two of Ra, rb, rc, rd and Re are represented by CN, and two are represented by a structure shown in a general formula (4);
when Rb represents CN, ra is the same as Rc, re is not the same as Rd or Re is the same as Rd, ra is not the same as Rc;
in the general formula (2), X 1 -X 6 Each independently represents N or C-R 1 ；
In the general formula (3), Y 1 -Y 8 Each independently represents N or C-R 2 (ii) a Z is O, S or N-R 3 ；
In the general formula (4), A 1 -A 8 Each independently is N or C-R 4 ；
R 1 、R 2 、R 4 Each occurrence is independently represented by H, deuterium atom, halogen atom, cyano, C 1 -C 10 Alkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 One of the heteroaryl groups of (a); any adjacent R 1 Can be connected into a ring; any adjacent R 2 Can be connected into a ring; any adjacent R 4 Can be connected into a ring;
R 3 is represented by substituted orOr unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 One of the heteroaryl groups of (a);
the substituents for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C 1 -C 10 Alkyl radical, C 3 -C 20 Cycloalkyl radical, C 6 -C 30 Aryl radical, C 3 -C 30 One of heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
Preferably, the structure of the compound is shown as a general formula (5):
in the general formula (5), rb and Re are represented by H, a structure shown in a general formula (2) or a structure shown in a general formula (3) which are the same or different; and Rb and Re are not H at the same time.
Preferably, when Rc is CN, only two of Ra, rb, re and Rd are represented by the general formula (4), and the other two are each H or any of the structures represented by the general formulae (2) to (3), and the number of H is 0 or 1.
Preferably, when Rb is CN, only two of Ra, rc, re and Rd are represented by the general formula (4), and the other two are each H or any of the structures represented by the general formulae (2) to (3), and the number of H is 0 or 1; and Ra is the same as Rc, and Re is not the same as Rd; alternatively, when Re is the same as Rd, ra is different from Rc.
Preferably, in the general formula (5), rb and Re are represented by H or a structure shown in the general formula (2) which are the same or different; and Rb and Re are not H at the same time.
Preferably, when Rc is CN, ra and Rd are represented by a structure shown in a general formula (4), rb and Re are represented by H, a structure shown in a general formula (2) or a structure shown in a general formula (3), and Rb and Re are not H at the same time; or Rb and Re represent a structure represented by a general formula (4); ra and Rd represent H, a structure represented by general formula (2) or general formula (3), and Ra and Rd are not H at the same time.
Preferably, when Rb represents CN, ra and Rc represent structures represented by a general formula (4), and Re and Rd represent H, a structure represented by a general formula (2) or a structure represented by a general formula (3); and Ra is the same as Rc, and Re is not the same as Rd; or when Re is the same as Rd, ra is different from Rc; re and Rd are not H at the same time.
In the preferable scheme, when Rb is represented by CN, re and Rd are represented by a structure shown in a general formula (4); ra and Rc represent H, a structure shown in a general formula (2) or a general formula (3); and Ra is the same as Rc, and Re is not the same as Rd; or, when Re is the same as Rd, ra is not the same as Rc; ra and Rc are not H at the same time.
In a preferred embodiment, the R 1 、R 2 、R 4 Each independently represents one of H, deuterium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, cyclohexyl group, adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted terphenylyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9, 9-dimethylfluorenyl group, and substituted or unsubstituted 9, 9-diphenylfluorenyl group; any adjacent R 1 To form a phenyl, naphthyl, phenanthryl, triphenylene, benzofuranyl, benzothienyl, or phenylindoline group; any adjacent R 2 To form a phenyl, naphthyl, benzofuranyl, benzothienyl or phenylindoline group; any adjacent R 4 To form a phenyl, phenanthryl, triphenylene, benzofuranyl, benzothienyl or phenylindoline group;
the R is 3 Represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl and substituted or unsubstituted terphenylyl;
the substituent for the substituent group is optionally selected from a halogen atom, a deuterium atom, a tritium atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a cyclohexyl group, a heptyl group, an adamantyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyrimidinyl group, a pyridyl group, a dibenzofuranyl group, a carbazolyl group or a dibenzothiophenyl group.
Preferably, the specific structure of the compound is any one of the following structures:
an organic electroluminescent device comprises an anode, a cathode and an organic luminescent functional layer between the anode and the cathode, wherein the organic luminescent functional layer contains the compound taking the pyridine derivative as the core.
The organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the organic compound taking the pyridine derivative as the core.
The light-emitting layer comprises a first host material, a second host material and a doping material, wherein the first host material is a TADF material, and the second host material is the compound taking the pyridine derivative as a core.
Compared with the prior art, the invention has the beneficial technical effects that:
when the compound is used as a light-emitting layer of an organic light-emitting element, the compound has a proper HOMO energy level, smaller delta Est and higher fluorescence quantum yield, so that the material can fully utilize triplet state energy when being used as a main material, and the light-emitting efficiency of a device is improved; the compound has cyanopyridine and two carbazole groups, so that the compound has shorter delay life and can prolong the service life of a device.
Drawings
FIG. 1 is a schematic diagram of the structure of an OLED device to which the compounds of the present invention are applied;
wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments and the drawings, and the embodiments and features in the embodiments of the present invention may be combined with each other without conflict. The invention is further described with reference to the following drawings and specific examples, which are not intended to be limiting.
In the present invention, unless otherwise specified, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule. Further, in the present invention, HOMO and LUMO energy levels are represented by absolute values, and the comparison between energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of the energy level.
Any numerical range recited herein is intended to include all sub-ranges subsumed within the range with the same numerical precision. For example, "1.0 to 10.0" is intended to include all sub-ranges between (and including 1.0 and 10.0) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, all sub-ranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limitation recited herein is intended to include all smaller numerical limitations subsumed therein, and any minimum numerical limitation recited herein is intended to include all larger numerical limitations subsumed therein. Accordingly, applicants reserve the right to modify the specification, including the claims, to specifically describe any sub-ranges that fall within the ranges specifically described herein.
In the drawings, the size of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, and other structures, terms such as "upper", "lower", "top", and "bottom" used to indicate orientations only indicate orientations in a certain specific state, and do not mean that the related structures can exist only in the orientations; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of the electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side away from the substrate is the "top" side.
In this specification, "aryl" refers to a group having at least one aromatic hydrocarbon moiety and substantially aromatic hydrocarbon moieties linked by a single bond and a non-aromatic fused ring comprising aromatic hydrocarbon moieties that are directly or indirectly fused. Aryl groups can be monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.
In the present specification, "heteroaryl" includes at least one heteroatom selected from N, O and S other than a cyclic group of carbon (C) of a cyclic compound, such as aryl, cycloalkyl, fused ring or a combination thereof. Each or all of the rings of the heteroaryl group may contain at least one heteroatom.
More precisely, substituted or unsubstituted C 6 -C 30 Aryl and/or substituted or unsubstituted C 3 -C 30 Heteroaryl means substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substitutedOr unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted paratriphenylene, substituted or unsubstituted metaterphenylene, substituted or unsubstituted terphenylene
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C according to the invention 1 -C 10 Alkyl (including straight-chain and branched-chain alkyl) means methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, and the like, but is not limited thereto.
The halogen atom in the present invention refers to a chlorine atom, a fluorine atom, a bromine atom or the like, but is not limited thereto.
C according to the invention 3 -C 20 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 20 carbon atoms as ring-forming atoms. In this context, preference is given to using C 4 -C 9 Cycloalkyl, more preferably C 5 -C 8 Cycloalkyl, particularly preferably C 5 -C 7 A cycloalkyl group. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, adamantyl and cycloheptyl.
Organic electroluminescent device
The invention provides an organic electroluminescent device, which comprises an anode, a cathode and an organic luminescent functional layer between the anode and the cathode, wherein the organic luminescent functional layer contains the compound taking pyridine derivatives as cores.
In a preferred embodiment of the present invention, the organic light-emitting functional layer includes a light-emitting layer containing the pyridine derivative-based compound as a core.
In a preferred embodiment of the present invention, the light-emitting layer includes a first host material, a second host material, and a dopant material, the first host material is a TADF material, and the second host material is the pyridine derivative-based compound.
Fig. 1 is a schematic structural diagram of the compound of the present invention applied to an OLED device, where 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples are transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
A first electrode may be formed on the substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), indium Tin Zinc Oxide (ITZO), or the like. When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, mg, al, pt, pd, au, ni, nd, ir, cr, or a metal mixture. The thickness of the first electrode layer depends on the material used and is typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.
The organic functional material layer arranged between the first electrode and the second electrode sequentially comprises a hole transport region, a light emitting layer and an electron transport region from bottom to top.
Herein, the hole transport region constituting the organic electroluminescent device may be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.
As the materials of the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.
Examples of the above-mentioned materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrylanthracene derivatives, styrylamine derivatives and like styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline-based copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene ethylene and derivatives thereof, polythiophene and derivatives thereof, conductive polymer oligomers such as poly-N-vinylcarbazole derivatives and thiophene oligomers, aromatic tertiary amine compounds, styrene amine compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4' -bis (diarylamine) biphenyls, and the like bis [4- (diarylamino) phenyl ] methanes, 4 '-bis (diarylamino) terphenyls, 4' -bis (diarylamino) quaterphenyls, 4 '-bis (diarylamino) diphenyl ethers, 4' -bis (diarylamino) diphenylsulfanes, bis [4- (diarylamino) phenyl ] dimethylmethanes, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes, 2-diphenylethylene compounds, and the like.
Furthermore, according to the matching requirements of the devices, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a superposition structure of a plurality of hole transport materials. In this context, the film thickness of the hole carrier conducting film layer having the above-described various functions is not particularly limited.
The hole injection layer comprises a host organic material that conducts holes and a P-type dopant material having a deep HOMO level (and correspondingly a deep LUMO level). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO level of the host organic material used for the anode interface buffer layer to conduct holes must have certain characteristics with the P-doped material, so that the generation of a charge transfer state between the host material and the doped material is expected to be realized, ohmic contact between the buffer layer and the anode is realized, and efficient injection from the electrode to hole injection conduction is realized.
In view of the above empirical summary, for the hole-type host materials with different HOMO levels, different P-doped materials need to be selected and matched to realize ohmic contact at the interface, so as to improve the hole injection effect.
Thus, in one embodiment of the present invention, for better hole injection, the hole injection layer further comprises a P-type dopant material having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"- ((1E, 1' E) -cyclopropane-1, 2, 3-trimethylenetri (cyanoformylidene)) tris (2, 3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type dopant material used is 99.
The thickness of the hole injection layer of the present invention may be 5 to 100nm, preferably 5 to 50nm and more preferably 5 to 20nm, but the thickness is not limited to this range.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 150nm and more preferably 20 to 100nm, but the thickness is not limited to this range.
The thickness of the electron blocking layer of the present invention may be 1 to 20nm, preferably 5 to 10nm, but the thickness is not limited to this range.
After the hole injection layer, the hole transport layer, and the electron blocking layer are formed, a corresponding light emitting layer is formed over the electron blocking layer.
The light-emitting layer may contain a host material using the pyridine derivative-based organic compound of the present invention and a dopant material.
In the light-emitting layer of the present invention, the ratio of the host material to the guest material used is 99.
The thickness of the light emitting layer may be adjusted to optimize light emitting efficiency and driving voltage. A preferable range of the thickness is 5nm to 50nm, further preferably 10 to 50nm, and more preferably 15 to 30nm, but the thickness is not limited to this range.
In the present invention, the electron transport region may include, in order from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed over the light emitting layer, but is not limited thereto.
The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light emitting layer to the cathode, thereby extending the lifetime of the device and improving the performance of the device. The hole blocking layer of the present invention may be disposed over the light emitting layer. As the hole-blocking layer material of the organic electroluminescent device of the present invention, compounds having a hole-blocking effect known in the art can be used, for example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, pyridine derivatives, pyrimidine derivatives such as 9,9'- (5- (6- ([ 1,1' -biphenyl ] -4-yl) -2-phenylpyrimidin-4-yl) -1, 3-phenylene) bis (9H-carbazole) (CAS No. 1345338-69-3), and the like. The hole blocking layer of the present invention may have a thickness of 2 to 200nm, preferably 5 to 150nm, and more preferably 10 to 100nm, but the thickness is not limited to this range.
The electron transport layer may be disposed over the light-emitting layer or, if present, the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, an electron transport layer material for organic electroluminescent devices known in the art, for example, in Alq, can be used 3 Metal complexes of hydroxyquinoline derivatives represented by BAlq and Liq, various rare earth metal complexes, triazole derivatives, pyridine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-pyridine (CAS No.: 1459162-51-6), 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG 201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silyl compound derivatives, and the like. The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
The electron injection layer may be disposed over the electron transport layer. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
The second electrode may be disposed over the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may comprise, for example, li, yb, ca, liF/Al, mg, baF, ba, ag, or compounds or mixtures thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, mg, yb, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Al, mo, ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20nm.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
A method for preparing the organic electroluminescent device of the present invention comprises sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, LITI, or the like may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum evaporation method. The individual process conditions in the vacuum evaporation process can be routinely selected by the person skilled in the art according to the actual requirements.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
The raw materials involved in the synthetic examples of the present invention are either commercially available or prepared by conventional preparation methods in the art;
example 1:
preparation of Compound 1
Starting material A1 (1.35 mmol), K 2 CO 3 (3.38mmol)，Pd(OAc) 2 (0.0405 mmol) and Pcy3 (0.122 mmol) were charged into a two-necked flask, which was evacuated and purged with nitrogen 3 times. To the reaction mixture was added the starting material B1 (3.0 mmol), 2-ethylhexanoic acid (0.135 mmol) and xylene (10 mL), and stirred at room temperature for 15 minutes, then heated to 140 ℃. After stirring for 18 hours, the reaction mixture was cooled to room temperature and diluted with CHCl 3 Diluted (10 mL) and water (10 mL) and filtered through a pad of celite, then with CHCl 3 And (5) washing. The aqueous layer was separated and washed with CHCl 3 (20 mL) was extracted. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate to give intermediate 1.LC-MS (m/z): theoretical value: 292.08, found: 293.15 ([ M + H)] + )。
Intermediate 1 (0.90 mmol), K 2 CO 3 (3.0 mmol), starting material C1 (2.20 mmol) and DMF (10 ml) were charged to a three-necked flask, which was then heated to 120 ℃. After stirring for 2 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the mixture was purified by column chromatography on silica gel using hexane/chloroform as eluent, to give compound 1. Elemental analysis Structure (C) 42 H 26 N 4 ) Theoretical values are as follows: c,85.98; h,4.47; n,9.55; test values are: c,85.96; h,4.50; and N,9.50.LC-MS (m/z): theoretical value: 586.22, found: 587.25 ([ M + H)] + )。
Examples 2-example 11 were prepared similarly to example 1, except that feedstock B and feedstock C were used, and the following table lists the structural formulae of feedstock B, feedstock C and the product.
TABLE 1
EXAMPLE 12 Synthesis of Compound 273
Starting materials D1 (1.34 mmol), K 2 CO 3 (3.38mmol)，Pd(OAc) 2 (0.0405 mmol) and Pcy3 (0.122 mmol) were charged in a two-necked flask, which was evacuated and purged with nitrogen 3 times. To the reaction mixture were added the starting material E1 (3.0 mmol), 2-ethylhexanoic acid (0.135 mmol) and xylene (10 mL), and stirred at room temperature for 15 minutes, then heated to 140 ℃. After stirring for 18 hours, the reaction mixture was cooled to room temperature and diluted with CHCl 3 Diluted (10 mL) and water (10 mL) and filtered through a pad of celite, then with CHCl 3 And (5) washing. The aqueous layer was separated and washed with CHCl 3 (20 mL) was extracted. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate to give intermediate F1.LC-MS (m/z): theoretical value: 292.08, found: 293.17 ([ M + H)] + )。
Intermediate F1 (0.90 mmol), K 2 CO 3 (2.03 mmol), starting material G1 (1.00 mmol) and DMF (10 ml) were charged to a three-necked flask, which was then heated to 120 ℃. After stirring for 2 hours, the reaction mixture was cooled to room temperature, poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the mixture was purified by column chromatography on silica gel using hexane/chloroform as eluent to give intermediate H1.LC-MS (m/z): theoretical values are as follows: 529.16, found: 530.20 ([ M + H ]] + )。
Intermediate H1 (0.90 mmol), K 2 CO 3 (2.03 mmol), starting material J1 (1.00 mmol) and DMF (10 ml) were charged to a three-necked flaskAnd then heated to 120 ℃. After stirring for 2 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the mixture was purified by column chromatography on silica gel using hexane/chloroform as eluent, to give compound 273. Elemental analysis Structure (C) 60 H 35 N 5 O) theoretical value: c,85.59; h,4.19; n,8.32; test values: c,85.58; h,4.25; and N,8.30.LC-MS (m/z): theoretical values are as follows: 841.28, found: 842.30 ([ M + H ]] + )。
EXAMPLE 13 Synthesis of Compound 289
Compound 289 was prepared analogously to example 12, with the exception that starting material G1 was replaced with starting material G2 to give intermediate H2, LC-MS (m/z): theoretical values are as follows: 439.15, found: 440.18 ([ M + H ]] + ) (ii) a The raw material J1 is replaced by the raw material J2 to obtain a compound 289 with an element analysis structure (C) 46 H 28 N 4 ) Theoretical values are as follows: c,86.77; h,4.43; n,8.80; test values: c,86.78; h,4.46; and N,8.76.LC-MS (m/z): theoretical value: 636.23, found: 637.29 ([ M + H ]] + )。
EXAMPLE 14 Synthesis of Compound 308
Compound 308 is prepared similarly to example 12, except that starting material J1 is replaced with starting material J2 to give compound 308, elemental analysis Structure (C) 52 H 32 N 4 O); theoretical values are as follows: c,85.69; h,4.43; n,7.69; test values are: c,85.70; h,4.45; and N,7.65.LC-MS (m/z): theoretical value: 728.26, found: 729.31 ([ M + H)] + )。
The compound of the present invention is used in a light-emitting device, and can be used as a material for a light-emitting layer. The physicochemical properties of the compounds prepared in the above examples of the present invention were measured, and the results are shown in table 2:
TABLE 2
Note: HOMO is the highest occupied molecular orbital energy level; Δ Est: singlet and triplet energy level differences; τ: transient fluorescence lifetime; PLQY: fluorescence quantum yield; the singlet energy level S1 and the triplet energy level T1 were measured by a Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 × 10 -5 A toluene solution of mol/L,. DELTA.Est = S1-T1; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is in an atmospheric environment; PLQY and τ were measured by Horiba's Fluorolog-3 series fluorescence spectrometer.
As can be seen from the data in the table above, the compound of the present invention has a suitable energy level, a short delayed fluorescence lifetime and a high fluorescence quantum yield, and can be applied to a light emitting layer of an OLED device as a main body, thereby obtaining an OLED device with high efficiency and long lifetime.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-14 and device comparative examples 1-3. Compared with the device comparative example 1, the device examples 1 to 14 and the device comparative examples 2 to 3 of the present invention have the same manufacturing process, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent, except that the material of the light emitting layer in the device is replaced. The layer structures and test results of the device embodiments are shown in tables 3 and 4, respectively.
Device comparative example 1
As shown in FIG. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (having a film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97. Then, HT-1 was evaporated to a thickness of 60nm as a hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, CBP is used as a first main body, ref-1 is used as a second main body, GD-1 is used as a green light doping material, the mass ratio of CBP, ref-1 and GD-1 is 67. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated, the mass ratio of ET-1 to Liq was 1, the film thickness was 30nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1.
Device comparative example 2, device comparative example 3, and device examples 1 to 14 were prepared in the same manner.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected using a well-known driving circuit, and the current efficiency, voltage, and lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 3.
TABLE 3
TABLE 4
Note: current efficiency, voltage were tested using the IVL (current-voltage-brightness) test system (frarda scientific instruments ltd, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95%; all data were at 10mA/cm 2 And (4) testing.
From the application of the data, compared with comparative examples 1-3 of devices, the OLED light-emitting device using the compound of the invention as a light-emitting layer material has greatly improved device efficiency and device service life compared with the OLED devices made of known materials, and has unexpected application effects and good industrialization prospects.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A compound with a pyridine derivative as a core is characterized in that the structure of the compound is shown as a general formula (1):
in the general formula (1), ra, rb, rc, rd and Re are respectively represented by H, CN, a structure shown in a general formula (2), a structure shown in a general formula (3) or a structure shown in a general formula (4) which are the same or different;
one and only two of Ra, rb, rc, rd and Re are represented by CN, and two are represented by a structure shown in a general formula (4);
when Rb represents CN, ra is the same as Rc, re is not the same as Rd or Re is the same as Rd, ra is not the same as Rc;
in the general formula (2), X 1 -X 6 Each independently represents N or C-R 1 ；
In the general formula (3), Y 1 -Y 8 Each independently is N or C-R 2 (ii) a Z is O, S or N-R 3 ；
In the general formula (4), A 1 -A 8 Each independently is N or C-R 4 ；
R 1 、R 2 、R 4 Each occurrence is independently represented by H, deuterium atom, halogen atom, cyano, C 1 -C 10 Alkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 One of the heteroaryl groups of (a); any adjacent R 1 Can be connected into a ring; any adjacent R 2 Can be connected into a ring; any adjacent R 4 Can be connected into a ring;
R 3 is represented by substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 One of the heteroaryl groups of (a);
the substituents for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C 1 -C 10 Alkyl radical, C 3 -C 20 Cycloalkyl radical, C 6 -C 30 Aryl radical, C 3 -C 30 One of heteroaryl;
the heteroatom in the heteroaryl is selected from one or more of oxygen, sulfur or nitrogen.
2. The pyridine derivative-based compound according to claim 1, wherein the structure of the compound is represented by general formula (5):
in the general formula (5), rb and Re are represented by H, a structure shown in a general formula (2) or a structure shown in a general formula (3) which are the same or different; and Rb and Re are not H at the same time.
3. The pyridine derivative-based compound according to claim 1, wherein when Rc represents CN, only two of Ra, rb, re and Rd represent a structure represented by the general formula (4), and the other two represent H and any one of the structures represented by the general formulae (2) to (3), and the number of H is 0 or 1; when Rb is CN, only two of Ra, rc, re and Rd are represented by a structure shown in a general formula (4), the other two are respectively represented by H and any one of structures shown in general formulas (2) to (3), and the number of H is 0 or 1; and Ra is the same as Rc, and Re is not the same as Rd; alternatively, when Re and Rd are the same, ra and Rc are not the same.
4. The pyridine derivative-based compound according to claim 2, wherein in the general formula (5), rb and Re may be the same or different and each represents H or a structure represented by the general formula (2); and Rb and Re are not H at the same time.
5. A pyridine derivative-based compound according to claim 3, wherein when Rc represents CN, ra and Rd represent a structure represented by general formula (4), rb and Re represent H, a structure represented by general formula (2) or a structure represented by general formula (3), and Rb and Re do not represent H at the same time; or Rb and Re represent a structure represented by a general formula (4); ra and Rd represent H, a structure shown in a general formula (2) or a general formula (3), and Ra and Rd are not H at the same time; when Rb is CN, ra and Rc are structures shown in a general formula (4), and Re and Rd are H, structures shown in a general formula (2) or a general formula (3); and Ra is the same as Rc, and Re is not the same as Rd; or, when Re is the same as Rd, ra is not the same as Rc; re and Rd are not H at the same time.
6. The compound having a pyridine derivative as a core according to claim 3, wherein when Rb is CN, re and Rd are represented by the formula (4); ra and Rc represent H, a structure represented by general formula (2) or general formula (3); and Ra is the same as Rc, and Re is not the same as Rd; or, when Re is the same as Rd, ra is not the same as Rc; ra and Rc are not H at the same time.
7. A pyridine derivative-based compound according to claim 1, wherein R is 1 、R 2 、R 4 Each independently represents one of H, deuterium atom, fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, cyclohexyl group, adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted terphenylyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9, 9-dimethylfluorenyl group, and substituted or unsubstituted 9, 9-diphenylfluorenyl group; any adjacent R 1 To form a phenyl, naphthyl, phenanthryl, triphenylene, benzofuranyl, benzothienyl, or phenylindoline group; any adjacent R 2 To form a phenyl, naphthyl, benzofuranyl, benzothienyl or phenylindoline group; any adjacent R 4 To form a phenyl, phenanthryl, triphenylene, benzofuranyl, benzothienyl, or phenylindoline group;
the R is 3 Represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted terphenyl;
the substituent for the substituent group is optionally selected from a halogen atom, a deuterium atom, a tritium atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a cyclohexyl group, a heptyl group, an adamantyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyrimidinyl group, a pyridyl group, a dibenzofuranyl group, a carbazolyl group or a dibenzothiophenyl group.
8. The pyridine derivative-based compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
9. an organic electroluminescent element comprising an anode and a cathode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer contains a pyridine derivative-based compound according to any one of claims 1 to 8; the organic light-emitting functional layer includes a light-emitting layer containing the pyridine derivative-based organic compound according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a first host material, a second host material and a dopant material, the first host material is a TADF material, and the second host material is the pyridine derivative-based compound according to any one of claims 1 to 8.
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