CN116969979A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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Publication number
CN116969979A
CN116969979A CN202210383108.8A CN202210383108A CN116969979A CN 116969979 A CN116969979 A CN 116969979A CN 202210383108 A CN202210383108 A CN 202210383108A CN 116969979 A CN116969979 A CN 116969979A
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substituted
unsubstituted
aryl
cycloalkyl
heteroaryl
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李熠烺
李国孟
王璐
曾礼昌
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Hefei Dingcai Technology Co ltd
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Hefei Dingcai Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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Abstract

The invention relates to a compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device. The compound has a structure shown in the following formula. The compound provided by the invention is beneficial to improving the red shift adjustment of the luminous spectrum of the device.

Description

Organic compound and application thereof
Technical Field
The invention relates to a boron-nitrogen-containing organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device.
Background
Deep red/near infrared luminescent materials have particular applications in phototherapy, biological imaging, communications, and night vision displays, and therefore, deep red/near infrared luminescent OLED materials are also receiving increasing attention. However, due to the influence of the energy gap rule, along with the red shift of the luminescence wavelength, the vibration coupling between the single-state zero vibration level and the ground state high vibration level of the dye is greatly enhanced, so that the high-performance deep red light/near infrared material is very rare
Recently, a series of organic small molecular materials DABCA-1 (adv. Mater.2016,28,2777-2781J. Mater. Chem. C, 2019,7,3082-3089) based on boron-nitrogen resonance type thermal excitation delayed fluorescence have been reported by the subject group of Japanese Takuji Hatakeyama and Junji Kido, etc., wherein boron atoms, nitrogen atoms and phenyl groups in the compounds form a rigid polycyclic aromatic resonance skeleton. Due to the strong molecular rigidity, vibration coupling between the singlet state and the ground state can be suppressed, thereby obtaining high luminous efficiency. However, the maximum emission wavelength of the molecules using the parent nucleus is generally 460-480nm, and the required photochromic phase for deep red/near infrared is far.
The researchers of the present invention have discovered a smart molecular design through careful thought and continuous experimentation and are described in detail below. Surprisingly, the compound disclosed by the invention can adjust the luminescence peak value to be more than 650nm on the basis of the boron-nitrogen resonance skeleton, and can be used as a good deep red light/near infrared material.
Disclosure of Invention
In order to solve the technical problems, the invention designs a kind of boron-nitrogen structure-containing resonant fluorescent dye with deep red light/near infrared light emission of a specific structure.
The invention provides a compound, which has a structure shown as a general formula (1):
in the formula (1): ring a represents one of a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group;
X 1 、X 2 、X 3 、X 4 、X 5 each independently is CR 2 Or N;
X 6 is CR (CR) 3 Or N;
Z 1 、Z 2 each independently selected from NR 4 One of O or S;
R 1 、R 2 、R 3 、R 4 each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
the R is 1 、R 2 、R 3 、R 4 Each independently linked or not to an adjacent substituent;
R 1 、R 2 、R 3 、R 4 and the substituents of the substituents in the ring A are each independently selected from one or two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl.
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are all shown above and are not repeated.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, unless otherwise specified, in general
In the present specification, "each independently" means that the subject has a plurality of subjects, and the subjects may be the same or different from each other.
Heteroatoms in the present specification generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably N, O, S.
In the present specification, unless otherwise specified, the expression of a chemical element generally includes the concept of isotopes having the same chemical properties, for example, the expression of "hydrogen (H)", and also includes the expression of isotopes having the same chemical properties 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., and are not described in detail.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings.
In the present specification, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and further preferably C6-C20 aryl groups. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as, for example: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed ring aryl refers to a group in which at least two aromatic rings are contained in the molecule, and the aromatic rings are not independent of each other but share two adjacent carbon atoms condensed with each other. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl,And a radical, a tetracenyl radical, a derivative thereof, and the like. The naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl groupA group and a 9-fluorenyl group; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethyl fluorenyl, 9-dipropyl fluorenyl, 9-dibutyl fluorenyl 9, 9-dipentylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
The C3-C60 heteroaryl group mentioned in the present specification includes monocyclic heteroaryl groups and condensed ring heteroaryl groups, preferably C3-C30 heteroaryl groups, further preferably C4-C20 heteroaryl groups, and further preferably C5-C12 heteroaryl groups. Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are linked by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl, and the like. Condensed ring heteroaryl means a group in which at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) are contained in a molecule and two adjacent atoms are fused together without being independent of each other. Examples of fused ring heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Examples of the C6-C30 arylamino group mentioned in the present specification include: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like.
Examples of the C3-C30 heteroarylamino group mentioned in the present specification include: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
In the present specification, the C1 to C20 linear or branched alkyl group, preferably C1 to C18 linear or branched alkyl group, more preferably C1 to C16 linear or branched alkyl group, still more preferably C1 to C10 linear or branched alkyl group, exemplarily includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.
In the present specification, the C3-C20 cycloalkyl group includes a monocycloalkyl group and a multicycloalkyl group; wherein, monocycloalkyl refers to an alkyl group having a single cyclic structure; polycycloalkyl refers to a structure in which two or more cycloalkyl groups are formed by sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present specification, the C3 to C20 heterocycloalkyl group, further preferably a C3 to C10 heterocycloalkyl group, i.e., a group in which at least 1 carbon atom in the cycloalkyl group listed above is replaced with a heteroatom (e.g., O, S or N, etc.), illustratively includes but is not limited to: tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, dioxane, and the like.
In the present specification, examples of the C1-C10 alkoxy group which is preferably substituted or unsubstituted C1-C20 alkoxy group, and which is preferably substituted or unsubstituted C1-C10 alkoxy group, may be given as follows: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, the aryloxy group is a monovalent group composed of the above aryl group and oxygen, and the heteroaryloxy group is a monovalent group composed of the above heteroaryl group and oxygen. The C6-C30 arylamino groups illustratively include, but are not limited to: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like. The C3-C30 heteroarylamino groups illustratively include, but are not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
Further, R is preferably 1 At least one selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; more preferably, R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and substituted or unsubstituted C6-C30 aryl; most preferably, R 1 And one of hydrogen, methyl, ethyl, isopropyl, tertiary butyl, phenyl, biphenyl, naphthyl, anthryl and phenanthryl.
Further, X is preferable 1 、X 2 、X 3 、X 4 、X 5 Each independently is CR 2 ；
Still further, X is preferred 1 、X 2 、X 3 、X 4 、X 5 Each independently is CR 2 The R is 2 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl; r is R 2 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
continuing further, preference is given to X 3 、X 4 、X 5 Each independently is CR 2 The R is 2 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl;
further, X is preferable 1 、X 5 Each independently is CR 2 The R is 2 Is hydrogen, preferably X 2 、X 3 、X 4 Each independently is CR 2 The R is 2 One selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
Further, X 6 Is CR (CR) 3 ；
Still further, R is preferably 3 Selected from hydrogen, substituted or unsubstituted C1-C10 chainsAlkyl, one of substituted or unsubstituted C3-C10 cycloalkyl, R 3 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
further, X is preferable 6 Is CR (CR) 3 The R is 3 Selected from hydrogen.
Further, Z 1 、Z 2 Each independently selected from NR 4 ；
Still further, it is preferable that R 4 At least one selected from the group consisting of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, R 4 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
continuing further, preferably the R 4 Is a substituted or unsubstituted C6-C30 aryl group, R 4 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
still further, it is preferable that R 4 One selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthryl or phenanthryl, R 4 Each of the substituents independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
Further, the ring a in the formula (1) has a structure as shown in the formula (a) or (b):
in the formulas (a) and (b), the dotted line represents a condensed connection position with the formula (1);
the Y is 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Each of which is a single pieceIndependently selected from CR 5 Or N, the R 5 One selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said two adjacent R 5 Are connected in a ring or are not connected;
R 5 wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
preferably, said Y 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Each independently selected from CR 5 ；
Still preferably, the Y 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Each independently selected from CR 5 And the R is 5 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl;
most preferably, said Y 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Are independently selected from CR 5 And the R is 5 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
The compound of the present invention preferably has a structure represented by the formula (1-1) or the formula (1-2):
wherein X is 1 -X 6 、Z 1 、Z 2 、R 1 Is defined as in formula (1), Y 1 -Y 6 The definition of (a) is the same as that in the formulae (a) and (b).
Further preferably, the compound of the present invention preferably has a structure as shown in any one of the formulae (1-a), (1-b), (1-c), (1-d) or (1-e):
wherein X is 1 -X 6 、Z 1 、Z 2 、R 1 Is defined as in formula (1), Y 1 -Y 6 Is as defined in formula (a) and formula (b);
further, a structure represented by the formula (1-a) or (1-b) is preferable.
Further, the organic compounds of the present invention may preferably be represented by the following specific structural compounds M1 to M116, which are merely representative and do not limit the scope of the present invention:
the compound adopts the azulene ring with five-membered ring and seven-membered ring as a mother nucleus structure, and the compound light color is red shifted due to the fact that the azulene ring has lower singlet state and triplet state energy levels, and deep red light/near infrared emission can be realized.
The preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification and is very suitable for industrial application.
As another aspect of the present invention, there is also provided the use of a compound as described above in an organic electroluminescent device. In particular, the compound disclosed by the invention has excellent luminescence property, has an emission wavelength of more than 650nm, is suitable to be used as a deep red light/near infrared luminescent material, and is applied to the fields of medical treatment, biological imaging, communication, night vision display and the like.
Since the compounds of the present invention can also be used as dyes to achieve good light-emitting layers together with host materials. Devices for which applications include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.
The invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and at least one or more luminescent functional layers interposed between the first electrode and the second electrode, wherein the luminescent functional layers contain at least one compound according to the invention.
The structure of the organic electroluminescent device is consistent with that of the existing device, for example, the organic electroluminescent device comprises an anode layer, a plurality of luminous functional layers and a cathode layer; the plurality of light-emitting functional layers include at least a light-emitting layer, wherein the light-emitting layer contains the above-described organic compound of the present invention.
OLED devices prepared using the compounds of the present invention have deep red/near infrared emission.
Detailed Description
The technical scheme of the invention is further more specifically described below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The compounds of the present invention may be obtained by known methods, for example, synthesized by known organic synthesis methods. Exemplary synthetic routes are given below, but may be obtained by other methods known to those skilled in the art.
Synthesis example 1
Synthesis of compound M4:
synthesis of intermediate M4-1:
raw material A (40 g,177.07 mmol), bis (4-t-butylphenyl) amine (49.84 g,177.07 mmol), dibenzylideneacetone dipalladium (3.24 g,3.54 mmol), tri-t-butylphosphine tetrafluoroborate (1.98 g,7.08 mmol), sodium t-butoxide (34.04 g, 354.15 mmol) and toluene (500 ml) were put into a 1000ml three-necked flask, nitrogen was substituted for 3 times, and the temperature was raised to 110℃for reaction for 5 hours.
Cooling the system to room temperature, spin-drying the solvent, performing silica gel sample column chromatography to obtain a white solid, and recrystallizing with toluene and ethanol to obtain intermediate M4-1.3 g.
Synthesis of intermediate M4-2:
m4-1 (50 g,117.53 mmol), 1-azulenyl-4-tert-butylphenylamine (32.37 g,117.53 mmol), pd132 (1.66 g, 2.35 mmol), sodium tert-butoxide (22.59, 235.05 mmol) and toluene (500 ml) were charged into a 1000ml three-necked flask, nitrogen was substituted 3 times, and the temperature was raised to 100℃for reaction for 8 hours.
Cooling the system to room temperature, spin-drying the solvent, performing silica gel sample column chromatography to obtain a white solid, and recrystallizing with toluene and ethanol to obtain intermediate M4-2.54 g.
Synthesis of product M4:
intermediate M4-2 (50 g,75.15 mmol) was added to a 2000ml three-necked flask, tert-butylbenzene (600 ml) was added, and after stirring for 20 minutes, the reaction system was cooled to 0℃and then tert-butyllithium (117.42 mL,1.6M,187.87 mmol) was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 60 ℃ and continuously heating for 2h. The reaction temperature was again lowered to 0℃and boron tribromide (56.48 g,225.44 mmol) was added under nitrogen, followed by stirring for 10 minutes and then heating to 60℃for 30 minutes. Diisopropylethylamine (38.85 g,300.59 mmol) was added thereto again after the temperature of the system was lowered to 0℃and finally the reaction system was heated to 120℃for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gives 9.1g of crude product, toluene/ethanol recrystallization gives 8.7g, purity 99.55%. Mass spectrometry determines molecular ion mass: 638.71 (theory: 638.71).
Synthesis example 2
Synthesis of Compound M20:
synthesis of intermediate M20-1:
the synthesis of M20-1 is identical to that of M4-1 except that the starting material A is replaced by the starting material Bg.
Synthesis of intermediate M20-2:
the synthesis of M20-2 was identical to that of M4-2, except that 1-azulenyl-4-tert-butylphenylamine was replaced with starting material C and intermediate M4-1 was replaced with M20-1
Synthesis of product M20:
m20 is synthesized identically to M4 except that M4-2 is replaced by M20-2
Synthesis example 3
Synthesis of Compound M44:
synthesis of intermediate M44-1:
the synthesis of M44-1 is identical to that of M20-1 except that the bis (4-t-butylphenyl) amine is replaced with 4-t-butylphenyl-4-biphenylamine.
Synthesis of intermediate M44-2:
the synthesis of M44-2 is identical to that of M20-2, except that the starting material C is replaced with starting material D and the intermediate M20-1 is replaced with M44-1.
Synthesis of product M44:
m44 is synthesized identically to M20 except that M20-2 is replaced with M44-2.
Synthesis example 4
Synthesis of Compound M49:
synthesis of intermediate M49-1:
the synthesis of M49-1 was identical to that of M4-1 except that the bis (4-t-butylphenyl) amine was replaced with 1-azulenyl-4-t-butylphenylamine.
Synthesis of intermediate M44-2:
the synthesis of M49-2 was identical to that of M4-2, except that the starting material 1-azulenyl-4-tert-butylphenylamine was replaced with 2-azulenyl-4-tert-butylphenylamine and intermediate M4-1 was replaced with M49-1.
Synthesis of product M44:
m49 is synthesized identically to M4 except that M4-2 is replaced with M49-2.
And (3) quantitative calculation:
the compounds C1, C2, C3 and C4 of the prior art shown in the following structures served as comparative compounds of the present invention.
Wherein C1 refers to the synthetic method in CN111253421 a; c2 refers to the synthetic method in KR1020210117931 a; the above compounds may also be synthesized by synthetic methods well known to those skilled in the art, with reference to the synthetic methods in CN112851700a for C3 and C4, and are not described in detail herein.
The results of the quantitative calculations for C1, C2, C3 and C4 for some of the compounds of the invention and for the comparative compounds are shown in table 1 below.
Table 1:
numbering of compounds S1/eV Luminescence peak/nm
M4 1.11 1120
M20 1.86 665
M44 1.86 665
M49 0.91 1365
M50 0.69 1789
M51 1.33 935
C1 2.70 459
C2 2.63 471
C3 2.71 458
C4 2.76 449
In table 1, the S1 state energy level refers to: the energy level of the first singlet state of the compound is calculated by the following steps: optimizing the structure of the compound by adopting a density functional method, and calculating the first singlet energy level of the compound by adopting a time-dependent density functional method (B3 LYP/6-31G); the luminescence peak refers to the maximum emission wavelength of the compound; the calculation method comprises the following steps: 1240/S1; when the luminescence peak is located in the 660-700nm range, the compound light color is deep red light; when the light-emitting peak is located in the range of 700-2500nm, the light color of the compound is near infrared, and when the light-emitting peak of the compound is located in the range of 400-500nm, the light color is blue light.
From the results of Table 1, the compounds of the present invention have lower S1 state energy levels than the comparative compounds C1, C2, C3 and C4, and the peak-to-peak luminescence is in the deep red/near infrared region, and the compounds of the present invention can achieve high-efficiency near infrared emission. This may be due to the introduction of a specific group "azulene ring" in the molecular structure of the compounds of the present invention, since the azulene ring has a unique planar conjugated structure, the band gap of the compounds may be reduced, resulting in red shift of the luminescence of the compounds. The light emission peaks of the contrast compounds C1, C2, C3 and C4 are all positioned in the blue light region, and the light color requirement of the deep red light/near infrared material cannot be met.
Device example:
the specific embodiment is as follows:
the OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) An oxide transparent conductive material such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-51; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1 through HI-3 described below; one or more compounds of HT-1 through HT-51 may also be used to dope one or more of HI-1 through HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-24 listed below.
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In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described below; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, but are not limited thereto.
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The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
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In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ,LiF,NaCl,CsF,Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca，Mg，Yb。
The preparation process of the organic electroluminescent device in this embodiment is as follows:
device example 1 fabrication method: the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with anode in vacuum chamber, vacuumizing to<1×10 -5 Pa, vacuum thermal evaporation is carried out on the anode layer film in sequence, wherein 10nm of HT-4:HI-3 (97/3,w/w) mixture is used as a hole injection layer, 60nm of compound HT-4 is used as a hole transmission layer, 5nm of compound HT-14 is used as an electron blocking layer, 20nm of compound BFH-4:M20 (100:3, w/w) binary mixture is used as a light emitting layer, 5nm of ET-23 is used as a hole blocking layer, 25nm of compound ET-69:ET-57 (50/50, w/w) mixture is used as an electron transmission layer,1nm LiF is used as an electron injection layer, and 150nm metallic aluminum is used as a cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Device example 2, and comparative examples 1, 2, 3, and 4 were fabricated in the same manner as device example 1, except that the dopant in the light-emitting layer was replaced with the compound M49 of the present invention and the comparative compounds C1, C2, C3, and C4 of the present invention, respectively.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the properties of the organic electroluminescent devices prepared in examples and comparative examples were measured at the same brightness using a digital source table and PR 650. Specifically, the light color of the resulting device may be directly tested on PR 650.
The performance data of the organic electroluminescent devices prepared in the examples and comparative examples of the respective devices are shown in Table 2 below.
Table 2:
device numbering Dopant(s) Photochromic light
Device example 1 M20 Deep red
Device example 2 M49 Near infrared
Device comparative example 1 C1 Blue light
Device comparative example 2 C2 Blue-green
Device comparative example 3 C3 Blue light
Device comparative example 4 C4 Blue light
From the results in table 2, the compounds of the present invention exhibited deep red or near infrared light emission, and the comparative compounds C1, C2, C3 and C4 exhibited blue or blue-green light emission, relative to the compounds C1, C2, C3 and C4, mainly because the introduction of the azulene ring of the large planar conjugated structure in the molecular structure of the compounds of the present invention reduced the S1 state energy level of the compounds, resulting in red shift of luminescence thereof. The above results prove that the compounds of the invention can be used as deep red light/near infrared materials with good performance.
The foregoing description of the embodiments has been provided for the purpose of illustrating the general principles of the invention, and is not meant to limit the invention thereto, but to limit the invention thereto, and any modifications, equivalents, improvements and equivalents thereof may be made without departing from the spirit and principles of the invention.

Claims (11)

1. A compound having a structure represented by formula (1):
in the formula (1): ring a represents one of a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group;
X 1 、X 2 、X 3 、X 4 、X 5 each independently is CR 2 Or N;
X 6 is CR (CR) 3 Or N;
Z 1 、Z 2 each independently selected from NR 4 One of O or S;
R 1 、R 2 、R 3 、R 4 each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
the R is 1 、R 2 、R 3 、R 4 Each independently linked or not to an adjacent substituent;
R 1 、R 2 、R 3 、R 4 and the substituents of the substituents in the ring A are each independently selected from one or two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl.
2. The compound according to claim 1, wherein the ring a in the formula (1) has a structure as shown in formula (a) or formula (b):
in the formulas (a) and (b), the dotted line represents a condensed connection position with the formula (1);
the Y is 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Each independently selected from CR 5 Or N, the R 5 One selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said two adjacent R 5 Are connected in a ring or are not connected;
R 5 wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
preferably, said Y 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Each independently selected from CR 5 ；
Still preferably, the Y 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Each independently selected from CR 5 And the R is 5 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl;
most preferably, said Y 1 、Y 2 、Y 3 、Y 4 、Y 5 And Y 6 Are independently selected from CR 5 And the R is 5 Selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentylA group or a cyclohexyl group.
3. The compound according to claim 2, which has a structure represented by formula (1-1) or formula (1-2):
wherein X is 1 -X 6 、Z 1 、Z 2 、R 4 Is defined as in formula (1), Y 1 -Y 6 The definition of (a) is the same as that in the formulae (a) and (b).
4. A compound according to claim 3, having a structure as shown in any one of formulae (1-a), (1-b), (1-c), (1-d) or (1-e):
wherein X is 1 -X 6 、Z 1 、Z 2 、R 1 Is defined as in formula (1), Y 1 -Y 6 Is as defined in formula (a) and formula (b);
further, it has a structure as shown in the formula (1-a) or (1-b).
5. The compound of any one of claims 1-4, wherein R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
preferably, R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and substituted or unsubstituted C6-C30 aryl; more preferably, R 1 Selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl,One of biphenyl, naphthyl, anthryl and phenanthryl.
6. The compound of any one of claims 1-4, wherein X is 1 、X 2 、X 3 、X 4 、X 5 Each independently is CR 2 ；
Further, the X 1 、X 2 、X 3 、X 4 、X 5 Each independently is CR 2 The R is 2 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl; r is R 2 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
continuing further, the X 3 、X 4 、X 5 Each independently is CR 2 The R is 2 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl;
further, the X 1 、X 5 Each independently is CR 2 The R is 2 Is hydrogen, preferably X 2 、X 3 、X 4 Each independently is CR 2 The R is 2 One selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
7. The compound of any one of claims 1-4, wherein X is 6 Is CR (CR) 3 ；
Further, the R 3 Selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, R 3 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
further, the X 6 Is CR (CR) 3 The R is 3 Is hydrogen.
8. The compound of any one of claims 1-4, wherein Z 1 、Z 2 Each independently is NR 4 ；
Further, the R 4 At least one selected from the group consisting of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, R 4 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
continuing further, the R 4 Is a substituted or unsubstituted C6-C30 aryl group, R 4 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
further, the R 4 One selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthryl or phenanthryl, R 4 Each of the substituents independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
9. The organic compound according to claim 1, having the structure shown below:
10. use of an organic compound according to any one of claims 1 to 9 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper;
preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a light-emitting dye in a light-emitting layer.
11. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 9;
preferably, the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 9.
CN202210383108.8A 2022-04-13 2022-04-13 Organic compound and application thereof Pending CN116969979A (en)

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