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CN114773286B - Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof - Google Patents

Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof Download PDF

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Publication number
CN114773286B
CN114773286B CN202210509454.6A CN202210509454A CN114773286B CN 114773286 B CN114773286 B CN 114773286B CN 202210509454 A CN202210509454 A CN 202210509454A CN 114773286 B CN114773286 B CN 114773286B
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compound
group
substituted
deuterium
nitrogen
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CN114773286A (en
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郭建华
韩春雪
孙月
陆影
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Changchun Hyperions Technology Co Ltd
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Changchun Hyperions Technology Co Ltd
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    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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Abstract

The invention provides a nitrogen-containing heterocyclic organic compound and an organic light-emitting device thereof. The compound of the invention takes arylene containing alkyl or condensed alicyclic as bridging, one side of which is connected with fluorene group, and the other side of which is connected with oxazole, thiazole or imidazole group. The compound has a proper LUMO value and a proper energy level between adjacent layers, is favorable for electron injection and migration, can effectively reduce driving voltage, has a higher electron migration rate, and can realize good luminous efficiency in an organic light-emitting device. The compound is applied to an electron transport layer and/or a hole blocking layer, can improve the luminous efficiency of the device, and can improve the service life of the device, thereby enhancing the durability of the device. The method can be widely applied to the technical field of information display, such as mobile phones, tablet personal computers, televisions, wearable equipment, VR, vehicle displays, vehicle taillights and the like.

Description

Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a nitrogen-containing heterocyclic organic compound and an organic light-emitting device thereof.
Background
Organic Light-Emitting Diodes (OLEDs), also known as Organic Light-Emitting semiconductors, are a new generation of all-solid-state flat panel display technology, and have been gradually introduced into daily life, such as smartphones, smartwatches, portable notebooks, etc., all of which employ OLED display technology. Compared with other display technologies, the OLED display technology has the characteristics of energy conservation, high response speed, stable color, strong environmental adaptability, no radiation, light weight, thin thickness, relatively simple device manufacturing process and the like. Compared with the prior display technology, the OLED has the remarkable characteristic that a bent or curled display screen can be manufactured, so that development of a proper organic film material is always the research focus of the OLED industry.
The current research on the OLED is very intensive, and the device structure of the OLED is generally that organic functional layers are added between an anode and a cathode, and the functional layers include a hole injection layer, a hole transport layer, a light emitting region, an electron transport layer, an electron injection layer and a cover layer. In order to balance the transport rate of electrons or holes, an electron blocking layer is sometimes added between the hole transport layer and the light emitting layer, or a hole blocking layer is added between the electron transport layer and the light emitting layer. Through certain energy level collocation, holes and electrons can be gathered in the luminous main body layer to collide, so that the luminous material can excite luminescence.
In an OLED material, the mobility of electrons is typically 2-3 orders of magnitude lower than the mobility of holes, and the number of holes in the OLED light-emitting host layer is much greater than the number of electrons. Therefore, the development of efficient electron transport materials is very important for improving the light emission efficiency of organic light emitting devices. The ideal electron transport material should have conditions of high electron mobility, suitable LUMO values, relatively high electron affinity, and the like. In order to meet the requirements of market application, the performance of the OLED device such as luminous efficiency, driving voltage, service life, etc. needs to be further enhanced and improved.
Disclosure of Invention
The invention aims to provide a nitrogen-containing heterocyclic organic compound and an organic light-emitting device thereof, and the organic light-emitting device prepared by using the nitrogen-containing heterocyclic organic compound is applied to an electron transport layer or a hole blocking layer to develop the organic light-emitting device with high efficiency and long service life, and the molecular structural general formula of the organic light-emitting device is shown as formula I:
wherein L is selected from one of the following groups:
the at least one R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C30 alkenyl, or two adjacent R can be combined with each other to form a substituted or unsubstituted three-to eight-membered aliphatic ring; the rest R is selected from hydrogen, deuterium and tritium;
The X are the same or different and are selected from CR' or N, and at least one X is selected from N;
r' is selected from hydrogen, deuterium, tritium;
the q is 1 Selected from 0, 1, 2, 3 or 4; the q is 2 Selected from 0, 1, 2, 3, 4, 5 or 6;
z is selected from any one of O, S or N (Ry); the Ry is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the Y is the same or different and is selected from CH or N;
the R is 1 、R 2 Independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R 1 、R 2 Can be combined with each other to form a substituted or unsubstituted spiro ring; r is R 1 、R 2 Any one of which can be directly bonded to the bridging L;
the R is a 、R b Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R a May be linked to form a substituted or unsubstituted aromatic or aliphatic ring; or two adjacent R b May be linked to form a substituted or unsubstituted aromatic or aliphatic ring;
the a 1 Selected from 0, 1, 2, 3 or 4; the a 2 Selected from 0, 1, 2, 3 or 4; the b is selected from 0, 1, 2, 3 or 4.
The invention provides an organic light-emitting device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises an electron transport layer, and the electron transport layer contains any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds.
The invention also provides an organic light-emitting device, wherein the organic layer comprises a hole blocking layer, and the hole blocking layer contains any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds.
The invention has the beneficial effects that:
the invention provides a nitrogen-containing heterocyclic organic compound and an organic light-emitting device thereof. On one hand, the compound contains alkyl groups, so that the solubility of the compound is enhanced, film formation is facilitated, and good film forming property and thermal stability are achieved. On the other hand, the compound has a proper LUMO value and a proper energy level between adjacent layers, is favorable for electron injection and migration, can effectively reduce driving voltage, has a higher electron migration rate, and can realize good luminous efficiency in an organic luminous device. The compound is applied to an electron transport layer and/or a hole blocking layer, can improve the luminous efficiency of the device, and can improve the service life of the device, thereby enhancing the durability of the device.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
In this specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, the number of the cells to be processed,can indicate->And so on.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed,can indicate-> Can indicate->And so on.
Halogen in the present invention means fluorine, chlorine, bromine and iodine.
The alkyl group according to the present invention is a hydrocarbon group having at least one hydrogen atom in the alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
The chain alkyl group having more than three carbon atoms according to the present invention includes isomers thereof, for example, propyl group includes n-propyl group, isopropyl group, butyl group includes n-butyl group, sec-butyl group, isobutyl group, tert-butyl group. And so on.
Cycloalkyl as used herein refers to a hydrocarbon group having at least one hydrogen atom in the cycloparaffin molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 3 to 6 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, etc., but are not limited thereto. The cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, or a norbornyl group.
The heterocycloalkyl group refers to a monovalent group in which at least one parent carbon atom in the heterocycloalkyl group is replaced with a heteroatom. Such heteroatoms include, but are not limited to, atoms as described below, N, O, S, si, B, P, and the like. Preferably having 3 to 30 carbon atoms, more preferably 3 to 15 carbon atoms, still more preferably 3 to 10 carbon atoms. Examples of heterocycloalkyl groups include, but are not limited to, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, azepanyl, homopiperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, and the like.
Aryl in the present invention refers to the generic term for monovalent radicals remaining after removal of one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having from 6 to 25 carbon atoms, more preferably from 6 to 20 carbon atoms, particularly preferably from 6 to 14 carbon atoms, and most preferably from 6 to 12 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, for example, but not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirobifluorenyl, and the like. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, or a spirobifluorenyl group.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms, including but not limited to oxygen, sulfur, nitrogen or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, most preferably 3 to 12 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom, or on a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl, polycyclic heteroaryl or fused ring heteroaryl. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, and the like. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzodibenzothienyl group, a benzodibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
The alkenyl refers to a monovalent group obtained by removing one hydrogen atom from an olefin molecule, and the alkenyl comprises mono alkenyl, di alkenyl, multi alkenyl and the like. Preferably from 2 to 60 carbon atoms, more preferably from 2 to 30 carbon atoms, particularly preferably from 2 to 15 carbon atoms, most preferably from 2 to 6 carbon atoms. Examples of the alkenyl group include vinyl, butadienyl, and the like, but are not limited thereto. The alkenyl group is preferably a vinyl group.
Alkenyl groups having more than three carbon atoms according to the present invention include isomers thereof, for example, propenyl group includes 1-propenyl group or 2-propenyl group, butenyl group includes 1-butenyl group, 2-butenyl group, or 3-butenyl group, pentenyl group includes 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, hexenyl group includes 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group. And so on.
The "substituted …" according to the present invention, such as a substituted alkyl group, a substituted cycloalkyl group, a substituted heterocycloalkyl group, a substituted alkenyl group, a substituted aryl group, a substituted heteroaryl group, etc., means that a group selected independently from deuterium, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C3 to C6 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C15 heteroaryl group, a substituted or unsubstituted amine group, etc., but not limited thereto, is mono-or poly-substituted, preferably with a group selected from deuterium, tritium, methyl, ethyl, isopropyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, benzophenyl, perylene, pyrenyl, benzyl, tolyl, fluorenyl, 9-dimethylfluorenyl, 9-diphenyl fluorenyl, 9-methyl-9-phenylfluorenyl, diphenylaminyl, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furyl, thienyl, benzothienyl, benzoxazolyl, benzothienyl, benzothiazolyl, dioxazine, or a polysubstituted phenoxazinyl group. In addition, the above substituents may be substituted with one or more substituents described for deuterium, tritium, halogen, cyano, alkyl, cycloalkyl, aryl.
Aliphatic as used herein refers to aliphatic hydrocarbons having from 1 to 60 carbon atoms, which may be fully unsaturated or partially unsaturated.
The aliphatic ring according to the present invention means a cyclic hydrocarbon having aliphatic nature, and the molecule contains a closed carbon ring, and may be a single-or multi-cyclic hydrocarbon formed of 3 to 18 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 7 carbon atoms, and may be fully saturated or partially saturated, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but is not limited thereto. The plurality of monocyclic hydrocarbons may also be linked in a variety of ways: two rings in the molecule can share one carbon atom to form a spiro ring; the two carbon atoms on the ring can be connected by a carbon bridge to form a bridge ring; several rings may also be interconnected to form a cage-like structure.
The term "ring" as used herein, unless otherwise specified, refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, which comprises a saturated or unsaturated ring.
The term "bonded to form a cyclic structure" as used herein means that two groups are attached to each other by a chemical bond and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane, cyclohexene, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
The invention provides a nitrogen-containing heterocyclic organic compound, the molecular structural general formula of which is shown as formula I:
the invention aims to provide a nitrogen-containing heterocyclic organic compound and an organic light-emitting device thereof, and the organic light-emitting device prepared by using the nitrogen-containing heterocyclic organic compound is applied to an electron transport layer or a hole blocking layer to develop the organic light-emitting device with high efficiency and long service life, and the molecular structural general formula of the organic light-emitting device is shown as formula I:
wherein L is selected from one of the following groups:
the at least one R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C30 alkenyl, or two adjacent R can be combined with each other to form a substituted or unsubstituted three-to eight-membered aliphatic ring; the rest R is selected from hydrogen, deuterium and tritium;
the X are the same or different and are selected from CR' or N, and at least one X is selected from N;
R' is selected from hydrogen, deuterium, tritium;
the q is 1 Selected from 0, 1, 2, 3 or 4; the q is 2 Selected from 0, 1, 2, 3, 4, 5 or 6;
z is selected from any one of O, S or N (Ry); the Ry is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the Y is the same or different and is selected from CH or N;
the R is 1 、R 2 Independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or R 1 、R 2 Can be combined with each other to form a substituted or unsubstituted spiro ring; r is R 1 、R 2 Any one of which can be directly bonded to the bridging L;
the R is a 、R b Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R a Can be connected with each otherTo a substituted or unsubstituted aromatic or aliphatic ring; or two adjacent R b May be linked to form a substituted or unsubstituted aromatic or aliphatic ring;
the a 1 Selected from 0, 1, 2, 3 or 4; the a 2 Selected from 0, 1, 2, 3 or 4; the b is selected from 0, 1, 2, 3 or 4.
Preferably, L is selected from one of the following groups:
the at least one R is selected from one of the following substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, butadienyl, cyclopentadienyl, cyclohexadienyl; the rest R is selected from one or more of hydrogen, deuterium and tritium, and when R is substituted by a plurality of substituents, the substituents are the same or different;
the q is 0 Selected from 0, 1 or 2; the q is 1 Selected from 0, 1, 2, 3 or 4; the q is 2 Selected from 0, 1, 2, 3, 4, 5 or 6; the q is 3 Selected from 0, 1, 2 or 3;
the s is 1 Selected from 0, 1 or 2; s is(s) 2 Selected from 0, 1, 2, 3 or 4; s is(s) 3 Selected from 0, 1, 2, 3, 4, 5 or 6; s is(s) 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; s is(s) 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; s is(s) 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.
Preferably, the at least one R is selected from one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethenyl, propenyl, butenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl; the rest R is selected from one or more of hydrogen, deuterium and tritium, wherein the substituent in the substituted or unsubstituted is selected from one or more of deuterium, tritium, methyl, ethyl, propyl, butyl, amyl, hexyl and heptyl, and when the substituent is substituted by a plurality of substituents, the substituents are the same or different from each other.
More preferably, the at least one R is selected from one of the following substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethenyl, propenyl, butenyl; the rest R is selected from one or more of hydrogen, deuterium and tritium; wherein the substituents in the "substituted or unsubstituted" are selected from deuterium or tritium.
Preferably, the "at least one" includes one, two, three, four, five, six, seven, eight, nine, ten, eleven or twelve.
Preferably, the "at least one" includes at least one, at least two, at least three, at least four, at least five, or at least six.
Preferably, the "at least one" includes at most seven, at most eight, at most nine, at most ten, at most eleven, or at most twelve.
Preferably, the saidR in (B) b Identical to or different from each other and independently selected from hydrogen, deuterium, tritium, or one of the following substituted or unsubstituted groups: one of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, canyl, norbornyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, cyano, fluoro, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzocyclopentenyl, benzocyclohexenyl, benzocyclopentenyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl; or two adjacent R b Can be connected to form benzene ring, naphthalene ring or three-to eight-membered aliphatic ring; wherein the substituents in the "substituted or unsubstituted" are One or more selected from deuterium, tritium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, canalkyl, norbornyl, phenyl, biphenyl, naphthyl, and in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.
More preferably, theAny one selected from the following groups:
preferably, said R 1 、R 2 Independently selected from any of hydrogen, deuterium, tritium, substituted or unsubstituted: C1-C6 alkyl, C3-C6 cycloalkyl, adamantyl, norbornyl, C6-C12 aryl, C2-C12 heteroaryl, benzocyclopentenyl, benzocyclohexenyl, benzocyclopentenyl, naphthocyclohexenyl, naphthocyclopentenyl, naphthocyclohexenyl; the substituent groups of the substituted or unsubstituted substituent groups can be any one or more than one of deuterium, tritium, C1-C12 alkyl and C3-C12 cycloalkyl;
or said R 1 、R 2 Can be formed intoAny one of the spiro structures:
The R is p Selected from hydrogen, deuterium, tritium, or substituted or unsubstituted groups of: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, cankyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, phenanthryl, triphenylyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, one or more substituents selected from deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated isopropyl, deuterated tert-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or adjacent R p Can be bonded to form a benzene ring or naphthalene ring;
ar is selected from one of isopropyl, tertiary butyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl and deuterated terphenyl;
The p is 1 Selected from 0, 1 or 2; p is p 2 Selected from 0, 1, 2, 3 or 4; p is p 3 Selected from 0, 1, 2, 3, 4, 5 or 6; p is p 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p is p 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; p is p 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; p is p 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.
Preferably, the saidAny one selected from the following groups:
the a is selected from 0, 1, 2 or 3; b is selected from 0, 1, 2, 3 or 4; c is selected from 0, 1, 2, 3, 4 or 5; e is selected from 0, 1, 2, 3, 4, 5 or 6; d is selected from 0, 1, 2, 3, 4, 5, 6 or 7; f is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; h is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; i is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
Preferably, said R a 、R b Independently selected from deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazolyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, and the above groups may also be substituted with one or more of deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated isopropyl, deuterated tert-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl 。
Preferably, said R a 、R b Independently selected from hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, deuterated isopropyl, deuterated tert-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornyl, or one of the groups shown below:
most preferably, the nitrogen-containing heterocyclic organic compound is selected from any one of the chemical structures shown below:
the preparation method of the nitrogen-containing heterocyclic organic compound shown in the formula I can be prepared through coupling reaction conventional in the art, for example, the preparation method can be prepared through the following synthetic route, but the invention is not limited to the following steps:
in nitrogen atmosphere, the intermediate A is obtained by Miyaura boration reaction of halogen compound a and bishalogen compound B, the intermediate B is obtained by Suzuki reaction of the intermediate A and bishalogen compound B, the intermediate C is obtained by Miyaura boration reaction of bisboronic acid ester, the intermediate C is reacted with halogen compound C, and the corresponding compound of formula I is obtained by reaction of the intermediate C and the corresponding catalyst, organic base, ligand, solution and corresponding temperature 0 、X 1 、X 2 、X 3 Selected from Cl, br or I.
The source of the raw materials used in the above-mentioned various reactions is not particularly limited, and can be obtained using commercially available raw materials or by using a preparation method well known to those skilled in the art. The present invention is not particularly limited to the above reaction, and conventional reactions well known to those skilled in the art may be employed. The compound has few synthesis steps and simple method, and is beneficial to industrial production.
The invention also provides an organic light-emitting device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises an electron transport layer, and the electron transport layer contains any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds.
Preferably, the organic layer comprises a hole blocking layer, and the hole blocking layer contains any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds.
The light emitting device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.
The anode of the organic light emitting device of the present invention may be formed by sputtering or depositing a material serving as the first electrode on the substrate. The anode can be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), or tin dioxide (SnO) 2 ) An oxide transparent conductive material such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The hole transport layer and the hole injection layer of the organic light-emitting device have good hole transport performance, and can effectively transport holes from the anode to the light-emitting layer. Other small and high molecular organic compounds may be included including, but not limited to, carbazole-based compounds, tri-aromatic amine-based compounds, biphenyl diamine-based compounds, fluorene-based compounds, phthalocyanine-based compounds, hexacyano hexa-triphenyl, 2,3,5, 6-tetrafluoro-7, 7', 8' -tetra-cyano dimethyl p-benzoquinone (F4-TCNQ), polyvinylcarbazole, polythiophene, polyethylene or polyphenylsulfonic acid.
The luminous layer of the organic luminous device has good luminous characteristics and can adjust the range of visible light according to the requirement. The following compounds may be selected, but are not limited to, naphthalene compounds, pyrene compounds, fluorene compounds, phenanthrene compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, diarylethene compounds, triphenylamine vinyl compounds, amine compounds, benzimidazole compounds, furan compounds, and organic metal chelates. As for the light emitting layer of the organic light emitting device of the present invention, a red light emitting material, a green light emitting material, or a blue light emitting material may be used as the light emitting material, and two or more light emitting materials may be mixed and used as necessary. The light-emitting material may be a host material alone or a mixture of a host material and a dopant material, and the light-emitting layer is preferably a mixture of a host material and a dopant material.
The electron transport material of the organic light emitting device of the present invention is required to have excellent electron transport properties, to be able to efficiently transport electrons from the cathode into the light emitting layer, and to have great electron mobility. In addition to the compound having the structural formula I of the present invention, the compound may also contain, but is not limited to, oxazazole, thiazole compounds, triazole compounds, triazazine compounds, triazabenzene compounds, quinoxaline compounds, diazoanthracene compounds, silicon-containing heterocyclic compounds, quinoline compounds, phenanthroline compounds, metal chelates (e.g., alq 3 ) Fluorine substituted benzene compounds and benzimidazole compounds.
The electron injection layer of the organic light emitting device of the present invention may effectively inject electrons from the cathode into the organic layer, and is mainly selected from alkali metals or alkali metal compounds, or alkaline earth metals or alkaline earth metal compounds or alkali metal complexes, and may be selected from, but not limited to, alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides or halides, alkaline earth metal oxides or halides, rare earth metal oxides or halides, alkali metals or alkaline earth metal organic complexes; preferred are lithium, lithium fluoride, lithium oxide, lithium nitride, lithium 8-hydroxyquinoline, cesium carbonate, cesium 8-hydroxyquinoline, calcium fluoride, calcium oxide, magnesium fluoride, magnesium carbonate, magnesium oxide, and these compounds may be used alone or in combination with other organic electroluminescent materials.
In the cathode material of the organic light-emitting device of the present invention, a metal material having a small work function is generally preferable for injecting electrons into the electron injection/transport layer or the light-emitting layer. For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, or an alloy of 2 or more of them, or an alloy of 1 or more of them with 1 or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or a graphite interlayer compound, etc. can be used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.
The cover layer material of the organic light-emitting device is used for reducing the total emission loss and waveguide loss in the OLED device and improving the light extraction efficiency. Alq can be used as the coating material of the present invention 3 Conventional capping materials known to those skilled in the art, TPBi, etc., or any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds described herein.
The film thickness of the hole transport layer and the electron transport layer may be selected depending on the material used, and may be selected so as to have a suitable value for the driving voltage and the luminous efficiency, but it is not preferable that the film thickness does not cause pinholes at least, and if the film thickness is too large, the driving voltage of the device is increased. Therefore, the film thickness of the hole transport layer and the electron transport layer is, for example, 1nm to 1um, preferably 2nm to 500nm, more preferably 5nm to 200nm. The total thickness of the organic layer of the organic light emitting device of the present invention is 1 to 1000nm, preferably 50 to 500nm.
Each of the organic layers in the organic light emitting device of the present invention may be prepared by vacuum evaporation, molecular beam evaporation, solvent-soluble dip coating, spin coating, bar coating, or ink-jet printing. The metal motor may be produced by a vapor deposition method or a sputtering method, and in the present invention, a vacuum vapor deposition method is preferably used.
The organic light-emitting device can be widely applied to the fields of information display technology, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signboards, signal lamps and the like. The information display aspect is widely applied to various information displays, such as mobile phones, tablet computers, televisions, wearable devices, VR, smart watches, digital cameras, vehicle displays, vehicle taillights, and the like.
The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.
Description of the starting materials, reagents and characterization equipment:
The source of the raw materials used in the following examples is not particularly limited and may be commercially available products or prepared by a preparation method well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis was carried out using a Vario EL cube organic elemental analyzer from Elementar, germany, and the sample mass was 5 to 10mg.
Synthesis of intermediates
Preparation of intermediate b-1
Synthetic intermediate M-1
To the reaction flask was added m-1 (22.60 g,110 mmol), pinacol diboronate (27.93 g,110 mmol), pd (PPh) 3 ) 4 (1.27g，1.10mmol)、K 2 CO 3 (23.49 g,170.00 mmol), DMF (500 mL), after heating and reacting for 2 hours, adding distilled water, extracting with dichloromethane, separating liquid, washing the organic phase with distilled water three times, drying with anhydrous magnesium sulfate, rotary evaporating and concentrating the solvent, cooling and crystallizing, suction filtering, and using toluene to obtain solid: ethanol=4: 1 recrystallisation to give intermediate M-1 (21.11 g, 76% yield); HPLC purity is not less than 98.85%. Mass spectrum m/z:252.1075 (theory: 252.1088).
Synthetic intermediate b-1
Under the protection of nitrogen, the intermediate M-1 (18.94 g,75 mmol), the raw material n-1 (21.22 g,75 mmol), potassium carbonate (16.58 g,120 mmol) and Pd (PPh) are added into a reaction bottle in sequence 3 ) 4 (1.04 g,0.90 mmol) was added 400mL of toluene/ethanol/water (2:1:1) mixed solvent and the mixture was stirred and the above reactant system was heated at reflux for 2 hours. After the reaction was completed, cooling to room temperature, adding toluene and separating the phases, washing the toluene phase three times with distilled water, drying over anhydrous magnesium sulfate, rotary evaporating the concentrated solvent, cooling to crystallize, suction filtering, and subjecting the obtained solid to toluene: ethanol=20: 3 to give intermediate b-1 (15.84 g, 75% yield). HPLC purity is more than or equal to 99.53%. Mass spectrum m/z:279.9666 (theory: 279.9654).
According to the above procedure, equimolar substitution of starting material m and starting material n was carried out, synthesizing the following intermediate b:
EXAMPLE 1 Synthesis of Compound 1
Preparation of intermediate A-1:
under the protection of nitrogen, the raw material a-1 (31.79 g,80.00 mmol), the bisboronic acid pinacol ester (20.32 g,80.00 mmol) and Pd (PPh) are added into a reaction bottle in sequence 3 ) 4 (1.15g，1.00mmol)、K 2 CO 3 (23.49 g,170.00 mmol), DMF (400 mL), then heating for 3.5 hours, cooling to room temperature after the reaction, adding 500mL of water, then extracting with ethyl acetate (500 mL. Times.3), drying the organic layer over anhydrous magnesium sulfate, rotary evaporating to remove the solvent, then toluene: ethanol=20: 1 recrystallisation and drying to give intermediate A-1 (29.51 g, 83% yield); HPLC purity is not less than 98.72%. Mass spectrum m/z:444.2277 (theory: 444.2261).
Preparation of intermediate B-1:
under the protection of nitrogen, the intermediate A-1 (24.44 g,55.00 mmol), the raw material b-1 (15.49 g,55.00 mmol) and Pd (PPh) are added into a reaction bottle in sequence 3 ) 4 (0.69g，0.60mmol)、K 2 CO 3 (11.06 g,80.00 mmol) and 300mL toluene, 100mL ethanol and 100mL water, and the mixture was stirred, and the above-mentioned system was heated under reflux for 3 hours; after the reaction is finished, cooling to room temperature, carrying out suction filtration to obtain a filter cake, flushing the filter cake with ethanol, and finally recrystallizing the filter cake with toluene to obtain an intermediate B-1 (21.70 g, yield 76%); HPLC purity is more than or equal to 99.41%. Mass spectrum m/z:518.1819 (theory: 518.1801).
Preparation of intermediate C-1:
to the reaction flask was added in sequence under nitrogen protection intermediate B-1 (20.76 g,40.00 mmol), pinacol diboronate (10.16 g,40.00 mmol), KOAc (8.83 g,90.00 mmol), pd (dppf) Cl 2 (0.73 g,1.00 mmol), 1, 4-dioxane (350 mL), then heated to reflux temperature for 4 hours, cooled to room temperature after the completion of the reaction, added with 350mL of water, then extracted with ethyl acetate (500 mL. Times.3), and the organic layer was dried over anhydrous MgSO 4 Drying, spin-evaporating to remove ethyl acetate, and then using tolueneRecrystallizing and drying to obtain an intermediate C-1 (19.54 g, yield 80%); the HPLC purity is more than or equal to 99.69 percent. Mass spectrum m/z:610.3032 (theory: 610.3043).
Preparation of Compound 1:
under the protection of nitrogen, the intermediate C-1 (15.27 g,25.00 mmol), the raw material C-1 (4.95 g,25.00 mmol) and Pd are added into a reaction bottle in sequence 2 (dba) 3 (0.27g，0.30mmol)、P(t-Bu) 3 (0.20g，1.00mmol)，K 2 CO 3 (5.53 g,40.00 mmol) and 150mL of tetrahydrofuran, the mixture was stirred, and the above reactant system was heated at reflux for 5 hours; after the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to give compound 1 (11.28 g, yield 75%); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:601.2420 (theory: 601.2406). Theoretical element content (%) C 45 H 31 NO: c,89.82; h,5.19; n,2.33. Measured element content (%): c,89.87; h,5.13; n,2.35.
EXAMPLE 2 Synthesis of Compound 5
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-5 and substituting b-1 with equimolar b-5, compound 5 (8.82 g) was synthesized, and the purity of the solid was ≡ 99.90% by HPLC. Mass spectrum m/z:415.1945 (theory: 415.1936). Theoretical element content (%) C 30 H 25 NO: c,86.71; h,6.06; n,3.37. Measured element content (%): c,86.74; h,6.02; n,3.40.
EXAMPLE 3 Synthesis of Compound 14
Using the same method as in Synthesis example 1, a compound was synthesized by substituting a-1 with equimolar a-14, substituting b-1 with equimolar b-14, substituting c-1 with equimolar c-14 Product 14 (10.28 g) showed a purity of > 99.78% by HPLC. Mass spectrum m/z:527.2257 (theory: 527.2249). Theoretical element content (%) C 39 H 29 NO: c,88.77; h,5.54; n,2.65. Measured element content (%): c,88.82; h,5.50; n,2.69.
EXAMPLE 4 Synthesis of Compound 29
Using the same method as in Synthesis example 1, compound 29 (10.66 g) was synthesized with equal molar substitution of a-29 for a-1, equal molar substitution of b-29 for b-1, equal molar substitution of c-29 for c-1, and a solid purity of > 99.83% as measured by HPLC. Mass spectrum m/z:490.3014 (theory: 490.3002). Theoretical element content (%) C 35 H 26 D 7 NO: c,85.67; h,8.21; n,2.85. Measured element content (%): c,85.72; h,8.17; n,2.88.
EXAMPLE 5 Synthesis of Compound 47
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-47 and b-1 with equimolar b-47, compound 47 (12.31 g) was synthesized, and the purity of the solid was ≡ 99.76% by HPLC. Mass spectrum m/z:648.3180 (theory: 648.3189). Theoretical element content (%) C 48 H 32 D 5 NO: c,88.85; h,6.52; n,2.16. Measured element content (%): c,88.81; h,6.55; n,2.13.
EXAMPLE 6 Synthesis of Compound 82
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-82 and b-1 with equimolar b-29, compound 82 (11.26 g) was synthesized with a purity of > 99.94% by HPLC. Mass spectrum m/z: 549.2110 (theory: 549.2093). Theoretical element content (%) C 41 H 27 NO: c,89.59; h,4.95; n,2.55. Measured element content (%): c,89.64; h,4.90; n,2.52.
EXAMPLE 7 Synthesis of Compound 85
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-85 and substituting b-1 with equimolar b-85, compound 85 (11.24 g) was synthesized, and the purity of the solid was ≡ 99.73% by HPLC. Mass spectrum m/z:671.3197 (theory: 671.3188). Theoretical element content (%) C 50 H 41 NO: c,89.38; h,6.15; n,2.08. Measured element content (%): c,89.42; h,6.17; n,2.02.
EXAMPLE 8 Synthesis of Compound 92
Using the same method as in Synthesis example 1, compound 92 (11.58 g) was synthesized with a purity of > 99.84% by HPLC, substituting a-1 with equimolar a-92, substituting b-1 with equimolar b-92, and substituting c-1 with equimolar c-92. Mass spectrum m/z:634.2678 (theory: 634.2669). Theoretical element content (%) C 46 H 26 D 5 NO 2 : c,91.98; h,6.57; n,1.45. Measured element content (%): c,92.04; h,6.53; n,1.51.
EXAMPLE 9 Synthesis of Compound 141
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-141, synthesis of Compound 141 (11.67 g), the purity of the solid was ≡ 99.66% by HPLC. Mass spectrum m/z:657.3024 (theory: 657.3032). Theoretical element content (%) C 49 H 39 NO：C,89.46; h,5.98; n,2.13. Measured element content (%): c,89.50; h,5.92; n,2.16.
EXAMPLE 10 Synthesis of Compound 269
Using the same method as in Synthesis example 1 except substituting a-1 with equimolar a-269 and b-1 with equimolar b-269, compound 269 (10.15 g) was synthesized, and the purity of the solid was ≡ 99.56% by HPLC. Mass spectrum m/z:605.2711 (theory: 605.2719). Theoretical element content (%) C 45 H 35 NO: c,89.22; h,5.82; n,2.31. Measured element content (%): c,89.26; h,5.80; n,2.28.
EXAMPLE 11 Synthesis of Compound 279
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-279, substituting b-1 with equimolar b-279, substituting c-1 with equimolar c-279, synthesized compound 279 (11.40 g) with a purity of > 99.59% by HPLC. Mass spectrum m/z:701.2167 (theory: 701.2179). Theoretical element content (%) C 53 H 35 NO: c,90.70; h,5.03; n,2.00. Measured element content (%): c,90.74; h,5.00; n,2.05.
EXAMPLE 12 Synthesis of Compound 339
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-339, substituting b-1 with equimolar b-339, substituting c-1 with equimolar c-339, synthesizing Compound 339 (11.90 g), the purity of the solid was ≡ 99.69% by HPLC. Mass spectrum m/z:670.2996 (theory: 670.2984). Theoretical element content (%) C 49 H 38 N 2 O：C,87.73；H,5.71；N,4.18。Measured element content (%): c,87.78; h,5.66; n,4.15.
EXAMPLE 13 Synthesis of Compound 341
Using the same method as in Synthesis example 1, a-1 was replaced with equimolar a-341, b-1 was replaced with equimolar b-341, and compound 341 (14.00 g) was synthesized, and the purity of the solid was ≡ 99.91% by HPLC. Mass spectrum m/z:781.4240 (theory: 781.4222). Theoretical element content (%) C 58 H 47 D 4 NO: c,89.08; h,7.09; n,1.79. Measured element content (%): 89.12; h,7.05; n,1.81.
EXAMPLE 14 Synthesis of Compound 394
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-394, substituting b-1 with equimolar b-394, substituting c-1 with equimolar c-394, synthetic compound 394 (11.65 g), HPLC detected a solid purity of ≡ 99.73%. Mass spectrum m/z:582.2688 (theory: 582.2671). Theoretical element content (%) C 42 H 34 N 2 O: c,86.57; h,5.88; n,4.81. Measured element content (%): c,86.62; h,5.82; n,4.83.
EXAMPLE 15 Synthesis of Compound 413
Using the same method as in Synthesis example 1, a-1 was replaced with equimolar a-413, b-1 was replaced with equimolar b-413, and compound 413 (13.07 g) was synthesized, and the purity of the solid was ≡ 99.81% by HPLC. Mass spectrum m/z:661.3182 (theory: 661.3190). Theoretical element content (%) C 49 H 23 D 10 NO: c,88.92; h,6.55; n,2.12. Measured element content (%): c,88.96;H,6.51；N,2.10。
EXAMPLE 16 Synthesis of Compound 461
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-461, substituting b-1 with equimolar b-461, substituting c-1 with equimolar c-461, synthetic compound 461 (14.91 g), the solid purity was. Mass spectrum m/z:805.3353 (theory: 805.3345). Theoretical element content (%) C 61 H 43 NO: c,90.90; h,5.38; n,1.74. Measured element content (%): c,90.95; h,5.34; n,1.72.
EXAMPLE 17 Synthesis of Compound 477
Using the same method as in Synthesis example 1, a-1 was replaced with equimolar a-477, b-1 was replaced with equimolar b-477, and Compound 477 (11.46 g) was synthesized, and the purity of the solid was ≡ 99.85% by HPLC. Mass spectrum m/z:587.3069 (theory: 587.3064). Theoretical element content (%) C 43 H 25 D 8 NO: c,87.87; h,7.03; n,2.38. Measured element content (%): c,87.80; h,7.08; n,2.35.
EXAMPLE 18 Synthesis of Compound 491
Using the same method as in Synthesis example 1 except substituting a-1 with equimolar a-491 and b-1 with equimolar b-491, compound 491 (11.94 g) was synthesized, and the purity of the solid was ≡ 99.69% by HPLC. Mass spectrum m/z:604.2462 (theory: 604.2453). Theoretical element content (%) C 44 H 24 D 4 N 2 O: c,87.39; h,5.33; n,4.63. Measured element content (%): c,87.33; h,5.36; n,4.66.
EXAMPLE 19 Synthesis of Compound 509
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-509 and substituting b-1 with equimolar b-509, compound 509 (13.06 g) was synthesized, and the purity of the solid was ≡ 99.72% by HPLC. Mass spectrum m/z:705.2789 (theory: 705.2780). Theoretical element content (%) C 51 H 35 N 3 O: c,86.78; h,5.00; n,5.95. Measured element content (%): c,86.82; h,5.02; n,5.89.
EXAMPLE 20 Synthesis of Compound 522
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-522, substituting b-1 with equimolar b-522, substituting c-1 with equimolar c-522, synthesized compound 522 (10.59 g), and detected by HPLC that the solid purity was ≡ 99.92%. Mass spectrum m/z:605.2478 (theory: 605.2467). Theoretical element content (%) C 43 H 31 N 3 O: c,85.26; h,5.16; n,6.94. Measured element content (%): c,85.29; h,5.12; n,6.98.
EXAMPLE 21 Synthesis of Compound 526
Using the same method as in Synthesis example 1, compound 526 (12.10 g) was synthesized with a molar equivalent of a-526 replacing a-1, a molar equivalent of b-526 replacing b-1, a molar equivalent of c-526 replacing c-1, and a solid purity of ≡ 99.93% by HPLC. Mass spectrum m/z:653.3405 (theory: 653.3393). Theoretical element content (%) C 47 H 27 D 9 N 2 O: c,86.33; h,6.93; n,4.28. Measured element content (%): c,86.37; h,6.90; n,4.24.
EXAMPLE 22 Synthesis of Compound 529
Using the same method as in Synthesis example 1, compound 529 (11.25 g) was synthesized with equal molar substitution of a-529 for a-1, equal molar substitution of b-529 for b-1, equal molar substitution of c-529 for c-1, and a solid purity of ≡99.86% as measured by HPLC. Mass spectrum m/z:725.2913 (theory: 725.2905). Theoretical element content (%) C 50 H 38 F 3 NO: c,82.74; h,5.28; n,1.93. Measured element content (%): c,82.78; h,5.23; n,1.97.
EXAMPLE 23 Synthesis of Compound 550
Using the same method as in Synthesis example 1, compound 550 (10.64 g) was synthesized with equal molar substitution of a-550 for a-1, equal molar substitution of b-550 for b-1, equal molar substitution of c-550 for c-1, and a solid purity of ≡ 99.63% by HPLC. Mass spectrum m/z:664.2895 (theory: 664.2878). Theoretical element content (%) C 50 H 36 N 2 : c,90.33; h,5.46; n,4.21. Measured element content (%): c,90.38; h,5.42; n,4.25.
EXAMPLE 24 Synthesis of Compound 569
Using the same method as in Synthesis example 1, compound 569 (11.17 g) was synthesized with equal molar substitution of a-569 for a-1, equal molar substitution of b-569 for b-1, equal molar substitution of c-569 for c-1, and a solid purity of ≡ 99.74% as measured by HPLC. Mass spectrum m/z:657.2478 (theory: 657.2490). Theoretical element content (%) C 48 H 35 NS: c,87.63; h,5.36; n,2.13. Measured element content (%): c,87.67; h,5.32; n,2.10.
EXAMPLE 25 Synthesis of Compound 666
Using the same method as in Synthesis example 1, compound 666 (9.71 g) was synthesized with a-666 replacing a-1, b-14 replacing b-1, c-666 replacing c-1, and an equivalent molar ratio of > 99.64% as measured by HPLC. Mass spectrum m/z:554.2368 (theory: 554.2358). Theoretical element content (%) C 40 H 30 N 2 O: c,86.61; h,5.45; n,5.05. Measured element content (%): c,86.66; h,5.42; n,5.00.
EXAMPLE 26 Synthesis of Compound 670
Using the same method as in Synthesis example 1, compound 670 (10.97 g) was synthesized with a molar equivalent of a-670 replacing a-1, a molar equivalent of b-14 replacing b-1, a molar equivalent of c-670 replacing c-1, and a solid purity of > 99.70% as measured by HPLC. Mass spectrum m/z:707.3177 (theory: 707.3188). Theoretical element content (%) C 53 H 41 NO: c,89.92; h,5.84; n,1.98. Measured element content (%): c,89.88; h,5.89; n,1.95.
Red organic light-emitting device (electron transport layer)
Comparative examples 1-4 device preparation examples:
comparative example 1: the organic light emitting device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: the ITO substrate is put in distilled water for 3 times, washed by ultrasonic waves for 15 minutes, washed by ultrasonic waves sequentially by solvents such as isopropanol, acetone, methanol and the like after the distilled water is washed, dried and dried at 120 ℃, and sent into an evaporator.
Evaporating a hole injection layer NPNPB/45nm, an evaporating hole transport layer beta-NPB/28 nm and an evaporating main body m-C on the prepared ITO transparent electrode by a layer-by-layer vacuum evaporation modeBP: ir doped (piq) 2 acac (mass content 97%:3% mixture)/26 nm, then evaporating an electron transport layer ET-1/27nm, an electron injection layer LiF/1.1nm, and a cathode Al/136nm. And sealing the device in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is shown as follows:
comparative example 2: the organic light emitting device of comparative example 2 was manufactured in the same manner as comparative example 1, except that the electron transport layer material ET-1 in comparative example 1 was replaced with ET-2.
Comparative example 3: the organic light emitting device of comparative example 3 was manufactured in the same manner as comparative example 1, except that the electron transport layer material ET-1 in comparative example 1 was replaced with ET-3.
Comparative example 4: the organic light emitting device of comparative example 4 was manufactured in the same manner as comparative example 1, except that the electron transport layer material ET-1 in comparative example 1 was replaced with ET-4.
Examples 1 to 26
Examples 1 to 26: the electron transport layer material ET-1 of the organic light-emitting device was changed to the inventive compounds 1, 5, 14, 29, 47, 82, 85, 92, 141, 269, 279, 339, 341, 394, 413, 461, 477, 491, 509, 522, 526, 529, 550, 569, 666, 670 in this order, and the other steps were the same as comparative example 1.
Test software, a computer, a K2400 digital source list manufactured by Keithley corporation, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research corporation, U.S. were combined into a single integrated IVL test system to test the luminous efficiency of an organic light emitting device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature. The results of the light emission characteristics test of the obtained organic light emitting device are shown in table 1. Table 1 shows the results of the light emitting characteristics test of the light emitting devices prepared with the compounds prepared in the examples of the present invention and the comparative substances.
TABLE 1 test of light emitting characteristics of light emitting device
Note that: t95 means that the current density is 10mA/cm 2 In the case, the time taken for the brightness of the device to decay to 95%;
as can be seen from the results of table 1, the nitrogen-containing heterocyclic organic compound of the present invention was used in an organic light-emitting device as an electron transport layer material, and exhibited the advantages of high light-emitting efficiency and long service life as compared with comparative examples 1 to 4, and was an electron transport material for an organic light-emitting device with good performance.
Green organic light emitting device (hole blocking layer)
Comparative example 5 device preparation example:
comparative example 5: the organic light emitting device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: the ITO transparent substrate is put in distilled water for 3 times, washed by ultrasonic waves for 15 minutes, washed by ultrasonic waves sequentially by solvents such as isopropanol, acetone, methanol and the like after the distilled water is washed, dried and dried at 120 ℃, and sent into an evaporator.
Evaporating a hole injection layer on the prepared ITO transparent substrate electrode in a layer-by-layer vacuum evaporation mode, evaporating a hole injection layer NPNPB/50nm, an evaporating hole transport layer beta-NPB/29 nm and an evaporating main body m-CBP on the prepared ITO transparent substrate electrode in a layer-by-layer vacuum evaporation mode: ir doped (ppy) 3 (mass content 95% to 5% mixture)/32 nm, then evaporating the hole blocking layer ET-1/29nm, evaporating the electron transport layer TMPYPB/25nm, the electron injection layer LiF/1nm and the cathode Al/134nm. And sealing the device in a glove box, thereby preparing an organic light emitting device. The preparation of the organic light-emitting device is completed according to the stepsAfter that, the photoelectric property of the device is measured, and the molecular structural formula of the related material is shown as follows:
Comparative example 6: the organic light emitting device of comparative example 6 was manufactured in the same manner as comparative example 1, except that the hole blocking layer material ET-1 in comparative example 1 was replaced with ET-2.
Examples 27 to 49
Examples 27 to 49: the hole blocking layer material ET-1 of the organic light emitting device was changed to the inventive compounds 1, 5, 14, 29, 47, 85, 92, 141, 269, 279, 339, 341, 394, 413, 461, 477, 491, 509, 522, 526, 529, 550, 569 in this order, and the other steps were the same as comparative example 5.
Test software, a computer, a K2400 digital source list manufactured by Keithley corporation, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research corporation, U.S. were combined into a single integrated IVL test system to test the luminous efficiency of an organic light emitting device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature. The results of the light emission characteristics test of the obtained organic light emitting device are shown in table 2. Table 2 shows the results of the light emitting characteristics test of the light emitting devices prepared with the compounds prepared in the examples of the present invention and the comparative substances.
TABLE 2 test of light emitting characteristics of light emitting device
As can be seen from the results of table 2, the nitrogen-containing heterocyclic organic compound of the present invention is applied to an organic light-emitting device, particularly as a hole blocking layer material, and significantly improves the light-emitting efficiency and the service life of the organic light-emitting device as compared with comparative examples 5 to 6, and is an organic light-emitting material having good performance.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims (7)

1. A nitrogen-containing heterocyclic organic compound is characterized in that the molecular structure is shown as a formula I:
the L is selected from one of the following groups:
r' is selected from one or more of hydrogen and deuterium;
the q is 1a Selected from 0, 1, 2, 3 or 4;
the X are the same or different and are selected from CR' or N, and one X is selected from N;
the saidAny one selected from the following groups:
z is selected from any one of O, S or N (Ry); the Ry is selected from any one of substituted or unsubstituted phenyl; the term "substituted …" refers to mono-or poly-substitution with a group selected from deuterium;
the saidAny one selected from the following groups:
the a is selected from 0, 1, 2 or 3; b is selected from 0, 1, 2, 3 or 4; e is selected from 0, 1, 2, 3, 4, 5 or 6;
the R is a Selected from deuterium;
the R is a1 Independently selected from deuterium, t-butyl, phenyl, and said t-butyl, phenyl may also be substituted with one or more of deuterium, when R a1 When selected from tertiary butyl and phenyl, b is selected from 1;
the R is a2 Independently selected from deuterium, t-butyl, and said t-butyl may also be substituted with one or more of deuterium, when R a2 When selected from tert-butyl, b is selected from 1.
2. A nitrogen-containing heterocyclic organic compound according to claim 1, wherein L is selected from one of the following groups:
3. a nitrogen-containing heterocyclic organic compound as described in claim 1, wherein theAny one selected from the following groups:
z is selected from any one of O, S or N (Ry); the Ry is selected from any one of substituted or unsubstituted phenyl; the term "substituted …" means mono-or poly-substituted with a group selected from deuterium.
4. A nitrogen-containing heterocyclic organic compound as described in claim 1, wherein theAny one selected from the following groups:
the R is a Selected from deuterium;
the R is a1 Selected from deuterium;
the R is a2 Selected from deuterium.
5. A nitrogen-containing heterocyclic organic compound, characterized in that the nitrogen-containing heterocyclic organic compound is selected from any one of the chemical structures shown below:
6. an organic light-emitting device comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises an electron transport layer comprising any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds as described in any one of claims 1 to 5.
7. An organic light-emitting device according to claim 6, wherein the organic layer comprises a hole blocking layer containing any one or a combination of at least two of the nitrogen-containing heterocyclic organic compounds according to any one of claims 1 to 5.
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