CN116003389A - Organic electroluminescent compounds and use thereof - Google Patents
Organic electroluminescent compounds and use thereof Download PDFInfo
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- CN116003389A CN116003389A CN202211737759.9A CN202211737759A CN116003389A CN 116003389 A CN116003389 A CN 116003389A CN 202211737759 A CN202211737759 A CN 202211737759A CN 116003389 A CN116003389 A CN 116003389A
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- substituted
- unsubstituted
- organic electroluminescent
- independently selected
- heteroaryl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 81
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- 239000000463 material Substances 0.000 claims description 47
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- 229910052805 deuterium Inorganic materials 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- -1 dibenzofuranyl Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 3
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- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 238000000034 method Methods 0.000 description 2
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 2
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- ULNROOMDGPXRQB-UHFFFAOYSA-N (4-pyrimidin-5-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=C1)C1=CN=CN=C1 ULNROOMDGPXRQB-UHFFFAOYSA-N 0.000 description 1
- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical compound C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JYPGHMDTTDKUEL-UHFFFAOYSA-N 2,4-dichloro-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 JYPGHMDTTDKUEL-UHFFFAOYSA-N 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Images
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention relates to the technical field of display, in particular to an organic electroluminescent compound and application thereof. The invention provides an organic electroluminescent compound, which has the following structure:
the organic electroluminescent device comprising the organic electroluminescent compound can have a lower driving voltage, higher current efficiency and longer lifetime.
Description
Technical Field
The invention relates to the technical field of display, in particular to an organic electroluminescent compound and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) convert electrical energy into light by applying electrical power to an organic electroluminescent material, which is considered to be the most promising display and lighting technology, typically comprise an anode, a cathode and an organic layer formed between the two electrodes. The organic layer of an organic light-emitting electronic version (organic EL) may include a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. The materials used in the organic layer may be classified into a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transporting material, an electron injecting material, and the like depending on their functions. In the device of the organic EL, holes from the anode and electrons from the cathode are injected into the light emitting layer by applying a voltage, and excitons having high energy are generated by recombination of the holes and electrons. Electrons of the organic electroluminescent material emit light by energy when they move to an excited state by energy and return to a ground state from the excited state.
However, the matching degree of the HOMO energy level and the LUMO energy level of the existing organic electroluminescent material with the adjacent energy levels is poor, so that the problems of low stability and unbalanced carrier mobility of the organic electroluminescent material are caused, the problems of high driving voltage and short service life of an organic electroluminescent device containing the organic electroluminescent material are caused, and the application of the organic electroluminescent device is severely limited.
Disclosure of Invention
The invention aims to solve the problems of low stability and unbalanced carrier mobility of the organic electroluminescent material caused by poor matching degree of HOMO and LUMO energy levels and adjacent energy levels of the conventional organic electroluminescent material, and the problems of low luminous efficiency and short service life of an organic electroluminescent device containing the organic electroluminescent material severely limit the application of the organic electroluminescent device, thereby providing an organic electroluminescent compound and application thereof.
Definition of substituent terms in the present invention:
as used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.
As used herein, the term "C1-C30 alkyl" refers to monovalent substituents derived from straight or branched chain saturated hydrocarbons having from 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.
As used herein, the term "C3-C30 cycloalkyl" refers to a mono-or polycyclic hydrocarbon derived from a hydrocarbon having from 1 to 30 ring backbone carbon atoms, which cycloalkanes may include cyclopropyl, cyclobutyl, adamantyl, and the like.
Aryl, arylene in the present invention includes monocyclic, polycyclic or fused ring aryl groups which may be interrupted by short non-aromatic units and may contain spiro structures, aryl groups including, but not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, and the like, arylene groups including, but not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracenyl, fluorenylene, spirobifluorenyl, and the like.
Heteroaryl, heteroarylene in the present invention includes monocyclic, polycyclic or fused ring heteroaryl groups, which rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, sulfur. Heteroaryl groups include, but are not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazayl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof, and the like; heteroarylene includes, but is not limited to, furanylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazaylene, pyridinyl, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, benzimidazolylene, benzothiazolylene, benzisothiazolylene, benzisoxazolylene, benzoxazolylene, isoquinolene, cinnolylene, cinnoline, quinazolinylene, quinoxaline, carbazolylene, phenazinylene, phenanthrenezine, phenanthrenedinylene, dioxolylene, dihydroacridine, and the like.
As used herein, the term "substituted" refers to a compound in which a hydrogen atom is replaced with another substituent. The position is not limited to a specific position as long as hydrogen at the position can be substituted with a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, unless otherwise indicated, hydrogen atoms include protium, deuterium, and tritium.
In the present invention, the definition of a group defines a range of carbon atoms, the number of carbon atoms being any integer within the defined range, for example, a C6-C30 aryl group, and the number of carbon atoms representing the aryl group may be any integer within the range of 6-60, for example, 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, or the like.
The scheme adopted by the invention is as follows:
the invention provides an organic electroluminescent compound, which has the following structure:
wherein Ar is 1 -Ar 3 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; wherein Ar is 1 -Ar 3 At least one of which is selected from the structures shown in formula 2,
wherein T is 1 ，T 2 ，T 3 ，T 4 ，T 5 Each independently selected from CR or N, R is selected from hydrogen or deuterium, and T 1 ，T 2 ，T 3 ，T 4 ，T 5 At least one selected from N;
L 1 -L 5 each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C60 heteroarylene;
Ar 5 selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
the substituent of the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C5-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C30 arylene and substituted C3-C60 heteroarylene is selected from one or two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl and C3-C12 heteroaryl;
wherein, the liquid crystal display device comprises a liquid crystal display device,
representing a connection key.
Preferably, the organic electroluminescent compound has a structure as shown below:
wherein Ar is 2 、Ar 3 、Ar 5 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
T 1 ，T 2 ，T 3 ，T 4 ，T 5 each independently selected from C or N, and T 1 ，T 2 ，T 3 ，T 4 ，T 5 At least one of which is selected from N;
L 2 、L 3 、L 5 each independently selected from the group consisting of a bond, a substituted or unsubstituted C1-C6 alkylene, a substituted or unsubstituted C6-C30 arylene, and a substituted or unsubstituted C3-C60 heteroarylene;
the substituent of the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C5-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C30 arylene and substituted C3-C60 heteroarylene is selected from one or two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl and C3-C12 heteroaryl;
x is selected from N.
Preferably, the L 1 -L 5 Each independently selected from the group consisting of a linkage, a substituted or unsubstituted C6-C30 arylene group.
Preferably, said Ar 1 -Ar 3 、Ar 5 Each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.
Preferably, L 2 、L 3 、L 5 Each independently selected from single bond, C6-C30 arylene;
Ar 2 、Ar 3 、Ar 5 each independently selected from the group consisting of C6-C30 aryl, C3-C18 heteroaryl;
x is selected from N.
Preferably T 1 Selected from N, T 2 ，T 3 ，T 4 ，T 5 Each independently selected from CR;
or T is 2 Selected from N, T 1 ，T 3 ，T 4 ，T 5 Each independently selected from CR;
or T is 1 ，T 5 Selected from N, T 2 ，T 3 ，T 4 Each independently selected from CR;
or T is 2 ，T 5 Selected from N, T 1 ，T 3 ，T 4 Each independently selected from CR;
or T is 1 ，T 4 Selected from N, T 2 ，T 3 ，T 5 Each independently selected from CR.
Preferably, L 2 、L 3 、L 5 Each independently selected from a single bond, phenylene, naphthylene;
Ar 2 、Ar 3 、Ar 5 each independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl.
The organic electroluminescent compound has a structure as shown below:
it will be appreciated that the bond La may be bonded to T 1 ，T 2 ，T 3 ，T 4 ，T 5 Any of the five elements representing C being joined, e.g. T 1 Selected from N, T 2 ，T 3 ，T 4 ，T 5 Independently of one another, from CR, la may be combined with T 2 ，T 3 ，T 4 ，T 5 Any one of which is connected; for example when T 3 When selected from CR, la may be combined with T 3 Directly connected.
It will be appreciated that the linkage Lb may be attached to any one of the C1-C4 carbon atoms in ring A.
Preferably, the compound is selected from the following:
the compound shown in formula 1 claimed in the present invention can be used as a host material of a light-emitting layer alone or together with other materials, and the invention is not limited in particular to the types of other materials, and can be a material of a light-emitting layer host as is conventional in the art, and further, the present invention also provides an organic electroluminescent composition comprising the above-mentioned organic electroluminescent compound and a compound having the following structure:
wherein Ar is W1 、Ar W2 、Ar W3 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, ar W1 、Ar W2 、Ar W3 Are not connected with each other or are connected with adjacent two to form a ring; l (L) W1 、L W2 、L W3 Each independently selected from the group consisting of a bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
the substituent of the substituted C6-C60 aryl, the substituted C3-C60 heteroaryl, the substituted C6-C30 arylene and the substituted C3-C30 heteroarylene is selected from one or two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl and C3-C12 heteroaryl.
Preferably, in formula 3, ar W1 、Ar W2 、Ar W3 Each independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted triazinyl, substituted or unsubstitutedA C3-C30 heteroaryl, a substituted or unsubstituted group Q, the group Q being selected from one of the following structures:
or Ar W1 、Ar W2 、Ar W3 Any two are linked to form a ring a, wherein ring a is:
wherein the substituent in the substituted phenyl, substituted biphenyl, substituted dibenzofuranyl, substituted naphthyl, substituted triphenylene, substituted triazinyl, substituted C3-C30 heteroaryl, and substituted group Q is selected from at least one of deuterium, phenyl, C1-C5 alkyl, and biphenyl;
R 10 -R 17 each independently selected from the group consisting of a bond, hydrogen, deuterium, halogen, cyano, C1-C30 alkyl, one or more subunits
C3-C30 alkyl, C7-C30 aralkyl, C6-C30 aryl, C3-C30 heteroaryl, C4-C30 heteroaralkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 cycloalkenyl, C1-C30 alkoxy, C6-C30 aryloxy each of which is substituted in a non-adjacent manner by an O atom and/or an S atom;
alternatively, R 10 -R 17 The two adjacent rings are connected with a ring B, wherein the ring B is selected from a C6-C30 aromatic ring and a C3-C30 heteroaromatic ring;
preferably, L W1 、L W2 、L W3 Each independently selected from the group consisting of a linkage, phenylene, biphenylene, and naphthylene.
Preferably, the connection bond is a single bond.
Preferably, the compound of formula 3 is selected from one of the following compounds:
the compound with the structure of the formula 3 is a known material and can be prepared by the conventional technical means.
Preferably, the mass ratio of any one of the above organic electroluminescent compounds to the compound having the structure of formula 3 is: 1:9-9:1;
preferably, the mass ratio of any one of the above organic electroluminescent compounds to the compound having the structure of formula 3 is: 2:8-8:2;
more preferably, the mass ratio of any one of the above organic electroluminescent compounds to the compound having the structure of formula 3 is: 3:7-7:3;
further preferably, the mass ratio of any one of the above organic electroluminescent compounds to the compound having the structure of formula 3 is: 4:6-6:4.
The invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises any one of the organic electroluminescent compounds.
Preferably, the organic layer includes a light emitting layer, and a material of the light emitting layer includes a host material and a guest material; the host material comprises any one of the above-described organic electroluminescent compounds or the above-described organic electroluminescent composition;
preferably, the guest material comprises a phosphorescent dopant or a thermally activated delayed fluorescence compound;
preferably, the phosphorescent dopant comprises a complex of a transition metal;
the organic electroluminescent device is an organic light emitting diode.
In an embodiment of the organic electroluminescent device, the first electrode of the organic electroluminescent device is an anode, the second electrode of the organic electroluminescent device is a cathode, the organic layer is composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer which are sequentially stacked, and the organic electroluminescent device further comprises a substrate, wherein the substrate is positioned on the surface of one side of the anode, which is opposite to the cathode.
Optionally, an electron blocking layer is further included between the hole transport layer and the light emitting layer.
Optionally, in the present invention, the synthetic route of any one of the above organic electroluminescent compounds includes the following steps:
step one:
step two:
step three:
wherein Y is halogen, preferably chlorine or bromine; x is N; t (T) 1 ，T 2 ，T 3 ，T 4 ，T 5 Wherein is equal to L 1 -L 3 Any one of which is linked to a member selected from C, T 1 ，T 2 ，T 3 ，T 4 ，T 5 Is not in conjunction with L 1 -L 3 At least one or both of the links is selected from N;
among the above reactions, the compound of formula (1) is synthesized mainly by using a Suzuki coupling reaction.
The invention has the beneficial effects that:
1. the organic electroluminescent compound provided by the invention is based on the structure of formula 1 and further limits Ar 1 -Ar 3 At least one of the structures shown in the formula 2 is selected from the structures, and the HOMO energy level and the LUMO energy level of the organic electroluminescent compound are matched with each other through the two structures so as to have higher matching degree with the adjacent energy level, so that the organic electroluminescent compound has higher stability and more balanced carrier mobility, and the organic electroluminescent device containing the organic electroluminescent material has lower driving voltage, higher current efficiency and longer service life.
2. The invention provides an organic electroluminescent composition, which is characterized in that a compound of formula 1 and a compound of formula 3 are combined with each other, so that the stability and carrier mobility balance of the organic electroluminescent composition are further improved, the driving voltage of an organic electroluminescent device comprising the organic electroluminescent composition is further reduced, the current efficiency is further improved, and the service life is further prolonged.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are needed in the description of the embodiments or the prior art will be briefly described, and it is obvious that the drawings in the description below are some embodiments of the present invention, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
FIG. 1 is a block diagram of an organic electroluminescent device in an embodiment of the device of the present invention
1-a substrate; 2-anode; 3-a hole injection layer; a 4-hole transport layer; a 5-light emitting layer; 6-an electron transport layer; 7-an electron injection layer; 8-cathode.
Detailed Description
The following examples are provided for a better understanding of the present invention and are not limited to the preferred embodiments described herein, but are not intended to limit the scope of the invention, any product which is the same or similar to the present invention, whether in light of the present teachings or in combination with other prior art features, falls within the scope of the present invention.
The specific experimental procedures or conditions are not noted in the examples and may be followed by the operations or conditions of conventional experimental procedures described in the literature in this field. The reagents or apparatus used were conventional reagent products commercially available without the manufacturer's knowledge.
The starting materials used in the following preparations of the present invention do not provide a synthetic method and are all commercially available starting material products. The solvents and reagents used in the present invention, such as tetrahydrofuran, potassium hydroxide, nitrobenzene, palladium catalyst and other chemical reagents, can be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai pichia pharmaceutical company or the carboline reagent company. In addition, the person skilled in the art can synthesize the compounds by known methods.
Example 1
The embodiment provides an organic electroluminescent compound N-44, and the preparation method of the compound N-44 specifically comprises the following steps:
step 1) Synthesis of intermediate N-B44 (reaction scheme above)
44-B Synthesis
Taking a 100 ml three-neck round bottom bottle, placing the bottle into a stirrer and an upper return pipe, adding raw material 4-chlorocarbazole (1 mmol), raw material 2-chloropyridine (1 mmol), DMF (10 ml), copper powder (0.1 mmol), potassium carbonate (2 mmol) and 18-crown ether-6 (0.1 mmol), heating to 140 ℃, reacting for 12 hours, cooling to room temperature, extracting with water and ethyl acetate, drying an organic phase by anhydrous magnesium sulfate, removing a solvent by using a rotary evaporator, separating a crude product by column chromatography (DCM: n-hexane=1:50), and obtaining an intermediate 44-B (yield 60%);
synthesis of 44-B-1
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, raw material 44-B (1 mmol), raw material 1-B (1 mmol), toluene (9 mL), ethanol (3 mL), water (3 mL), tetrakis triphenylphosphine palladium (0.05 mmol), potassium carbonate (2 mmol) were added, heated to 90℃and reacted for 12 hours, cooled to room temperature, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: n-hexane=1:50) to give intermediate 44-B-1 (yield 70%).
Synthesis of 44-B-2
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper return tube, 44-B-1 (1 mmol), (methoxymethyl) triphenylphosphine chloride (1.8 mmol) as a raw material, THF (10 mL) was added, the temperature was lowered to-10 ℃, and a tetrahydrofuran (150 mL) solution of t-BuOK (27 g) was slowly added dropwise with a constant pressure dropping funnel, and the temperature was maintained below-5 ℃. After the completion of the dropwise addition, the reaction was carried out at this temperature for 20 minutes. Then slowly heating to room temperature, and after the reaction liquid reaches the room temperature, continuing the reaction for 1h, and stopping the reaction. The reaction was extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: n-hexane=1:50) to give intermediate 44-B-2 (yield 82%).
Synthesis of 44-B-3
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, 44-B-2 (1 mmol) and hexafluoroisopropanol (14 mL) were added. Under the protection of nitrogen, the temperature is reduced to-10 ℃, after the temperature is reached, the triflic acid (3 mmol) is slowly added dropwise by using a constant pressure dropping funnel, and the temperature is always kept below-5 ℃. After the completion of the dropwise addition, the reaction was carried out at this temperature for 20 minutes. Then slowly heating to room temperature, and after the reaction liquid reaches the room temperature, continuing the reaction for 1h, and stopping the reaction. The reaction was extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: n-hexane=1:50) to give intermediate 44-B-3 (yield 78%).
Synthesis of N-B44
Taking 100 ml of a three-necked round bottom bottle, placing the bottle into a stirrer and an upper return pipe, adding raw material 44-B-3 (1 mmol), raw material duplex-frequency na alcohol borate (1 mmol), dioxane (10 ml), adding 1,1' -bis-diphenylphosphine ferrocene palladium dichloride (0.05 mmol), potassium acetate (2 mmol), heating to 110 ℃, reacting for 12 hours, cooling to room temperature, extracting with water and ethyl acetate, drying an organic phase with anhydrous magnesium sulfate, removing a solvent by using a rotary evaporator, separating a crude product by using column chromatography (DCM: N-hexane=1:50), and obtaining intermediate N-B44 (yield 77%);
step 2) Synthesis of intermediate N-A44 (reaction scheme above)
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, raw material N-B44 (1 mmol), 2-bromo-5- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) pyrimidine (1.05 mmol), toluene (9 mL), ethanol (3 mL), water (3 mL), and tetrakis triphenylphosphine palladium (0.05 mmol) were added, potassium carbonate (2 mmol) was heated to 90℃and reacted for 12 hours, after completion of the reaction, cooled to room temperature, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: N-hexane=1:50) to give intermediate N-A44 (yield 83%).
Step 3) Synthesis of Compound N-44 (reaction scheme above)
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, intermediate N-C44 (1.05 mmol), N-A44 (0.95 mmol) toluene (9 mL), water (3 mL), palladium 132 (0.05 mmol), sodium bicarbonate (2 mmol) were added, the temperature was heated to 90℃and the reaction was allowed to proceed for 12 hours, after completion of the reaction, the temperature was lowered to room temperature, water and ethyl acetate were used for extraction, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: N-hexane=1:50) to give compound N-44 (yield 81%).
Elemental analysis: c (C) 55 H 34 N 8 Theoretical value: c,81.87; h,4.25; n,13.89; actual measurement value: c,81.88; h,4.26; n,13.87; HRMS (ESI) M/z (m+): theoretical value: 806.30; actual measurement value: 807.29.
example 2
The embodiment provides an organic electroluminescent compound N-77, and the preparation method of the compound N-77 specifically comprises the following steps:
synthesis of intermediate N-C77
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, intermediate 2- ([ 1,1 '-biphenyl ] -4-yl) -4, 6-dichloro-1, 3, 5-triazine (1.05 mmol) was added, toluene (0.95 mmol) of (4- (pyrimidin-5-yl) phenyl) boronic acid (9 mL), water (3 mL) was added, 1' -bis-diphenylphosphine ferrocene palladium dichloride (0.05 mmol), sodium carbonate (2 mmol) was added, heating to 90℃and reaction was carried out for 12 hours, after the reaction was completed, cooled to room temperature, extracted with water and ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: N-hexane=1:50) to obtain intermediate N-C77 (yield 74%).
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, intermediate N-C77 (1.05 mmol), N-A44 (0.95 mmol) toluene (9 mL), water (3 mL), palladium 132 (0.05 mmol), sodium bicarbonate (2 mmol) were added, the temperature was heated to 90℃and the reaction was allowed to proceed for 12 hours, after completion of the reaction, the temperature was lowered to room temperature, water and ethyl acetate were used for extraction, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: N-hexane=1:50) to give compound N-77 (yield 79%).
Elemental analysis: c (C) 54 H 33 N 9 Theoretical value: c,80.28; h,4.12; n,15.60; actual measurement value: c,80.31; h,4.12; n,15.57; HRMS (ESI) M/z (m+): theoretical value: 807.28; actual measurement value: 808.37.
example 3
The embodiment provides an organic electroluminescent compound N-87, and the preparation method of the compound N-87 specifically comprises the following steps:
synthesis of intermediate N-A87 (shown in the above formula)
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, raw material N-B44 (1 mmol), 2-bromo-5- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) pyridine (1.05 mmol), toluene (9 mL), ethanol (3 mL), water (3 mL), tetrakis triphenylphosphine palladium (0.05 mmol), potassium carbonate (2 mmol) were added, heated to 90℃for 12 hours, after completion of the reaction, cooled to room temperature, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: N-hexane=1:50) to give intermediate N-A87 (yield 81%).
Synthesis of Compound N-87 (represented by the above formula)
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, intermediate N-C87 (1.05 mmol), N-A87 (0.95 mmol) toluene (9 mL), water (3 mL), palladium 132 (0.05 mmol), sodium bicarbonate (2 mmol) were added, the temperature was heated to 90℃and the reaction was allowed to proceed for 12 hours, after completion of the reaction, the temperature was lowered to room temperature, water and ethyl acetate were used for extraction, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: N-hexane=1:50) to give compound N-87 (yield 80%).
Elemental analysis: c (C) 49 H 30 N 6 Theoretical value: c,83.74; h,4.30; n,11.96; actual measurement value: c,83.76; h,4.30; n,11.95; HRMS (ESI) M/z (m+): theoretical value: 702.25; actual measurement value: 703.43.
example 4
The embodiment provides an organic electroluminescent compound N-139, and the preparation method of the compound N-139 specifically comprises the following steps:
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, intermediate N-C139 (1.05 mmol), N-A139 (0.95 mmol), toluene (9 mL), water (3 mL), palladium 132 (0.05 mmol), sodium bicarbonate (2 mmol) were added, the temperature was heated to 90℃and the reaction was allowed to proceed for 12 hours, after completion of the reaction, the temperature was lowered to room temperature, water was extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: N-hexane=1:50) to give compound N-139 (yield 80%).
Elemental analysis: c (C) 55 H 34 N 6 Theoretical value: c,84.81; h,4.40; n,10.79; actual measurement value: c,84.82; h,4.41; n,10.77; HRMS (ESI) M/z (m+): theoretical value: 778.28; actual measurement value: 779.31。
Example 5
The embodiment provides an organic electroluminescent compound N-178, and the preparation method of the compound N-178 specifically comprises the following steps:
step 1) Synthesis of intermediate N-B178 (reaction scheme above)
Synthesis of 178-B
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, 4-chlorocarbazole (1 mmol) as a raw material, 2-chloropyrimidine (1 mmol) as a raw material, DMF (10 mL) as a raw material, copper powder (0.1 mmol), potassium carbonate (2 mmol), 18-crown-6 (0.1 mmol) were added, the mixture was heated to 140℃for 12 hours, after the reaction was completed, cooled to room temperature, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: n-hexane=1:50) to obtain intermediate 178-B (yield 60%).
Synthesis of 178-B-1
100 mL of a three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, 178-B (1 mmol) as a raw material, 1-B (1 mmol) as a toluene (9 mL), ethanol (3 mL), water (3 mL), tetrakis triphenylphosphine palladium (0.05 mmol) as a potassium carbonate (2 mmol) were added, heated to 90℃for 12 hours, cooled to room temperature after the reaction was completed, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: n-hexane=1:50) to give intermediate 178-B-1 (yield 70%).
Synthesis of 178-B-2
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper return tube, 178-B-1 (1 mmol) of (methoxymethyl) triphenylphosphine chloride (1.8 mmol) as a raw material was added, THF (10 mL) was cooled to-10℃and a solution of t-BuOK (27 g) in tetrahydrofuran (150 mL) was slowly added dropwise through a constant pressure dropping funnel, and the temperature was maintained below-5℃all the time. After the completion of the dropwise addition, the reaction was carried out at this temperature for 20 minutes. Then slowly heating to room temperature, and after the reaction liquid reaches the room temperature, continuing the reaction for 1h, and stopping the reaction. The reaction was extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: n-hexane=1:50) to give intermediate 178-B-2 (yield 82%).
Synthesis of 178-B-3
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, and 178-B-2 (1 mmol) and hexafluoroisopropanol (14 mL) were added. Under the protection of nitrogen, the temperature is reduced to-10 ℃, after the temperature is reached, the triflic acid (3 mmol) is slowly added dropwise by using a constant pressure dropping funnel, and the temperature is always kept below-5 ℃. After the completion of the dropwise addition, the reaction was carried out at this temperature for 20 minutes. Then slowly heating to room temperature, and after the reaction liquid reaches the room temperature, continuing the reaction for 1h, and stopping the reaction. The reaction was extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: n-hexane=1:50) to give intermediate 178-B-3 (yield 78%).
Synthesis of N-B178
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, 178-B-3 (1 mmol) as a raw material, 1 mmol) as a bispinacol borate, 10mL of dioxane, 1' -bis-diphenylphosphino ferrocene palladium dichloride (0.05 mmol) as a raw material, potassium acetate (2 mmol) as a raw material, heating to 110℃for 12 hours, cooling to room temperature after the reaction, extracting with water and ethyl acetate, drying the organic phase with anhydrous magnesium sulfate, removing the solvent using a rotary evaporator, and separating the crude product by column chromatography (DCM: N-hexane=1:50) to obtain intermediate N-B178 (yield 75%).
Step 2) Synthesis of intermediate N-A178 (reaction scheme above)
A100 mL three-necked round bottom flask was taken and placed in a stirrer and an upper reflux tube, raw material N-B178 (1 mmol), 2-bromo-5- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) pyrimidine (1.05 mmol), toluene (9 mL), ethanol (3 mL), water (3 mL), and tetrakis triphenylphosphine palladium (0.05 mmol) were added, potassium carbonate (2 mmol) was heated to 90℃and reacted for 12 hours, after completion of the reaction, cooled to room temperature, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (DCM: N-hexane=1:50) to give intermediate N-A178 (yield 84%).
Step 3) Synthesis of Compound N-178 (reaction scheme above)
A100 mL three-necked round bottom flask was taken and placed in a stirrer and upper reflux tube, intermediate N-C178 (1.05 mmol), N-A178 (0.95 mmol) toluene (9 mL), water (3 mL), palladium 132 (0.05 mmol), sodium bicarbonate (2 mmol) were added, heated to 90℃for 12 hours, cooled to room temperature after the reaction was completed, extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was isolated by column chromatography (DCM: N-hexane=1:50) to give compound N-178 (yield 77%).
Elemental analysis: c (C) 52 H 31 N 9 Theoretical value: c,79.88; h,4.00; n,16.12; actual measurement value: c,79.90; h,4.01; n,16.09; HRMS (ESI) M/z (m+): theoretical value: 781.27; actual measurement value: 782.52.
examples 6 to 28
The synthetic route of the compound N-N is as follows:
wherein N-An and N-Cn are commercially available raw material products or intermediate products prepared in examples 1-5, and specific reaction steps refer to step 3) of example 1, wherein N-An is substituted for N-A44 and N-Cn is substituted for N-C44; the yields of N-An, N-Cn, N-N and N-N are shown in Table 1, and the results of elemental analysis are shown in Table 2.
TABLE 1
TABLE 2
Device embodiment
The embodiment provides an organic electroluminescent device, as shown in fig. 1, including an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a cathode 8, which are sequentially stacked on a substrate 1, wherein the device structure is as follows: substrate + anode (indium tin oxide (ITO) coated glass substrate)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/light emitting layer (EML)/Electron Transport Layer (ETL)/Electron Injection Layer (EIL)/cathode (Al).
The materials for manufacturing the organic electroluminescent device are as follows:
the preparation of the organic electroluminescent device comprises the following steps:
1) Cleaning a substrate:
the glass substrate coated with transparent ITO is subjected to ultrasonic treatment in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are that the glycol solvent is less than or equal to 10wt percent and the triethanolamine is less than or equal to 1wt percent), then washed in deionized water, subjected to ultrasonic degreasing in a mixed solvent of acetone and ethanol (the volume ratio of the acetone to the ethanol is 1:1), baked in a clean environment until the moisture is completely removed, and then cleaned by ultraviolet light and ozone.
2) Organic layer preparation:
transferring ITO transparent substrate into vapor deposition equipment, and vacuumizing to 1×10 -6 Up to 2X 10 -4 Pa, sequentially evaporating a 10nm Hole Injection Layer (HIL)/80 nm Hole Transport Layer (HTL)/38 nm light emitting layer (EML)/30 nm Electron Transport Layer (ETL)/1 nm Electron Injection Layer (EIL)/80 nm thick cathode (Al) on the anode film.
Wherein:
the Hole Injection Layer (HIL) is made of a mixture of NDP-9 and HT, wherein the mass ratio of the NDP-9 to the HT is 3:97;
the Hole Transport Layer (HTL) is made of HT;
the material of the light emitting layer (EML) comprises a host material and a guest material, wherein the host material is the organic electroluminescent composition prepared by the method and/or the organic electroluminescent composition, and the guest material is (piq) 2Ir (acac); the specific materials and the proportions are shown in Table 3;
the materials of the Electron Transport Layer (ETL) are shown in table 3;
the material of the Electron Injection Layer (EIL) is LiQ;
the organic electroluminescent device part layer, and materials and thicknesses thereof are shown in table 3.
TABLE 3 Table 3
Test case
The organic electroluminescent devices obtained in device examples 1 to 25 and comparative examples 1 to 4 in device examples were tested.
Instrument: the characteristics of current, voltage, brightness, luminescence spectrum and the like of the device are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;
test conditions: photoelectric characteristic test conditions: the current density was 10mA/cm2.
Life test: the current density was 50mA/cm2 and the time (in hours) was recorded when the device brightness was reduced to 95% of the original brightness. The device performance test results are shown in table 4:
TABLE 4 Table 4
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (15)
1. An organic electroluminescent compound characterized by having the structure shown below:
wherein Ar is 1 -Ar 3 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; wherein Ar is 1 -Ar 3 At least one of which is selected from the structures shown in formula 2,
wherein T is 1 ，T 2 ，T 3 ，T 4 ，T 5 Each independently selected from C or N, and T 1 ，T 2 ，T 3 ，T 4 ，T 5 At least one selected from N;
L 1 -L 5 each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C60 heteroarylene;
Ar 5 selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
the substituent of the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C5-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C30 arylene and substituted C3-C60 heteroarylene is selected from one or two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl and C3-C12 heteroaryl;
x is selected from N.
2. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound has a structure as shown below:
wherein Ar is 2 、Ar 3 、Ar 5 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
T 1 ，T 2 ，T 3 ，T 4 ，T 5 each independently selected from CR or N, R is selected from hydrogen or deuterium, and T 1 ，T 2 ，T 3 ，T 4 ，T 5 At least one of which is selected from N;
L 2 、L 3 、L 5 each independently selected from the group consisting of a bond, a substituted or unsubstituted C1-C6 alkylene, a substituted or unsubstituted C6-C30 arylene, and a substituted or unsubstituted C3-C60 heteroarylene;
the substituent of the substituted C1-C30 alkyl, substituted C3-C30 cycloalkyl, substituted C5-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C30 arylene and substituted C3-C60 heteroarylene is selected from one or two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl and C3-C12 heteroaryl;
x is selected from N.
3. The organic electroluminescent compound according to claim 1, wherein the L 1 -L 5 Each independently selected from the group consisting of a linkage, a substituted or unsubstituted C6-C30 arylene group.
4. The organic electroluminescent compound according to claim 1 or 2, wherein Ar is as described above 1 -Ar 3 、Ar 5 Each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstitutedSubstituted C5-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.
5. The organic electroluminescent compound as claimed in claim 1 or 2, wherein L 2 、L 3 、L 5 Each independently selected from single bond, C6-C30 arylene;
Ar 2 、Ar 3 、Ar 5 each independently selected from the group consisting of C6-C30 aryl, C3-C18 heteroaryl;
x is selected from N.
6. The organic electroluminescent compound as claimed in claim 1 or 2, wherein,
T 1 selected from N, T 2 ，T 3 ，T 4 ，T 5 Each independently selected from CR;
or T is 2 Selected from N, T 1 ，T 3 ，T 4 ，T 5 Each independently selected from CR;
or T is 1 ，T 5 Selected from N, T 2 ，T 3 ，T 4 Each independently selected from CR;
or T is 2 ，T 5 Selected from N, T 1 ，T 3 ，T 4 Each independently selected from CR;
or T is 1 ，T 4 Selected from N, T 2 ，T 3 ，T 5 Each independently selected from CR.
7. The organic electroluminescent compound as claimed in claim 1 or 2, wherein,
L 2 、L 3 、L 5 each independently selected from a single bond, phenylene, naphthylene;
Ar 2 、Ar 3 、Ar 5 each independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl.
8. An organic electroluminescent compound according to any one of claims 1 to 3, wherein the compound is selected from the group consisting of:
9. an organic electroluminescent composition comprising the organic electroluminescent compound as claimed in any one of claims 1 to 8, and a compound having a structure as shown below:
wherein Ar is W1 、Ar W2 、Ar W3 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, ar W1 、Ar W2 、Ar W3 Are not connected with each other or are connected with adjacent two to form a ring;
L W1 、L W2 、L W3 each independently selected from the group consisting of a bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
the substituent of the substituted C6-C60 aryl, the substituted C3-C60 heteroaryl, the substituted C6-C30 arylene and the substituted C3-C30 heteroarylene is selected from one or two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl and C3-C12 heteroaryl.
10. The organic electroluminescent composition according to claim 9, wherein in formula 3, ar W1 、Ar W2 、Ar W3 Each independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted diphenylAnd furyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted triazinyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted group Q, the group Q being selected from one of the following structures:
or Ar W1 、Ar W2 、Ar W3 Any two are linked to form a ring a, wherein ring a is:
wherein the substituent in the substituted phenyl, substituted biphenyl, substituted dibenzofuranyl, substituted naphthyl, substituted triphenylene, substituted triazinyl, substituted C3-C30 heteroaryl, and substituted group Q is selected from at least one of deuterium, phenyl, C1-C5 alkyl, and biphenyl;
R 10 -R 17 each independently selected from the group consisting of a bond, hydrogen, deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 alkyl wherein one or more methylene groups are each substituted in a non-adjacent manner by-O-and/or-S atoms, C7-C30 aralkyl, C6-C30 aryl, C3-C30 heteroaryl, C4-C30 heteroaralkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 cycloalkenyl, C1-C30 alkoxy, C6-C30 aryloxy;
alternatively, R 10 -R 17 The two adjacent rings are connected with a ring B, wherein the ring B is selected from a C6-C30 aromatic ring and a C3-C30 heteroaromatic ring;
preferably, L W1 、L W2 、L W3 Each independently selected from the group consisting of a linkage, phenylene, biphenylene, and naphthylene.
11. The organic electroluminescent composition according to claim 9 or 10, wherein the compound of formula 3 is selected from one of the following compounds:
12. the organic electroluminescent composition according to any one of claims 9 to 11, wherein the mass ratio of the organic electroluminescent compound according to any one of claims 1 to 8 to the compound having the structure of formula 3 is: 1:9-9:1;
preferably, the mass ratio of the organic electroluminescent compound according to any one of claims 1 to 8 to the compound having the structure of formula 3 is: 2:8-8:2;
more preferably, the mass ratio of the organic electroluminescent compound according to any one of claims 1 to 8 to the compound having the structure of formula 3 is: 3:7-7:3;
further preferably, the mass ratio of the organic electroluminescent compound according to any one of claims 1 to 8 to the compound having the structure of formula 3 is: 4:6-6:4.
13. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer comprising the organic electroluminescent compound of any one of claims 1-8.
14. The organic electroluminescent device of claim 13, wherein the organic layer comprises an electron transport layer comprising the organic electroluminescent compound of any one of claims 1-8.
15. The organic electroluminescent device according to claim 13 or 14, wherein the organic layer comprises a light-emitting layer, and a material of the light-emitting layer comprises a host material and a guest material; the host material comprising the organic electroluminescent composition of any one of claims 9-12;
preferably, the guest material comprises a phosphorescent dopant or a thermally activated delayed fluorescence compound;
preferably, the phosphorescent dopant comprises a complex of a transition metal;
the organic electroluminescent device is an organic light emitting diode.
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| KR20180031385A (en) * | 2016-09-20 | 2018-03-28 | 에스에프씨 주식회사 | Novel organic compounds and organic light-emitting diode therewith |
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| KR20180031385A (en) * | 2016-09-20 | 2018-03-28 | 에스에프씨 주식회사 | Novel organic compounds and organic light-emitting diode therewith |
| KR20190143188A (en) * | 2018-06-20 | 2019-12-30 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
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