CN117088872A - Condensed-cyclic compound, organic electroluminescent device and electronic device - Google Patents
Condensed-cyclic compound, organic electroluminescent device and electronic device Download PDFInfo
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- CN117088872A CN117088872A CN202210853393.5A CN202210853393A CN117088872A CN 117088872 A CN117088872 A CN 117088872A CN 202210853393 A CN202210853393 A CN 202210853393A CN 117088872 A CN117088872 A CN 117088872A
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000002346 layers by function Substances 0.000 claims description 14
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 13
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
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- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application relates to the technical field of organic electroluminescent materials, and provides a condensed ring compound, an organic electroluminescent device and an electronic device containing the condensed ring compound. When the compound is used as a main material of a luminescent layer, the compound can improve carrier balance in the luminescent layer, widen a carrier recombination region, improve exciton generation and utilization efficiency, and improve luminous efficiency and service life of a device.
Description
Technical Field
The application relates to the technical field of organic electroluminescent materials, in particular to a condensed-cyclic compound, an organic electroluminescent device and an electronic device containing the condensed-cyclic compound.
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. An organic electroluminescent device (OLED) generally includes a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. 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.
In the existing organic electroluminescent devices, the most important problems are represented by the service life and efficiency, and along with the large area of the display, the driving voltage is also improved, and the luminous efficiency and the current efficiency are also required to be improved, so that it is necessary to continuously develop novel materials to further improve the performance of the organic electroluminescent devices.
Disclosure of Invention
In view of the foregoing problems in the prior art, an object of the present application is to provide a condensed-cyclic compound, and an organic electroluminescent device and an electronic apparatus including the same, wherein the condensed-cyclic compound is used in the organic electroluminescent device, and the performance of the device can be improved.
According to a first aspect of the present application, there is provided a condensed-cyclic compound having a structure represented by the following formula 1,
the group A is selected from the group shown in a-1, a-2 or a-3:
L、L 1 、L 2 、L 3 、L 4 and L 5 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 3 selected from the group represented by a-4 or a-5:
ring E, F, P and Q are each independently selected from 6-14 membered aromatic rings;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms and contains at least 2 nitrogen atoms;
Ar 1 And Ar is a group 2 The same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
Ar 4 、Ar 5 and Ar is a group 6 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;
each R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And R is 7 The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms and cycloalkyl groups with 3 to 10 carbon atoms;
n 1 、n 2 and n 3 Each independently selected from 0, 1, 2, 3 or 4;
n 4 selected from 0, 1, 2 or 3;
n 5 、n 6 and n 7 Each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8;
Ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 and L 5 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, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, haloaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; Optionally, any two adjacent substituents may form a saturated or unsaturated 3-to 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 fused ring 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 compound of the application comprises a macrocyclic condensed ring mother nucleus structure formed by phenanthroindole and a benzene ring, and the mother nucleus is respectively connected with triarylamine, carbazole groups or nitrogen-containing electron-deficient heteroaryl. Wherein, the benzene ring connected with the nitrogen atom in the mother nucleus is connected with the 1-position carbon atom on the phenanthrene ring through a covalent bond, and the specific connection mode forms a condensed ring macrocyclic structure with a large conjugated system, thereby endowing the phenanthroindole group with more excellent hole transmission capability. When the compound is used as a hole transport type material or a single 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 light-emitting efficiency and the service life of a device can be 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 serve to explain, without limitation, 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 application.
In a first aspect, the present application provides a condensed-cyclic compound having a structure represented by the following formula 1,
the group A is selected from the group shown in a-1, a-2 or a-3:
L、L 1 、L 2 、L 3 、L 4 and L 5 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 3 selected from the group represented by a-4 or a-5:
ring E, F, P and Q are each independently selected from 6-14 membered aromatic rings;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms and contains at least 2 nitrogen atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
Ar 4 、Ar 5 and Ar is a group 6 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;
each R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And R is 7 The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms and cycloalkyl groups with 3 to 10 carbon atoms;
n 1 、n 2 And n 3 Each independently selected from 0, 1, 2, 3 or 4;
n 4 selected from 0, 1, 2 or 3;
n 5 、n 6 and n 7 Each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8;
Ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 and L 5 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, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, haloaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3-15 membered ringA ring.
The compound of the application comprises a macrocyclic condensed ring mother nucleus structure formed by phenanthroindole and a benzene ring, and the mother nucleus is respectively connected with triarylamine, carbazole groups or nitrogen-containing electron-deficient heteroaryl. Wherein, the benzene ring connected with the nitrogen atom in the mother nucleus is connected with the 1-position carbon atom on the phenanthrene ring through a covalent bond, and the specific connection mode forms a condensed ring macrocyclic structure with a large conjugated system, thereby endowing the phenanthroindole group with more excellent hole transmission capability. When the parent nucleus is connected with triarylamine or carbazole groups, the hole transmission capacity of the compound can be further improved, and the compound is more suitable for being used as a hole transmission type main body material in a mixed main body material; when the parent nucleus is connected with the nitrogen-containing electron-deficient heteroaryl group, the material is more suitable as a bipolar host material with excellent electron and hole transport capacity.
In the present disclosure, 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 ring" means that the two substituents may or may not form a ring, i.e., include: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring. As another example, "Ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 And L 5 In which, optionally, any two adjacent substituents form a ring "means Ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 And L 5 Any two adjacent substituents of (a) are linked to form a ring, or Ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 And L 5 Any two adjacent substituents of (a) may be present independently of each other. Any two adjacent atoms can include two substituents on the same atom, and can also include two adjacent atoms with one substituent respectively; wherein the method comprises the steps ofWhen 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 of "… …" and "… …" and "… …" are used interchangeably and are to be understood in a broad sense, and refer to the fact 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, 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 aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, deuteroalkyl, halogenated aryl, cycloalkyl, etc. The number of substitutions may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.
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).
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
In the present 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 condensed ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon single bond conjugation, a monocyclic aryl group and a condensed ring aryl group linked by carbon-carbon single bond conjugation, two or more condensed ring aryl groups linked by carbon-carbon single bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon single bond may also be considered as aryl groups of the present application 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 may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.
In the present application, arylene refers to a divalent or polyvalent group formed by further loss of one or more hydrogen atoms from an aryl group.
In the present application, the terphenyl group includes
In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group, for example, a substituted aryl group having 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents being 18.
In the present application, the substituted or unsubstituted aryl (arylene) group may have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38, 40 or the like. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 40 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms.
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 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 And L 5 For example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.
In the present application, a 6-14 membered aromatic ring means an aromatic ring having 6 to 14 ring atoms, such as, but not limited to, a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring.
Heteroaryl in the context of the present application refers to 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 conjugated through a single carbon-carbon bond, and either aromatic ring system may be 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, the term "heteroarylene" refers to a divalent or polyvalent group formed by further losing one or more hydrogen atoms.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group may be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 3 to 40 carbon atoms, in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 3 to 30 carbon atoms, and in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 5 to 12 carbon atoms.
In the present application, ar is 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 And L 5 Heteroaryl groups of substituents of (a) such as, but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl, dibenzofuranyl.
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. 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, 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 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, or iodine.
In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
In the present application, specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application, specific examples of deuterated alkyl groups include, but are not limited to, tridentate methyl.
In the present application, deuterated aryl refers to aryl having deuteration such as, but not limited to, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, and the like.
In the present application, halogenated aryl means aryl having halogen substituent, such as but not limited to, fluorophenyl, fluoronaphthyl, fluorobiphenyl, and the like.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3, 4, 5, 6, 7, 8 or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring system“-#”、/>Which represents theOne end of the bond may 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 formula (f), the naphthyl group represented by formula (f) is linked to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in 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 the formula (X ' -1) to (X ' -4) includes any possible linkage as shown in the formula (X ' -1):
by an off-site substituent in the context of the present application is meant 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 formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means that it includes any of the possible linkages shown in formulas (Y-1) to (Y-7):
In some embodiments, the fused ring compound has a structure represented by the following formulas (1-1) to (1-4):
in some embodiments, rings E, F, P and Q are each independently selected from benzene rings, naphthalene rings, or phenanthrene rings.
Alternatively, rings E, F, P and Q are each independently selected from the following structures:
the position represents the fusion site.
In some embodiments, het is selected from the group consisting of:
- # represents a bond to L,represents a bond to L1, +.>Represents a bond to L2; wherein->Represents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
Alternatively, het is selected from the following groups:
- # represents a bond to L,represents a bond to L1, +.>Represents a bond to L2; wherein->Represents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
In some embodiments, L, L 1 、L 2 、L 3 、L 4 And L 5 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.
In some embodiments, L, L 1 、L 2 、L 3 、L 4 And L 5 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, or 15 carbon atoms, a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
Optionally L, L 1 、L 2 、L 3 、L 4 And L 5 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, phenyl or naphthyl.
In some embodiments, L, L 1 、L 2 、L 3 、L 4 And L 5 Identical or different and are each independently selected from single bonds, substituted or unsubstitutedSubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolylene.
Optionally L, L 1 、L 2 、L 3 、L 4 And L 5 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, trimethylsilyl or phenyl.
In some embodiments, L is selected from the group consisting of a single bond or:
in some embodiments, L 3 Selected from the group consisting of single bonds or:
in some embodiments, L 1 、L 2 、L 4 And L 5 Each independently selected from the group consisting of a single bond or:
In some embodiments, ar 1 、Ar 4 、Ar 5 And Ar is a group 6 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 7 to 20 carbon atoms; ar (Ar) 2 Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 7 to 20 carbon atoms.
In some embodiments of the present invention, in some embodiments,Ar 1 、Ar 4 、Ar 5 and Ar is a group 6 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 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
Alternatively, ar 2 A substituted or unsubstituted aryl group selected from hydrogen, a substituted or unsubstituted aryl group 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 a substituted or unsubstituted heteroaryl group having 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
In some embodiments, ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 Each of the substituents is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuteroalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, optionally any two adjacent substituents forming a benzene ring or a fluorene ring.
In some embodiments, ar 1 、Ar 4 、Ar 5 And Ar is a group 6 Each independently selected from the group consisting of substituted or unsubstituted groups V; ar (Ar) 2 A group V selected from hydrogen, substituted or unsubstituted; wherein the unsubstituted group V is selected from the group consisting of:
the substituted group V has one or more than two substituents, the substituents of the group V are each independently selected from deuterium, fluorine, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of the substituents on the group V is more than 1, the substituents are the same or different.
In some embodiments, ar 1 、Ar 4 And Ar is a group 5 Selected from the group consisting of; ar (Ar) 2 Selected from the group consisting of hydrogen or:
in some embodiments, ar 6 Selected from the group consisting of:
in some embodiments, ar 3 Selected from the group consisting of:
in some embodiments, ar 3 Selected from the group consisting of:
in some embodiments of the present invention, in some embodiments,selected from the following groups: />
In some embodiments of the present invention, in some embodiments, And->Each independently selected from the group consisting of->Selected from hydrogen or the following groups: />
In some embodiments, group a is selected from the following groups:
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in some embodiments, each R 1 、R 2 、R 3 、R 4 、R 5 、R 6 And R is 7 Identical or different and are each independently selected from deuterium, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.
Optionally, the fused ring compound is selected from the group consisting of the compounds shown below:
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in a second aspect of the present application, there is provided 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 the fused ring compound according to the first aspect of the present application.
The condensed-cyclic compound provided by the application can be used for forming at least one organic film layer in the functional layer so as to improve the luminous efficiency, the service life and other characteristics of the organic electroluminescent device.
Optionally, the functional layer includes an organic light emitting layer including the condensed ring compound. The organic light-emitting layer can be composed of the condensed-cyclic compound provided by the application or can be composed of the condensed-cyclic compound provided by the application and other materials.
According to a specific embodiment, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (hole auxiliary layer) 322, an organic light emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked.
In the present application, the anode 100 includes an anode material, which is preferably a material having 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. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
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, the first hole transport layer 321 consists of HT-1.
In one embodiment, second hole transport layer 322 is comprised of HT-2 or HT-3.
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 selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 is selected from, for example, the following compounds or any combination thereof;
in one embodiment, hole injection layer 310 is comprised of PD.
In the present 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. Optionally, the host material comprises a fused ring compound 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 in the present application. 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 phosphorescent dopants include but are not limited to,
in one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light emitting layer 330 comprises the fused ring compound of the present application. The guest material is, for example, RD-1 or GD.
In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light emitting layer 330 comprises the fused ring compound of the present application. The guest material may be, for example, fac-Ir (ppy) 3 。
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, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application is not particularly limited by comparison. 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 may be composed of ET-1 and LiQ, or of ET-2 and LiQ.
In the present 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, 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 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).
A third aspect of the application provides an electronic device comprising an organic electroluminescent device according to the second aspect of the 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 synthesis method of the condensed-cyclic compound of the present application is specifically described below with reference to synthesis examples, but the present disclosure 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 many of the organic compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the application can 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. All compounds of the synthesis process not mentioned in the present application are commercially available starting products.
Synthesis of Sub-a 1:
9-phenanthreneboronic acid (12.21 g,55 mmol), o-bromonitrobenzene (10.10 g,50 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.58g,0.5 mmol), anhydrous potassium carbonate (13.82 g,100 mmol), toluene (120 mL), anhydrous ethanol (30 mL) and deionized water (30 mL), stirring and heating were turned on, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure, Crude product is obtained. Purification of the crude product by silica gel column chromatography using n-heptane/dichloromethane as mobile phase gave Sub-a1 (11.67 g, 78% yield) as a white solid.
Sub-a2 to Sub-a4 were synthesized by referring to the method of Sub-a1, except that the o-bromonitrobenzene was replaced with reactant a shown in table 1.
Table 1: synthesis of Sub-a2 to Sub-a4
Synthesis of Sub-b 1:
to a 250mL three-necked flask under nitrogen atmosphere, sub-a1 (14.96 g,50 mmol), triphenylphosphine (32.78 g,125 mmol) and o-dichlorobenzene (150 mL) were added, stirring and heating were turned on, and the temperature was raised to reflux for 16h. After the system is cooled to room temperature, the solvent is removed by reduced pressure distillation, and the crude product is obtained. The crude product was purified by silica gel column chromatography using n-heptane as mobile phase to give Sub-b1 (7.48 g, yield 56%) as a white solid.
Sub-B2 through Sub-B4 were synthesized by referring to the method of Sub-a1, except that reactant B shown in Table 2 was used instead of Sub-a1.
Table 2: synthesis of Sub-b2 to Sub-b4
Synthesis of Sub-c 1:
sub-b1 (13.36 g,50 mmol), 2, 4-dichloro-1-iodobenzene (15.00 g,55 mmol), tris (dibenzylideneacetone) dipalladium (Pd) were sequentially added to a 500mL three-necked flask under nitrogen atmosphere 2 (dba) 3 ，0.916g,1 mmol), 2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl (XPhos, 0.95g,2 mmol), sodium tert-butoxide (9.61 g,100 mmol) and toluene (150 mL), and then heated to reflux and stirred for overnight; after the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using n-heptane/dichloromethane as mobile phase to give Sub-c1 (15.05 g, 73% yield) as a white solid.
Sub-C2 to Sub-C7 were synthesized with reference to the method of Sub-C1, except that reactant C shown in table 3 was used instead of Sub-b1 and reactant D was used instead of 2, 4-dichloro-1-iodobenzene.
Table 3: synthesis of Sub-c2 to Sub-c11
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Synthesis of Sub-d 1:
to a 250mL three-necked flask, sub-c1 (10.31 g,25 mmol), dichlorobis (tricyclohexylphosphine) palladium (0.92 g,1.25 mmol), t-valeric acid (5.10 g,50 mmol), cesium carbonate (16.29 g,50 mmol) and dimethylacetamide (100 mL) were added under nitrogen atmosphere, and the mixture was heated to reflux and stirred for 6 hours. After the reaction system was cooled to room temperature, the organic layer was extracted with methylene chloride (50 mL. Times.3 times), the organic phases were combined and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure after filtration to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane/ethyl acetate as mobile phase to give Sub-d1 (3.94 g, yield 42%) as a white solid.
Sub-d2 through Sub-d7 were synthesized by referring to the method of Sub-d1, except that reactant E shown in Table 4 was used instead of Sub-c1.
Table 4: synthesis of Sub-d2 to Sub-d7
Synthesis of Sub-e 1:
sub-d1 (18.79 g,50 mmol), pinacol biborate (15.24 g,60 mmol), potassium acetate (10.80 g,110 mmol) and 1, 4-dioxane (180 mL) were added sequentially to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating were turned on, tris (dibenzylideneacetone) dipalladium (0.46 g,0.5 mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxy-1, 1' -biphenol (SPhos, 0.41g,1.0 mmol) were rapidly added until the system warmed to 40℃and the temperature was continued to rise to reflux, stirring and reacting overnight. After the system is cooled to room temperature, 200mL of water is added into the system, the mixture is fully stirred for 30min, and filter cakes are collected after decompression and suction filtration; the filter cake was dissolved in methylene chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure after filtration to obtain a crude product. The crude product was purified by column chromatography on silica gel using n-heptane/dichloromethane as mobile phase to finally give Sub-e1 as a white solid (17.29 g, yield 74%).
Sub-e2 through Sub-e7 were synthesized by referring to the method of Sub-e1, except that reactant F shown in Table 5 was used instead of Sub-d1.
Table 5: synthesis of Sub-e2 to Sub-e7
Synthesis of Sub-f 1:
to a 500mL three-necked flask under nitrogen atmosphere was successively added Sub-e1 (23.37 g,50 mmol), m-chlorobromobenzene (9.57 g,50 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.58g,0.5 mmol), anhydrous potassium carbonate (13.82 g,100 mmol), toluene (240 mL), anhydrous ethanol (60 mL) and deionized water (60 mL), stirring and heating were turned on, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification of the crude product by silica gel column chromatography using n-heptane/dichloromethane as mobile phase gave Sub-f1 (17.85 g, 79% yield) as a white solid.
Sub-f2 to Sub-f17 were synthesized with reference to the method of Sub-f1, except that reactant G shown in table 6 was used instead of Sub-e1 and reactant H was used instead of m-chlorobromobenzene.
Table 6: synthesis of Sub-f2 to Sub-f17
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Synthesis of Sub-g 1:
to a 500mL three-necked flask under nitrogen atmosphere was added Sub-f1 (11.29 g,25 mmol), pinacol ester of biboron (7.62 g,30 mmol), potassium acetate (5.40 g,55 mmol) and 1, 4-dioxane (120 mL) in this order, stirring and heating were turned on, tris (dibenzylideneacetone) dipalladium (0.43 g,0.25 mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxy-1, 1' -biphenol (SPhos, 0.21g,0.5 mmol) were rapidly added until the system warmed to 40℃and the temperature was continued to rise to reflux, stirring reaction overnight. After the system is cooled to room temperature, 200mL of water is added into the system, the mixture is fully stirred for 30min, and a crude product is obtained after decompression and suction filtration; the crude product is dissolved by methylene dichloride and dried by anhydrous sodium sulfate, and the solvent is removed by reduced pressure distillation after filtration, thus obtaining the crude product. The crude product was purified by silica gel column chromatography using n-heptane/dichloromethane as mobile phase to give sub-g1 as a white solid (8.42 g, 62% yield).
Sub-g2 through Sub-g13 were synthesized by referring to the method of Sub-g1, except that reactant J shown in Table 7 was used instead of Sub-f1.
Table 7: synthesis of Sub-g2 to Sub-g13
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Synthesis of Compound A-12:
sub-d2 (9.40 g,25 mmol), RA-1 (CAS: 897671-78-2,7.75g,26.25 mmol), tris (dibenzylideneacetone) dipalladium (0.46 g,0.5 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxy-1, 1' -biphenol (SPhos, 0.41g,1 mmol), sodium t-butoxide (4.8 g,50 mmol) and xylene (100 mL) were added sequentially to a 500mL three-necked flask under nitrogen, warmed to reflux, and stirred overnight; after the system was cooled to room temperature, it was extracted with methylene chloride (50 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification of the crude product by silica gel column chromatography using n-heptane/dichloromethane as mobile phase gave compound A-12 (8.25 g; yield 52)％)，m/z＝635.2[M+H] + 。
The compounds of the present application were synthesized by referring to the method for compound A-12, except that reactant K was used instead of Sub-d2 and reactant L was used instead of RA-1, and the synthesized compounds, the yields thereof, and the mass spectrum characterization results are shown in Table 8.
Table 8: synthesis of the Compounds of the application
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Synthesis of Compound B-5:
RM-2 (CAS: 1883265-40-4,9.35g,25 mmol), sub-g6 (14.95 g,27.5 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.29g,0.25 mmol), anhydrous potassium carbonate (6.91 g,50 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 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification of the crude product by silica gel column chromatography using n-heptane/dichloromethane as mobile phase gave compound B-5 (10.0 g, 53% yield) as a white solid, m/z=755.2 [ m+h ]] + 。
The compounds of the present application were synthesized by referring to the method for compound B-5, except that reactant M was used in place of RM-2 and reactant N was used in place of Sub-g6, and the synthesized compounds and their yields and mass spectrum characterization results are shown in Table 9.
Table 9: synthesis of the Compounds of the application
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Nuclear magnetic data of partial compounds:
compound a-51 nuclear magnetism: 1 H-NMR(400MHz,CD 2 Cl 2 )δppm 8.51(d,1H),8.22-8.08(m,5H),8.01(d,1H),7.97-7.93(m,2H),7.68(d,1H),7.62(t,1H),7.56-7.37(m,12H),7.32(t,1H),7.26(s,1H),7.18(t,1H),7.06(d,1H),6.63(d,1H),6.46(d,2H)。
compound B-50 nuclear magnetism: 1 H-NMR(400MHz,CD 2 Cl 2 )δppm 8.88(s,1H),8.76(s,1H),8.69(d,1H),8.63(d,1H),8.53(d,1H),8.37(d,1H),8.28(d,1H),8.21-8.16(m,2H),8.11(t,1H),8.05-7.98(m 5H),7.92-7.86(m,2H),7.79-7.72(m,3H),7.70-7.43(m,8H),7.42-7.31(m,3H),7.18(t,1H)。
organic electroluminescent device preparation and evaluation:
example 1: red organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turnThe ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum evaporating PD on an experimental substrate (anode) to form a film with a thickness ofIs then vacuum evaporated onto the Hole Injection Layer (HIL) to form HT-1 with a thickness of +.>Is provided.
Vacuum evaporating compound HT-2 on the first hole transport layer to form a film of thicknessIs provided.
Then, on the second hole transport layer, the compound A-12:RH-N:RD-1 is subjected to co-evaporation at an evaporation rate ratio of 49 percent to 2 percent to form a film with a thickness ofRed light emitting layer (EML).
On the light-emitting layer, mixing and evaporating the compounds ET-1 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) in a 1:9 ratioIs deposited on the electron injection layer by vacuum evaporation to form a film having a thickness of +.>Is provided.
Further, CP-1 is vacuum deposited on the cathode to form a cathode having a thickness of Thereby completing the manufacture of the red organic electroluminescent device.
Examples 2 to 27
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound X in table 10 below was used instead of the compound a-12 in example 1 when the light-emitting layer was prepared.
Comparative examples 1 to 3
An organic electroluminescent device was prepared by the same method as in example 1, except that compound a, compound B, and compound C were used in place of compound a-12 in example 1, respectively, when the light-emitting layer was prepared.
Among these, the structures of the compounds used in examples 1 to 27 and comparative examples 1 to 3 were as follows:
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performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 27 and comparative examples 1 to 3, specifically at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 10.
Table 10
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Referring to table 10 above, it can be seen that when the compound of the present invention is used as a hole transport host material for a red organic electroluminescent device, the luminous efficiency of the device is improved by at least 14.2%, and the T95 lifetime is improved by at least 12.7%.
Example 28: red organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turn The ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum evaporating PD on an experimental substrate (anode) to form a film with a thickness ofIs then vacuum evaporated onto the Hole Injection Layer (HIL) to form HT-1 with a thickness of +.>Is provided.
Vacuum evaporating compound HT-3 on the first hole transport layer to form a film having a thickness ofIs provided.
Then, on the second hole transport layer, the compound B-5:RD-1 is subjected to co-evaporation at an evaporation rate ratio of 98 percent to 2 percent to form a film with a thickness ofRed light emitting layer (EML).
On the light-emitting layer, mixing and evaporating the compounds ET-2 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +.>Is provided.
Further, CP-1 is vacuum deposited on the cathode to form a cathode having a thickness ofThereby completing the manufacture of the red organic electroluminescent device.
Examples 29 to 57
An organic electroluminescent device was prepared by the same method as in example 28, except that the compound Y in Table 11 below was used instead of the compound B-5 in example 28 in the preparation of the light-emitting layer.
Comparative examples 4 to 6
An organic electroluminescent device was prepared by the same method as in example 28, except that compound D, compound E, and compound F were used in place of compound B-5 in example 28, respectively, when the light-emitting layer was prepared.
Among these, in examples 28 to 57 and comparative examples 4 to 6, the structures of the compounds used were as follows:
performance test was performed on the red organic electroluminescent devices prepared in examples 28 to 57 and comparative examples 4 to 6, specifically at 10mA/cm 2 Is tested under the condition of (2)IVL performance of the device is achieved, and service life of the T95 device is 20mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 11.
TABLE 11
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Referring to Table 11 above, it can be seen that when the compound of the present application is used as a bipolar light-emitting host material for a red organic electroluminescent device, the luminous efficiency of the device is improved by at least 10.3%, and the T95 lifetime is improved by at least 14.7%.
The reason for the above test results is that the compound of the present application includes a macrocyclic condensed ring mother nucleus structure formed by phenanthroindole and a benzene ring, and the mother nucleus is respectively connected with triarylamine, carbazole group or electron-deficient heteroaryl containing nitrogen. Wherein, the benzene ring connected with the nitrogen atom in the mother nucleus is connected with the 1-position carbon atom on the phenanthrene ring through a covalent bond, and the specific connection mode forms a condensed ring macrocyclic structure with a large conjugated system, thereby endowing the phenanthroindole group with more excellent hole transmission capability. When the compound is used as a hole transport type material or a single 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 light-emitting efficiency and the service life of a device can be improved. When the parent nucleus is connected with triarylamine or carbazole groups, the hole transmission capacity of the compound can be further improved, and the compound is more suitable to be used as a hole transmission type main body material in a mixed main body material; when the parent nucleus is connected with a nitrogen-containing electron-deficient heteroaryl group, the parent nucleus is more suitable for being used as a bipolar host material with excellent electron and hole transmission capacity.
The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, 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 (15)
1. A fused ring compound having a structure represented by the following formula 1:
the group A is selected from the group shown in a-1, a-2 or a-3:
L、L 1 、L 2 、L 3 、L 4 and L 5 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 3 selected from the group represented by a-4 or a-5:
ring E, F, P and Q are each independently selected from 6-14 membered aromatic rings;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms and contains at least 2 nitrogen atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
Ar 4 、Ar 5 and Ar is a group 6 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;
Each R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 And R is 7 The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms and cycloalkyl groups with 3 to 10 carbon atoms;
n 1 、n 2 and n 3 Each independently selected from 0, 1, 2, 3 or 4;
n 4 selected from 0, 1, 2 or 3;
n 5 、n 6 and n 7 Each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8;
Ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 、L、L 1 、L 2 、L 3 、L 4 and L 5 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, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, haloaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms and cycloalkyl having 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3-to 15-membered ring.
2. The fused ring compound according to claim 1, wherein each of rings E, F, P and Q is independently selected from a benzene ring, a naphthalene ring or a phenanthrene ring.
3. The fused ring compound according to claim 1, wherein Het is selected from the group consisting of:
- # represents a bond to L,representation and L 1 The key of the connection->Representation and L 2 A linked bond; wherein the formula does not containRepresents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
4. The fused ring compound according to claim 1, wherein Het is selected from the group consisting of:
- # represents a bond to L,representation and L 1 The key of the connection->Representation and L 2 A linked bond; wherein the formula does not containRepresents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
5. The fused ring compound according to claim 1, wherein L, L 1 、L 2 、L 3 、L 4 And L 5 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;
optionally L, L 1 、L 2 、L 3 、L 4 And L 5 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, phenyl or naphthyl.
6. The fused ring compound according to claim 1, wherein L, L 1 、L 2 、L 3 、L 4 And L 5 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 phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group;
optionally L, L 1 、L 2 、L 3 、L 4 And L 5 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, trimethylsilyl or phenyl.
7. The fused ring compound according to claim 1, wherein Ar 1 、Ar 4 、Ar 5 And Ar is a group 6 The same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and from 7 to 10 carbon atoms20 or an unsubstituted or substituted heteroaryl; ar (Ar) 2 Selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 7 to 20 carbon atoms;
alternatively, ar 1 、Ar 2 、Ar 4 、Ar 5 、Ar 6 Each of the substituents is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuteroalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, optionally any two adjacent substituents forming a benzene ring or a fluorene ring.
8. The fused ring compound according to claim 1, wherein Ar 1 、Ar 4 、Ar 5 And Ar is a group 6 Each independently selected from the group consisting of substituted or unsubstituted groups V; ar (Ar) 2 A group V selected from hydrogen, substituted or unsubstituted; wherein the unsubstituted group V is selected from the group consisting of:
the substituted group V has one or more than two substituents, the substituents of the group V are each independently selected from deuterium, fluorine, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of the substituents on the group V is more than 1, the substituents are the same or different.
9. The fused ring compound according to claim 1, wherein Ar 3 Selected from the group consisting of:
10. the fused ring compound according to claim 1, wherein,selected from the following groups:
11. the fused ring compound according to claim 1, wherein,each independently selected from the group consisting of->Selected from hydrogen or the following groups:
12. the fused ring compound according to claim 1, wherein the group a is selected from the group consisting of:
13. The fused ring compound according to claim 1, wherein the fused ring compound is selected from the group consisting of:
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14. 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; characterized in that the functional layer comprises the condensed-cyclic compound according to any one of claims 1 to 13;
optionally, the functional layer comprises an organic light-emitting layer comprising the fused ring compound.
15. An electronic device comprising the organic electroluminescent device as claimed in claim 14.
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