CN112876455B - Nitrogen-containing compound, and organic electroluminescent device and electronic device using same - Google Patents
Nitrogen-containing compound, and organic electroluminescent device and electronic device using same Download PDFInfo
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- CN112876455B CN112876455B CN202110024392.5A CN202110024392A CN112876455B CN 112876455 B CN112876455 B CN 112876455B CN 202110024392 A CN202110024392 A CN 202110024392A CN 112876455 B CN112876455 B CN 112876455B
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Abstract
The application belongs to the technical field of organic materials, and provides a nitrogen-containing compound, and an organic electroluminescent device and an electronic device using the nitrogen-containing compound, wherein the nitrogen-containing compound has a structure shown in a formula I; wherein, X 1 、X 2 、X 3 Each independently selected from N or CH, and at least one is N. The nitrogen-containing compound is used in an organic electroluminescent device, and can improve the performance of the device.
Description
Technical Field
The application belongs to the technical field of organic materials, and particularly provides a nitrogen-containing compound, and an organic electroluminescent device and an electronic device using the nitrogen-containing compound.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
Taking an organic electroluminescent device as an example, the organic electroluminescent device generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
At present, the problems of low luminous efficiency, overhigh driving voltage and the like exist in the using process of an organic electroluminescent device, so that the performance of the organic electroluminescent device is reduced.
Disclosure of Invention
In view of the above problems in the prior art, the present application aims to provide a nitrogen-containing compound used in an organic electroluminescent device to improve the performance of the organic electroluminescent device, and an organic electroluminescent device and an electronic apparatus using the same.
In order to achieve the above object, the first aspect of the present application provides a nitrogen-containing compound, which has a structure represented by formula I:
wherein, X 1 、X 2 、X 3 Are identical or different from each other, are each independently selected from N or CH, and at least one is N;
Ar 1 and Ar 2 The same or different from each other, each is independently selected from substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L 1 and L 2 The same or different from each other, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
y is selected from C (R) 1 R 2 )、Si(R 1 R 2 ) O, S orN(R 3 )；R 1 、R 2 And R 3 The same or different from each other, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms; optionally, R 1 And R 2 Form a ring together with the atoms to which they are commonly attached;
Ar 1 and Ar 2 Wherein the substituents are the same or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and optionally, any two adjacent substituents form a ring;
L、L 1 、L 2 wherein the substituents are the same or different from each other and each is independently selected from deuterium, a halogen group, cyano, phenyl, naphthyl, pyridyl, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms;
R a 、R b and R c Identical or different from each other and each independently selected from deuterium, a halogen group, a cyano group, a group A, a trialkylsilyl group having 3 to 7 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms; the group A is selected from substituted or unsubstituted aryl with 6-15 carbon atoms or substituted or unsubstituted heteroaryl with 4-10 carbon atoms, and the substituent in the group A is selected from deuterium, fluorine, cyano and alkyl with 1-4 carbon atoms;
n a 、n b and n c Each represents R a 、R b And R c The number of (2); n is a Selected from 0, 1,2, 3 or 4When n is a When greater than 1, any two R a The same or different; n is b Selected from 0, 1 or 2, when n b When it is 2, two R b The same or different; n is c Selected from 0, 1,2, 3 or 4, when n is c When greater than 1, any two R c The same or different.
In a second aspect, the present application provides an organic electroluminescent device comprising a nitrogen-containing compound as described in the first aspect of the present application.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
The nitrogen-containing compound is asymmetric in the whole molecule in the structure, so that the amorphous property of the material is increased, and the charge transmission becomes smoother; the nitrogen-containing heterocycle and the carbazole have a certain rotation angle in a molecular configuration, so that the HOMO value of the nitrogen-containing compound can be adjusted, the HOMO value of the nitrogen-containing compound can be matched with an adjacent film layer, and the driving voltage of the organic electroluminescent device can be reduced; in addition, the HOMO and the LUMO in the structure are respectively arranged at different positions of the molecule, thereby being beneficial to improving T 1 Thereby improving the luminous efficiency.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light-emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. an electronic device.
Detailed Description
The following detailed description of specific embodiments of the present disclosure is provided in connection with the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula I:
wherein, X 1 、X 2 、X 3 Are the same or different from each other, are each independently selected from N or CH, and at least one is N;
Ar 1 and Ar 2 The same or different from each other, each is independently selected from substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L 1 and L 2 The same or different from each other, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
y is selected from C (R) 1 R 2 )、Si(R 1 R 2 ) O, S or N (R) 3 )；R 1 、R 2 And R 3 The same or different from each other, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms; optionally, R 1 And R 2 Form a ring together with the atoms to which they are commonly attached;
Ar 1 and Ar 2 Wherein the substituents are the same or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and optionally, any two adjacent substituents form a ring;
L、L 1 、L 2 wherein the substituents are the same or different from each other and each independently selected from deuterium, a halogen group, cyano, phenyl, naphthyl, pyridyl, a trialkylsilyl group having 3 to 7 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms;
R a 、R b and R c Identical or different from each other and each independently selected from deuterium, a halogen group, a cyano group, a group A, a trialkylsilyl group having 3 to 7 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms; the group A is selected from substituted or unsubstituted aryl with 6-15 carbon atoms or substituted or unsubstituted heteroaryl with 4-10 carbon atoms, and the substituent in the group A is selected from deuterium, fluorine, cyano and alkyl with 1-4 carbon atoms;
n a 、n b and n c Each represents R a 、R b And R c The number of (2); n is a radical of an alkyl radical a Selected from 0, 1,2, 3 or 4, when n is a When greater than 1, any two R a The same or different; n is b Selected from 0, 1 or 2, when n b When it is 2, two R b The same or different; n is c Selected from 0, 1,2, 3 or 4, when n is c When greater than 1, any two R c The same or different.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. For example,') "
Wherein each q is independently 0, 1,2 or 3, each R' is independently selected from hydrogen, deuterium, fluorine, chlorine ",the meaning is that: the formula Q-1 represents that Q substituent groups R ' exist on a benzene ring, each R ' can be the same or different, and the options of each R ' do not influence each other; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as R x ). For example, "substituted or unsubstituted aryl" means having a substituent R x Or an unsubstituted aryl group. Wherein the above-mentioned substituents are R x For example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, a triarylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, or the like may be mentioned. In addition, "two adjacent substituents" includes the following two cases: with two substituents R attached to the same atom x And two adjacent atoms are respectively connected with a substituent R x The case (1). When two substituents R are attached to the same atom x When two substituents R are present x May be independently present or attached to each other to form a ring with said atoms; when two adjacent atoms present on the functional group are each bound by a substituent R x When two adjacent substituents R are present x May be present independently or may be fused to form a ring with the functional group to which it is attached.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked in conjugation by a carbon-carbon bond, by a carbon-carbon bondMonocyclic aryl and fused ring aryl groups linked in conjugation, two or more fused ring aryl groups linked in conjugation by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. Specific examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, reference to heteroarylene is to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
The non-positional connection key referred to in this application
Refers to a single bond extending from the ring system, which means that one end of the connecting bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) to the naphthyl represented by the formula (f-10) includes any possible connection mode.
As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, the number of carbon atoms of the aryl group as a substituent is, for example, 6 to 20, 6 to 18, 6 to 15, etc., the number of carbon atoms is, for example, 6, 10, 12, 14, 15, etc., and specific examples of the aryl group include, but are not limited to, phenyl, naphthyl, biphenyl, etc.
In the present application, the number of carbon atoms of the heteroaryl group as a substituent is, for example, 3 to 20, 3 to 18, 5 to 15, 6 to 12, etc., and the number of carbon atoms is, for example, 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, etc., and specific examples of the heteroaryl group include, but are not limited to, a pyridyl group, a quinolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, etc.
In the present application, the number of carbon atoms of the trialkylsilyl group may be 3 to 12, 3 to 7, etc., and specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, etc.
In the present application, the number of carbon atoms of the cycloalkyl group may be 3 to 10, 5 to 6, etc., and specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, etc.
In the present application, in the formula I,
represents:
r in (1) b Any two adjacent CH's and
the resulting groups are attached at the "#", "###" junctions, respectively. For example, when n is a 、n b And n c When both are 0 and Y is S,
is specifically composed of
Specifically, the nitrogen-containing compound has a structure represented by any one of formulas 2-1 to 2-6:
in the application, X 1 、X 2 、X 3 At least one of which is N, in particular, X 1 、X 2 、X 3 1,2 or 3 of which are N.
Alternatively, L, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms. For example, L, L 1 、L 2 Each independently selected from a single bond, or from a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms, or from a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15 carbon atoms.
Alternatively, L, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a new subunit group formed by interconnecting a phenylene group and a naphthylene group.
Alternatively, L, L 1 、L 2 Wherein the substituents in (A) are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, trifluoromethyl and phenyl.
Alternatively, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 6 to 12 carbon atoms.
Alternatively, L is selected from a single bond or from the group consisting of:
alternatively, L 1 、L 2 Each independently selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
Alternatively, L 1 、L 2 Each independently selected from a single bond, substituted or unsubstituted phenylene. For example, L 1 、L 2 Each independently selected from a single bond or phenylene.
Alternatively, Ar 1 And Ar 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms. For example, Ar 1 And Ar 2 Each independently selected from substituted or unsubstituted aryl having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms or substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.
Alternatively, L 1 And Ar 1 Has a total number of carbon atoms of 6 to 20, L 2 And Ar 2 The total number of carbon atoms of (a) is 6 to 20.
In some embodiments, Ar 1 And Ar 2 Are the same or different from each other and are each independently selected from the group consisting of:
wherein the content of the first and second substances,
represents a chemical bond, M 1 Selected from a single bond or
G 1 ～G 5 Each independently selected from N or C (F) 1 ) And G is 1 ～G 5 At least one is selected from N; when G is 1 ～G 5 Two or more of C (F) 1 ) When, two arbitrary F 1 The same or different;
G 6 ～G 13 each independently selected from N or C (F) 2 ) And G is 6 ～G 13 At least one is selected from N; when G is 6 ～G 13 Two or more selected from C (F) 2 ) When, two arbitrary F 2 The same or different;
G 14 ～G 23 each independently selected from N, C or C (F) 3 ) And G is 14 ～G 23 At least one is selected from N; when G is 14 ～G 23 Two or more of C (F) 3 ) When, two arbitrary F 3 The same or different;
G 24 ～G 33 each independently selected from N, C or C (F) 4 ) And G is 24 ～G 33 At least one is selected from N; when G is 24 ～G 33 Two or more of C (F) 4 ) When, two arbitrary F 4 The same or different;
Z 1 selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms and alkylthio having 1 to 10 carbon atoms;
Z 2 ～Z 9 、Z 13 each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3-12 carbon atoms, alkyl having 1-10 carbon atoms, haloalkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, alkoxy having 1-10 carbon atoms, alkylthio having 1-10 carbon atoms, heteroaryl having 3-18 carbon atoms, and triphenylsilyl;
Z 10 ～Z 20 、F 1 ～F 4 each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, or a mixture thereof6-18 aryl, 3-18 heteroaryl and triphenyl silyl; optionally, any two adjacent Z 19 Forming a ring; optionally, any two adjacent Z 20 Forming a ring;
h 1 ～h 21 in h is given by k Is represented by Z 1 ～Z 21 With Z k K is a variable and represents an arbitrary integer of 1 to 21, h k Represents a substituent H k The number of (2); wherein, when k is selected from 5 or 17, h k Selected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k Selected from 1,2, 3 or 4; when k is selected from 1,3, 4,6, 9 or 14, h k Selected from 1,2, 3,4 or 5; when k is 13, h k Selected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, h k Selected from 1,2, 3,4, 5, 6 or 7; when k is 20, h k Selected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, h k Selected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when h is k When greater than 1, any two Z k The same or different;
K 1 selected from O, S, N (Z) 22 )、C(Z 23 Z 24 )、Si(Z 23 Z 24 ) (ii) a Wherein, Z 22 、Z 23 、Z 24 Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or Z 23 And Z 24 Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked;
K 2 selected from single bond, O, S, N (Z) 25 )、C(Z 26 Z 27 )、Si(Z 26 Z 27 ) (ii) a Wherein Z is 25 、Z 26 、Z 27 Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or Z 26 And Z 27 Are linked to each other so as to form a carbon number of 3 to 15 with the atoms to which they are commonly linkedSaturated or unsaturated rings.
In the formulae i-13 to i-15, F 2 To F 4 Fi, where i is a variable, may represent 2, 3, or 4. For example, when i is 2, Fi means F 2 . It should be understood that when the delocalized bond is connected to c (Fi), Fi in c (Fi) is not present. For example, in the chemical formula i-13, when
Is connected to G 12 When, G 12 Only C atoms can be represented, i.e. the structure of formula i-13 is specified as:
in the present application, Z is as defined above 23 And Z 24 Z above 26 And Z 27 In both groups, the ring formed by the interconnection of the two groups in each group may be saturated or unsaturated, for example a saturated or unsaturated 3 to 13 membered ring may be formed. For example, in the formula i-10, when K is 2 And M 1 Are all single bonds, Z 19 Is hydrogen, and K 1 Is C (Z) 23 Z 24 ) When Z is above 23 And Z 24 When they are linked to each other so as to form a 5-membered ring with the atoms to which they are commonly attached, formula i-10 is
Likewise, the formula i-10 can also be represented
I.e. H 23 And H 24 The atoms that are linked to each other to be commonly bound to them form a partially unsaturated 13-membered ring.
Alternatively, Ar 1 And Ar 2 Each substituent in (a) is independently selected from: deuterium, fluorine, cyano group, alkyl group having 1 to 4 carbon atoms, heteroaryl group having 5 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, cycloalkyl group having 5 to 10 carbon atoms, and a pharmaceutically acceptable salt thereof,Alkoxy group having 1 to 4 carbon atoms and alkylthio group having 1 to 4 carbon atoms.
Ar 1 And Ar 2 Specific examples of the substituent in (1) include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, phenyl, naphthyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methoxy, methylthio, and the like, respectively.
Alternatively, Ar 1 And Ar 2 Are identical or different and are each independently selected from substituted or unsubstituted radicals V 1 Unsubstituted radicals V 1 Selected from the group consisting of:
substituted radicals V 1 Wherein the substituent group is independently selected from deuterium, fluorine, cyano, alkyl group having 1 to 4 carbon atoms, trifluoromethyl, cycloalkyl group having 5 to 10 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms, and phenyl; when the number of the substituents is more than 1, the substituents may be the same or different.
Optionally, a substituted group V 1 The substituents in (a) are independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, cyclopentyl, cyclohexyl, trimethylsilyl, phenyl.
Further optionally, Ar 1 And Ar 2 Each independently selected from the group consisting of:
alternatively, R 1 、R 2 And R 3 Each independently selected from alkyl with 1-4 carbon atoms and aryl with 6-12 carbon atoms; optionally, R 1 And R 2 Form a ring together with the atoms to which they are commonly attached.
In this application, when Y is C (R) 1 R 2 ) And R is 1 And R 2 When they form a ring together with the atom (C atom) to which they are commonly attached, Y may have, for example, a structure of:
alternatively, R 1 And R 2 Each independently selected from methyl, phenyl; r 3 Selected from phenyl, naphthyl or biphenyl.
In the present application, optionally n a 、n b And n c Each independently selected from 0 or 1.
Alternatively, R a 、R b And R c Each independently selected from deuterium, fluoro, cyano, phenyl, biphenyl, naphthyl, trialkylsilyl having 3-7 carbon atoms, alkyl having 1-4 carbon atoms, fluoromethyl, cycloalkyl having 5-10 carbon atoms, pyridyl, fluoro-substituted phenyl, deuterium-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl.
Alternatively, R a 、R b And R c Each independently selected from deuterium, fluoro, cyano, phenyl, biphenyl, naphthyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, fluoromethyl, cyclopentyl, cyclohexyl, pyridyl, fluoro-substituted phenyl, deuterium-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl.
In one embodiment, Y is selected from O, S or N (R) 3 )，R 3 Selected from phenyl, naphthyl and biphenyl.
Preferably, Y is selected from O or S, in which case the nitrogen-containing compound can further increase the lifetime of the OLED device.
Optionally, the nitrogen-containing compound is selected from the group consisting of:
the synthesis method of the nitrogen-containing compound provided by the present application is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the preparation method provided by the synthesis examples section of the present application in combination with the nitrogen-containing compound. In other words, the synthesis examples section of the present invention illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All of the nitrogen-containing compounds provided herein are available to those skilled in the art from these exemplary preparative methods and all specific preparative methods for preparing the nitrogen-containing compounds will not be described in detail herein and should not be construed as limiting the application to which the skilled artisan is entitled.
A second aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises a nitrogen-containing compound according to the first aspect of the present application.
The nitrogen-containing compound provided by the present application can be used to form at least one organic film layer in a functional layer to improve efficiency characteristics and lifetime characteristics of an organic electroluminescent device.
In a specific embodiment, the functional layer includes an organic light-emitting layer including the nitrogen-containing compound. Generally, the organic light emitting layer may include a host material and a guest material, wherein the host material includes the nitrogen-containing compound of the present application.
As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO 2 Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the first hole transport layer 321 and the second hole transport layer 322 each include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. The host material of the organic light emitting layer 330 may contain the nitrogen-containing compound of the present application. Further alternatively, the organic light emitting layer 330 may be composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, and the exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application.
According to a specific embodiment, the organic electroluminescent device is a green device, wherein the host material in the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application. The host material may be comprised of the nitrogen-containing compounds provided herein; alternatively, it may be composed of the nitrogen-containing compounds provided herein in combination with other materials.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO 2 Al, LiF/Ca, LiF/Al and BaF 2 and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, hole injection layer 310 may be comprised of F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include LiQ.
In a third aspect, the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
The method for synthesizing the nitrogen-containing compound of the present application will be specifically described below with reference to the synthesis examples.
The compounds of the present invention were synthesized using the following methods.
And (3) synthesis of an intermediate D-I:
1. intermediates D-I
(1) 2-bromocarbazole (9.10g,37mmol), methyl 2-aminobenzoate (8.41g,37mmol) and toluene (100 mL) are added into a 500mL three-neck flask with a nitrogen protection and condensation reflux device, stirring and heating are started, sodium tert-butoxide (5.28g,55mmol), 2-dicyclohexylphosphonium-2, 6-dimethoxy-biphenyl (S-phos) (0.15g,0.37mmol) and tris (dibenzylideneacetone) dipalladium (Pd) are added in sequence when the temperature rises to 50 DEG C 2 (dba) 3 ) (0.1g,0.18 mmol); heating to toluene for refluxing, reacting for 6h, stopping stirring and heating after the reaction is finished, and starting to process the obtained reaction liquid when the temperature is reduced to room temperature; adding 80mL of ultrapure water into the reaction solution, stirring and separating the solution, extracting the water phase twice by using 100mL of toluene each time, combining the organic phases, and washing the organic phases for three times by using 100mL of ultrapure water each time; drying with anhydrous sodium sulfate, passing through silica gel column, eluting the column with 200mL of toluene after passing, concentrating the organic phase to 80mL of the remaining, heating to completely dissolve the solid, cooling to crystallize, filtering the solid, and recrystallizing with 45mL of dichloroethane to obtain intermediate B-1 as a white solid (7.26g, 50% yield).
(2) Adding an intermediate B-1(14.52g,37mmol), THF (120 mL) and 2mol/L hydrochloric acid solution (30mL) into a 500mL three-neck flask, starting stirring and heating, heating to 60 ℃, reacting for 8 hours, stopping stirring and heating after the reaction is finished, and starting treatment when the temperature is reduced to room temperature; separating liquid, extracting the water phase twice by using 100mL of dichloromethane each time, combining organic phases, and washing three times by using 100mL of ultrapure water each time; drying with anhydrous sodium sulfate, concentrating the filtrate to dryness, beating twice with 80mL n-heptane, cooling to room temperature and filtering to obtain intermediate B-2(9.80g, yield 70%).
(3) Adding the intermediate B-2(14.00g,37mmol) and 112mL of glacial acetic acid into a 500mL three-necked flask, starting stirring and heating, heating to 60 ℃, adding 1mL of concentrated sulfuric acid (98 wt%), reacting for 10h, filtering after the reaction is finished, beating twice with 80mL of anhydrous ethanol, cooling to room temperature, filtering, separating by a column, and eluting with THF and n-heptane (3: 1, volume ratio) to obtain an intermediate D-1(4.99g, yield 37.5%).
2. The intermediates D-I listed in Table 1 were synthesized by referring to the method for the intermediate D-1, except that the raw material I was used instead of 2-bromocarbazole and the raw material II was used instead of methyl 2-aminobenzoate, and the structures of the main raw materials, the intermediate D-I and the total yield thereof were as shown in Table 1.
TABLE 1
Synthesis example 1: synthesis of Compound 1
Adding the intermediate D-1(13.41g,37mmol) and 100mL of N, N-Dimethylformamide (DMF) into a 500mL three-necked flask, introducing nitrogen for protection, starting stirring, cooling to 5-10 ℃, adding NaH (1.15g,48mmol), dissolving 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (9.86g,37mmol) in 40mL of DMF, and dropwise addingAnd (2) reacting for 6 hours in a reaction system, filtering after the reaction is finished, pulping with 60mL of acetone, separating a product through a column, wherein eluent is petroleum ether and ethyl acetate (4: 1, volume ratio) to obtain a compound 1(8.78g, yield 40%), and mass spectrum: 592.2[ M + H ] M/z] + 。
Synthesis examples 2 to 4
The compounds in table 2 were synthesized with reference to the synthesis method of compound 1, except that intermediate D-I was used instead of intermediate D-1, and the main raw materials, compounds, and their structures, yields, and mass spectrum characterization structures used are shown in table 2.
TABLE 2
Synthesis of intermediate C-I
1. Synthesis of intermediate C-1
(1) Adding 100mL of 1-fluorocarbazole (12.95g,70mmol), 2- (methoxycarbonyl) phenol (10.65g,70mmol), cesium carbonate (34.21,105mmol) and DMF (dimethyl formamide) into a 500mL three-neck flask with a nitrogen protection and condensation reflux device, introducing nitrogen protection, starting heating and stirring, heating to 120 ℃, reacting for 18 hours, cooling the reaction solution to room temperature after the reaction is finished, extracting with 200mL of toluene, washing with 800mL of ultrapure water, drying with anhydrous sodium sulfate, passing through a silica gel column after the extraction is finished, concentrating the column-passing solution to the residual 80mL, heating to completely dissolve solids, slowly cooling for recrystallization, separating the product through the column, and obtaining the product intermediate A-13(13.32g, yield 60%) by using petroleum ether and THF (volume ratio is 4: 1).
(2) Adding the intermediate A-13(11.74g,37mmol), THF (120 mL) and 2mol/L hydrochloric acid (30mL) into a 500mL three-neck flask, starting stirring and heating, heating to 60 ℃, reacting for 8 hours, stopping stirring and heating after the reaction is finished, and starting treatment reaction when the temperature is reduced to room temperature; separating, extracting the water phase twice by using 100mL of dichloromethane each time, combining the organic phases, and washing three times by using 100mL of ultrapure water each time; drying was carried out with anhydrous sodium sulfate, and after the filtrate was concentrated to dryness, it was subjected to thermal beating twice with 80mL of n-heptane and then filtered by cooling to room temperature to obtain intermediate B-13(6.73g, yield 60%).
(3) Adding the intermediate B-13(11.22g,37mmol) and 112mL of glacial acetic acid into a 500mL three-neck flask, starting stirring and heating, and heating to 60 ℃; 1mL of concentrated sulfuric acid (98 wt%) was added to the reaction mixture, the reaction was carried out for 10 hours, filtration was carried out after completion of the reaction, the mixture was thermally slurried twice with 80mL of anhydrous ethanol, cooled to room temperature and filtered, and the filtrate was separated by column chromatography using THF and n-heptane (3: 1, volume ratio) as leacheate to obtain intermediate C-1(7.60g, yield 72%).
2. The intermediates C-I listed in Table 3 were synthesized by referring to the method for the intermediate C-1, using the raw material I in place of 1-fluorocarbazole and the raw material II in place of 2- (methoxycarbonyl) phenol, and the structures of the main raw material, the intermediates C-I and the total yields thereof are shown in Table 3.
TABLE 3
Synthesis example 5: synthesis of Compound 13
Adding an intermediate C-1(10.55g,37mmol) and 100mL of DMF (dimethyl formamide) into a 500mL three-necked flask, introducing nitrogen for protection, starting stirring, cooling to 5-10 ℃, adding NaH (1.15g,48mmol), dissolving 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (9.86g,37mmol) with 40mL of DMF, dropwise adding into a reaction system, reacting for 5h, filtering after the reaction is finished, pulping with 60mL of acetone, separating the product by using a column, wherein the eluent is petroleum ether and ethyl acetate (6: 1, volume ratio), obtaining a compound 13(8.60g, yield 45%), and mass spectrum: m/z 517.2[ M + H ═ M] + 。
Synthesis examples 6 to 13
The compounds of table 4 were synthesized with reference to the synthesis of compound 13, except that intermediate C-I was used instead of intermediate C-1 and starting material a was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, and the main starting materials, compounds and their structures, yields and mass spectrometric characterization structures used are shown in table 4.
TABLE 4
Nuclear magnetic resonance of compound 55: 1 H NMR(400MHz,CD 2 Cl 2 ):8.72(d,1H),8.58(d,4H),8.38(d,1H),8.10(d,1H),7.73(dd,1H),7.68-7.61(m,6H),7.61-7.56(m,2H),7.51-7.40(m,7H),7.02(t,1H)。
synthesis example 14: synthesis of Compound 37
Adding intermediate D-1(13.41g,37mmol) and DMF 100mL into 500mL three-necked flask, introducing nitrogen for protection, stirring, cooling to 5-10 deg.C, adding NaH (1.15g,48mmol), and adding NaH 40mAfter 2-chloro-4- (biphenyl-4-yl) -6-phenyl-1, 3, 5-triazine (12.72g,37mmol) is dissolved in DMF of L, the solution is dripped into a reaction system for reaction for 8 hours, 50mL of deionized water is added after the reaction is finished, stirring is carried out for 30min, filtering is carried out, 60mL of ethanol is used for pulping, products are separated through a column, and eluent is petroleum ether and THF (3: 1, volume ratio) to obtain a compound 37(12.39g, yield 50%) mass spectrum: 668.2[ M + H ] M/z] + 。
Synthesis examples 15 to 18
The compounds of table 5 were synthesized with reference to the synthesis of compound 37, except that intermediate D-I was used instead of intermediate D-1, and starting material a was used instead of 2-chloro-4- (biphenyl-4-yl) -6-phenyl-1, 3, 5-triazine, and the main starting materials, compounds, and their structures, yields, and mass spectrometric characterization structures used are shown in table 5.
TABLE 5
Synthesis of intermediate a-12:
in a 500mL three-necked flask with nitrogen protection and a condensing reflux device, 2, 4-dichloro-6-naphthalen-2-yl- [1,3,5] triazine (19.06g,70mmol), dibenzofuran-2-boronic acid (14.84g,70mmol), potassium carbonate (30.69g,140mmol), tetrabutylammonium bromide (4.5g,14mmol), and 120mL of toluene, 30mL of ethanol, and 30mL of ultrapure water (30mL) were charged; introducing nitrogen for protection, starting heating and stirring, adding tetratriphenylphosphine palladium (0.45g,0.4mmol) when the temperature rises to 40 ℃, heating to reflux reaction for 18 hours, cooling reaction liquid to room temperature after the reaction is finished, extracting with 200mL toluene, washing with 400mL ultrapure water, drying with anhydrous sodium sulfate, concentrating until no liquid flows out, purifying with silica gel column, wherein the eluent is petroleum ether and ethyl acetate (3: 1, volume ratio), and obtaining a-12(16.97g, yield 60%).
Synthesis of intermediates A-I
1. Synthesis of intermediate A-1
Adding 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (18.73g,70mmol), p-bromophenylboronic acid (14.00g,70mmol), potassium carbonate (30.69g,140mmol), tetrabutylammonium bromide (4.5g,14mmol), toluene 120mL, ethanol 30mL and ultrapure water 30mL into a 500mL three-neck flask with a nitrogen protection and condensation reflux device, introducing nitrogen protection, starting heating and stirring, adding tetratriphenylphosphine palladium (0.45g,0.4mmol) when the temperature rises to 40 ℃, heating to reflux for reaction for 5 hours, after the reaction is finished, cooling the reaction solution to room temperature, extracting with 200mL of toluene, washing with 400mL of ultrapure water, drying with anhydrous sodium sulfate, concentrating until no liquid flows out, purifying the product by a column, and eluting with petroleum ether and ethyl acetate (4: 1, volume ratio), intermediate A-1(8.15g, yield 30%) was obtained.
2. The intermediates A-I listed in Table 6 were synthesized by referring to the method of the intermediate A-1, except that the starting material A was used in place of 2, 4-dichloro-6-naphthalen-2-yl- [1,3,5] triazine and the starting material B was used in place of dibenzofuran-2-boronic acid, and the structures of the main starting materials, the intermediates A-I and the yields thereof are shown in Table 6.
TABLE 6
Synthesis example 19: synthesis of Compound 12
Adding intermediate C-4(10.55g,37mmol) and DMF 100mL into a 500mL three-necked flask, introducing nitrogen for protection, stirring, cooling to 5-10 deg.C,adding NaH (1.15g,48mmol), dissolving intermediate a-12(14.95g,37mmol) with 40mL of DMF, dropwise adding into the reaction system, reacting for 5h, filtering after the reaction is finished, pulping with 60mL of acetone, separating the product through a column, eluting with petroleum ether and ethyl acetate (6: 1, volume ratio), obtaining compound 12(10.87g, yield 45%), mass spectrum: 657.18[ M + H ] M/z] + 。
Synthesis examples 20 to 28
The compounds of table 6 were synthesized with reference to the synthesis of compound 12, except that intermediate C-I was used instead of intermediate C-4, and starting material IV (including a-I) was used instead of intermediate a-12, and the main starting materials, compounds and their structures, yields and mass spectrometry characterization structures used are shown in table 6.
TABLE 6
Preparation and evaluation of organic electroluminescent device
Example 1: green organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on the test substrate (anode) to a thickness of
And NPB is vapor-deposited on the hole injection layer to form a layer having a thickness of
The hole transport layer of (1).
Vacuum evaporating compound HT-1 on the hole transport layer to a thickness of
The hole adjusting layer of (1).
On the hole adjusting layer, compound 1: GH-N1: ir (ppy) 3 The mixture is evaporated at a thickness ratio of 45 percent to 10 percent to form a film with a thickness of
The green light emitting layer of (2).
ET-1 and LiQ were formed by vapor deposition at a film thickness ratio of 1:1
A thick electron transport layer formed by vapor depositing Yb on the electron transport layer
Then magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer at a film thickness ratio of 1: 9 to form a layer having a thickness of
The cathode of (2).
The thickness of the vapor deposition on the cathode is set to
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Example 2 example 28
An organic electroluminescent device was produced in the same manner as in example 1, except that in the formation of the light-emitting layer, compounds shown in table 8 below were used instead of compound 1.
Comparative example 1 to comparative example 4
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, compound C, and compound D in table 8 below were each substituted for compound 1 in forming a light-emitting layer.
The structures of the main materials used in examples 1 to 28 and comparative examples 1 to 4 are shown in Table 7.
TABLE 7
For the organic electroluminescent devices prepared in the above examples and comparative examples, at 20mA/cm 2 The device performance was analyzed under the conditions of (1) and the results are shown in table 8.
TABLE 8
As can be seen from the results of table 8, the organic electroluminescent devices of examples 1 to 28 using the nitrogen-containing compounds of the present application as the organic light-emitting layer showed a reduction in driving voltage of at least 0.24V, an increase in luminous efficiency (Cd/a) of at least 12.6%, and an increase in external quantum efficiency (EQE/%) of at least 12.7% as compared to the devices of comparative examples 1 to 4 using known compounds as the organic light-emitting layer; it can be seen that the nitrogen-containing compounds used in examples 1 to 28 can further improve the photoelectric efficiency of the device and reduce the driving voltage of the device. In addition, the nitrogen-containing compounds used in examples 1 to 28 can also provide higher yield of the organic electroluminescent device, for example, the lifetime can be increased by more than 21.4%, and can be increased by more than 75 hours at most.
The preferred embodiments of the present disclosure are described in detail with reference to the accompanying drawings, however, the present disclosure is not limited to the specific details of the embodiments, and various simple modifications may be made to the technical solution of the present disclosure within the technical idea of the present disclosure, and these simple modifications all belong to the protection scope of the present disclosure.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.
In addition, any combination of the various embodiments of the present application can be made, and the same shall be considered as the disclosure of the present application as long as the idea of the present application is not violated.
Claims (9)
1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is represented by formula I:
wherein, X 1 、X 2 、X 3 Are identical or different from each other, are each independently selected from N or CH, and X 1 、X 2 、X 3 2 or 3 are N;
Ar 1 and Ar 2 Are identical or different from one another and are each independently selected from substituted or unsubstituted radicals V 1 Unsubstituted radicals V 1 Selected from the group consisting of:
substituted radicals V 1 Wherein the substituent group is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, and phenyl; when the number of the substituents is more than 1, the substituents are the same or different;
l is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; l is a radical of an alcohol 1 、L 2 Each independently selected from a single bond, substituted or unsubstituted phenylene;
L、L 1 、L 2 wherein the substituents in (A) are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, and a phenyl group;
y is selected from O or S;
R a 、R b and R c Identical to or different from each other and each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms;
n a 、n b and n c Each represents R a 、R b And R c The number of (2); n is a Selected from 0, 1,2, 3 or 4, when n is a When greater than 1, any two R a The same or different; n is a radical of an alkyl radical b Selected from 0, 1 or 2, when n b When it is 2, two R b The same or different; n is c Selected from 0, 1,2, 3 or 4, when n c When greater than 1, any two R c The same or different.
2. The nitrogen-containing compound according to claim 1, wherein Ar 1 And Ar 2 Each independently selected from the group consisting of:
3. the nitrogen-containing compound according to claim 1, wherein n is a 、n b And n c Each independently selected from 0 or 1.
4. The nitrogen-containing compound according to claim 1, wherein R a 、R b And R c Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl.
5. A nitrogen-containing compound selected from the group consisting of:
6. an organic electroluminescent device, comprising an anode and a cathode which are oppositely arranged, and a functional layer which is arranged between the anode and the cathode; the functional layer contains the nitrogen-containing compound according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the functional layer comprises an organic light-emitting layer containing a host material containing the nitrogen-containing compound and a guest material.
8. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent device is a green device.
9. An electronic device comprising the organic electroluminescent element as claimed in any one of claims 6 to 8.
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| KR20160060572A (en) * | 2014-11-19 | 2016-05-30 | 주식회사 엠비케이 | Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus |
| CN111518106A (en) * | 2014-04-09 | 2020-08-11 | 斗山索如始株式会社 | Organic compound and organic electroluminescent element comprising same |
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| CN111518106A (en) * | 2014-04-09 | 2020-08-11 | 斗山索如始株式会社 | Organic compound and organic electroluminescent element comprising same |
| KR20160060572A (en) * | 2014-11-19 | 2016-05-30 | 주식회사 엠비케이 | Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus |
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