CN112521340B - Organic electroluminescent material and application thereof - Google Patents
Organic electroluminescent material and application thereof Download PDFInfo
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- CN112521340B CN112521340B CN202011332883.8A CN202011332883A CN112521340B CN 112521340 B CN112521340 B CN 112521340B CN 202011332883 A CN202011332883 A CN 202011332883A CN 112521340 B CN112521340 B CN 112521340B
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- organic electroluminescent
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- 125000005843 halogen group Chemical group 0.000 description 17
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Abstract
The invention relates to an organic compound, the structural formula of which is shown as the formula (I):
Description
Technical Field
The invention belongs to the technical field of materials for organic electroluminescent elements, and particularly relates to an organic electroluminescent material and a preparation method and application thereof.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have already entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport properties, electroluminescent properties of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting element has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from radiative transition of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transition of triplet excitons is 75%. It is urgent to use 75% of the energy of triplet excitons. Forrest et al in 1997 discovered that the phosphorescence electroluminescence phenomenon breaks through the limitation of 25% efficiency of the quantum efficiency of the organic electroluminescence material, and arouses people to pay extensive attention to the metal complex phosphorescence material. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a novel organic compound and use thereof, which can be used as a raw material for an organic electroluminescent element material to provide an organic electroluminescent element having a reduced starting voltage, an improved luminous efficiency, and an improved luminance.
The structural formula of the organic compound is as follows:
wherein R is 1 ～R 10 Same or different, selected from hydrogen, deuterium, having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 Or alkenyl or alkynyl, or one of an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R 1 ～R 10 Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar 1 、Ar 2 identical or different, from aromatic or heteroaromatic ring systems having from 5 to 60 carbon atoms, which may be mono-or polysubstitutedA plurality of groups R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 3 ) 2 、N(R 12 ) 2 、C(＝O)Ar 3 、C(＝O)R 12 、P(＝O)(Ar 3 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Or alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, or an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 12 Substituted, or a combination of these systems; in which one or more non-adjacent-CHs 2 The radicals may be substituted by R 12 C＝CR 12 、C≡C、Si(R 12 ) 2 、Ge(R 12 ) 2 、Sn(R 12 ) 2 、C＝O、C＝S、C＝Se、C＝NR 12 、P(＝O)(R 12 )、SO、SO 2 、NR 12 O, S or CONR 12 And wherein one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups; wherein two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R 12 Substitution;
R 12 each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 3 ) 2 、N(R 13 ) 2 、C(＝O)Ar 3 、C(＝O)R 13 、P(＝O)(Ar 3 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Of one of an alkenyl or alkynyl group, an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, an aryloxy or heteroaryloxy group having 5 to 60 carbon atoms, R 12 Each radical in (a) may be substituted by one or more radicals R 13 Substituted, or a combination of these systems; in which one or more non-adjacent-CHs 2 The radicals may be substituted by R 13 C＝CR 13 、C≡C、Si(R 13 ) 2 、Ge(R 13 ) 2 、Sn(R 13 ) 2 、C＝O、C＝S、C＝Se、C＝NR 13 、P(＝O)(R 13 )、SO、SO 2 、NR 13 O, S or CONR 13 And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups; in which two or more adjacent substituents R 12 Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R 13 Substitution;
Ar 3 identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R 13 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 3 Can also be selected from N (R) through a single bond 13 )、C(R 13 ) 2 Oxygen or sulfur bridging groups;
R 13 selected from hydrogen atoms, deuterium atoms, fluorine atoms, nitrile groups, having C 1 ～C 20 An aromatic or heteroaromatic ring system having from 5 to 30 carbon atoms, wherein R 13 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 13 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
Aromatic or heteroaromatic ring systems in the sense of the present invention are intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, for example C, N, O or an S atom. Thus, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9,9' -spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, and the like are also considered to refer to aromatic ring systems in the sense of the present invention.
Aryl in the sense of the present invention contains from 5 to 60 carbon atoms and heteroaryl in the sense of the present invention contains from 5 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which a single hydrogen atom or-CH 2 The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably to be understood as meaning the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. Alkoxy, preferably alkoxy having from 1 to 40 carbon atoms, is to be understood as meaning methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy. Heteroalkyl is preferably alkyl having 1 to 40 carbon atoms, meaning groups in which the individual hydrogen atoms or-CH 2-groups may be substituted by oxygen, sulfur, halogen atoms, and is understood to mean alkoxy, alkylthio, fluoroAlkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present 2 The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms or nitrile groups.
The aromatic or heteroaromatic ring atoms according to the invention may in each case also be substituted by the abovementioned radicals R 13 Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6]Quinoline, quinoline and quinoline derivatives,Benzo [6,7]Quinoline, benzo [7,8]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaft 3925, pyrazine, phenazine, phenoxazine, phenothiazine, fluoranthene, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 5483, 54545454545427-triazole, 359692-triazole, 359635-triazole, 359692-triazole, 359635, a-429692, a combination of these oxadiazole-429635, oxadiazole-429652, and oxadiazole systems.
Preferably, said R 1 ～R 10 The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, and the R is 1 ～R 10 Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
ar is 1 、Ar 2 Identical or different, from aromatic or heteroaromatic ring systems having from 5 to 60 carbon atoms, which may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 3 ) 2 、N(R 12 ) 2 、C(＝O)Ar 3 、C(＝O)R 12 、CJHP(＝O)(Ar 3 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), having C 2 ～C 40 Or alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, or an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 12 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radical may be represented by R 12 C＝CR 12 、C≡C、Si(R 12 ) 2 、Ge(R 12 ) 2 、Sn(R 12 ) 2 、C＝O、C＝S、C＝Se、C＝NR 12 、CJHP(＝O)(R 12 )、SO、SO 2 、NR 12 O, S or CONR 12 And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R 12 Substitution;
R 12 each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 3 ) 2 、N(R 13 ) 2 、C(＝O)Ar 3 、C(＝O)R 13 、P(＝O)(Ar 3 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, R 12 Each radical in (a) may be substituted by one or more radicals R 13 By substitution, or combinations of these systems, in which one or more non-adjacent-CH is/are not adjacent 2 The radicals may be substituted by R 13 C＝CR 13 、C≡C、Si(R 13 ) 2 、Ge(R 13 ) 2 、Sn(R 13 ) 2 、C＝O、C＝S、C＝Se、C＝NR 13 、CJHP(＝O)(R 13 )、SO、SO 2 、NR 13 O, S or CONR 13 And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R 12 Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R 13 Substitution;
Ar 3 identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R 13 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 3 Can also be selected from N (R) through a single bond 13 )、C(R 13 ) 2 Oxygen or sulfur bridging groups;
R 13 selected from hydrogen atoms, deuterium atoms, fluorine atoms, nitrile groups, having C 1 ～C 20 An aromatic or heteroaromatic ring system having from 5 to 30 carbon atoms, wherein R 13 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 13 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
Further, the specific structural formula of the organic compound is shown as CJHP489-CJHP 663:
further, the specific structural formula of the organic compound is as follows:
the R is 1 ～R 10 The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, and the R is 1 ～R 10 Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
further, said R 1 ～R 10 Identical or different, selected from hydrogen or deuterium;
ar is 1 、Ar 2 Identical or different, from aromatic or heteroaromatic ring systems having from 5 to 60 carbon atoms, which may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 3 ) 2 、N(R 12 ) 2 、C(＝O)Ar 3 、C(＝O)R 12 、P(＝O)(Ar 3 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Or alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, or an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R 12 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radicals may be substituted by R 12 C＝CR 12 、C≡C、Si(R 12 ) 2 、Ge(R 12 ) 2 、Sn(R 12 ) 2 、C＝O、C＝S、C＝Se、C＝NR 12 、P(＝O)(R 12 )、SO、SO 2 、NR 12 O, S or CONR 12 And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R 12 Substitution;
R 12 each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar) 3 ) 2 、N(R 13 ) 2 、C(＝O)Ar 3 、C(＝O)R 13 、P(＝O)(Ar 3 ) 2 Having a structure of C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an aryloxy or heteroaryloxy group having from 5 to 60 carbon atoms, R 12 Each radical in (a) may be substituted by one or more radicals R 13 Substituted, or combinations of these systems, wherein one or more non-adjacent-CH 2 The radical may be represented by R 13 C＝CR 13 、C≡C、Si(R 13 ) 2 、Ge(R 13 ) 2 、Sn(R 13 ) 2 、C＝O、C＝S、C＝Se、C＝NR 13 、P(＝O)(R 13 )、SO、SO 2 、NR 13 O, S or CONR 13 And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R 12 Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R 13 Substitution;
Ar 3 identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R 13 Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom 3 Can also be selected from N (R) or through a single bond 13 )、C(R 13 ) 2 Oxygen or sulfur bridging groups;
R 13 selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C 1 ～C 20 An aromatic or heteroaromatic ring system having from 5 to 30 carbon atoms, wherein R 13 Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R 13 They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
The invention also relates to the use of the organic compounds according to the invention for producing materials for organic components.
Further, the organic element is an organic electroluminescent element, an organic field effect transistor or an organic thin film solar cell.
Furthermore, aiming at the organic electroluminescent element, the organic combination is applied to the preparation of a luminescent layer material, an electron transport layer material, a hole transport layer material or an encapsulation layer material.
An organic electroluminescent element comprising a first electrode, a second electrode and a plurality of organic layers disposed between the first electrode and the second electrode, at least one of the organic layers being prepared from the organic compound of the present invention.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light-emitting layer, or it may include a plurality of light-emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises, according to the invention, a compound according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-injecting and hole-transporting layer and in the electron-injecting and electron-transporting layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, an organic electroluminescent element is preferred which uses the sublimation methodApplying one or more layers, wherein the temperature is below 10 in a vacuum sublimation device -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10 -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermography, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which one or more layers are applied, for example, from solution and one or more further layers are applied by vapor deposition.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A display device includes the organic electroluminescent element.
An illumination device comprising the organic electroluminescent element.
The organic device material of the present invention contains the compound of the present invention. The material for organic devices may be composed of the compound of the present invention alone or may contain other compounds.
The compound of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light-emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, and an encapsulation layer.
Compared with the prior art, the invention has the beneficial effects that: the novel compound has high triplet state energy level and high carrier mobility, is suitable for being used as a material for an organic electroluminescent element, and has the characteristics of low starting voltage, high luminous efficiency and high brightness. The compound of the present invention has excellent thermal stability and film-forming properties, and can be used for materials for organic electroluminescent elements, display devices, and lighting devices, and can prolong the service life thereof, thereby reducing the production costs of the materials for organic electroluminescent elements, the display devices, and the lighting devices.
Drawings
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
fig. 2 is a schematic view of one example of top emission of the organic electroluminescent device of the present invention.
In the figure, 1-substrate, 2-anode, 3-hole injection layer, 4-hole transmission/electron blocking layer, 5-luminescent layer, 6-hole transmission/electron transmission layer, 7-electron injection layer and 8-cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
Example 1
The preparation method of the compound CJHP517 comprises the following steps:
the first step is as follows: preparation of Compound Int-1
25.0mmol 1,8-dibromonaphthalene, 25.0mmol 9,9-dimethyl-2-aminofluorene, 30.0mmol sodium tert-butoxide and 0.25mmol Pd 2 (dba) 3 And 0.5mmol of Xanphos, adding 80mL of toluene, heating to 100 ℃ under the protection of nitrogen, stirring for reaction for 12 hours, cooling to room temperature, adding 300mL of water for dilution, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain the compound Int-1 with the yield of 72%.
The second step is that: preparation of Compound Int-2
20.0mmol of the intermediate Int-1 prepared in the first step is dispersed in 100mL of toluene, 22.0mmol of o-iodobromobenzene, 40.0mmol of anhydrous potassium carbonate and 2.0mmol of cuprous iodide are added, 4.0mmol of N, N' -dimethylethylenediamine is added, the mixture is heated under reflux and stirred for reaction for 20 hours under the protection of nitrogen, the mixture is cooled to room temperature, filtered, decompressed, concentrated and dried in the filtrate, and separated and purified by a silica gel column to obtain a white solid compound Int-2 with the yield of 87%.
The third step: preparation of compound CJHP517
10.0mmol of the secondDissolving the intermediate Int-2 prepared in step (b) in 80mL of dry toluene, adding 10.0mmol of 2-amino-9,9' -spirobifluorene and 30.0mmol of sodium tert-butoxide under the protection of nitrogen, and then adding 0.1mmol of Pd 2 (dba) 3 CHCl 3 And 0.02mL of 10% tri-tert-Ding Lin toluene solution, heating to 100 ℃, stirring for reaction for 16 hours, cooling to room temperature, adding 50mL of water for dilution, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain the compound CJHP517 as a yellow solid with a yield of 65%.
MS and of compound CJHP517 1 The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 739.3129[M+H] + ； 1 HNMR(δ、CDCl 3 )：7.67～7.65(3H,m)；7.54～7.48(2H,m)；7.31～7.10(16H,m)；7.00～6.93(4H,m)；6.82～6.80(2H,m)；6.72～6.57(4H,m)；6.39(1H,s)；1.02(6H,s)。
example 2
Preparation of CJHP489-CJHP 516, CJHP 518-CJHP 520, CJHP 531-CJHP 539, CJHP 546-CJHP 555, and CJHP 637-CJHP 639 referring to the preparation method of CJHP517 in example 1, the compounds CJHP489-CJHP 516, CJHP 518-CJHP 520, CJHP 531-CJHP 539, CJHP 546-CJHP 555-CJHP 637 639 were prepared by replacing 9,9-dimethyl-2-aminofluorene of the first step in example 1 with a different amine substrate, replacing 2-amino-9,9' -spirobifluorene of the third step in example 1 with a different amine substrate, and adjusting other experimental parameters as usual.
Example 3
Preparation of compound group CJHP597, comprising the steps of:
by T 1 Is selected as
The product number is: CJHP597-1 is an example:
the first step is as follows: preparation of Compound Int-4
10.0mmol of intermediate Int-3 (prepared according to the first and second synthesis steps of example 1) was dissolved in 80mL of dry xylene under nitrogen, 10.0mmol of tritylamine and 30.0mmol of sodium tert-butoxide were added, and 0.1mmol of Pd was added 2 (dba) 3 CHCl 3 And 0.02mL of 10% tri-tert-Ding Lin toluene solution, heating to 110 ℃, stirring for reaction for 16 hours, cooling to room temperature, adding 50mL of water for dilution, filtering, washing the filter cake with water and ethanol, and separating and purifying by a silica gel column to obtain the intermediate Int-4 as a white solid with a yield of 62%.
The second step is that: preparation of intermediate Int-5
Dispersing 10.0mmol of intermediate Int-4 in 150mL of 75% acetic acid aqueous solution, heating, refluxing, stirring, reacting for 24 hours, cooling to room temperature, adding 150mL of water for dilution, filtering, washing a filter cake with water, saturated sodium bicarbonate aqueous solution and ethanol to obtain intermediate Int-5 as a white solid with the yield of 90%.
The third step: preparation of compound CJHP597-1
Dissolving 10.0mmol of intermediate Int-5 in 60mL of dry dimethyl sulfoxide, cooling to 5 ℃ with an ice-water bath under the protection of nitrogen, adding 12.0mmol of 65% sodium hydride solid in batches, stirring for reaction for 1 hour, adding 12.0mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, heating to room temperature, stirring for reaction for 12 hours, adding 200mL of water for dilution, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain a compound CJHP597-1, a white solid with the yield of 66%.
MS and of compound CJHP597-1 1 The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 755.2941[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.58～8.55(4H,m)；8.19～8.15(2H,m)；7.93～7.88(3H,m)；7.72～7.70(5H,m)；7.66～7.53(11H,m)；7.35～7.28(4H,m)；7.16～7.09(3H,m)；6.98～6.96(2H,m)。
example 4
Preparation of compounds CJHP586 to CJHP636 and CJHP646 to CJHP661 referring to the preparation of compound CJHP597 of example 3, compounds CJHP586 to CJHP636 and CJHP646 to CJHP661 HP were prepared by replacing 2-chloro-4,6-diphenyl-1,3,5-triazine in the third step of example 3 with different halides and by performing general adjustment of other experimental parameters.
Example 5
The preparation method of the compound CJHP571 comprises the following steps:
the first step is as follows: preparation of Compound Int-7
10.0mmol of intermediate Int-6 (prepared according to the first and second synthesis steps of example 1) was dissolved in 80mL of dry toluene, 10.0mmol of p-chloroaniline and 30.0mmol of sodium tert-butoxide were added under nitrogen, and 0.1mmol of Pd were added 2 (dba) 3 CHCl 3 And 0.02mL of 10% tri-tert-Ding Lin toluene solution, heating to 100 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with toluene, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-7 which is a white solid with the yield of 72%.
The second step is that: preparation of intermediate Int-8
8.0mmol of the intermediate Int-7 prepared in the first step is dissolved in 50mL of dry THF, the temperature is reduced to-80 ℃ by liquid nitrogen under the protection of nitrogen, 4.0mL of 2.5M N-butyllithium N-hexane solution is dropwise added, the mixture is stirred and reacted for 30 minutes, 10.0mmol of trimethyl borate solution in THF is dropwise added, the mixture is stirred and reacted for 1 hour, the temperature is raised to the room temperature, 20mL of 3N diluted hydrochloric acid aqueous solution is added, the mixture is stirred for 30 minutes, the ethyl acetate is used for extraction, an organic phase is collected, dried and filtered, the filtrate is decompressed, concentrated and dried, petroleum ether is added for dispersion and filtered, and the intermediate Int-8 is obtained, a white solid is obtained, and the yield is 82%.
The third step: preparation of compound CJHP571
10.0mmol of the intermediate Int-8 prepared in the second step is dissolved in 60mL of toluene, under the protection of nitrogen, 8.3mmol of 9- (4-chloro-6-phenyl-1,3,5-triazin-2-yl) carbazole, 20.0mmol of anhydrous potassium carbonate and 0.001mmol of Pd132 catalyst are added, the mixture is heated up, refluxed and stirred for reaction for 8 hours, cooled to room temperature, 50mL of water is added for dilution, dichloromethane is used for extraction, a lower organic phase is collected, dried and filtered, filtrate is concentrated under reduced pressure to dryness, and a solid is separated and purified by a silica gel column to obtain a compound CJHP571, a yellow solid with the yield of 82%.
MS and of compound CJHP571 1 The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 705.2783[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.95(2H,s)；8.56～8.51(4H,m)；8.16～8.14(2H,d)；7.56～7.43(7H,m)；7.39～7.37(4H,m)；7.31～7.21(6H,m)；7.14～7.10(3H,m)；6.96～6.92(4H,m)。
example 6
Preparation of compounds CJHP 521-CJHP 530, CJHP 540-CJHP 545, CJHP 556-CJHP 585, CJHP663 referring to the preparation method of example 5, compounds CJHP 521-CJHP 530, CJHP 540-CJHP 545, CJHP 556-CJHP 585 and CJHP663 in compound formula I were prepared by replacing 9- (4-chloro-6-phenyl-1,3,5-triazine-2-yl) carbazole in the third step of example 5 with different halides and by general adjustment of other experimental parameters.
Example 7
The preparation method of the compound CJHP640 comprises the following steps:
the first step is as follows: preparation of Compound Int-10
15.0mmol of intermediate Int-9 (prepared according to the first and second synthesis steps of example 3) was dissolved in 60mL of dry toluene, 6.8mmol of 4,4' -dibromodiphenyl sulfide and 45.0mmol of sodium tert-butoxide were added under nitrogen protection, and 0.2mmol of Pd were added 2 (dba) 3 CHCl 3 And 0.04mL of 10% tri-tert-Ding Lin toluene solution, heating to 100 ℃, stirring for reaction for 24 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with toluene, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-10 as a white solid with the yield of 56%.
The second step is that: preparation of compound CJHP640
10.0mmol of the intermediate Int-10 prepared in the first step is dissolved in 120mL of dichloromethane, 40.0mmol of 85% m-chloroperoxybenzoic acid is added, the temperature is increased, reflux and stirring are carried out for reaction for 12 hours, the reaction solution is cooled to room temperature and filtered, filtrate is washed by sodium bicarbonate aqueous solution, an organic phase is collected, the drying and the filtration are carried out, the filtrate is decompressed and concentrated to dryness, and the compound CJHP640 is obtained after separation and purification by a silica gel column, and the white solid is obtained with the yield of 86%.
MS and of compound CJHP640 1 The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 831.2808[M+H] + ； 1 HNMR(δ、CDCl 3 )：7.66～7.64(2H,m)；7.58～7.54(2H,m)；7.24～7.21(2H,m)；7.18～7.16(4H,m)；7.12～7.10(2H,m)；6.89～6.86(3H,m)；6.76～6.72(4H,m)。
example 8
Preparation of CJHP641 to CJHP645 and CJHP662 Compounds CJHP641 to CJHP645 and CJHP662 in formula I were prepared by substituting different intermediates for the intermediate Int-9 of the first step in example 7 with reference to the preparation method of example 7.
Comparative example 1
This comparative example also relates to a compound of the formula:
comparative example 2
This comparative example also relates to a compound of the formula:
examples of the experiments
This example relates to an organic electroluminescent element prepared from the following compounds:
the organic compound or the compound A is used as a green light main body material, the following compound B is used as a green light doping material, the compound C is used as a hole injection material, the compound D is used as a hole transport material, the compound G is used as an electron transport doping material, and LiQ is used as an electron transport main body material.
Compound C
/D
/A+B(5％)
/LiQ+G(50％)
/LiF
Al (2 nm) was sequentially deposited on ITO glass by an EL deposition apparatus manufactured by SNU to produce a green light element, and an organic electroluminescent element as a green light was produced.
The results of measuring the properties of the obtained organic electroluminescent element are shown in Table 1, wherein the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), the full width at half maximum (FWHM) were obtained under the condition that the current density of the element was 10mA/cm2, and the voltage, LE, FWHM and LT90% were subjected to data normalization processing with respect to the reference element.
TABLE 1 test results of device Properties
As is clear from Table 1, the device produced from the organic material of the present invention has a lower driving voltage, a higher current efficiency, a good color purity, and an initial emission luminance of 2000cd/cm in comparison with the device produced in comparative example 1 2 Under the initial conditions, the service life of the element using the compound of the present invention as a host material is greatly improved.
The properties of only some of the compounds in CJHP489-CJHP663 are listed in Table 1, and the properties of other compounds are substantially identical to the structures of the compounds listed in the tables, and are not listed any more due to space limitation.
Test example 2
Compound a was used as a green host material, the following compound B was used as a green dopant material, compound C was used as a hole injection material, compound D or the organic compound of the present invention was used as a hole transport material, compound G was used as an electron transport dopant material, and LiQ was used as an electron transport host material.
An organic electroluminescent element was prepared in accordance with the method of comparative example 1.
The results of measuring the properties of the obtained element are shown in Table 2, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm 2 Conditions were obtained and the voltage, LE, FWHM and LT90% were normalized to the reference.
TABLE 2 test results of device performance
As can be seen from the results of the device performance test in table 2, the device prepared from the organic material of the present invention has significantly lower driving voltage, high current efficiency, and good luminescent color purity, compared to the device prepared in comparative example 2. At an initial luminance of 2000cd/cm 2 Under the initial conditions, the LT90% lifetime of the element using the compound of the present invention as a hole material was 1.0 times or more as long as that of the comparative element.
In Table 2, only some of the properties of CJHP489-CJHP663 are listed, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, which are not listed any more due to space limitation.
As shown in fig. 1 and 2, which are a schematic view of a bottom emission example of the organic electroluminescent device of the present invention and a schematic view of a top emission example of the organic electroluminescent device, respectively, the organic compound prepared by the present invention is contained in the light-emitting layer 5 or in the hole transport layer 4 or in the hole blocking layer 6.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto without departing from the scope of the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (7)
1. An organic compound having the structure CJHP489-CJHP 663:
the T is 1 Each independently selected from-O-, -S-, or any of the following structures:
2. Use of an organic compound according to claim 1 as a material for organic components in the production of organic components.
3. The use according to claim 2, wherein the organic device is an organic electroluminescent device, an organic field effect transistor or an organic thin film solar cell.
4. Use of the organic compound according to claim 1 for the preparation of a light-emitting layer material, an electron transport layer material, a hole transport layer material or an encapsulation layer material in an organic electroluminescent device.
5. An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers is prepared from the organic compound according to claim 1.
6. A display device comprising the organic electroluminescent element according to claim 5.
7. A lighting device comprising the organic electroluminescent element according to claim 5.
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