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CN117603209A - Organic compound, organic electroluminescent device and electronic device comprising the same - Google Patents

Organic compound, organic electroluminescent device and electronic device comprising the same Download PDF

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Publication number
CN117603209A
CN117603209A CN202310560094.7A CN202310560094A CN117603209A CN 117603209 A CN117603209 A CN 117603209A CN 202310560094 A CN202310560094 A CN 202310560094A CN 117603209 A CN117603209 A CN 117603209A
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organic compound
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刘文强
张鹤鸣
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application belongs to the technical field of organic electroluminescence, and provides an organic compound, an organic electroluminescent device comprising the same and an electronic device. The organic compound has a structure shown in formula I, and is used as an organic light-emitting layerThe prepared organic electroluminescent device has good photoelectric performance.

Description

Organic compound, organic electroluminescent device and electronic device comprising the same
Technical Field
The invention relates to the field of organic electroluminescence, in particular to an organic compound, an organic electroluminescent device comprising the same and an electronic device comprising the same.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transporting layer, an electron transporting layer, and the like. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.
At present, in the use process of the material of the luminous layer, the material is easy to crystallize due to repeated charge and discharge, and the uniformity of the film is destroyed, so that the service life of the material is influenced. Therefore, it is necessary to develop a stable and efficient organic material, thereby reducing a driving voltage, improving a light emitting efficiency of the device, and extending a lifetime of the device, to further improve performance of the organic electroluminescent device.
Disclosure of Invention
The object of the present application is to provide an organic compound, an organic electroluminescent device and an electronic apparatus including the same, which can improve the performance of the device by using the organic compound in the organic electroluminescent device.
According to a first aspect of the present application, there is provided an organic compound having a structure represented by formula I:
wherein X is N (R) 3 ) O or S, R 3 Selected from substituted or unsubstituted phenyl, substituted or unsubstitutedPhenylene of (a);
R 3 the substituents on the substrate are independently selected from deuterium, cyano, halogen, alkyl with 1-5 carbon atoms, deuterated aryl with 6-12 carbon atoms or aryl with 6-12 carbon atoms;
ring A is selected from aromatic rings with 6-14 carbon atoms;
L 1 、L 2 and L 3 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
R 1 and R is 2 The same or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 3 to 20 carbon atoms;
n 1 is R 1 Number n of (n) 1 Selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 is R 2 Number n of (n) 2 Selected from 0, 1,2, 3 or 4; when n is 2 When the number is greater than 1, any two R 2 The same or different;
L 1 、L 2 、L 3 and Ar are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, deuteroaryl group having 6 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar may form a saturated or unsaturated 3-15 membered ring.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
In the molecular structure of the organic compound, the heteroaromatic ring formed by the benzo seven-membered heterocycle has large plane conjugation performance, so that not only can the glass transition temperature of the material be improved, but also the conjugation between molecules can be enhanced, and the deep HOMO is formed, and meanwhile, the high LUMO is formed. Meanwhile, the N bonding of the heteroaromatic ring and the indolocarbazole can increase the molecular conjugation, so that the efficiency is effectively improved, and further, a high-efficiency device of the material is realized. Even in a smaller molecular weight, the organic compound of the present application has a high Tg, and thus can prevent recrystallization at the time of driving, with higher stability. Therefore, the compound is used as an organic light-emitting layer material to be evaporated into the organic electroluminescent device, so that the luminous efficiency of the device can be improved, and the working voltage can be improved to a certain extent.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
321. First hole transport layer 322, second hole transport layer 330, organic light emitting layer 340, and electron transport layer
350. Electron injection layer 400 and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In a first aspect, the present application provides an organic compound having a structure represented by formula I:
wherein X is N (R) 3 ) O or S, R 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted phenylene;
R 3 the substituents on the substrate are independently selected from deuterium, cyano, halogen, alkyl with 1-5 carbon atoms, deuterated aryl with 6-12 carbon atoms or aryl with 6-12 carbon atoms;
ring A is selected from aromatic rings having 6-14 carbon atoms;
L 1 、L 2 and L 3 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
R 1 and R is 2 Identical or different and are each independently selected from deuterium, halogen radicals, cyano radicals, alkyl radicals having 1 to 10 carbon atoms, cycloalkyl radicals having 3 to 10 carbon atoms, carbon atomsA haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;
n 1 is R 1 Number n of (n) 1 Selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 is R 2 Number n of (n) 2 Selected from 0, 1,2, 3 or 4; when n is 2 When the number is greater than 1, any two R 2 The same or different;
L 1 、L 2 、L 3 and Ar are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, deuteroaryl group having 6 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar may form a saturated or unsaturated 3-15 membered ring.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: any two adjacent substituents form a ring, and any two adjacent substituents each independently exist, and do not form a ring. Any two adjacent atoms can include two substituents on the same atom, and can also include two adjacent atoms with one substituent respectively; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring.
In the present application, the descriptions "… …" and "… …" and "… …" are used interchangeably and are to be understood in a broad sense as meaning that they are expressed between the same symbols in different groupsThe specific options of (a) do not affect each other, or it may be expressed that the specific options expressed between the same symbols do not affect each other in the same group. For example, the number of the cells to be processed,wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an aryl group having no substituent. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl or the like. The number of substituents may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2,3, 4, 5, 6, etc.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms.
The hydrogen atoms in the structures of the compounds of the present application include various isotopic atoms of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
"D" in the structural formula of the compound of the present application represents deuteration.
In this application, "aryl" refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more linked by carbon-carbon bond conjugationA monocyclic aryl group, a monocyclic aryl group and a condensed ring aryl group which are connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups which are connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.
As used herein, "arylene" refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.
In the present application, terphenyl includes
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group may be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having from 6 to 30 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having from 6 to 20 carbon atoms.
In this application, the fluorenyl group may be substituted with 1 or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be:and the like, but is not limited thereto.
In the present application, R is 3 、L 1 、L 2 、L 3 And aryl groups of substituents of Ar such as, but not limited toPhenyl, naphthyl, phenanthryl, biphenyl pentadeuterated phenyl, and the like.
In the present application heteroaryl means a monovalent aromatic ring or derivative thereof containing 1,2, 3,4, 5 or 6 heteroatoms in the ring, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.
In the present application, reference to heteroarylene refers to a divalent or multivalent radical formed by the further loss of one or more hydrogen atoms from the heteroaryl group.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group may be selected from 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.
In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total number of carbon atoms of 5 to 25.
In the present application, R is 3 、L 1 、L 2 、L 3 Heteroaryl groups of substituents for Ar such as, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolylOxazolyl, benzothiazolyl, benzimidazolyl.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of trialkylsilyl groups herein include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.
In the present application, the deuterated alkyl group having 1 to 10 carbon atoms has, for example, 1,2, 3,4, 5, 6, 7, 8 or 10 carbon atoms. Specific examples of deuterated alkyl groups include, but are not limited to, tridentate methyl.
In the present application, the number of carbon atoms of the haloalkyl group having 1 to 10 is, for example, 1,2, 3,4, 5, 6, 7, 8 or 10. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered ring. By 3-15 membered ring is meant a cyclic group having 3-15 ring atoms. The 3-15 membered ring is, for example, cyclopentane, cyclohexane, fluorene ring, benzene ring, etc.
In the present application,refers to chemical bonds that interconnect other groups.
In the present application, the connecting key is not positionedInvolving single bonds extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
In particular, in formula I of the present application L1 And the radical in brackets->The connection mode of (C) includes any one of possible connection modes shown in the formulas (Z-1) to (Z-7).
Wherein in formula (Z-7), X is N (R) 3 ) And R is 3 Is a substituted or unsubstituted phenylene group.
An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by the same includes any one of possible linkages as shown in the formulae (Y-1) to (Y-7).
In some embodiments of the present application, ring a is selected from a benzene ring or a naphthalene ring.
In some embodiments of the present application, the organic compound is selected from structures represented by formulas I-1 through I-16:
therein, X, L 1 、L 2 、L 3 、Ar、R 1 、R 2 、n 1 、n 2 Is defined as in formula I.
In some embodiments, R 1 And R is 2 Identical or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl or tert-butyl.
In some embodiments, n 1 And n 2 Are all 0.
In some embodiments, R 3 The substituents of (a) are selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
In some embodiments, L 1 、L 2 And L 3 Identical or different and are each independently selected from single bonds, carbonA substituted or unsubstituted arylene group having 6 to 18 atoms, a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms. For example L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, or 15 carbon atoms. L (L) 1 、L 2 And L 3 The substituents of (3) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, trialkylsilicon group having 3 to 8 carbon atoms, phenyl, pentadeuterated phenyl, naphthyl, biphenyl or pyridyl.
In some embodiments, L 1 、L 2 And L 3 And are each independently selected from a single bond, a substituted or unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of:
the substituted group Q has one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, pentadeuterophenyl, naphthyl, biphenyl or pyridyl.
In some embodiments, L 1 Selected from the group consisting of single bonds or:
in some embodiments, L 2 Selected from single bonds or radicalsGroup consisting of bolus:
in some embodiments, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments, L 3 Selected from the group consisting of single bonds or:
- # represents the sum L 2 The key to be connected to the key,represents a bond to Ar.
In some embodiments, L 3 Selected from the group consisting of single bonds or:
- # represents the sum L 2 The key to be connected to the key,represents a bond to Ar.
In some embodiments, ar is selected from the group consisting of a substituted or unsubstituted aryl group having from 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having from 4 to 18 carbon atoms. For example Ar is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 4, 5, 6, 7, 8, 9,10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
Optionally, the substituents in Ar are selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 5 to 12 carbon atoms.
In some embodiments, ar is selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
the substituted group W has one or more substituents independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, biphenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents in the group W is greater than 1, the substituents are the same or different. In some embodiments, ar is selected from the group consisting of:
in some embodiments, ar is selected from the group consisting of:
in some embodiments of the present invention, in some embodiments,selected from the group consisting of single bonds or: />
In some embodiments of the present invention, in some embodiments,selected from the group consisting of:
specifically, the organic compound may be selected from the group consisting of:
in a second aspect, the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises an organic compound according to the first aspect of the present application.
According to one embodiment, the structure of the organic electroluminescent device is shown in fig. 1, and includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound provided herein.
Optionally, the functional layer 300 includes an organic light emitting layer 330, wherein the organic light emitting layer 330 comprises an organic compound provided herein.
The light-emitting layer may be composed of an organic compound provided herein, or may be composed of an organic compound provided herein together with other materials. The light emitting layer may be one layer or two or more layers.
In one embodiment of the present application, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked. The organic compound can be applied to the organic light-emitting layer 330 of the organic electroluminescent device, so that the light-emitting efficiency of the organic electroluminescent device is effectively improved, and the driving voltage of the organic electroluminescent device is reduced.
In this application, anode 100 includes an anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof;metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Optionally, a transparent electrode comprising Indium Tin Oxide (ITO) as anode is included.
Optionally, the first hole transport layer 321 and the second hole transport layer 322 each include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. The first hole transport layer 321 may be composed of a compound HT-1. The second hole transport layer 322 may be composed of the compound HT-2.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 is selected from, for example, the following compounds or any combination thereof;
in one embodiment of the present application, hole injection layer 310 is composed of NDP-9 and the composition HT-1.
Optionally, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
Optionally, the host material of the organic light emitting layer 330 includes an organic compound provided herein. The host material of the organic light emitting layer 330 may be one compound, a combination of two or more compounds.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. Guest materials are also known as doping materials or dopants.
In some embodiments of the present application, the guest material of the organic light emitting layer 330 is GHP1 or GHN1.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in this application. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:
in one embodiment of the present application, electron transport layer 340 is comprised of ET-01 and LiQ.
In this application, cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as a lanthanide metal, an alkali metal sulfide, an alkali metal halide, or a complex of an alkali metal and an organic material. In one embodiment of the present application, electron injection layer 350 comprises metallic Yb.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthetic method of the organic compound of the present application is specifically described below with reference to synthetic examples, but the present application is not limited thereto.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare a number of organic compounds of the present application, and that other methods for preparing compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those compounds not exemplified in accordance with the present application may be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. None of the compounds mentioned in this application as synthetic methods are commercially available starting products.
1. Synthesis of intermediates
(1) Synthesis of intermediates Sub-a-1 to Sub-g-1:
reaction A (80.0 g,220.7 mmol), reaction B (80.48 g,485.6 mmol), tetrakis triphenylphosphine palladium (2.55 g,2.2 mmol), potassium carbonate (91.52 g, 6)62.2 mmol), tetrabutylammonium bromide (7.2 g,22.1 mmol) was added to the flask, and a mixed solvent of toluene (640 mL), ethanol (160 mL) and water (160 mL) was added thereto, and the temperature was raised to 80℃under nitrogen protection, and the mixture was stirred at the maintained temperature for 18 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using methylene chloride/n-heptane as the mobile phase afforded intermediate a-1 (40.0 g, 65% yield) as a white solid by mass spectrometry: m/z=279.0 (m+h) + 。
Using reactant 1 instead of reactant a and reactant 2 instead of reactant B in table 1, the following intermediates were synthesized using a similar method:
TABLE 1
(2) Synthesis of intermediates Sub-A to Sub-Z:
indolo [2,3-A ] carbazole (50.0 g,195.1 mmol), sodium hydrogen (5.62 g,234.1 mmol) and N, N-dimethylformamide (400 mL) were added to the flask, the mixture was stirred and dissolved at 20℃under nitrogen protection, a dropwise addition of an N, N-dimethylformamide (100 mL) solution of intermediate Sub-c-1 (54.37 g,195.1 mmol) was started, the solution became clear after the dropwise addition, a large amount of white solid was generated after 0.5h, and the sampling detection conversion was 83.3% after 2.5 h. Adding 500mL of water into the reaction solution for water washing, and filtering to separate out solid; leaching with 200mL ethanol, and draining to obtain crude product. The crude product was purified by silica gel column chromatography using methylene chloride/n-heptane system to give intermediate Sub-a (60.30 g, yield 62.0%) as a white solid.
Using reactant 3 in Table 2 in place of indolo [2,3-A ] carbazole and reactant 4 in place of intermediate Sub-c-1, each intermediate shown in Table 2 was synthesized by the method of synthesizing intermediate Sub-A:
TABLE 2
2. Synthesis of the Compounds: take compound 1 as an example
Intermediate Sub-A (7.0 g,14.0 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.76 g,14.0 mmol), 4-dimethylaminopyridine (0.86 g,7.0 mmol), cesium carbonate (11.4 g,35.0 mmol) and dimethyl sulfoxide (70 mL) were added to a round bottom flask, and the mixture was stirred and heated to 100deg.C under nitrogen protection to react for 10 hours. And after the reaction is finished, cooling to room temperature, filtering, leaching a filter cake by using water and ethanol, and drying to obtain a crude product. The crude product was purified by recrystallization from toluene to give compound 1 (5.43 g, yield 53%) as a yellow solid, mass spectrum: m/z= 730.2 (m+h) + 。
Using reactant 5 in table 3 instead of intermediate Sub-a and reactant 6 instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, the compounds shown in the following table were synthesized using a similar procedure:
TABLE 3 Table 3
The nuclear magnetic data of some compounds are shown in table 4:
TABLE 4 Table 4
Example 1
The anode was prepared by the following procedure: the ITO/Ag/ITO thickness isThe ITO substrate of (C) was cut into a size of 40mm (length). Times.40 mm (width). Times.0.7 mm (thickness), and a photolithography step was used to prepare an experimental substrate having cathode, anode and insulating layer patterns, and ultraviolet ozone and O were used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
Compound HT-1 and NDP-9 were mixed in 97% on the experimental substrate (anode): co-evaporation is carried out at a thickness ratio of 3% to form a film with a thickness ofIs then vacuum evaporated with HT-1 on the hole injection layer to form a layer thickness +.>Is provided.
Vacuum evaporating HT-2 on the first hole transport layer to form a film with a thickness ofIs provided.
On the second hole transport layer, compound GH-P1: compound 1: ir (ppy) 3 47 percent: 47%: co-evaporation is carried out at a thickness ratio of 6% to form a film with a thickness ofGreen light emitting layer (EML).
Co-evaporating ET-1 and LiQ according to the thickness ratio of 1:1 to formA thick Electron Transport Layer (ETL).
Vacuum evaporating metal Yb on the electron transport layer to form a layer with a thickness ofThen on the electron injection layer, magnesium (Mg) and silver (Ag) were mixed at 1:9, and forming a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAn organic capping layer (CPL) is formed, thereby completing the fabrication of the organic light emitting device, the structure of which is shown in fig. 1.
Example 2-example 40
An organic electroluminescent device was fabricated by the same method as in example 1, except that the luminescent layer materials shown in table 6 below were used instead of the luminescent layer in example 1 when forming the luminescent layer.
Comparative example 1-comparative example 4
An organic electroluminescent device was fabricated by the same method as in example 1, except that the luminescent layer materials shown in the following table were used instead of the luminescent layer in example 1 when forming the luminescent layer.
Wherein, in the preparation of the organic electroluminescent device, the structures of the respective materials used in the comparative example and the examples are as follows in table 5:
TABLE 5
The green organic electroluminescent devices prepared in examples 1 to 26 and comparative examples 1 to 4 were subjected to performance test, particularly at 10mA/cm 2 Under the condition of testing IVL performance of the device, T 95 The service life of the device is 30mA/cm 2 Is performed under the conditions, and the test results are shown in the following table 6:
TABLE 6
As can be seen from the above table, examples 1 to 40, in which the compounds of the present application were used as a green light-emitting layer mixed host material, were used as a device T as compared with comparative examples 1 to 4 95 Under the condition of similar service life, the working voltage and the luminous efficiency are improved. Specifically, the devices of examples 1-32 exhibited at least a 0.24V reduction in operating voltage and a significant improvement in luminous efficiency of at least 16.8% over the devices of comparative examples 1-2. To implementThe devices of examples 33-40 have at least a 0.18V reduction in operating voltage and a significant improvement in luminous efficiency of at least 14.4% compared to the devices of comparative examples 3-4.
Therefore, when the organic compound is used for preparing a green organic electroluminescent device, the luminous efficiency of the device can be effectively improved, and the working voltage can be improved to a certain extent.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.

Claims (13)

1. An organic compound having a structure represented by formula I:
wherein X is N (R) 3 ) O or S, R 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted phenylene;
R 3 the substituents on the substrate are independently selected from deuterium, cyano, halogen, alkyl with 1-5 carbon atoms, deuterated aryl with 6-12 carbon atoms or aryl with 6-12 carbon atoms;
ring A is selected from aromatic rings having 6-14 carbon atoms;
L 1 、L 2 and L 3 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
R 1 and R is 2 Identical or different and are each independently selected from deuterium, halogen radicals, cyano radicals, alkyl radicals having 1 to 10 carbon atoms, and carbon atomsCycloalkyl having 3 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms or heteroaryl having 3 to 20 carbon atoms;
n 1 is R 1 Number n of (n) 1 Selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different; n is n 2 Is R 2 Number n of (n) 2 Selected from 0, 1,2, 3 or 4; when n is 2 When the number is greater than 1, any two R 2 The same or different;
L 1 、L 2 、L 3 and Ar are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, deuteroaryl group having 6 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar may form a saturated or unsaturated 3-15 membered ring.
2. An organic compound according to claim 1, wherein ring a is selected from benzene rings or naphthalene rings.
3. The organic compound according to claim 1, wherein L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms;
alternatively, L 1 、L 2 Or L 3 The substituents of (3) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, trialkylsilicon group having 3 to 8 carbon atoms, phenyl, pentadeuterated phenyl, naphthyl, biphenyl or pyridyl.
4. The organic compound according to claim 1, wherein L 1 、L 2 And L 3 Identical or different and eachAnd is selected from the group consisting of a single bond, a substituted or unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of:
the substituted group Q has one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, pentadeuterophenyl, naphthyl, biphenyl or pyridyl.
5. The organic compound according to claim 1, wherein L 1 Selected from the group consisting of single bonds or:
alternatively, L 2 Selected from the group consisting of single bonds or:
6. the organic compound according to claim 1, wherein L 3 Selected from the group consisting of single bonds or:
- # denotes and L 2 The key to be connected to the key,represents a bond to Ar.
7. The organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 18 carbon atoms;
optionally, the substituents in Ar are selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 5 to 12 carbon atoms.
8. An organic compound according to claim 1, wherein Ar is selected from the group consisting of substituted or unsubstituted groups W, wherein unsubstituted groups W are selected from the group consisting of:
the substituted group W has one or more substituents independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, biphenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents in the group W is greater than 1, the substituents are the same or different.
9. The organic compound according to claim 1, wherein Ar is selected from the group consisting of:
10. the device according to claim 1An organic compound, wherein,selected from the group consisting of:
11. the organic compound according to claim 1, wherein the compound is selected from the group consisting of:
12. the organic electroluminescent device comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1 to 11;
preferably, the functional layer includes an organic light emitting layer including the organic compound.
13. An electronic device comprising the organic electroluminescent device of claim 12.
CN202310560094.7A 2023-05-17 2023-05-17 Organic compound, organic electroluminescent device and electronic device comprising the same Pending CN117603209A (en)

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