CN117603195A - 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 PDFInfo
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- CN117603195A CN117603195A CN202310568582.2A CN202310568582A CN117603195A CN 117603195 A CN117603195 A CN 117603195A CN 202310568582 A CN202310568582 A CN 202310568582A CN 117603195 A CN117603195 A CN 117603195A
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- 238000013461 design Methods 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The present application relates to an organic compound, and an organic electroluminescent device and an electronic device including the same. The organic compoundThe organic compound has the structure shown in the formula 1, and can be applied to an organic electroluminescent device to remarkably improve the performance of the device.
Description
Technical Field
The application relates to the technical field of organic electroluminescent materials, in particular to an organic compound, an organic electroluminescent device comprising the same and an electronic device.
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. In recent years, organic electroluminescent devices (OLEDs) have been gaining attention by researchers, and the more materials and components involved have been studied. Among them, the OLED device generally includes a cathode and an anode disposed opposite to each other with a functional layer disposed therebetween. 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 through the cathode and anode electrodes, electrons on the cathode side move to the organic light-emitting layer through the electron transmission layer under the action of an electric field generated by the anode and cathode electrodes, holes on the anode side move to the organic light-emitting layer through the hole transmission layer, the electrons and the holes are combined in the organic light-emitting layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the organic light-emitting layer emits light outwards.
At present, the large-area use trend of the organic electroluminescent device enables the performance optimization of the display device to be embodied in service life, efficiency and driving voltage. Therefore, the structural design and use of the new material are important points for satisfying the research of higher performance OLED components, and it is necessary to continue to develop new materials to further improve the performance of the organic electroluminescent device.
Disclosure of Invention
In view of the problems existing in the prior art, an 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 1:
wherein X is selected from O, S, C (R 5 R 6 ) Or N (R) 7 )；
R 5 、R 6 And R is 7 The same or different and are each independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, and carbon atomsDeuterated aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
R 1 and R is 2 The same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
R 1 And R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, deuteroalkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms or aryl group with 6-20 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
L 1 and L 2 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、L 1 and L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 24 carbon atoms, aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms or heteroaryl having 3 to 20 carbon atoms;
Each R is 4 Independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
n is R 4 N is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two R 4 The same or different.
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.
The organic compound is structurally characterized in that dibenzo five-membered rings are trisubstituted on the same benzene ring, one of three substitution sites is directly connected with a triazinyl group with electron deficiency, and the other two substitution sites are connected with aryl groups; on the one hand, the hydrogen bond action between the hydrogen on the dibenzo five-membered ring and the nitrogen atom in the triazine group enables the triazine and the dibenzo five-membered ring to be basically positioned in the same plane, which is beneficial to intermolecular accumulation and enhances the carrier transmission capability of the compound; on the other hand, two aryl groups extend outwards of the molecule, and the aspect ratio of the molecule is increased, so that the horizontal orientation of the compound along the substrate direction is improved, and the carrier mobility of the compound is further enhanced. When the compound is used as an electron transport type main body material in a mixed main body material, the carrier balance in a light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the current efficiency and the service life of a device can be remarkably improved.
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 diagram of an electronic device according to an embodiment of the present application.
Description of the 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 1:
wherein X is selected from O, S, C (R 5 R 6 ) Or N (R) 7 )；
R 5 、R 6 And R is 7 The two are the same or different and are each independently selected from alkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms, aryl groups with 6-20 carbon atoms, deuterated aryl groups with 6-20 carbon atoms or heteroaryl groups with 3-20 carbon atoms;
R 1 and R is 2 The same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
R 1 and R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, deuteroalkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms or aryl group with 6-20 carbon atoms;
Ar 1 and Ar is a group 2 Identical or differentAnd each is independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
L 1 and L 2 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, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 24 carbon atoms, aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms or heteroaryl having 3 to 20 carbon atoms;
each R is 4 Independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
n is R 4 N is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two R 4 The same or different.
In this application, the descriptions "each … … is independently" and "… … is independently" and can be used interchangeably, and should be understood in a broad sense, which refers to that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. 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, each R ' can be the same or different, and each R ' has different optionsSounding; 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 aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, deuterated alkyl, trialkylsilyl, triarylsilyl, aryl, deuterated aryl, heteroaryl, or the like.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
In this application, "D" in the structural formula represents deuteration.
Aryl in this application 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 condensed ring aryl group, a spiro aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups 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. For example, in the present application, examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, 9' -spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylenyl, perylenyl, benzo [9,10]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.
In the present application, reference to arylene means a divalent group formed by further loss of one or more hydrogen atoms from the aryl group.
In the present application, a substituted aryl group may be one in which one or more hydrogen atoms in the aryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, triarylsilyl groups, alkyl groups, haloalkyl groups, deuterated alkyl groups, deuterated aryl groups, and the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
In the present application heteroaryl means a monovalent aromatic ring or derivative thereof containing 1, 2, 3, 4, 5, 6 or 7 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 group formed by further loss of one or more hydrogen atoms from the heteroaryl group.
In the present application, a substituted heteroaryl group may be one in which one or more of the hydrogen atoms in the heteroaryl group is substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, a triarylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, or the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, ar is 1 、Ar 2 、L 1 And L 2 The aryl group of the substituent(s) may have 6 to 20 carbon atoms, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, anthracenyl,A base.
In the present application, the fluorenyl group may be substituted with 1 or more substituents. 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, ar is 1 、Ar 2 、L 1 And L 2 The heteroaryl group of the substituent(s) may have 3 to 20 carbon atoms, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and specific examples of the heteroaryl group as the substituent(s) include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, quinolinyl, isoquinolinyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl, dibenzofuranyl.
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, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.
Specific examples of deuterated alkyl groups herein include, but are not limited to, tridentate methyl.
Specific examples of deuterated aryl groups herein include, but are not limited to, pentadeuterated phenyl, heptadeuterated naphthyl.
Specific examples of trialkylsilyl groups herein include, but are not limited to, trimethylsilyl, triethylsilyl.
Specific examples of triarylsilyl groups in the present application include, but are not limited to, triphenylsilyl groups.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring system It 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 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).
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, the organic compounds described herein are selected from structures represented by formulas a-C:
in some embodiments of the present application, R 1 And R is 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms. For example, R 1 And R is 2 Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
In some embodiments of the present application, R 1 And R is 2 The substituents in (a) are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 6 carbon atoms or aryl having 6 to 12 carbon atoms.
In some embodiments, R 1 And R is 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl.
Alternatively, R 1 And R is 2 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl or naphthyl.
In some embodiments, R 1 And R is 2 Each independently selected from the group consisting of:
in some embodiments, R 1 And R is 2 Each independently selected from the group consisting of:
in some embodiments of the present application, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms. For example, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.
In some embodiments, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, deuteroalkyl with 1-5 carbon atoms, trialkylsilyl with 3-6 carbon atoms and aryl with 6-12 carbon atomsA group or a heteroaryl group having 5 to 12 carbon atoms.
In some embodiments, ar 1 And Ar is a group 2 And are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9' -spirobifluorenyl, and substituted or unsubstituted triphenylenyl.
Alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, tridentate methyl, phenyl, naphthyl, biphenyl, dibenzothienyl, dibenzofuranyl or carbazolyl.
In some embodiments, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups Q selected from the group consisting of:
wherein the substituted group Q has one or more substituents which are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, tridentate methyl, phenyl, naphthyl, biphenyl, dibenzothienyl, dibenzofuranyl or carbazolyl.
In some embodiments, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the following groups:
in some embodiments, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the following groups:
in some embodiments of the present application, L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms. For example, L 1 And L 2 And are the same or different and are 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 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
In some embodiments, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.
In some embodiments, L 1 And L 2 And are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
Alternatively, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl orPhenyl.
In some embodiments, L 1 And L 2 Identical or different, and are each independently selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:
wherein the substituted group V has one or more substituents thereon, each substituent being the same or different and each being independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl or phenyl.
In some embodiments, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
In some embodiments of the present invention, in some embodiments,each independently selected from the following groups:
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in some embodiments of the present invention, in some embodiments,each independently selected from the following groups:
in some embodiments of the present application, R 5 、R 6 And R is 7 The same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, tridentate methyl, phenyl, naphthyl, biphenyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
In some embodiments of the present application, each R 4 Independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, tridentate methyl, pentadeuterated phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
In some embodiments of the present application, the organic compounds described herein are selected from structures represented by formulas 2-1 to 2-12:
optionally, the organic compound is selected from the group consisting of:
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in a second aspect, the present application provides 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; wherein the functional layer comprises an organic compound according to the first aspect of the present application.
Optionally, the functional layer comprises an organic light emitting layer comprising an organic compound of the present application.
Alternatively, the organic light-emitting layer may be composed of either the organic compound of the present application or the organic compound of the present application and other materials together.
Optionally, the organic electroluminescent device is a red organic electroluminescent device or a green organic electroluminescent device.
In one embodiment of the present application, the organic electroluminescent device includes an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked as shown in fig. 1.
In this application, anode 100 comprises an anode material, which is preferably 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. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the compounds shown below or any combination thereof:
in one embodiment of the present application, the first hole transport layer 321 is HT-12 and the second hole transport layer 322 is HT-15.
In another embodiment of the present application, the first hole transport layer 321 is HT-12 and the second hole transport layer 322 is HT-10.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first 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 may be selected from, for example, the following compounds or any combination thereof:
In one embodiment, hole injection layer 310 is comprised of PD and HT-12.
In this application, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, 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.
The host material of the organic light emitting layer 330 may include a metal chelating compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials.
In one embodiment of the present application, the host material of the organic light emitting layer 330 is an organic compound and compound RH-P of the present application.
In another embodiment of the present application, the host material of the organic light emitting layer 330 is the organic compound and the compound GH-P of the present application.
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. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. Specific examples of the phosphorescent dopant include, but are not limited to;
In some embodiments of the present application, the guest material of the organic light emitting layer 330 is RD.
In some embodiments of the present application, the guest material of the organic light emitting layer 330 is GD.
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, BTB, liQ, ET-1, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application is not particularly limited. 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-1 and LiQ.
In this application, the cathode 200 may include a cathode material, which is a material having 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, comprises magnesium and silverIs used 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 an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).
In a third aspect, 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 apparatus 400 is provided that 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 methods of the compounds of the present application are specifically described below in connection with synthetic examples, but the present disclosure is not thereby limited in any way.
Synthesis of intermediates
1. Synthesis of Sub-a 1:
RM-1 (21.48 g,50 mmol), pinacol diboronate (15.24 g,60 mmol), potassium acetate (KOAc, 12.26g,125 mmol) and toluene (220 mL) are added in sequence to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating are turned on, and [1,1' -bis (diphenylphosphino) ferrocene is rapidly added until the system is warmed to 40 DEG C ]Palladium dichloride (Pd (dppf) Cl) 2 0.73g,1 mmol) and the reaction was continued with stirring at 80℃for 24h. After the system is cooled to room temperature, 200mL of water is added into the system, the system is fully stirred for 30min, the pressure is reduced, the filtration cake is washed to be neutral by deionized water, and then 100mL of absolute ethyl alcohol is used for leaching, so that a gray solid crude product is obtained; the crude product is beaten once by n-heptane,after 150mL of toluene was dissolved, the mixture was passed through a silica gel column, the catalyst was removed, and the mixture was concentrated to give Sub-a1 (16.0 g, yield: 67%) as a white solid.
Sub-aX listed in Table 1 below was synthesized in the same manner as Sub-a1 except that reactant A was used in place of RM-1, and the main raw material, the synthesized intermediate and the yields thereof were as shown in Table 1.
TABLE 1
2. Synthesis of Sub-b 1:
RM-2 (17.14 g,50 mmol), sub-a1 (26.22 g,55 mmol), tetrabutylammonium bromide (TBAB, 1.61g,5 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.58g,0.5 mmol), anhydrous potassium carbonate (K) 2 CO 3 13.82g,100 mmol), toluene (PhMe, 260 mL), tetrahydrofuran (THF, 65 mL) and deionized water (65 mL), stirring and heating were turned on and the temperature was raised to reflux for 24h. After the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, and precipitating a large amount of precipitate; filtering, taking and fixing, and leaching and fixing with deionized water until neutral to obtain a crude product; the crude product was recrystallized from toluene to give Sub-b1 (27.59 g, yield: 84%) as an off-white solid.
Sub-bX listed in Table 2 below was synthesized in the same manner as Sub-B1 except that reactant B was used in place of RM-2 and reactant C was used in place of Sub-a1, wherein the main raw materials used, the synthesized intermediates and the yields thereof are shown in Table 2.
TABLE 2
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3. Synthesis of Sub-c 1:
to a 1000mL three-necked flask, sub-b1 (32.85 g,50 mmol), phenylboronic acid (6.7 g,55 mmol), tetrabutylammonium bromide (1.61 g,5 mmol), tetrakis (triphenylphosphine) palladium (0.58 g,0.5 mmol), anhydrous potassium carbonate (13.82 g,100 mmol), toluene (320 mL), tetrahydrofuran (80 mL) and deionized water (80 mL) were sequentially added under nitrogen atmosphere, and stirring and heating were turned on and the temperature was raised to reflux reaction for 24h. After the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, and precipitating a large amount of precipitate; filtering, taking and fixing, and leaching and fixing with deionized water until neutral to obtain a crude product; the crude product was recrystallized from toluene to give Sub-c1 as an off-white solid (19.90 g, yield: 68%).
Sub-cX listed in table 3 below was synthesized in the same manner as Sub-c1 except that reactant D was used instead of Sub-b1 and reactant E was used instead of phenylboronic acid, wherein the main raw materials used, the synthesized intermediates, and the yields thereof are shown in table 3.
TABLE 3 Table 3
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4. Synthesis of Sub-d 1:
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RM-1 (21.48 g,50 mmol), phenylboronic acid (13.41 g,110 mmol), tetrabutylammonium bromide (3.22 g,10 mmol), tetrakis (triphenylphosphine) palladium (1.16, 1.0 mmol), anhydrous potassium carbonate (27.64 g,200 mmol), toluene (220 mL), tetrahydrofuran (55 mL), and deionized water (55 mL) were added sequentially under a nitrogen atmosphere, stirring and heating were turned on, and the temperature was raised to reflux reaction for 24h. After the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, and precipitating a large amount of precipitate; filtering, taking and fixing, and leaching and fixing with deionized water until neutral to obtain a crude product; the crude product was recrystallized from toluene to give Sub-d1 (11.0 g, yield: 62%) as an off-white solid.
Sub-d2 listed in Table 4 below was synthesized in the same manner as Sub-d1 except that reactant F was used in place of RM-1, and the main raw material used, the synthesized intermediate and the yields thereof are shown in Table 4.
TABLE 4 Table 4
5. Synthesis of Sub-e 1:
sub-d1 (17.74 g,50 mmol), pinacol diboronate (15.24 g,60 mmol), potassium acetate (10.8 g,110 mmol) and dimethyl sulfoxide (DMSO, 200 mL) were added sequentially to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating were turned on, and tris (dibenzylideneacetone) dipalladium (Pd) was added rapidly until the system warmed to 40 ℃ 2 (dba) 3 0.46g,0.50 mmol) and 2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl (XPhos, 0.48g,1.0 mmol), the reaction was stirred for 24h with continued heating to 80 ℃. After the system is cooled to room temperature, 200mL of water is added into the system, the mixture is fully stirred for 30min, the pressure is reduced, the filtration cake is washed to be neutral by deionized water, and then 100mL of absolute ethyl alcohol is used for leaching, so that gray solid is obtained; the crude product was slurried once with n-heptane, purified by 200mL of toluene, passed through a silica gel column, the catalyst was removed, and the organic phase was concentrated to give Sub-e1 (11.82 g, yield: 53%) as a white solid.
Sub-e2 listed in Table 5 below was synthesized in the same manner as Sub-e1 except that reactant G was used in place of Sub-d1, and the main raw materials used, the synthesized intermediates and their yields are shown in Table 5.
TABLE 5
Synthesis of Compounds
1. Synthesis of Compound 3:
to a 500mL three-necked flask under nitrogen atmosphere, sub-c1 (14.62 g,25 mmol), phenylboronic acid (3.35 g,27.5 mmol) and palladium acetate (Pd (OAc) were sequentially added 2 42mg,0.25 mmol), 2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl (0.24 g,0.5 mmol), anhydrous potassium carbonate (6.9 g,50 mmol), tetrabutylammonium bromide (0.8 g,2.5 mmol), toluene (140 mL), tetrahydrofuran (35 mL) and deionized water (35 mL), stirring and heating were turned on, and the temperature was raised to reflux for 24h. After the system is cooled to room temperature, pouring the reaction solution into 250mL of deionized water, and precipitating a large amount of precipitate; filtering, taking and fixing, and leaching and fixing with deionized water until neutral to obtain a crude product; the crude product was dissolved by heating with toluene, passed through a heat-preserving column, the catalyst was removed, and the organic phase was concentrated and recrystallized with toluene to give compound 3 (11.28 g, yield: 72%) as a white solid, mass spectrum (m/z) =627.21 [ m+h ] ] + 。
Compound X of the present application in table 6 below was synthesized in the same manner as compound 3 except that reactant H was used instead of Sub-c1 and reactant I was used instead of phenylboronic acid, wherein the main raw materials used, the synthesized compound X, and mass spectra and yields thereof are shown in table 6.
TABLE 6
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2. Synthesis of Compound 328:
RM-3 (8.60 g,25 mmol), sub-e1 (12.27 g,27.5 mmol), palladium acetate (42 mg,0.25 mmol), 2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl (XPhos, 0.24g,0.5 mmol), anhydrous potassium carbonate (6.9 g,50 mmol), tetrabutylammonium bromide (0.8 g,2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL), and deionized water (2 mL) were sequentially added under a nitrogen atmosphere, and stirring and heating were turned on, and the temperature was raised to reflux reaction for 24h. After the system is cooled to room temperature, pouring the reaction solution into 150mL of deionized water, and precipitating a large amount of precipitate; filtering, taking and fixing, and leaching and fixing with deionized water until neutral to obtain a crude product; the crude product was dissolved by heating with toluene, passed through a heat-preserving column, the catalyst was removed, and the organic phase was concentrated and recrystallized with toluene to give compound 328 (8.94 g, yield: 57%) as a white solid, mass spectrum (m/z) =628.23 [ m+h ]] + )。
Compound 369 shown in table 7 below was synthesized in the same manner as compound 328 except that reactant G was used instead of RM-3 and reactant K was used instead of Sub-e1, wherein the main raw materials used, the synthesized compound and mass spectrum and yield thereof are shown in table 7.
TABLE 7
Nuclear magnetic data of compound 31: 1 H-NMR(400MHz,Methylene-Chloride-D 2 )δppm9.41(s,2H),8.87(d,2H),8.71(d,1H),8.55(s,1H),8.08(d,2H),8.04(d,2H),7.96(d,2H),7.65-7.55(m,5H),7.51(t,1H),7.44-7.20(m,11H)。
device embodiment
Example 1: red organic electroluminescent device
Sequentially the thickness isThe ITO/Ag/ITO substrate 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 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 is used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
First, PD: HT-12 was co-evaporated on an experimental substrate (anode) at an evaporation rate ratio of 3:97 to form a film having a thickness ofAnd vacuum evaporating HT-12 on the hole injection layer to form a layer having a thickness +.>Is provided.
Vacuum evaporating compound HT-15 on the first hole transport layer to form a film having a thickness ofIs provided.
On the second hole transport layer, the compound 3:RH-P:RD is co-evaporated at an evaporation rate ratio of 49:49:2 to form a film with a thickness ofIs provided.
On the organic light-emitting layer, the compound ET-1 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to formA thick electron transport layer formed by vapor deposition of Yb on the electron transport layer to a thickness +. >Then magnesium and silver are vacuum evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a film with a thickness of +.>Is provided.
Finally, vacuum vapor plating CP-1 on the cathode to form a film with a thickness ofThereby completing the fabrication of the red organic electroluminescent device.
Examples 2 to 23
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound shown in table 9 below was used as a host material of the light emitting layer instead of the compound 3 at the time of preparing the organic light emitting layer.
Comparative examples 1 to 4
An organic electroluminescent device was prepared by the same method as in example 1, except that compound a, compound B, compound C and compound D were used as a host material of the light emitting layer instead of compound 3 when the organic light emitting layer was prepared.
The main material structures used in the above examples and comparative examples are shown in table 8 below.
TABLE 8
The devices prepared in examples and comparative examples were subjected to performance tests in which IVL performance (driving voltage, current efficiency, color coordinates) of the devices was 10mA/cm 2 T95 lifetime at 20mA/cm 2 The results are shown in Table 9.
TABLE 9
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According to the test results of table 9, when the compounds of the present application were used as electron transport type host materials in the mixed red light host materials of the red organic electroluminescent device, the driving voltage of the devices prepared from the compounds of the present application was reduced by at least 0.25V, the current efficiency was increased by at least 10.04%, and the lifetime was increased by at least 10.92% as compared with comparative examples 1 to 4.
Example 24: green organic electroluminescent device
Sequentially the thickness isThe ITO/Ag/ITO substrate 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 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 is used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
Firstly, PD: HT-12 is co-evaporated on an experimental substrate (anode) at an evaporation rate ratio of 2:98 to form a film with a thickness ofAnd vacuum evaporating HT-12 on the hole injection layer to form a layer having a thickness +.>Is provided.
Vacuum evaporating compound HT-10 on the first hole transport layer to form a film having a thickness ofIs provided.
On the second hole transport layer, the compound 120 to GH-P to GD is co-evaporated at an evaporation rate ratio of 60 to 40 to 10 to form a film with a thickness ofIs provided.
On the organic light-emitting layer, the compound ET-1 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to formA thick electron transport layer formed by vapor deposition of Yb on the electron transport layer to a thickness +. >Then magnesium and silver are vacuum evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a film with a thickness of +.>Is provided.
Finally, vacuum vapor plating CP-1 on the cathode to form a film with a thickness ofIs an organic compound of (2)And (5) covering the layer, thereby completing the manufacture of the green organic electroluminescent device.
Examples 25 to 44
An organic electroluminescent device was produced by the same method as in example 24, except that the compound shown in table 11 was used as a host material of the light-emitting layer instead of the compound 120 when the organic light-emitting layer was produced.
Comparative examples 5 to 8
An organic electroluminescent device was fabricated by the same method as in example 24, except that compound E, compound F, compound G and compound H were used as a host material of the light-emitting layer instead of compound 120 in the fabrication of the organic light-emitting layer.
The main material structures used in the above examples and comparative examples are shown in table 10 below.
Table 10
The devices prepared in examples and comparative examples were subjected to performance tests in which IVL performance (driving voltage, current efficiency, color coordinates) of the devices was 10mA/cm 2 T95 lifetime at 20mA/cm 2 The results are shown in Table 11.
TABLE 11
According to the test results of table 11, when the compound of the present application was used as an electron transport host material in a mixed green host material of a green organic electroluminescent device, the driving voltage of the device prepared from the organic compound of the present application was reduced by at least 0.22V, the current efficiency was increased by at least 16.41%, and the lifetime was increased by at least 15.94% as compared with comparative examples 5 to 8.
Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the application following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the application pertains.
Claims (13)
1. An organic compound, characterized in that the organic compound has a structure represented by formula 1:
wherein X is selected from O, S, C (R 5 R 6 ) Or N (R) 7 )；
R 5 、R 6 And R is 7 The two are the same or different and are each independently selected from alkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms, aryl groups with 6-20 carbon atoms, deuterated aryl groups with 6-20 carbon atoms or heteroaryl groups with 3-20 carbon atoms;
R 1 and R is 2 The same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
R 1 and R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, deuteroalkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms or aryl group with 6-20 carbon atoms;
Ar 1 And Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
L 1 and L 2 Identical or different and each is independentA single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、L 1 and L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 24 carbon atoms, aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms or heteroaryl having 3 to 20 carbon atoms;
each R is 4 Independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms or heteroaryl with 3-20 carbon atoms;
n is R 4 N is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two R 4 The same or different.
2. The compound of claim 1, wherein R 1 And R is 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms;
alternatively, R 1 And R is 2 The substituents in (a) are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 6 carbon atoms or aryl having 6 to 12 carbon atoms.
3. The compound of claim 1, wherein R 1 And R is 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl;
alternatively, R 1 And R is 2 Each substituent of (a) is independently selected fromDeuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl or naphthyl.
4. The compound of claim 1, wherein Ar 1 And Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms;
Alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuteroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 6 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.
5. The compound of claim 1, wherein Ar 1 And Ar is a group 2 And are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9,9' -spirobifluorenyl, and substituted or unsubstituted triphenylenyl;
alternatively, ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, tridentate methyl, phenyl, naphthyl, biphenyl, dibenzothienyl, dibenzofuranyl or carbazolyl.
6. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Identical or different and are each independently selected from the following groups:
7. the compound of claim 1, wherein L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms;
alternatively, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.
8. The compound of claim 1, wherein L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group;
alternatively, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl or phenyl.
9. The compound of claim 1, wherein L 1 And L 2 Each independently selected from the group consisting of a single bond or:
10. the organic compound according to claim 1, wherein each R 4 Independently selected from deuterium, fluorine, cyano,Methyl, ethyl, isopropyl, tert-butyl, tridentate methyl, pentadeuterated phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl;
preferably, R 5 、R 6 And R is 7 The same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, tridentate methyl, phenyl, naphthyl, biphenyl, pentadeuterated phenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
11. The organic compound according to claim 1, wherein the organic compound is selected from the following structures:
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12. an organic electroluminescent device comprising an anode and a cathode which are disposed opposite to each other, and a functional layer provided between the anode and the cathode, characterized in that the functional layer comprises the organic compound according to any one of claims 1 to 11;
Optionally, the organic electroluminescent device is a red organic electroluminescent device;
optionally, the organic electroluminescent device is a green organic electroluminescent device;
optionally, the functional layer includes an organic light emitting layer, the organic light emitting layer including the organic compound.
13. An electronic device comprising the organic electroluminescent device as claimed in claim 12.
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