CN119638746A - A phosphine oxide compound and an organic electroluminescent device containing the compound - Google Patents
A phosphine oxide compound and an organic electroluminescent device containing the compound Download PDFInfo
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- CN119638746A CN119638746A CN202311194549.4A CN202311194549A CN119638746A CN 119638746 A CN119638746 A CN 119638746A CN 202311194549 A CN202311194549 A CN 202311194549A CN 119638746 A CN119638746 A CN 119638746A
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Abstract
The invention belongs to the technical field of organic electroluminescence, and particularly relates to a phosphine oxide compound and an organic electroluminescent device containing the same. A phosphine oxide compound having a structure represented by formula (1):
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to a phosphine oxide compound and an organic electroluminescent device containing the same.
Background
The organic electroluminescent device (Organiclightemittingdiode) is a self-luminous display device based on an organic electroluminescent material, has the characteristics of no backlight source and thin thickness unlike the conventional liquid crystal display device, and is a technology suitable for a flexible device (flexible light-emitting display device). The organic light emitting device has an anode and a cathode, and a structure in which an organic thin film is disposed between the two electrodes. A simple device comprising a single light emitting unit or a serial device of a plurality of light emitting units. Simple devices typically include a hole transport layer, a light emitting layer, and an electron transport layer. Because the electron mobility of the electron transport layer material is far lower than that of the hole transport layer material, the unbalance of holes and electrons entering the light-emitting layer is caused, and the light-emitting efficiency and the service life of the device are affected. Tandem devices typically provide charge generation layers between the light emitting cells to ensure efficient charge distribution to the light emitting stacks while improving current efficiency in the individual light emitting layers. Generally, the charge generation layer has a PN junction in which an N-type charge generation layer and a P-type charge generation layer are stacked in order.
Since the injection barrier of electrons from the N-type charge generation layer to the adjacent electron transport layer is relatively large, electrons accumulate at the interface between the N-type charge generation layer and the adjacent electron transport layer, which is likely to cause deterioration of the interface, shortening the lifetime of the device, and the energy level difference between the electron transport layer and the N-type charge generation layer may cause an increase in driving voltage.
Therefore, development of novel materials is urgently required to improve the luminous efficiency and the lifetime of the device.
Disclosure of Invention
The present invention is directed to a phosphine oxide compound, and an organic electroluminescent device prepared using the same can achieve improved luminous efficiency, reduced driving voltage, and durable service life.
The technical scheme adopted for solving the technical problems is as follows:
A phosphine oxide compound having a structure represented by formula (1):
Wherein X is selected from CR or N,
R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, L 1-L2 is independently selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene,
R 1-R4 is each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,
-L 1R1、-L2R2 are identical or different and,
The substituent is selected from one or combination of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl and C3-C30 heteroaryl when substituted or unsubstituted;
the hetero atom of the heteroaryl group is selected from one or more of oxygen, sulfur and nitrogen.
Preferably, the X is selected from CH or N, -L 2R2 is not hydrogen or deuterium when-L 1R1 is hydrogen, -L 2R2 is not hydrogen or deuterium when-L 1R1 is deuterium.
Preferably, said X is selected from CH.
Preferably, the X is selected from N.
Preferably, the R 3 is selected from phenyl.
Preferably, the R 4 is selected from phenyl.
Preferably, at least one of L 1、L2、R1、R2 is selected from substituted or unsubstituted heteroaryl groups containing 1 to 3N.
Preferably, L 1 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridylene, substituted or unsubstituted bipyridylene, substituted or unsubstituted terpyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted phenazinylene, substituted or unsubstituted pyrazinylene;
preferably, L 2 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridylene, substituted or unsubstituted bipyridylene, substituted or unsubstituted terpyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted phenazinylene, substituted or unsubstituted pyrazinylene;
preferably, R 1 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted pyrazinyl;
Preferably, R 2 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted triazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted pyrazinyl.
Preferably, the L 1、L2 groups are each independently selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstitutedA group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenalkenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted bipyridyl group, a substituted or unsubstituted terpyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9, 9-dimethyl fluorene, a substituted or unsubstituted spirofluorene, a substituted or unsubstituted fluorene.
Preferably, each of the L 1、L2 is independently selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted pyrenylene, and substituted or unsubstituted fluoranthenylene.
Preferably, each R 1、R2 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted adamantylA group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenalkenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted bipyridyl group, a substituted or unsubstituted terpyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted pyrrolyl group substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted indenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9, 9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzopyreneA group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted carboline group.
Preferably, the substituents when substituted in "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 carbocyclyl, and substituted or unsubstituted C3-C60 heterocyclyl.
Preferably, the substituents in the "substituted or unsubstituted" substituents are each independently selected from deuterium, halogen, cyano, methyl, ethyl, t-butyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluoranthenyl, triphenylenyl, and,A combination of one or more of a group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a phenazinyl group, a quinolinyl group, an isoquinolinyl group.
An organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer having one or more, at least one organic layer comprising the phosphine oxide compound of the present invention.
Preferably, the organic layer comprises at least two light emitting units, wherein the light emitting units comprise at least one layer of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer and an electron transport layer, a charge generation layer is arranged between the two light emitting units, the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer comprises the phosphine oxide compound.
Preferably, the organic layer comprises at least one layer of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer and an electron transport layer, and the electron transport layer comprises the phosphine oxide compound of the present invention.
Preferably, the electron transport layer comprises an electron transport layer of each light emitting unit, and the phosphine oxide compound of the present invention is contained in at least one of the N-type charge generation layer and the electron transport layer, and the electron transport layer comprises one N-type charge generation layer containing the phosphine oxide compound of the present invention, or a plurality of N-type charge generation layers containing the phosphine oxide compound of the present invention, or one electron transport layer of one light emitting unit contains the phosphine oxide compound of the present invention, or one electron transport layer of one N-type charge generation layer and each of a plurality of light emitting units contains the phosphine oxide compound of the present invention, or each electron transport layer of a plurality of N-type charge generation layers and a plurality of light emitting units contains the phosphine oxide compound of the present invention, etc. When 2 or more layers contain the phosphine oxide compound of the present invention, the phosphine oxide compounds are the same or different.
An electronic device includes one or more of a display, a monitor, and a lighting device including an organic electroluminescent element according to the present invention, and a control section for driving the display device.
Compared with the prior art, the invention has the beneficial effects that:
the organic electroluminescent compound has a phosphine oxide structure, improves the injection and transmission capacity of electrons, and can realize improved luminous efficiency, reduced driving voltage and durable service life.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device according to application example 1, wherein a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, an N-type charge generation layer 6, a P-type charge generation layer 7, a hole transport layer 8, a light emitting layer 9, an electron transport layer 10, an electron injection layer 11, and a second electrode layer 12, wherein 100 is a first light emitting unit, and 200 is a second light emitting unit.
Fig. 2 is a schematic structural diagram of the organic electroluminescent device according to application example 2, wherein the first electrode layer 110, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, the electron injection layer 160, and the second electrode layer 170 are disposed.
Detailed Description
Embodiments of the present invention are provided for more complete description of the present invention to those skilled in the art. The scope of the present invention is not limited to the following embodiments. These embodiments will provide a thorough and complete description of the present invention and will fully convey the concept of the invention to those skilled in the art.
The experimental methods used in the following examples are conventional methods unless otherwise specified, and the reagents, materials, etc. used in the following examples are commercially available unless otherwise specified.
As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.
As used herein, the term "C1-C10 alkyl" refers to monovalent substituents derived from straight or branched chain saturated hydrocarbons having from 1 to 10 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-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornane, adamantane, and the like.
As used herein, the term "heterocycloalkyl of C2-C10 has a mono-or polycyclic monovalent substituent of 2 to 10 carbon atoms and at least one heteroatom in the ring selected from O, S, N, P, si.
As used herein, the term "alkoxy" refers to a straight, branched, or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited herein, but the alkoxy group preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, benzyloxy.
As used herein, the term "aryl of C6-C60" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such aryl groups may have a form in which two or more rings are simply flanked by each other or are fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9, 9-dimethylfluorene, 9-diphenylfluorene, spirobifluorenyl, and the like.
As used herein, the term "arylene" refers to a divalent aryl radical derived from an "aryl" radical by removal of one hydrogen atom, e.g., phenyl to phenylene and naphthyl to naphthylene.
As used herein, the term "heteroaryl of C3-C60" refers to a monovalent substituent derived from a mono-or polyheterocyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbons in the ring is replaced by a heteroatom, such as N, O, S, P, B or Si. Furthermore, such heteroaryl groups may have a form in which two or more rings are simply pendant from each other or are fused to each other or to an aryl group. Examples of such heteroaryl groups include, for example, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridinyl, purinyl, phenanthroline, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and the like, to which the present invention is not limited.
As used herein, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" group by removal of one hydrogen atom, e.g., a pyridyl group removes one hydrogen atom to a pyridylene group.
As used herein, "L 1R1 is hydrogen" means that L 1 is selected from a single bond, R 1 is selected from hydrogen, and "L 2R2 is hydrogen" means that L 2 is selected from a single bond, R 2 is selected from hydrogen.
As used herein, "the number of carbon atoms of" AA-BB "in the expression of" the number of carbon atoms of the Z group of AA-BB "or" the number of carbon atoms of the Z group of C (AA-BB) "means the number of carbon atoms of the Z group when unsubstituted, excluding the number of carbon atoms of the substituent when substituted, for example, the aryl group of C6-C30, means any integer of 6 to 30 carbon atoms in the aryl group when unsubstituted, that is, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.
As used herein, the term "single bond" refers to a direct attachment of a group, e.gWherein L 1 is a single bond, means
As used herein, the term "substituted (substituted)" means that a hydrogen atom in a compound is substituted with another substituent. The position where the substitution occurs may be a position where a hydrogen atom is substituted. That is, the position is not limited to a specific position as long as hydrogen at the position can be substituted with a substituent. For example, the carbazolyl group includes any of the following groups unless otherwise specified in the present specification, but is not limited thereto,
Indicating the substitution position. "unsubstituted" means that hydrogen atoms are retained, in which case the hydrogen atoms include protium, deuterium, tritium.
As used herein, the term "phenylene naphthyl" refers to
As used herein, the term "phenylnaphthyl" includes
Refers to the substitution position.
As used herein, the term "1-3N heteroaryl" includes any of, but is not limited to,
Indicating the connection location.
When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, hydrogen atoms include protium, deuterium, and tritium. The compounds of the present invention may contain deuterium atoms of natural origin, or deuterium atoms may be introduced by deuterating a portion or all of the starting compounds. If deuterium atoms are introduced from the raw material, the deuteration rate may be 100%, or less than 95%, or less than 90%, or less than 80%, or 1% or more, or 5% or more, or 10% or more. Such as a deuteration ratio of not 100%, meaning a mixture of deuterated and non-deuterated compounds, or a mixture of fully deuterated and non-fully deuterated compounds, or a mixture of fully deuterated and non-deuterated compounds, respectively.
As used in the present invention, the terms 1,2, A, B, etc. are used. The above terms are used only to distinguish the constituent elements, and the nature and order of the constituent elements are not limited to the terms.
Organic electroluminescent element
The structure used for the organic electroluminescent element of the present invention is a disclosed structure comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprising the compound of the present invention.
The organic layer further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.
The light-emitting element of the present invention may emit fluorescence or phosphorescence or a combination thereof, and may emit light singly or in a series of a plurality of light-emitting units.
The simple light emitting element is exemplified by, but not limited to,
(1) Hole transport layer/fluorescent light emitting layer/electron transport layer;
(2) Hole transport layer/phosphorescent light emitting layer/electron transport layer;
(3) A hole transport layer/a first fluorescent light emitting layer/a second fluorescent light emitting layer/an electron transport layer;
(4) A hole transport layer/a first phosphorescent light emitting layer/a second phosphorescent light emitting layer/an electron transport layer;
(5) Hole transport layer/fluorescent light emitting layer/spacer layer/phosphorescent light emitting layer/electron transport layer;
(6) Hole transport layer/electron blocking layer/fluorescent light emitting layer/electron transport layer;
(7) Hole transport layer/electron blocking layer/fluorescent light emitting layer/hole blocking layer/electron transport layer;
(8) Hole transport layer/electron blocking layer/phosphorescent light emitting layer/electron transport layer;
(9) Hole transport layer/electron blocking layer/phosphorescent light emitting layer/hole blocking layer/electron transport layer;
(10) Hole injection layer/hole transport layer/phosphorescent light emitting layer/electron transport layer/electron injection layer;
(11) A hole injection layer/a hole transport layer/a fluorescent light emitting layer/an electron transport layer/an electron injection layer;
(12) A hole injection layer/a hole transport layer/an electron blocking layer/a phosphorescent light emitting layer/an electron transport layer/an electron injection layer;
(13) A hole injection layer/a hole transport layer/an electron blocking layer/a fluorescent light emitting layer/an electron transport layer/an electron injection layer;
The above-described phosphorescent/fluorescent light-emitting layers may each emit light of a different color.
The tandem organic electroluminescent element may be an anode, a first light-emitting unit, an intermediate layer, a second light-emitting unit, or a cathode, and the intermediate layer may be generally referred to as a charge generation layer, an electron extraction layer, a connection layer, or the like.
When the organic light emitting element includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
The organic electroluminescent element of the present specification may be manufactured by materials and methods known in the art, except that one or more of the organic material layers are manufactured by using a compound comprising formula (1).
As the anode material, a material having a relatively large work function may be used, and a transparent conductive oxide, a metal, a conductive polymer, or the like may be used.
As the cathode material, a material having a low work function is generally used to promote electron injection into the organic material layer, and a metal, a metal oxide, a conductive polymer, or the like can be used.
The hole injection layer is a layer that injects holes from an electrode and has the ability to transport holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on an aromatic amine compound, and other materials having hole transporting ability may be used.
The hole transporting layer is a layer that receives holes from the hole injecting layer and transports the holes to the light emitting layer, and the hole transporting material may suitably receive holes from the anode or the hole injecting layer and transfer the holes to a material having high hole mobility of the light emitting layer.
The light emitting material may be a material that receives holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and combines the holes and the electrons to emit light in the visible light region. The light emitting layer material comprises a host material and a doping material. Red, green, or blue light emitting materials may be used, and two or more light emitting materials may be mixed as needed. As the light-emitting material, a fluorescent material or a phosphorescent material can be used. As the luminescent material, a single-component material or a multi-component material may be used.
The electron transporting layer receives electrons from the electron injecting layer and transports the electrons to the layer of the light emitting layer, and the electron transporting material may receive electrons from the cathode and transfer the electrons to the material of the light emitting layer having high electron mobility, and metal complexes of triazine derivatives, oxadiazole derivatives, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, fluorenone derivatives thereof, diphenyldicyanoethylene and derivatives thereof, 8-hydroxyquinoline and derivatives thereof, and the like may be used, and polymer materials and small molecular materials may also be used.
The electron injection layer is a layer that injects electrons from the electrode.
The hole blocking layer is a layer that blocks holes from reaching the cathode.
An electron blocking layer is a layer that blocks electrons from reaching the anode.
The organic light emitting element of the present specification may be a top light emitting element, a bottom light emitting element, or a dual emission element, depending on the materials used.
The charge generation layer refers to an intermediate layer located between the anode and the cathode in the series structure element, and is a layer that generates holes and electrons by charge separation. The charge generation layer is typically formed of a P-type layer on the cathode side and an N-type layer on the anode side, and is effective for charge separation and efficient carrier transport.
In one embodiment of the present invention, in formula (1), X is selected from CH;
L 1、L2 is each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluoranthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted benzopyrene group, a substituted or unsubstituted phenylene group A group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted pyridylene group;
R 1、R2 is each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted A group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenalkenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted bipyridyl group, a substituted or unsubstituted terpyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted pyrrolyl group substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted indenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9, 9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzopyreneA group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted carboline group;
R 3、R4 is selected from phenyl.
Preferably, at least one of L 1、L2、R1、R2 is selected from heteroaryl groups containing 1-3N.
Preferably, L 1 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridylene, substituted or unsubstituted bipyridylene, substituted or unsubstituted terpyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted phenazinylene, and substituted or unsubstituted pyrazinylene.
Preferably, L 2 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridylene, substituted or unsubstituted bipyridylene, substituted or unsubstituted terpyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted phenazinylene, and substituted or unsubstituted pyrazinylene.
Preferably, R 1 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted triazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted pyrazinyl.
Preferably, R 2 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted triazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted pyrazinyl.
In one embodiment of the present invention, in formula (1), X is selected from N;
L 1、L2 is each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluoranthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted benzopyrene group, a substituted or unsubstituted phenylene group A group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted pyridylene group;
R 1、R2 is each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted A group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenalkenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted bipyridyl group, a substituted or unsubstituted terpyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted pyrrolyl group substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted indenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9, 9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzopyreneA group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted carboline group;
R 3、R4 is selected from phenyl.
Preferably, at least one of L 1、L2、R1、R2 is selected from heteroaryl groups containing 1-3N.
Preferably, L 1 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridylene, substituted or unsubstituted bipyridylene, substituted or unsubstituted terpyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted phenazinylene, and substituted or unsubstituted pyrazinylene.
Preferably, L 2 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridylene, substituted or unsubstituted bipyridylene, substituted or unsubstituted terpyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted phenazinylene, and substituted or unsubstituted pyrazinylene.
Preferably, R 1 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted triazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted pyrazinyl.
Preferably, R 2 is selected from substituted or unsubstituted heteroarylene containing 1-3N, more preferably L 1 is selected from substituted or unsubstituted pyridinyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted triazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted pyrazinyl.
In one embodiment of the present invention, the phosphine oxide compound is selected from any of the following compounds numbered 1-192:
the general formula is only one synthetic mode of the compound of the invention, the compound of the invention can be synthesized by other modes,
Wherein X, L 1、L2、R1-R4 has the same meaning as X, L 1、L2、R1-R4 in formula (1).
Preparation of Compounds example
The present invention is specifically described by way of compound examples 1-3.
Compound example 1 synthesis of compound 32
Under a nitrogen atmosphere, 2-chloropyrimidine (10 g,87.7 mmol), hexamethylditin (15 mL,96.4 mmol), tetraphenylpalladium phosphide (1 g,1.7 mmol) and xylene (100 mL) were added sequentially. After refluxing at elevated temperature for 2 hours, 100mL of xylene was added again, intermediate 48-2 (30 g,61.23 mmol) was added, and refluxing at elevated temperature for 2 hours. Cooling, filtering to obtain filtrate, concentrating under reduced pressure, and pulping with ethanol to obtain compound 32 (15 g,28 mmol).
LC-MS:[M+H]+=533.17
1HNMR(400MHz,MethyleneChloride-d2)δ8.81(d,3H),8.75–8.62(m,3H),7.96–7.82(m,4H),7.75–7.66(m,4H),7.64–7.60(m,1H),7.58(dd,1H),7.57–7.51(m,2H),7.49–7.41(m,5H),7.25(t,1H).
Compound example 2
1. Synthesis of intermediate 48-1
2, 6-Dichloro-4-iodopyridine (3.8 g,14 mmol), diphenyloxyphosphine (2.26 g,11 mmol), tetrakis (triphenylphosphine) palladium (0.8 g,0.7 mmol) and potassium carbonate (3.87 g,28 mmol) were added to a four-port reaction flask under a nitrogen atmosphere, DMF150mL was added, and refluxed for 1 hour. The reaction solution is cooled to room temperature, water is added to separate out solid, the solid is filtered by suction, the filter cake is washed by ethanol and hexane, and yellow solid is obtained after the filter cake is dried by suction. The solid was purified by column chromatography (n-hexane: ethyl acetate volume ratio=1:5 as developing solvent). Thus, intermediate 48-1 was obtained as a white solid (3.0 g, yield 60%).
LC-MS(APCI):348.15(M+H)+.
2. Synthesis of intermediate 48-2
Under a nitrogen atmosphere, intermediate 48-1 (2.56 g,7.3 mmol), 9-phenanthreneboronic acid (1.36 g,6 mmol), tetrakis (triphenylphosphine) palladium (0.21 g,0.18 mmol) and potassium carbonate (4.55 g,12.2 mmol) were added to a four-port reaction flask, 50mL of tetrahydrofuran and 15mL of water were added, and reflux was continued for 2 hours. The reaction solution was cooled to room temperature, extracted with ethyl acetate, and the organic phase was concentrated on a column (developing solvent n-hexane: ethyl acetate volume ratio=1:3). Thus, intermediate 48-2 was obtained as a white solid (2.0 g, yield 67%).
LC-MS(APCI):490.31(M+H)+.
3. Synthesis of Compound 48
Under a nitrogen atmosphere, intermediate 48-2 (4.6 g,94 mmol), 2-pyridineboronic acid (1.2 g,9.9 mmol), [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride (0.20 g,0.28 mmol) and potassium carbonate (2.59 g,18 mmol) were added to a four-port reaction flask, 60mL of 1, 4-dioxane was added, and reflux was continued for 2 hours. The reaction solution was cooled to room temperature, extracted with dichloromethane, and the organic phase was concentrated through a chromatography column (n-hexane: ethyl acetate volume ratio=1:2). Thus, compound 48 was obtained as a white solid (3.4 g, yield 68%).
LC-MS(APCI):533.38(M+H)+.
1HNMR(400MHz,MethyleneChloride-d2)δ8.81(dd,1H),8.79–8.70(m,2H),8.67(ddd,1H),8.49(dt,1H),8.17(dd,1H),8.02–7.93(m,3H),7.86–7.50(m,15H),7.34(ddd,1H).
Compound example 3
1. Synthesis of intermediate 84-1
To a 1L four-necked flask, 1-bromo-3-chloro-5-iodobenzene (50.00 g,157.55 mmol), 9-phenanthreneboronic acid (35.00 g,157.55 mmol), potassium carbonate (43.55 g,315.10 mmol), tetrakis (triphenylphosphine) palladium (1.82 g,1.57 mmol), tetrahydrofuran (400 mL), water (100 mL) and nitrogen were sequentially added, and after replacement with nitrogen, the mixture was refluxed for 2 hours. After the completion of the reaction, the reaction mixture was separated by extraction with DCM and water and subjected to column chromatography (eluting with n-hexane) to give intermediate 84-1 (52 g, yield 90%).
LC-MS(APCI):[M+H]+=367.12.
2. Synthesis of intermediate 84-2
To a 1L four-necked flask, intermediate 84-1 (52 g,141.43 mmol), tetrahydrofuran (500 mL) and nitrogen were added, followed by substitution at an ultra-low temperature (-78 ℃) and then n-butyllithium in-hexane solution (155.57 mmol) was injected into the system, followed by reaction at an elevated temperature for 2 hours, and then 200mL of tetrahydrofuran solution (24.74g in 200mL THF,155.57mmol) was injected into the system and then water quenching was performed at 200mL after reaction at an elevated temperature for 2 hours, and after extraction with dichloromethane, column chromatography (n-hexane: dichloromethane volume ratio=10:1) gave intermediate 84-2 (45 g, yield 87%).
LC-MS(APCI):[M+H]+=367.35.
3. Synthesis of Compound 84
To a 1L four-necked flask, intermediate 84-2 (45 g,122.66 mmol), diphenylphosphino (37.20 g,183.99 mmol), potassium carbonate (33.90 g,245.32 mmol), bis (triphenylphosphine) nickel dichloride (4.00 g,6.133 mmol), tetrahydrofuran (500 mL) and nitrogen were added in this order, and the mixture was refluxed for 3 hours. After the completion of the reaction, the mixture was filtered, and the filtrate was concentrated and subjected to column chromatography (elution with methylene chloride) to give compound 84 (59 g, yield 90%)
LC-MS(APCI):[M+H]+=533.42.
1H NMR(400MHz,MethyleneChloride-d2)δ8.93–8.84(m,2H),8.83–8.71(m,4H),7.98–7.89(m,2H),7.87–7.75(m,6H),7.74–7.48(m,10H),7.25(td,1H).
Device preparation examples
The effect of the compound of the present invention applied as an N-type charge generation layer in a device is illustrated by application example 1.
Application example 1
Device comparative example 1
The present embodiment provides an organic electroluminescent element, as shown in fig. 1, including a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, an N-type charge generation layer 6, a P-type charge generation layer 7, a hole transport layer 8, a light emitting layer 9, an electron transport layer 10, an electron injection layer 11, and a second electrode layer 12, which are stacked, wherein the hole injection layer 2, the hole transport layer 3, the light emitting layer 4, and the electron transport layer 5 are a first light emitting unit 100, the hole transport layer 8, the light emitting layer 9, the electron transport layer 10, and the electron injection layer 11 are a second light emitting unit 200.
The specific element structure is as follows:
ITO(100nm)/NPD:F4-TCNQ(10％)(10nm)/NPD(120nm)/BH:BD(3％)(20nm)/TmPyPB(10nm)/Bphen:Li(2％)(10nm)/NPD:F4-TCNQ(10％)(20nm)/NPD(20nm)/BH:BD(3％)(20nm)/Alq3(10nm)/LiF(0.5nm)/Al(200nm).
The element preparation process comprises the following steps:
The bottom emission glass substrate used in this example was purchased from Guangdong Xinli display technology Co., ltd, and 100nm ITO was used as the first electrode layer 1. Firstly, the bottom luminescent glass substrate is cleaned by using ITO cleaning agent, deionized water and isopropanol in sequence, and then baked for 30 minutes at 180 ℃ to be dried.
Then, the bottom emission glass substrate was placed in an evaporation chamber, and organic layers were sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 Angstrom/second under a vacuum of about 10 -8 Torr. Wherein F4-TCNQ (mass content 10%) was incorporated into NPD to form a thickness of 10nm as a hole injection layer. NPD is formed to a thickness of 120nm as a hole transporting layer, a pyrene dopant 1,6-bis (diphenylamino) pyrene having a mass content of 3% is doped on an anthracene host ADN (9, 10-di (naptha-2-yl-) antacene), a blue light emitting layer having a thickness of 20nm is formed, tmPyPB is formed to a thickness of 10nm as a first electron transporting layer, li having a mass content of 2% is doped in a comparative compound Ref1, an N-type charge generating layer 6 having a thickness of 10nm is formed, F4-TCNQ having a mass content of 10% is doped on NPD, a P-type charge generating layer having a thickness of 20nm is formed, NPD is formed to a thickness of 20nm as a hole transporting layer, a pyrene dopant 1,6-bis (diphenylamino) pyrene having a mass content of 3% is doped on an anthracene host ADN (9, 10-di (naptha-2-yl-) antacene) is formed, an Alin 3 (Alin a thickness of 20 nm) is formed, and an Alin-35- (35-35) is formed as an electron transporting layer having a thickness of 200nm as an electron transporting layer, and LiF-200.35 nm is formed as an electron transporting layer.
Finally, the element was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the element, designated as organic electronic element 1.
Synthesis of comparative Compounds
2,3,4, 5-Tetraphenyl-pyrrole (30.0 g,80.8 mmol) was charged to a four-necked flask under nitrogen atmosphere, and about 300mL of THF was added for dissolution. The temperature in the system is reduced to below-78 ℃ by liquid nitrogen, then n-butyllithium is slowly dripped, and the temperature is reduced by Wen Xu hours after dripping is finished, and stirring is carried out for 1 hour. Then slowly dripping diphenyl phosphinoyl chloride, stirring for 1h at Wen Xu ℃ after dripping, removing the cold bath, and stirring for 2h at room temperature. The organic phases were combined and dried by extraction with DCM and H 2 O. The crude product obtained above was purified by silica gel column chromatography (n-hexane: dichloromethane=1:3 as developing solvent) and recrystallized from chlorobenzene to give a white comparative compound Ref1 (12.7 g, yield 28%).
1HNMR(400MHz,CD2CL2)δ7.42–7.32(m,4H),7.13–7.08(m,2H),7.07–7.00(m,8H),6.99–6.89(m,10H),6.86–6.77(m,6H).
LC-MS(APCI):572.46(M+H+).
Device example 1
Charge generation layer an N-type charge generation layer 6 was prepared using the compound prepared in example 1 of the compound of the present invention instead of the comparative compound material, and an organic electronic device 2 was fabricated in the same manner.
Device example 2
Charge generation layer N-type charge generation layer 6 was prepared using the compound prepared in example 2 of the compound of the present invention instead of the comparative compound material, and organic electronic device 3 was fabricated in the same manner.
Device example 3
Charge generation layer an N-type charge generation layer 6 was prepared using the compound prepared in example 3 of the compound of the present invention instead of the comparative compound material, and an organic electronic device 4 was fabricated in the same manner.
The lifetime test method was to apply a voltage to the obtained organic electroluminescent element so that the current density became 30mA/cm 2, and to measure the time (LT 95 (unit: hours)) until the luminance became 95% with respect to the initial luminance.
The driving voltage and the current efficiency were measured at a current density of 15mA/cm 2, and the results are shown in Table 1.
TABLE 1
| Drive voltage, V | Current efficiency, cd/a | LT95,h | |
| Organic electronic element 1 | 15.46 | 12.34 | 65 |
| Organic electronic element 2 | 7.06 | 17.44 | 71 |
| Organic electronic element 3 | 6.96 | 17.55 | 94 |
| Organic electronic element 4 | 7.20 | 17.69 | 97 |
In conclusion, compared with the organic electroluminescent element prepared by the comparative compound Ref1, the organic electroluminescent element prepared by the compound of the invention has the advantages of obviously reduced driving voltage, improved current efficiency and service life, and is suitable for being used as a material for the organic electroluminescent element.
The effect of the compound of the present invention applied as an electron transport layer in a device is illustrated by application example 2.
Application example 2
Device comparative example 2
The present embodiment provides an organic electroluminescent device, as shown in fig. 2, including a first electrode layer 110, a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode layer 170.
The specific device structure is as follows:
ITO(100nm)/NPD:F4-TCNQ(10％)(10nm)/NPD(120nm)/BH:BD(3％)(20nm)/Alq3:Liq(50％)(10nm)/LiF(0.5nm)/Al(200nm).
The preparation process of the device comprises the following steps:
The bottom emission glass substrate used in this example was purchased from Guangdong Silites display technologies Inc., and 100nm ITO was used as the first electrode layer 110. Firstly, the bottom luminescent glass substrate is cleaned by using ITO cleaning agent, deionized water and isopropanol in sequence, and then baked for 30 minutes at 180 ℃ to be dried.
Then, the bottom emission glass substrate was placed in an evaporation chamber, and organic layers were sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 Angstrom/second under a vacuum of about 10 -8 Torr. Wherein F4-TCNQ (2, 3,5, 6-Tetrafluoro-tetracyanoquinodimethane) having a mass content of 10% is doped on NPD to form a thickness of 10nm, NPD is formed to a thickness of 120nm as a hole injection layer, a pyrene dopant 1,6-bis (diphenylamino) pyrene having a mass content of 3% is doped on an anthracene host ADN (9, 10-di (naphthalene-2-yl-) amine) as a hole transport layer, a blue light emitting layer having a thickness of 20nm is formed, alq 3 (Tris- (8-hydroxyquinolinato) aluminum) doped with 50% Liq is formed to an electron transport layer having a thickness of 10nm, liF (LithiumFluoride) is formed to a thickness of 0.5nm as an electron injection layer, and Al is formed to a thickness of 200nm as a cathode.
Finally, the device is transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device, denoted as organic electronic element 5.
Device example 4
An electron transport layer was prepared using the compound produced in example 2 of the present invention instead of Alq 3, and an organic electronic device 6 was produced in the same manner.
Test results
The lifetime test method was to apply a voltage to the obtained organic electroluminescent element so that the current density became 30mA/cm 2, and to measure the time (LT 95 (unit: hours)) until the luminance became 95% with respect to the initial luminance.
The driving voltage and the current efficiency were measured at a current density of 15mA/cm 2, and the measurement results are shown in Table 2.
TABLE 2
| Drive voltage, V | Current efficiency, cd/a | Life LT95 hours | |
| Organic electronic element 5 | 5.44 | 5.38 | 14 |
| Organic electronic element 6 | 5.52 | 5.47 | 375 |
Organic electronic components using the compounds of the present invention for the electron transport layer have lower driving voltages, higher current efficiencies and longer service lives than the component 5. Therefore, the compound can be used as an electron transport layer material for manufacturing an organic electroluminescent element.
In this specification, each embodiment is described in a progressive manner, and each embodiment is mainly described in a different point from other embodiments, so that the same or similar parts between the embodiments are referred to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant points refer to the description of the method section.
The phosphine oxide compound and the organic electroluminescent device containing the same provided by the invention are described in detail. The principles and embodiments of the present invention have been described herein with reference to specific examples, the description of which is intended only to facilitate an understanding of the method of the present invention and its core ideas. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the invention can be made without departing from the principles of the invention and these modifications and adaptations are intended to be within the scope of the invention as defined in the following claims.
Claims (10)
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