CN117683048A - Organic compound, organic electroluminescent device, and electronic device - Google Patents

Organic compound, organic electroluminescent device, and electronic device Download PDF

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CN117683048A
CN117683048A CN202211711030.4A CN202211711030A CN117683048A CN 117683048 A CN117683048 A CN 117683048A CN 202211711030 A CN202211711030 A CN 202211711030A CN 117683048 A CN117683048 A CN 117683048A
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carbon atoms
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夏博宇
王士攀
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Guangdong Juhua Printing Display Technology Co Ltd
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Guangdong Juhua Printing Display Technology Co Ltd
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Abstract

The application relates to the field of organic materials, and provides an organic compound, an organic electroluminescent device and an electronic device. The organic compoundThe organic compound has a structure shown in a formula 1, and can be applied to a light-emitting layer of an organic electroluminescent device as an organic light-emitting material, so that the performance of the device can be improved.。

Description

Organic compound, organic electroluminescent device, and electronic device
Technical Field
The present application relates to the field of organic materials, and in particular, to an organic compound, an organic electroluminescent device, and an electronic device.
Background
With the advent of the information age, display technology has gained popularity and application in life production. Organic light-emitting devices (Organic Light Emission Diodes, OLEDs) belong to a new generation of display lighting technology, and compared with inorganic material LED technology, organic light-emitting materials have low production cost, light weight, flexibility and controllable photophysical characteristics, and can be produced and prepared into flexible curved folding screens with pure chromaticity and larger size, so that the organic light-emitting devices have larger application scenes and spaces. In addition, the organic light-emitting micromolecules have the advantages of simple synthesis and easy regulation, so that the organic light-emitting micromolecules become the first choice of materials of the OLEDs light-emitting layer.
Currently, organic luminescent materials are mainly classified into conventional fluorescent materials, heavy metal organic complex phosphorescent materials, and thermally activated delayed fluorescence materials (TADF). The theoretical exciton utilization rate of the traditional fluorescent material can only reach 25% at most, while the theoretical exciton utilization rate of the heavy metal organic complex phosphorescent material can reach 100%, the heavy metals used are noble metals, the price is high, the resources are limited, and the use of the organic luminescent material is limited. Therefore, to further develop OLED technology, the development of novel organic light emitting materials has become extremely urgent and desired.
As a third-generation organic luminescent material, the theoretical exciton utilization rate of the thermal activation delay fluorescent material can reach 100 percent, and the organic luminescent material is easy to synthesize and prepare, has low manufacturing cost and gradually becomes a hot spot for researching the organic luminescent material. However, when the thermally activated delayed fluorescent material is applied to an OLED device as a light-emitting layer, there are still problems of serious device efficiency roll-off and short lifetime. Therefore, in order to make OLED devices more commercially useful, it is desirable to design a class of thermally activated delayed fluorescence materials with higher stability to improve the performance of OLED devices.
Disclosure of Invention
The application aims to provide an organic compound and application thereof, and an organic electroluminescent device and an electronic device. The organic compound is applied to an organic electroluminescent device as an organic luminescent material, and can improve the performance of the device.
In a first aspect, the present application provides an organic compound having a structure as shown in formula 1:
wherein X represents O, S or C (R a R b )，
R a And R is b The same or different and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms;
R 1 and R is 2 The same or different and are each independently an alkyl group having 1 to 10 carbon atoms;
L、L 1 and L 2 The same or different and each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms;
a is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group having 3 to 40 carbon atoms;
A 1 and A 2 The same or different and each independently is hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group having 3 to 40 carbon atoms;
L、L 1 、L 2 、A、A 1 and A 2 Wherein the substituents are the same or different and are each independently deuterium, halogen group, cyano group, hydroxyl group, nitro group, carbonyl group, malononitrile group, alkenyl group having 2 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, alkoxy group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylformyl group having 6 to 18 carbon atoms, arylsulfonyl group having 6 to 18 carbon atoms or arylsulfinyl group having 6 to 18 carbon atoms.
In a second aspect, the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other; and an organic light emitting layer disposed between the anode and the cathode, wherein the organic light emitting layer comprises the organic compound.
In a third aspect, the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
The organic compound provided by the application is diindole [3,2-c:2',3' -h ] xanthene ring derivatives as diindole [3,2-c:2',3' -h ] xanthene ring is a donor, has a larger three-dimensional rigid structure, so that an organic compound (thermally activated delayed fluorescent molecule) formed by combining the xanthene ring with different acceptors shows a larger torsion angle between the acceptors and the donor, the single-triplet state splitting energy of an organic luminescent material is effectively reduced, the rapid energy transfer of a luminescent layer is ensured, and annihilation of triplet state excitons is relieved.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Description of the reference numerals
100: organic electroluminescent device 1: anode 2: hole injection layer 3: hole transport layer
4: organic light emitting layer 5: electron transport layer 6: electron injection layer 7: cathode electrode
Detailed Description
In order to facilitate an understanding of the present application, a more complete description of the present application will now be provided with reference to the relevant figures. Preferred embodiments of the present application are shown in the accompanying drawings. This application may, however, be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
The inventors of the present application found in the study that diindole [3,2-c: the 2',3' -h ] xanthene ring has a plurality of sites containing nitrogen atoms, the nitrogen atoms play a role in electron donating conjugation, and can improve the electron cloud density of the diindole [3,2-c:2',3' -h ] xanthene ring unit, and the structure belongs to a structural unit with good power supply performance; in addition, the diindole [3,2-c:2',3' -h ] xanthene ring unit has more modification sites, is easy to carry out halogenation substitution and metal coupling reaction, and is convenient to further construct novel luminescent layer organic molecules according to the modification sites; meanwhile, the nitrogen atom on the indole ring is convenient to modify, and the solubility of the organic molecule can be regulated and controlled by introducing alkyl chains and the like; and the diindole [3,2-c:2',3' -h ] xanthene ring unit with a hepta-ring structure has larger stereo rigidity, and is combined with different acceptors to form a thermally activated delayed fluorescent molecule, so that a larger torsion angle is shown between the acceptors and the donor, the rapid transfer of energy in a luminescent layer is ensured, and annihilation of triplet excitons can be inhibited. Accordingly, the present application is presented.
A first aspect of the present application provides an organic compound having a structure as shown in formula 1:
wherein X represents O, S or C (R a R b )，
R a And R is b The same or different and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms;
R 1 and R is 2 Identical or different and are each independently a carbon atomAlkyl having a number of 1 to 10;
L、L 1 and L 2 The same or different and each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms;
a is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group having 3 to 40 carbon atoms;
A 1 and A 2 The same or different and each independently is hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group having 3 to 40 carbon atoms;
L、L 1 、L 2 、A、A 1 and A 2 Wherein the substituents are the same or different and are each independently deuterium, halogen group, cyano group, hydroxyl group, nitro group, carbonyl group, malononitrile group, alkenyl group having 2 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, alkoxy group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylformyl group having 6 to 18 carbon atoms, arylsulfonyl group having 6 to 18 carbon atoms or arylsulfinyl group having 6 to 18 carbon atoms.
In the present application, the term "substituted or unsubstituted" means that the functional group described later in the term may have a substituent or not. For example, "substituted or unsubstituted phenyl" refers to phenyl having a substituent or unsubstituted phenyl. Wherein the number of substituents may be 1 or 2 or more, deuterium, halogen group, cyano, hydroxy, nitro, carbonyl, malononitrile group, alkenyl, alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, arylformyl, arylsulfonyl, arylsulfinyl and the like. It should be understood that when the functional group has a substituent, the number of carbon atoms refers to the total number of carbon atoms of the functional group and its substituent. For example, when a is methyl-substituted phenyl, then a has a total carbon number of 7, i.e., a is methyl-substituted phenyl having 7 carbon atoms.
Aryl in this application refers to an aromatic hydrocarbon radical derived from an aromatic ring compound by the loss of one hydrogen atom. The aryl group may be a monocyclic aryl group (e.g., phenyl), a condensed ring aryl group (e.g., naphthyl), two or more monocyclic aryl groups (e.g., biphenyl) connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. Specific examples of aryl groups include, but are not limited to, phenyl, naphthyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10]Phenanthryl, pyrenyl, benzofluoranthenyl,Radicals, dibenzocycloalkyl radicals (e.g., fluorenyl, dihydroanthracene), and the like.
As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, a heterocyclic group refers to a monocyclic group or a polycyclic group having a heteroatom (-X-) in the cyclic structure and/or a heteroatom group (=x) attached to the cyclic structure. The heteroatom X may be at least one of B, O, N, P, si, se and S. Specifically, in the heterocyclic group, at least one of the hetero atoms in the ring structure is B, O, N, S, for example, and the hetero atom group attached to the ring structure is carbonyl (=o), for example. The heterocyclic group is, for example, a saturated or unsaturated 3-to 15-membered heterocyclic group. Saturated heterocyclic groups include heterocycloalkyl groups, unsaturated heterocyclic groups include heteroaryl groups, heterocyclic alkenyl groups, the number of unsaturated double bonds in the heterocyclic alkenyl groups may be 1 or 2 or more, examples of heterocyclic alkenyl groups include, but are not limited to, pyranyl groups.
In the present application, heteroaryl refers to a group formed by replacing at least one carbon atom with a heteroatom on the basis of aryl, the heteroatom may be at least one of B, O, N, P, si, se and S, and the number of heteroatoms in the heteroaryl may be 1, 2,3, 4, 5 or more. Heteroaryl groups may be monocyclic heteroaryl groups, fused ring heteroaryl groups. It is understood that condensed aromatic (hetero) groups having one or more (2 or more) carbonyl groups attached thereto are also considered heteroaryl groups. Specific examples of heteroaryl groups include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothioyl, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzop-dioxanyl, quinazolinonyl, benzothiadiazolyl, benzotriazole, thianthrenyl, phenothiazinyl, phenoxathioyl, thianthrene tetraoxide, phenothiazine dioxide, anthraquinone, phenothiazine dioxide, thioxanthene dioxide, and the like.
In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, "alkenyl" refers to a monovalent residue comprising a hydrocarbon having at least one site of unsaturation, i.e., a carbon-carbon sp2 double bond, losing one hydrogen atom. The phrase containing the term, for example, "alkenyl group having 2 to 10 carbon atoms" means a straight chain alkenyl group having 2 to 10 carbon atoms, a branched alkenyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkenyl group is, for example, 2,3, 4, 5,6, 7, 8, 9 or 10. Specific examples of alkenyl groups include, but are not limited to: vinyl (-ch=ch) 2 ) Allyl (-CH) 2 CH＝CH 2 )。
In the present application, the alkyl group may be an alkyl group having 1 to 10 carbon atoms, and the alkyl group may have 1, 2,3, 4, 5,6, 7, 8, 9, or 10 carbon atoms, for example. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, 1-butyl (n-Bu, n-butyl, -CH) 2 CH 2 CH 2 CH 3 ) 2-methyl-1-propyl (i-Bu, i-butyl, -CH) 2 CH(CH 3 ) 2 ) 2-butyl (s-Bu, s-butyl, -CH (CH) 3 )CH 2 CH 3 ) 2-methyl-2-propyl (t-Bu, t-butyl, -C (CH) 3 ) 3 ) 1-pentyl (n-pentyl, -CH) 2 CH 2 CH 2 CH 2 CH 3 ) 2-pentyl (-CH (CH 3) CH2CH2CH 3), 3-pentyl (-CH (CH) 2 CH 3 ) 2 ) 2-methyl-2-butyl (-C (CH) 3 ) 2 CH 2 CH 3 ) 3-methyl-2-butyl (-CH (CH) 3 )CH(CH 3 ) 2 ) 3-methyl-1-butyl (-CH) 2 CH 2 CH(CH 3 ) 2 ) 2-methyl-1-butyl (-CH) 2 CH(CH 3 )CH 2 CH 3 ) 1-hexyl (-CH) 2 CH 2 CH 2 CH 2 CH 2 CH 3 ) 2-hexyl (-CH (CH) 3 )CH 2 CH 2 CH 2 CH 3 ) 3-hexyl (-CH (CH) 2 CH 3 )(CH 2 CH 2 CH 3 ) 2-methyl-2-pentyl (-C (CH) 3 ) 2 CH 2 CH 2 CH 3 ) 3-methyl-2-pentyl (-CH (CH) 3 )CH(CH 3 )CH 2 CH 3 ) 4-methyl-2-pentyl (-CH (CH) 3 )CH 2 CH(CH 3 ) 2 ) 3-methyl-3-pentyl (-C (CH) 3 )(CH 2 CH 3 ) 2 ) 2-methyl-3-pentyl (-CH (CH) 2 CH 3 )CH(CH 3 ) 2 ) 2, 3-dimethyl-2-butyl (-C (CH) 3 ) 2 CH(CH 3 ) 2 ) 3, 3-dimethyl-2-butyl (-CH (CH) 3 )C(CH 3 ) 3 And octyl.
In the present application, "alkoxy" refers to a group of the structure-OR, i.e. the alkyl group R as defined above is attached to an adjacent group via an oxygen atom. The phrase containing the term, for example, "an alkoxy group having 1 to 10 carbon atoms" means that the alkyl moiety contains 1 to 10 carbon atoms. Examples of alkoxy groups include, but are not limited to: methoxy (-O-CH) 3 or-OMe), ethoxy (-O-CH 2 CH 3 or-OEt) and t-butoxy (-O-C (CH) 3 ) 3 or-OtBu).
In this application, halogen groups include chlorine, fluorine, bromine, iodine.
In the present application, examples of the arylsulfonyl group having 6 to 18 carbon atoms include, for example, 6, 12, 18 carbon atoms, arylsulfonyl groups include, but are not limited to, phenylsulfonyl groups
In the present application, examples of the aryl sulfinyl group having 6 to 18 carbon atoms such as 6, 12, 18 carbon atoms include, but are not limited to, phenyl sulfinyl
In the present application, examples of the arylformyl group having 6 to 18 carbon atoms having, for example, 6, 12, 18 carbon atoms include, but are not limited to, phenylformyl
In the present application, the number of carbon atoms of the aryl group as a substituent may be 6 to 18, for example, 6, 10, 12, 13, 14, 18. Examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, and the like.
In the present application, the heteroaryl group as a substituent may have a carbon number of 3 to 18, for example, 3, 4,6, 10, 12, 13, 14, 18. Examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, pyrimidinyl, quinolinyl, piperazinyl, and the like.
In the present application,indicating a connection, the reference to a non-positive connection being a reference to a connection extending from the ring systemIt is meant that one end of the linkage may be attached to any position in the ring system through which the linkage extends, the other end being attached to the remainder of the molecule. For example, as shown in the following formula (Q), the naphthyl group represented by the formula (Q) is substituted by two benzene rings penetrating through the different benzene ringsIs linked to other positions of the molecule, and is represented by any one of the possible linkages represented by the formulae (Q-1) to (Q-6):
for another example, as shown in the following formula (Z), the naphthyl group represented by the formula (Z) is linked to other positions of the molecule through an unositioned linkage extending from the middle of one benzene ring, and the linkage includes any linkage represented by the formula (Z-1) and the formula (Z-2):
an delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in formula (E), substituent R in formula (E) is attached to the naphthalene ring via an unoositioned bond, which means, including any possible attachment means shown in formulas (E-1) to (E-14):
in the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 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.
In the present application, the number of carbon atoms of the substituted or unsubstituted heterocyclic group may be 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.
In some embodiments, the organic compound has a structure of one of the following formulas 1-1 to 1-4:
in some embodiments, R a And R is b The same or different and are each independently hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl.
In some embodiments, R 1 And R is 2 The same or different and are each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl or n-hexyl.
Optionally L, L 1 And L 2 And are identical or different and are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.
Optionally L, L 1 And L 2 The same or different and are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
Optionally L, L 1 And L 2 Each of the substituents in (a) is independently deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
In a specific embodiment, L, L 1 And L 2 Identical or different, and are each independently a single bond and one of the following groups:
in some embodiments, A is an alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, or a substituted or unsubstituted unsaturated heterocyclic group having from 5 to 25 carbon atoms.
In some embodiments, a 1 And A 2 Identical or different and are each independently hydrogen, substituted or unsubstituted aryl having 6 to 25 carbon atoms, or substituted or unsubstituted aryl having 3 to 25 carbon atomsUnsubstituted unsaturated heterocyclic group.
Optionally A, A 1 And A 2 Wherein each heteroatom in the heterocyclyl is independently one or more of O, S, N and B.
Alternatively, A 1 And A 2 And are identical or different and are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 18 carbon atoms.
Optionally A, A 1 And A 2 The substituents in (a) are each independently deuterium, fluorine, cyano, hydroxyl, nitro, carbonyl, malononitrile, alkenyl having 2 to 5 carbon atoms, alkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkoxy having 1 to 4 carbon atoms, aryloxy having 6 to 12 carbon atoms, arylformyl having 6 to 12 carbon atoms, arylsulfonyl having 6 to 12 carbon atoms or arylsulfinyl having 6 to 12 carbon atoms.
In some embodiments, A is an alkyl group having 1 to 10 carbon atoms, or is substituted with one or more substituents M 1 A substituted or unsubstituted group W, wherein the group W is selected from one of the following groups:
each substituent M 1 Independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenoxy, phenyl, naphthyl, benzoyl, phenylsulfonyl or phenylsulfinyl.
Alternatively, a is methyl, ethyl, n-propyl, isopropyl, t-butyl or one of the following groups:
in some embodiments, a 1 And A 2 Identical or different and are each independently: hydrogen, alkyl having 1 to 4 carbon atoms, or by one or more substituents M 2 A substituted or unsubstituted group Z, wherein the group Z is selected from one of the following groups:
each substituent M 2 Independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenoxy, phenyl, naphthyl, benzoyl, phenylsulfonyl or phenylsulfinyl.
Further alternatively, A 1 And A 2 The same or different and are each independently hydrogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl and one of the following groups:
in some embodiments, in formula 1, L 1 And L 2 All are single bonds, A 1 And A 2 All are H, namely, the structure of the organic compound is shown as a formula A:
in a specific embodiment, L 1 And L 2 Are all single bonds, and A 1 And A 2 Are all H, andis one of the following groups:
in a further specific embodiment of the present invention,is->And->Identical or different and are each independently one of the following groups:
in some embodiments of the present invention, in some embodiments,the same applies.
In some embodiments, the organic compound has a structure of one of the following formulas 2-1 to 2-50:
wherein X is O, S or C (R a R b )，R a And R is b All are H or all are methyl.
In the present application "-C in chemical structure 6 H 13 "all means n-hexyl," -C 4 H 9 "means n-butyl.
Optionally, the organic compound is one of the following compounds:
the synthetic method of the organic compound provided in the present application is not particularly limited, and a person skilled in the art can determine a suitable synthetic method from the preparation method provided in the organic compound of the present application in combination with the synthesis example section. In other words, the synthesis examples section of the present application illustratively provides a process for the preparation of organic compounds, the starting materials employed being commercially available or obtainable by methods well known in the art. All organic compounds provided herein can be obtained by one skilled in the art from these exemplary preparation methods, and all specific preparation methods for preparing the organic compounds are not described in detail herein, and should not be construed as limiting the present application.
The organic compound is used as an organic luminescent material, has higher stability, more matched energy band gap and faster energy transfer, and is used as a luminescent layer to construct an OLED device, so that the annihilation effect between exciton triplet states in the luminescent layer is relieved, and the improvement of the device efficiency and the extension of the service life are realized. The organic luminescent material can form a functional layer of the OLED device by spin coating, ink-jet printing, vacuum evaporation and the like.
A second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other; and an organic light emitting layer disposed between the anode and the cathode, wherein the organic light emitting layer comprises the organic compound.
In some embodiments, the organic light emitting layer comprises a host material and a guest material, wherein the guest material comprises an organic compound described herein.
In the present application, the host material of the organic light emitting layer may be a metal chelating compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in the present application. In some embodiments, the host material includes at least one of TATC (CAS number 139092-78-7), CBP (CAS number 58328-31-7), TPD (CAS number 65181-78-4), and mCP (CAS number 550378-78-4).
The material of the anode is not particularly limited in the present application, and may be various anode materials capable of transporting holes. The anode material includes, for example, one or a combination of several of a metal, a metal oxide, and a conductive polymer. In some embodiments, the anode material is selected from at least one of Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and Indium Gallium Zinc Oxide (IGZO).
The material of the cathode is not particularly limited in the present application, and may be various cathode materials capable of transporting electrons. The cathode material may include a metal, such as one or a mixture of two or more of magnesium (Mg), calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum (Al), silver (Ag), tin, and lead, or an alloy of at least two thereof. In some embodiments, the cathode material is selected from at least one of Al, ag, mg, and mg—ag alloys.
In some embodiments, the organic electroluminescent device further comprises a hole functional layer disposed between the anode and the organic light emitting layer, and an electron functional layer disposed between the cathode and the organic light emitting layer. Wherein the hole functional layer comprises a hole injection layer and/or a hole transport layer, and the electron functional layer comprises an electron injection layer and/or an electron transport layer.
In one embodiment, as shown in fig. 1, an organic electroluminescent device 100 includes an anode 1, a hole injection layer 2, a hole transport layer 3, an organic light emitting layer 4, an electron transport layer 5, an electron injection layer 6, and a cathode 7, which are sequentially stacked.
In the present application, the material of the hole injection layer 2 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative or other materials, which is not particularly limited in the present application. In a specific embodiment, the hole injection layer 2 is made of HAT-CN.
In the present application, the hole transport material of the hole transport layer 3 may be selected from various electron rich organic materials that are favorable for hole transport, for example, arylamine derivatives, carbazole derivatives, and the like. In a specific embodiment, the hole transport material is NPB.
In this application, the material of the electron transport layer 5 may generally include a metal complex and/or a nitrogen-containing heterocyclic derivative, and specific examples include, but are not limited to, TPBi, BCP, bphen, NBphen, DBimiBphen, bimiBphen, and the like. In a specific embodiment, the material of the electron transport layer is TPBi.
In this application, the electron injection layer 6 may enhance the ability of electrons to be injected from the cathode 7 into the electron transport layer 5. The electron injection layer 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 a specific embodiment, the material of the electron injection layer is LiQ.
A third aspect of the present application provides an electronic device comprising the organic electroluminescent device.
In the present application, the electronic device may be a display device, a lighting device, an optical communication device, or other types of electronic devices, and specific examples include, but are not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, and an optical module.
The present application will be described below with reference to specific examples and examples.
Unless otherwise indicated, the synthetic routes for the organic compounds may be as follows:
z is H or Br.
Synthesis example 1
Synthesis of compound M1:
(1) 10H-phenoxazine (1.83 g,10 mmol), 4 '-bromo- [1,1' -biphenyl]-2,4, 6-Trinitrile (3.68 g,12 mmol), pd 2 (dba) 3 (320 mg,0.35 mmol), sodium t-butoxide (3.84 g,40 mmol) and tri-t-butylphosphine (0.5 g,2.5 mmol) were added to 200mL toluene, stirred and heated to 85℃for 24h, extracted with dichloromethane, dried and passed through the column to give intermediate M1-1 (3.36 g, 82% yield).
(2) Intermediate M1-1 (2.05 g,5 mmol) was added to 100mL of THF and stirred under ice bath for 10min, then NBS (1.78 g,10 mmol) was slowly added dropwise to the reaction apparatus, the reaction was completed for 10min, the ice bath was removed and warmed to 25℃for 40min, 20mL of aqueous sodium sulfite (1.04 g,10 mmol) was added to quench the reaction, extracted with dichloromethane, dried and passed through a column to give intermediate M1-2 (2.68 g, yield 95%).
(3) Intermediate M1-2 (2.98 g,5 mmol), pinacol biborate (5.08 g,20 mmol), potassium acetate (1.96 g,20 mmol) and Pd (dppf) Cl 2 (181 mg,0.25 mmol) was added to 150mL of redistilled dioxane, stirred and heated to refluxAnd the reaction was continued for 24 hours, extracted with methylene chloride, dried and passed through a column to give intermediate M1-3 (2.75 g, yield 83%).
(4) Intermediate M1-3 (3.31 g,5 mmol), o-bromonitrobenzene (3.03 g,15 mmol), potassium phosphate (12.7 g,60 mmol) and Pd (PPh) 3 ) 4 (0.29 g,0.25 mmol) was added to a mixture of 200mL toluene, 40mL ethanol and 252.6mL water, stirred and heated to 85deg.C, the reaction was continued for 24h, extracted with dichloromethane, dried and passed through a column to give intermediate M1-4 (2.6 g, 79% yield).
(5) M1-4 (0.65 g,1 mmol), PPh 3 (2 g,8 mmol) was dissolved in 20mL of o-dichlorobenzene (ODB), stirred and heated to reflux and the reaction was continued for 24 hours, the reaction was stopped, o-dichlorobenzene was removed by distillation under reduced pressure, the obtained crude product was separated by column chromatography to obtain a earthy yellow solid, the solid was directly fed to the next reaction, and a solution of 1-iodomethane (846 mg,6 mmol) and potassium hydroxide (336 mg,6 mmol) in dimethyl sulfoxide (40 mL) was added, stirred and heated to 85℃and the reaction was continued for 24 hours; extraction with dichloromethane, drying and column passage gave compound M1 (308 mg, 50% yield), mass spectrum: m/z=617.20 [ m+h ]] + 。
Nuclear magnetic data of compound M1: 1 HNMR(400MHz,CDCl 3 )δ8.35(s,2H),7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,4H),7.25-7.20(m,6H),6.99-6.97(m,2H),4.37(s,6H)。
synthesis example 2
Synthesis of compound M2:
(1) M2-4 was synthesized according to the procedure of M1-1, except that 4 '-bromo- [1,1' -biphenyl ] -2,4, 6-trimethylnitrile was replaced with 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine, to give intermediate M2-1 (4.32 g, yield 88%).
(2) M2-2 was synthesized by the method of M1-2, except that intermediate M1-1 was replaced with intermediate M2-1 to give intermediate M2-2 (3.0 g, yield 93%).
(3) M2-3 was synthesized by the method of M1-3 except that intermediate M1-2 was replaced with M2-2 to give intermediate M2-3 (3.15 g, yield 85%).
(4) M2-4 was synthesized by the method of M1-4, except that intermediate M1-3 was replaced with M2-3 to give intermediate M2-4 (2.75 g, yield 75%).
(5) M2 was synthesized following the procedure of M1, except that intermediate M1-4 was replaced with M2-4, which was passed through the column to give compound M2 (415 mg, 60% yield), mass spectrum: m/z=697.26 [ m+h ]] + 。
Nuclear magnetic data of compound M2: 1 HNMR(400MHz,CDCl 3 )δ8.67(dd,4H,J＝8.3Hz,1.4Hz),7.98-7.96(m,2H),7.85-7.84(m,2H),7.58(t,2HJ＝7.2Hz),7.54(t,4H,J＝7.2Hz),7.47-7.42(m,4H),7.25-7.20(m,6H),6.99-6.97(m,2H),4.37(s,6H).
synthesis example 3
Synthesis of Compound M3
(1) M3-1 was synthesized according to the procedure of M1-1, except that 4 '-bromo- [1,1' -biphenyl ] -2,4, 6-trimethylnitrile was replaced with 4-bromobenzoyl benzene, to give intermediate M3-1 (3.27 g, yield 90%).
(2) M3-2 was synthesized by the method of M1-2, except that intermediate M1-1 was replaced with M3-1 to give intermediate M3-2 (2.48 g, yield 96%).
(3) M3-3 was synthesized by the method of M1-3 except that intermediate M1-2 was replaced with M3-2 to give intermediate M3-3 (2.52 g, yield 82%).
(4) M3-4 was synthesized by the method of M1-4, except that intermediate M1-3 was replaced with M3-3 to give intermediate M3-4 (2.57 g, yield 85%).
(5) M3 was synthesized following the procedure of M1, except that intermediate M1-4 was replaced with M3-4, which was passed through a column to give compound M3 (256 mg, yield 45%). Mass spectrometry: m/z=570.21 [ m+h ]] + 。
Nuclear magnetic data of compound M3: 1 HNMR(400MHz,CDCl 3 )δ7.98-7.96(m,2H),7.85-7.84(m,2H),7.81-7.74(m,4H),7.69-7.65(m,1H),7.47-7.42(m,4H),7.25-7.20(m,6H),6.99-6.97(m,2H),4.37(s,6H).
synthesis examples 4 to 15
Compounds were prepared as in Synthesis example 1, except that 4 '-bromo- [1,1' -biphenyl ] -2,4, 6-trimethylnitrile was replaced with starting material 1, and in addition, in the synthesis of M9, methyl iodide in step (5) was replaced with 1-iodohexane, and the prepared compounds, the total yields thereof and the mass spectrometry results are shown in Table 1.
TABLE 1
Synthesis examples 16 to 22
The compounds listed in Table 2 were prepared in the same manner as in Synthesis example 1 except that 10H-phenoxazine in step (1) was replaced with raw material 2, and 4 '-bromo- [1,1' -biphenyl ] -2,4, 6-trimethylnitrile in step (1) was replaced with raw material 3, and the prepared compounds, the total yields thereof and mass spectrometry results are shown in Table 2.
TABLE 2
Synthesis example 23
Synthesis of Compound M23
(1) M11 (63.8 mg,0.13 mmol) was dissolved in 30mL of redistilled THF, and two vials were wrapped with tinfoil paper and placed in ice bath under stirring for 10min, N-bromosuccinimide (NBS, 71.2mg,0.4 mmol) was dissolved in 10mL of redistilled THF and slowly injected into the reaction vial by aspiration with a syringe, the reaction was continued under ice bath for 1h, the reaction was continued at 25℃for 3h, 10mL of aqueous sodium thiosulfate (30 wt% concentration) was added to the reaction vial, the reaction was quenched, then extracted, dried and the filtrate was collected to give crude product which was isolated using column chromatography to give intermediate M23-6 (64.7 mg, 77% yield).
Nuclear magnetic data of M23-6: 1 H NMR(500MHz,CDCl 3 )δ7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,4H),7.25-7.20(m,4H),6.99-6.97(m,2H),4.37(s,6H).
(2) M23-6 (1.16 g,1.8 mmol), 2',4',6 '-tricyano- [1,1' -diphenyl]-4-yl) boronic acid (1.48 g,5.41 mmol), potassium phosphate (1.40 g,6.6 mmol), pd (PPh) 3 ) 4 (0.21 g,0.18 mmol) in 50mL toluene, 10mL ethanol and 5mL water, stirring and heating to 85deg.C for 24h, extraction with dichloromethane, drying, and column chromatography to give compound M23 (1.36 g, 80% yield), mass spectrum: m/z=945.28 [ m+h ]] + 。
Nuclear magnetic data of compound M23: 1 HNMR(500MHz,CDCl 3 )δ9.11(s,4H),7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,12H),7.25-7.20(m,4H),6.99-6.97(m,2H),4.37(s,6H).
synthesis example 24
(1) M23-6 (1.17 g,1.8 mmol), pinacol diboronate (1.82 g,7.2 mmol), potassium acetate (704 mg,7.2 mmol) and Pd (dppf) Cl 2 (132 mg,0.18 mmol) was added to 50mL of redistilled dioxane, stirred and heated to 110deg.C, the reaction was continued for 24h, extracted with dichloromethane, dried and passed through a column to give boric acid intermediate M24-1 (1.15 g, 86% yield).
(2) M24-1 (1.54 g,1.8 mmol), 4-bromobenzo [ c ]][1,2,5]Thiadiazole-5, 6-dinitrile (1.43 g,5.41 mmol), potassium phosphate (1.40 g,6.6 mmol), pd (PPh 3 ) 4 (0.21 g,0.18 mmol) in 50mL toluene, 10mL ethanol and 5mL water, stirring and heating to 85deg.C for 24h, extraction with dichloromethane, drying, and column chromatography to give compound M24 (927 mg, 60% yield), mass spectrum: m/z=859.15 [ m+h ]] + 。
Nuclear magnetic data of compound M24: 1 HNMR(500MHz,CDCl 3 )δ8.54(s,2H),7.98-7.96(m,2H),7.85-7.84(m,2H),7.47-7.42(m,4H),7.25-7.20(m,4H),6.99-6.97(m,2H),4.37(s,6H).
example 1: preparation of organic electroluminescent device
The OLED device of this embodiment has the following composition: ITO/HAT-CN (30 nm)/NPB (50 nm)/TCTA: M1 (60 nm)/TPBi (50 nm)/LiQ (1 nm)/Al (120 nm). The preparation method comprises the following steps:
the ITO substrate (thickness 45 nm) was first cleaned in the following order: 5wt% KOH solution is subjected to ultrasonic treatment for 15min, pure water is subjected to ultrasonic treatment for 15min, isopropanol is subjected to ultrasonic treatment for 15min, and the drying is performed for 1h; the substrate was then transferred to a UV-OZONE apparatus for surface treatment for 15min, and immediately transferred to a glove box after the treatment.
HAT-CN was vacuum evaporated on a clean ITO substrate to form a Hole Injection Layer (HIL) with a thickness of 30 nm. NPB was vacuum-deposited on the hole injection layer to form a Hole Transport Layer (HTL) having a thickness of 50 nm.
The compound M1 as a guest material (dopant) and a host material TCTA were coated on a hole transport layer (the mass ratio of the dopant to the host material is 2:98, the solvent is xylene, the material concentration of the light-emitting layer is 20 mg/mL) by means of ink-jet printing, and dried at 140℃to form an organic light-emitting layer (EML) with a thickness of 60 nm.
Then, TPBi was vacuum-evaporated on the organic light emitting layer to form an Electron Transport Layer (ETL) having a thickness of 50 nm. LiQ was vacuum-deposited on the electron transport layer to form an Electron Injection Layer (EIL) having a thickness of 1 nm.
Subsequently, al was vapor-deposited on the electron injection layer to form a cathode having a thickness of 120 nm.
Finally, the OLED device is prepared by UV curing encapsulation and heating and baking for 20 min.
Examples 2 to 24
An organic electroluminescent device was fabricated according to the method of example 1, except that the compound listed in table 3 below ("guest material" column) was used instead of the compound M1 of example 1 in forming an organic light emitting layer, respectively.
Comparative example 1
An organic electroluminescent device was prepared as in example 1, except that Pm2 was used instead of the compound M1 of example 1 in forming an organic light-emitting layer.
In the above examples and comparative examples, the structures of the main materials used are as follows:
the performance of the organic electroluminescent devices prepared in examples and comparative examples was analyzed, in which the efficiency of the devices was tested under dark ambient conditions at 25℃in the light-shielding place at 1000Cd/m 2 The lifetime of the device at 80% decay in brightness was tested under brightness conditions and the results are shown in table 3.
TABLE 3 Table 3
From the above, the organic compound is used as the guest material of the light-emitting layer, so that the external quantum efficiency of the OLED device can be effectively improved, and the service life of the device can be prolonged.
The technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples merely represent a few embodiments of the present application, which are described in more detail and are not to be construed as limiting the scope of the invention. It should be noted that it would be apparent to those skilled in the art that various modifications and improvements could be made without departing from the spirit of the present application, which would be within the scope of the present application. Accordingly, the scope of protection of the present application is to be determined by the claims appended hereto.

Claims (13)

1. An organic compound, characterized in that the organic compound has a structure as shown in formula 1:
wherein X represents O, S or C (R a R b )，
R a And R is b The same or different and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms;
R 1 and R is 2 The same or different and are each independently an alkyl group having 1 to 10 carbon atoms;
L、L 1 and L 2 The same or different and each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms;
a is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group having 3 to 40 carbon atoms;
A 1 and A 2 The same or different and each independently is hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted saturated or unsaturated heterocyclic group having 3 to 40 carbon atoms;
L、L 1 、L 2 、A、A 1 and A 2 Wherein the substituents are the same or different and are each independently deuterium, halogen group, cyano group, hydroxyl group, nitro group, carbonyl group, malononitrile group, alkenyl group having 2 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, alkoxy group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylformyl group having 6 to 18 carbon atoms, arylsulfonyl group having 6 to 18 carbon atoms or arylsulfinyl group having 6 to 18 carbon atoms.
2. The organic compound according to claim 1, wherein R a And R is b The same or different and are each independently hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl; and/or
R 1 And R is 2 The same or different and are each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl or n-hexyl.
3. The organic compound according to claim 1, wherein L, L 1 And L 2 The same or different, and each independently is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group;
optionally L, L 1 And L 2 Each of the substituents in (a) is independently deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.
4. The organic compound according to claim 1, wherein L, L 1 And L 2 The same or a different one of the above,and each independently is a single bond or one of the following groups:
5. the organic compound according to claim 1, wherein a is an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted unsaturated heterocyclic group having 5 to 25 carbon atoms;
A 1 and A 2 The same or different and each independently is hydrogen, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted unsaturated heterocyclic group having 3 to 25 carbon atoms;
optionally A, A 1 And A 2 Wherein each heteroatom in the heterocyclyl is independently one or more of O, S, N and B;
optionally A, A 1 And A 2 The substituents in (a) are each independently deuterium, fluorine, cyano, hydroxyl, nitro, carbonyl, malononitrile, alkenyl having 2 to 5 carbon atoms, alkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkoxy having 1 to 4 carbon atoms, aryloxy having 6 to 12 carbon atoms, arylformyl having 6 to 12 carbon atoms, arylsulfonyl having 6 to 12 carbon atoms or arylsulfinyl having 6 to 12 carbon atoms.
6. The organic compound according to claim 1, wherein A is an alkyl group having 1 to 10 carbon atoms or is substituted with one or more substituents M 1 A substituted or unsubstituted group W, wherein the group W is one of the following groups:
each substituent M 1 Independent and independentDeuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenoxy, phenyl, naphthyl, benzoyl, phenylsulfonyl or phenylsulfinyl;
alternatively, a is methyl, ethyl, n-propyl, isopropyl, t-butyl or one of the following groups:
7. the organic compound according to claim 1, wherein a 1 And A 2 Identical or different and are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or are substituted by one or more substituents M 2 A substituted or unsubstituted group Z, wherein the group Z is one of the following groups:
each substituent M 2 Independently deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, methoxy, ethoxy, phenoxy, phenyl, naphthyl, benzoyl, phenylsulfonyl or phenylsulfinyl;
alternatively, A 1 And A 2 The same or different and are each independently hydrogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl and one of the following groups:
8. the organic compound according to claim 1, wherein in formula 1, L 1 And L 2 All are single bonds, A 1 And A 2 All are H.
9. The organic compound according to claim 1, wherein in formula 1, L 1 And L 2 All are single bonds, A 1 And A 2 Are all H, andis one of the following groups:
or alternatively
Is->Identical or different and are each independently one of the following groups:
10. the organic compound according to claim 1, wherein the organic compound is one of the following compounds:
11. an organic electroluminescent device, characterized in that the organic electroluminescent device comprises:
an anode and a cathode which are oppositely arranged; and
an organic light-emitting layer disposed between the anode and the cathode, wherein the organic light-emitting layer comprises the organic compound of any one of claims 1-10.
12. The organic electroluminescent device of claim 11, wherein the organic light-emitting layer comprises a host material and a guest material, wherein the guest material comprises the organic compound;
optionally, the host material comprises at least one of TATC, CBP, TPD and mCP.
13. An electronic device comprising the organic electroluminescent device as claimed in claim 11 or 12.
CN202211711030.4A 2022-12-29 2022-12-29 Organic compound, organic electroluminescent device, and electronic device Pending CN117683048A (en)

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