WO2018095397A1 - 含硼有机化合物及应用、有机混合物、有机电子器件 - Google Patents
含硼有机化合物及应用、有机混合物、有机电子器件 Download PDFInfo
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- WO2018095397A1 WO2018095397A1 PCT/CN2017/112724 CN2017112724W WO2018095397A1 WO 2018095397 A1 WO2018095397 A1 WO 2018095397A1 CN 2017112724 W CN2017112724 W CN 2017112724W WO 2018095397 A1 WO2018095397 A1 WO 2018095397A1
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- Prior art keywords
- group
- boron
- atoms
- organic compound
- containing organic
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/20—Delayed fluorescence emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the invention relates to the technical field of organic photoelectric materials, in particular to a boron-containing organic compound and an application thereof, an organic mixture and an organic electronic device.
- Organic semiconductor materials are versatile in synthesis, which has great advantages for organic light-emitting diodes (OLEDs), which are relatively low in manufacturing cost and excellent in optical and electrical properties, so that they are in optoelectronic devices. There are great potentials for applications such as flat panel displays and lighting.
- OLEDs organic light-emitting diodes
- Organic light-emitting diodes using fluorescent materials have high reliability, but their internal electroluminescence quantum under electrical excitation. The efficiency is limited to 25% because the branch ratio of the singlet excited state to the triplet excited state of the exciton is 1:3.
- organic light-emitting diodes using phosphorescent materials have achieved nearly 100% internal electroluminescence quantum efficiency.
- the Roll-off effect that is, the luminous efficiency rapidly decreases with increasing current or brightness, which is particularly disadvantageous for high brightness applications.
- phosphorescent materials with practical use value are rhodium and platinum complexes, which are rare and expensive, and the synthesis of complexes is complicated, so the cost is also quite high.
- Adachi proposed the concept of reverse intersystem crossing, which can be achieved by using organic compounds, ie without using metal complexes. High efficiency compared to phosphorescent OLEDs. This concept has been achieved through a combination of materials such as: 1) using a composite exciplex, see Adachi et al, Nature Photonics, Vol 6, p 253 (2012); 2) using thermally excited delayed fluorescence (TADF) materials.
- TADF thermally excited delayed fluorescence
- a boron-containing organic compound and its use, organic mixture, organic electronic device are provided that solve one or more of the problems involved in the background art.
- Ar 1 to Ar 7 are the same or different, and Ar 1 to Ar 7 are independently selected from aromatic, heteroaromatic or non-aromatic ring systems having 2 to 20 carbon atoms; and groups having Ar 1 to Ar 7 have a group R 1 , the group R 1 being the same or different at each occurrence;
- L1 to L6 are the same or different, and L1 to L6 are independently selected from a hydrogen bond, a linear alkane having 1 to 15 carbon atoms, a branched alkane having 1 to 15 carbon atoms, and a ring having 1 to 15 carbon atoms.
- Y 1 to Y 6 are the same or different, and Y 1 to Y 6 are independently selected from a single bond, a second bridge or a triple bridge group, and Y 1 to Y 6 independently have a single bond or a double bond with three groups adjacent thereto. Connected
- R 1 is selected from the group consisting of -H, -F, -Cl, Br, I, -D, -CN, -NO 2 , -CF 3 , B(OR 2 ) 2 , Si(R 2 ) 3 , linear alkane, alkane An ether, an alkane sulfide having 1 to 10 carbon atoms, a branched alkane, a cycloalkane or an alkane ether group having 3 to 10 carbon atoms;
- R 2 is selected from the group consisting of H, D, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched chain of 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, and a thioalkoxy group having 3 to 20 C atoms a group, a silyl group having 3 to 20 C atoms, a substituted keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 An aryloxycarbonyl group of a C atom, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group or
- a polymer in which at least one repeating unit comprises the above boron-containing organic compound comprises the above boron-containing organic compound.
- An organic mixture for an organic electronic device comprising at least one organic functional material and the above boron-containing organic compound or the above polymer;
- the organic functional material is selected from the group consisting of a hole injecting material, a hole transporting material, A hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, an organic host material, or a light emitting material.
- An ink for an organic electronic device comprising an organic solvent and the above boron-containing organic compound or the above polymer or the above organic mixture.
- An organic electronic device comprising a functional layer comprising the above boron-containing organic compound or the above polymer or the above organic mixture, or the functional layer is prepared from the above ink.
- compositions, printing inks, and inks have the same meaning and are interchangeable.
- the host material, matrix material, Host material, and Matrix material have the same meaning and are interchangeable.
- Metal organic complexes, metal organic complexes, and organometallic complexes have the same meaning and are interchangeable.
- the structure of the boron-containing organic compound of one embodiment is as shown in the general formula (1):
- Ar 1 to Ar 7 are the same or different, and Ar 1 to Ar 7 are independently selected from aromatic, heteroaromatic or non-aromatic ring systems having 2 to 20 carbon atoms; and groups having Ar 1 to Ar 7 have a group R 1 , the group R 1 being the same or different at each occurrence;
- L1 to L6 are the same or different, and L1 to L6 are independently selected from a hydrogen bond, a linear alkane having 1 to 15 carbon atoms, a branched alkane having 1 to 15 carbon atoms, and a ring having 1 to 15 carbon atoms.
- Y 1 to Y 6 are the same or different, and Y 1 to Y 6 are independently selected from a single bond, a second bridge or a triple bridge group, and Y 1 to Y 6 independently have a single bond or a double bond with three groups adjacent thereto. Connected
- R 1 is selected from the group consisting of -H, -F, -Cl, Br, I, -D, -CN, -NO 2 , -CF 3 , B(OR 2 ) 2 , Si(R 2 ) 3 , linear alkane, alkane An ether, an alkane sulfide having 1 to 10 carbon atoms, a branched alkane, a cycloalkane or an alkane ether group having 3 to 10 carbon atoms;
- R 2 is selected from the group consisting of H, D, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched chain of 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, and a thioalkoxy group having 3 to 20 C atoms a group, a silyl group having 3 to 20 C atoms, a substituted keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 An aryloxycarbonyl group of a C atom, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group or
- the above boron-containing organic compound can be used in an organic electronic device, particularly as a light-emitting layer material in an organic electronic device.
- the D group of the above boron-containing organic compound and the A group are simultaneously contained in the same conjugated ring, thereby facilitating realization in a non-DA structure such that it has thermal excitation delayed fluorescence luminescence characteristics, and the first three of the boron-containing organic compound The energy level difference between the re-excited state T 1 and its first singlet excited state S 1 is small.
- the boron-containing organic compound can be used as a TADF luminescent material, since the difference in energy level between the first triplet excited state T 1 of the boron-containing organic compound and its first singlet excited state S 1 is small, thereby making the triplet state thereof
- the excitons can be internally converted to singlet excitons by reverse, so that by virtue of their cooperation with a suitable host material, the luminous efficiency and lifetime of the organic electronic device can be improved, thereby making the manufacturing cost of the organic electronic device low, and having High efficiency, long life, low roll-off and so on.
- Ar 1 to Ar 7 are independently selected from aromatic or heteroaromatic rings having 2 to 20 carbon atoms. It should be noted that the hydrogen on the ring of Ar 1 to Ar 7 may be substituted or unsubstituted by one or more groups R 1 , and the group R 1 may be the same or different at each occurrence. Further, the aryl or heteroaryl group in the aromatic ring and/or heteroaromatic ring may be selected from benzene, naphthalene, anthracene, phenanthrene, pyridine, perylene or thiophene.
- L1 to L6 represented by the formula (1) may be the same or different, and L1 to L6 are independently selected from linear alkanes having 1 to 15 carbon atoms and having 1 to 15 carbon atoms. Branched alkane, cycloalkane having 1 to 15 carbon atoms, aromatic having 2 to 20 carbon atoms, heteroaromatic having 2 to 20 carbon atoms or non-aromatic having 2 to 20 carbon atoms Ring system.
- n and m shown in the general formula (1) are each selected from 0 or 1.
- Y 1 -Y 6 are independently selected from a single bond or a second or triple bridge group having one or more of the following structural groups:
- R 3 , R 4 and R 5 are independently selected from -H, -F, -Cl, Br, I, -D, -CN, -NO2, -CF3, B(OR 2 ) 2 , Si(R 2 ) 3 a linear alkane, an alkane ether, an alkane sulfide having 1 to 10 carbon atoms, a branched alkane, a cycloalkane or an alkane ether group having 3 to 10 carbon atoms;
- a dashed bond indicates a bond to which the structural group is bonded to its adjacent structural unit.
- Y 1 to Y 6 are independently selected from a single bond or any of the above two bridges or triple bridge groups.
- the aromatic ring system contains 5 to 10 carbon atoms in the ring system.
- the heteroaromatic ring system contains from 1 to 10 carbon atoms and at least one hetero atom in the ring system, wherein the total number of carbon atoms and heteroatoms is at least 4.
- the hetero atom is selected from one or more of Si, N, P, O, S, and Ge, and is particularly preferably one or more selected from the group consisting of Si, N, P, O, and S.
- the aromatic or heteroaromatic ring system includes not only an aromatic or heteroaromatic system, but also a plurality of aryl or heteroaryl groups may be interrupted by short non-aromatic units ( ⁇ 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Therefore, a system such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine or diaryl ether is also considered to be an aromatic ring system for the purpose of the present invention.
- the non-aromatic ring system contains from 1 to 10 carbon atoms in the ring system, and includes not only saturation but also a partially unsaturated cyclic system.
- the hydrogen on the ring may be unsubstituted or mono- or polysubstituted by the group R 1 , the groups R 1 may be the same or different in each occurrence, and may also contain one or more heteroatoms.
- the hetero atom may be Si, N, P, O, S and/or Ge, and particularly preferably selected from Si, N, P, O and/or S. These may, for example, be cyclohexyl- or piperidine-like systems or ring-like octadiene ring systems.
- the term also applies to fused non-aromatic ring systems.
- the non-aromatic ring system may contain from 1 to 3 carbon atoms in the ring system.
- H atom on the boron-containing organic compound or an NH group bridging CH 2 group may be substituted R 1 groups, R 1 can be selected from an alkyl group having 1 to 10 carbon atoms, An alkoxy group having 1 to 10 carbon atoms or an aryl or heteroaryl group having 2 to 10 carbon atoms.
- the alkyl group having 1 to 10 carbon atoms may be selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and ring.
- the alkoxy group having 1 to 10 carbon atoms may be selected from the group consisting of methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy Base or 2-methylbutoxy.
- An aryl or heteroaryl group having 2 to 10 carbon atoms may be monovalent or divalent depending on the use, and in each case may also be substituted by the above-mentioned group R 1 and may be passed through any desired The position is linked to an aromatic or heteroaromatic ring.
- the aryl or heteroaryl group having 2 to 10 carbon atoms may be selected from the group consisting of benzene, naphthalene, anthracene, anthracene, anthracene, fluorene, fluorene, butyl, pentane, benzopyrene , furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, thiopurine, pyrrole, hydrazine, isoindole, carbazole, pyridine, quinoline, isoquine Porphyrin, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, hydrazine Azole, imidazole, benzimide, imidazole
- aromatic and heteroaromatic ring systems are considered to be especially in addition to the above-mentioned aryl and heteroaryl groups, and also refer to biphenylylene, linethylene, hydrazine, stilbene, dihydrophenanthrene, tetrahydroanthracene. It is combined with cis or trans.
- Ar 1 -A 7 independently comprise one or more of the following structural groups:
- X 3 is selected from CR 6 or N;
- R 6 , R 7 , R 8 , R 9 , R 10 , R 11 are independently selected from H, D, a linear alkyl group having 1 to 20 C atoms, and an alkoxy group having 1 to 20 C atoms.
- R 6, R 7, R 8, R 9, R 10, R 11 forming at least one aliphatic mono or polycyclic structural groups of the ring or bonded An aromatic ring, or at least two of R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are bonded to each other to form a monocyclic or polycyclic aliphatic or aromatic ring.
- Ar 1 -A 7 may be independently selected from any of the above groups.
- Ar 1 -A 7 are independently selected from phenyl.
- boron-containing organic substance is selected from one of the structures represented by the following general formulae (2) to (7):
- L1 to L6 may be the same or different, and L1 to L6 are independently selected from a hydrogen bond, a linear alkane having 1 to 15 carbon atoms, a branched alkane having 1 to 15 carbon atoms, and 1 to 15 carbons. a cycloalkane of an atom, an aromatic having 2 to 20 carbon atoms, a heteroaromatic having 2 to 20 carbon atoms or a non-aromatic ring system having 2 to 20 carbon atoms; and when Y 1 to Y 6 When one or more of the single bond or the second bridge group, the corresponding L is a hydrogen bond;
- Y 1 to Y 6 may be the same or different, and Y 1 to Y 6 are independently selected from a single bond, a second bridge or a triple bridge group, and Y 1 to Y 6 are independently a single bond or a double bond with three groups adjacent thereto. Key connected;
- L1 to L6 in the general formulae (1) to (7) may be the same or different, and L1 to L6 are independently selected from linear alkane having 1 to 15 carbon atoms, and 1 to 15 a branched alkane of a carbon atom or a cycloalkane having 1 to 15 carbon atoms.
- L1 to L6 may be the same or different, and the L1 to L6 independently comprise one or more of the following structural units:
- n is selected from 1, 2, 3 or 4.
- L1 to L6 may be the same or different, and L1 to L6 are independently selected from any of the groups in the above table.
- the compounds according to the invention facilitate the obtaining of thermally excited delayed fluorescent TADF properties.
- thermal excitation delayed fluorescent TADF material see Adachi et al., Nature Vol 492, 234, (2012)
- the triplet excitons of the organic compound can pass Reverse internal conversion to singlet excitons for efficient illumination.
- TADF materials are obtained by electron donating (Donor) to electron-deficient or acceptor groups, i.e., having a distinct DA structure.
- the boron-containing organic compound has ⁇ E(S 1 -T 1 ) ⁇ 0.30 eV, preferably ⁇ 0.25 eV, more preferably ⁇ 0.20 eV, and most preferably ⁇ 0.10 eV.
- ⁇ E(S 1 -T 1 ) represents an energy level difference between the first triplet excited state T 1 of the boron-containing organic compound and the first singlet excited state S 1 of the boron-containing organic compound.
- At least one of L1-L6 comprises an electron donating group.
- the electron donating group may be selected from the group consisting of:
- At least one of L1-L6 comprises an electron withdrawing group.
- the electron withdrawing group may be selected from a structure which may be selected from F, a cyano group or a group containing the following groups.
- n is selected from 1, 2 or 3;
- X 1 -X 8 are independently selected from CR 12 or N, and at least one of X 1 -X 8 is selected from N;
- Z 1 -Z 3 are independently selected from C (R) 12 ) 2 , O or S; wherein R 12 is selected from a hydrogen bond, an alkyl group, an alkoxy group, an amino group, an alkene group, an alkyne group, an aralkyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
- the electron withdrawing group may be selected from a group selected from F, a cyano group or any of the above groups.
- At least one of L1-L6 comprises an electron-donating group, and at least one of L1-L6 comprises an electron-withdrawing group.
- the electron-donating group is as described above, and the electron-withdrawing group is also as described above.
- the above boron-containing organic compound can be used as an organic functional material in organic electronic devices, especially OLEDs.
- Organic functional materials can be classified into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injecting materials (EIM), electron blocking materials (EBM), and hole blocking materials (HBM). , Emitter, Host and organic dyes.
- HIM hole injection materials
- HTM hole transport materials
- ETM electron transport materials
- EIM electron injecting materials
- EBM electron blocking materials
- HBM hole blocking materials
- HBM hole blocking materials
- Emitter Host and organic dyes.
- the boron-containing organic compound can be used as a host material, an electron transport material or a hole transport material. Further, the boron-containing organic compound can be used as a phosphorescent host material or a co-host material.
- the boron-containing organic compound When the boron-containing organic compound is used as a phosphorescent host material, the boron-containing organic compound must have an appropriate triplet level.
- the boron-containing organic compound has T 1 ⁇ 2.2 eV; wherein T 1 represents the first triplet excited state of the boron-containing organic compound.
- T 1 ⁇ 2.4 eV more preferably T 1 ⁇ 2.6 eV, more preferably T 1 ⁇ 2.65 eV, most preferably T 1 ⁇ 2.7 eV.
- the function of the boron-containing organic compound depends on the substitution pattern, and the organic compounds according to the general formulae (1) to (7) can have various functions including, but not limited to, hole transport function, electron transport function. , illuminating function, exciton blocking function, etc.
- the substituents L1 to L6 which compounds are particularly suitable for which functions.
- the substituents L1 to L6 have an influence on the electronic properties of the units of the general formulae (1) to (8).
- At least one of the hydrogens on the ring of the boron-containing compound is deuterated. Further, the deuterated hydrogen on the ring of the boron-containing compound accounts for 5% to 50%, preferably 10%, of the total hydrogen on the ring of the boron-containing compound, more preferably 20%. The H is replaced, and even better, 30% of the H is replaced, preferably 40% of the H is replaced.
- the triplet level T1 of the organic compound depends on the substructure of the organic compound having the largest conjugated system. Generally, T1 decreases as the conjugated system increases. In one embodiment, in the general formula (1), the substructure shown by the formula (1a) has the largest conjugated system.
- the formula (1a) has no more than 36 ring atoms, preferably no more than 30, more preferably no more than 26, and most preferably no more than 36 substituents. 20.
- the boron-containing organic compound having the formula (1a) has a T1 ⁇ 2.3 eV, preferably ⁇ 2.5 eV, more preferably ⁇ 2.7 eV, still more preferably ⁇ 2.75 eV, preferably ⁇ 2.8eV.
- the boron-containing organic compound When the boron-containing organic compound is used as a phosphorescent host material, it is required to have high thermal stability.
- the boron-containing organic compound has a glass transition temperature T g ⁇ 100 ° C. Further, T g ⁇ 120 ° C. Further, T g ⁇ 140 ° C. Further, T g ⁇ 160 ° C. Further, T g ⁇ 180 ° C.
- the boron-containing organic compound has TADF properties and acts as a co-host or auxiliary host material.
- the boron-containing organic compound can also be used as an illuminant.
- Examples of preferred units of the general formulae (2) to (7) are the following structures. These structures can be substituted at all possible points of substitution.
- the boron-containing organic compound is a small molecule material.
- the boron-containing organic compound can be used for an evaporation type OLED.
- the boron-containing organic compound has a molecular weight of 1000 g/mol or less.
- the boron-containing organic compound has a molecular weight of 900 g/mol or less.
- the boron-containing organic compound has a molecular weight of 850 g/mol or less.
- the molecular weight of the boron-containing organic compound is less than or equal to 800 g / mol.
- the boron-containing organic compound has a molecular weight of 700 g/mol or less.
- small molecule refers to a molecule that is not a polymer, oligomer, dendrimer, or blend. In particular, there are no repeating structures in small molecules.
- the molecular weight of the small molecule is ⁇ 3000 g/mol, preferably ⁇ 2000 g/mol, preferably ⁇ 1500 g/mol.
- the polymer that is, the polymer, includes a homopolymer, a copolymer, and a block copolymer.
- the high polymer also includes a dendrimer.
- the conjugated polymer is a high polymer, and its backbone backbone is mainly composed of sp 2 hybrid orbitals of C atoms. Famous examples are: polyacetylene polyacetylene and poly(phenylene vinylene).
- the C atom on the chain can also be substituted by other non-C atoms, and is still considered a conjugated polymer when the sp 2 hybrid on the backbone is interrupted by some natural defects.
- the conjugated high polymer also includes an aryl amine, an aryl phosphine and other heteroarmotics, and an organometallic complexes in the main chain. )Wait.
- the boron-containing organic compound has a molecular weight of 700 g/mol or more.
- the boron-containing organic compound can be used for a printed OLED.
- the boron-containing organic compound has a molecular weight of 800 g/mol or more.
- the boron-containing organic compound has a molecular weight of 900 g/mol or more.
- the boron-containing organic compound has a molecular weight of 1000 g/mol or more.
- the molecular weight of the boron-containing organic compound is 1100 g/mol or more.
- the boron-containing organic compound has a solubility in toluene of greater than or equal to 10 mg/ml at 25 °C. Further, the boron-containing organic mixture has a solubility in toluene of 15 mg/ml or more at 25 °C. Further, the boron-containing organic mixture has a solubility in toluene of 20 mg/ml or more at 25 °C.
- the above boron-containing organic compound can be used in organic functional materials.
- the above boron-containing organic compounds can also be used in inks.
- the above boron-containing organic compounds can also be used in organic electronic devices.
- the polymer of one embodiment, wherein at least one of the repeating units comprises the above boron-containing organic compound comprises the above boron-containing organic compound.
- the polymer can be a conjugated high polymer or a non-conjugated high polymer. When the polymer is a non-conjugated high polymer, the above boron-containing organic compound is on the side chain of the high polymer.
- the use of the above polymers in organic functional materials can also be used in inks.
- the above polymers can also be used in organic electronic devices.
- the organic mixture of an embodiment comprises at least one organic functional material and the above boron-containing organic compound.
- the organic functional material is selected from the group consisting of a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, an organic host material, or a light emitting material.
- Various organic functional materials are described in detail in, for example, WO2010135519A1, US20090134784A1, and WO 2011110277A1, the entire disclosure of each of each of The organic functional material may be a small molecule and a high polymer material.
- the luminescent material is selected from the group consisting of a fluorescent illuminant, a phosphorescent illuminant, an organic thermally excited delayed fluorescent material, or a luminescent quantum dot material.
- the organic functional material is selected from the group consisting of a phosphorescent emitter and a boron-containing organic compound as a host material; and the weight percentage of the organic functional material is greater than 0 and less than or equal to 30%. Further, the weight percentage of the organic functional material is greater than 0 and less than or equal to 25%. Further, the weight percentage of the organic functional material is greater than 0 and less than or equal to 20%.
- the organic functional material is selected from the group consisting of organic host materials.
- a boron-containing organic compound is used as the luminescent material.
- the weight percentage of the boron-containing organic compound is greater than 0 and less than or equal to 30%. Further, the weight percentage of the boron-containing organic compound is greater than 0 and less than or equal to 25%. Further, the weight percentage of the boron-containing organic compound is greater than 0 and less than or equal to 20%. Further, the weight percentage of the boron-containing organic compound is greater than 0 and less than or equal to 15%.
- the organic functional material is selected from the group consisting of a phosphorescent emitter and an organic host material, and a boron-containing organic compound
- the material is an auxiliary luminescent material or an auxiliary host material; the weight ratio of the boron-containing organic compound to the phosphorescent illuminant is (1:2)-(2:1).
- the first triplet excited state of the boron-containing organic compound may be higher than the first triplet excited state of the phosphorescent emitter.
- the organic functional material is selected from the group consisting of TADF materials.
- the singlet emitter, the triplet emitter, and the TADF material are described in further detail below (but are not limited thereto).
- the example of the triplet host material is not particularly limited, and any metal complex or organic compound may be used as the host as long as its triplet energy is higher than that of the illuminant, particularly the triplet illuminant or the phosphorescent illuminant.
- metal complexes that can be used as the triplet host include, but are not limited to, the following general structure:
- M is a metal
- (Y 3 -Y 4 ) is a two-dentate ligand, Y 3 and Y 4 are independently selected from C, N, O, P or S
- L is an auxiliary ligand
- m is an integer, and its value The maximum coordination number from 1 to this metal
- m+n is the maximum coordination number of the metal.
- the metal complex that can be used as the triplet host has the following form:
- (O-N) is a bidentate ligand; the metal is coordinated to the O and N atoms.
- M can be selected from Ir or Pt.
- Examples of the organic compound which can be used as the host of the triplet state are selected from compounds containing a cyclic aromatic hydrocarbon group such as benzene, biphenyl, triphenyl, benzo, anthracene; compounds containing an aromatic heterocyclic group such as dibenzothiophene, Dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, carbazole, pyridinium, pyrrole dipyridine, pyrazole, imidazole, three Azole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazide, dioxazin, hydrazine Anthracen
- the groups may be the same or different types of cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups, and are bonded to each other directly or through at least one of the following groups, such as an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, A phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group.
- each of Ar may be further substituted, and the substituent may be hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl or heteroaryl.
- the triplet host material can be selected from compounds comprising at least one of the following groups:
- R 1 -R 7 are independently selected from hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl or heteroaryl; when they are aryl or heteroaryl When they are the same as Ar 1 and Ar 2 described above; n is selected from 0-20
- X 1 -X 8 are independently selected from CH or N; and X 9 is selected from CR 1 R 2 or NR 1 .
- Phosphorescent materials are also called triplet emitters.
- the triplet emitter is a metal complex having the general formula M(L)n; wherein M is a metal atom; and L is an organic ligand, which may be the same or different each time it appears, by one or more The position is bonded or coordinated to the metal atom M.
- n is an integer greater than one.
- n is selected from 1, 2, 3, 4, 5 or 6.
- the metal complexes are coupled to a polymer by one or more locations, preferably by an organic ligand.
- the metal atom M is selected from a transition metal element, a lanthanide element or a lanthanide element. Further, the metal atom M is selected from the group consisting of Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag. Further, the metal atom M is selected from the group consisting of Os, Ir, Ru, Rh, Re, Pd or Pt.
- the triplet emitter comprises a chelating ligand, ie a ligand, coordinated to the metal by at least two bonding sites, and it is particularly preferred to consider that the triplet emitter comprises two or three identical Or different bidentate or multidentate ligands.
- Chelating ligands are beneficial for increasing the stability of metal complexes.
- the organic ligand may be selected from the group consisting of a phenylpyridine derivative, a 7,8-benzoquinoline derivative, a 2(2-thienyl)pyridine derivative, a 2(1-naphthyl)pyridine derivative, or a 2-phenylquinoline.
- a morphine derivative All of these organic ligands may be substituted, for example by fluorine or trifluoromethyl.
- the ancillary ligand may be selected from the group consisting of acetone acetate or picric acid.
- the general formula of the metal complex used as the triplet emitter is as follows:
- M is a metal and M is selected from a transition metal element or a lanthanide or a lanthanide;
- Ar 1 is a cyclic group which may be the same or different at each occurrence, and Ar 1 contains at least one donor atom, that is, an atom having a lone pair of electrons, such as nitrogen or phosphorus, through which a cyclic group and a metal Coordination linkage;
- Ar 2 is a cyclic group, which may be the same or different at each occurrence, Ar 2 contains at least one C atom through which a cyclic group is bonded to the metal;
- Ar 1 and Ar 2 are covalently
- the linkages are linked together and may each carry one or more substituent groups, which may also be joined together by a substituent group;
- L may be the same or different at each occurrence, and L is an auxiliary ligand, preferably a double-sided chelate a ligand, preferably a monoanionic bidentate chelate ligand;
- m is selected from 1, 2 or 3, preferably 2 or 3, particularly preferably 3;
- n is selected from 0, 1, or 2,
- TDF Thermally activated delayed fluorescent luminescent material
- the thermally activated delayed fluorescent luminescent material is a third generation organic luminescent material developed after organic fluorescent materials and organic phosphorescent materials.
- Such materials generally have a small singlet-triplet energy level difference ( ⁇ E st ), and triplet excitons can be converted into singlet exciton luminescence by inter-system crossing. This can make full use of the singlet excitons and triplet excitons formed under electrical excitation.
- the quantum efficiency in the device can reach 100%.
- the TADF material needs to have a small singlet-triplet energy level difference, typically ⁇ Est ⁇ 0.3 eV, preferably ⁇ Est ⁇ 0.2 eV, more preferably ⁇ Est ⁇ 0.1 eV, and most preferably ⁇ Est ⁇ 0.05 eV.
- TADF has better fluorescence quantum efficiency.
- Some TADF luminescent materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064( A1), Adachi, et.al. Adv.
- Adachi et. al. Appl. Phys. Lett., 98, 2011, 083302, Adachi, et. al. Appl. Phys. Lett ., 101, 2012, 093306, Adachi, et. al. Chem. Commun., 48, 2012, 11392, Adachi, et. al. Nature Photonics, 6, 2012, 253, Adachi, et. al. Nature, 492, 2012,234,Adachi,et.al.J.Am.Chem.Soc,134,2012,14706,Adachi,et.al.Angew.Chem.Int.Ed,51,2012,11311,Adachi,et.al.
- TADF luminescent materials Some examples of suitable TADF luminescent materials are listed in the table below.
- the organic electronic device has higher luminous efficiency and lifetime.
- the organic mixture of an embodiment comprises at least one organic functional material and the above polymer.
- the performance and selection of the organic functional material are as described in the above embodiment, and are not described herein again.
- the ink of an embodiment comprises an organic solvent and the above boron-containing organic compound.
- the ink is the composition.
- the viscosity and surface tension of the ink are important parameters when the composition is used in a printing process. Suitable surface tension parameters for the ink are suitable for the particular substrate and the particular printing method.
- the surface tension of the ink at the operating temperature or at 25 ° C is in the range of from about 19 dyne/cm to 50 dyne/cm; more preferably in the range of from 22 dyne/cm to 35 dyne/cm; preferably at 25 dyne/cm. Up to 33dyne/cm.
- the viscosity of the ink at the operating temperature or at 25 ° C is in the range of from about 1 cps to about 100 cps; preferably in the range of from 1 cps to 50 cps; more preferably in the range of from 1.5 cps to 20 cps; preferably at 4.0 Cps to 20cps range. This makes the composition more convenient for ink jet printing.
- the viscosity can be adjusted by different methods, such as by selection of a suitable solvent and concentration of the functional material in the ink.
- An ink containing a metal organic complex or a polymer facilitates the adjustment of the printing ink to an appropriate range in accordance with the printing method used.
- the weight ratio of the organic functional material contained in the composition is from 0.3% to 30% by weight, preferably from 0.5% to 20% by weight, more preferably from 0.5% to 15% by weight, still more preferably from 0.5% to 10% by weight. %, preferably from 1% to 5% by weight.
- the organic solvent comprises a first solvent selected from the group consisting of aromatic and/or heteroaromatic based solvents.
- the first solvent may be an aliphatic chain/ring-substituted aromatic solvent, or an aromatic ketone solvent, or an aromatic ether solvent.
- Examples of the first solvent are, but not limited to, aromatic or heteroaromatic based solvents: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene.
- the first solvent may also be selected from aliphatic ketones, for example, 2-nonanone, 3-fluorenone, 5-fluorenone, 2-nonanone, 2,5-hexanedione, 2,6,8 - trimethyl-4-indolone, phorone, di-n-pentyl ketone, etc.; or an aliphatic ether, for example, pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol II Ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, One or more of triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.
- aliphatic ketones for example, 2-nonanone, 3-fluorenone, 5-fluor
- the organic solvent further includes a second solvent selected from the group consisting of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, Anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4 dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-benzene Oxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl One or more of a sulfoxide, tetrahydronaphthalene, decalin, and anthracene.
- a second solvent selected from the group consisting of methanol, ethanol,
- the ink can be a solution or suspension. This is determined based on the compatibility between the boron-containing organic compound and the organic solvent.
- the percentage by weight of the boron-containing organic compound in the composition is from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight, more preferably from 0.2 to 10% by weight, most preferably from 0.25 to 5% by weight.
- Organic compound is from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight, more preferably from 0.2 to 10% by weight, most preferably from 0.25 to 5% by weight.
- the above composition is used in the preparation of an organic electronic device.
- its use as a coating or printing ink in the preparation of an organic electronic device is particularly preferred by a printing or coating preparation method.
- suitable printing or coating techniques include, but are not limited to, inkjet printing, Nozzle Printing, typography, screen printing, dip coating, spin coating, blade coating, roller printing, torsion rolls. Printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing or slit-type extrusion coating. Preferred are gravure, inkjet and inkjet printing.
- the composition may further include a component example, and the cap component is selected from one or more of a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobic agent, and a binder, thereby being used for adjusting viscosity. , film forming properties, improved adhesion and the like.
- the use of the above boron-containing organic compound in an organic electronic device may be selected from an Organic Light-Emitting Diode (OLED), an Organic Photovoltaic (OPV), an Organic Light Emitting Battery (OLEEC), an organic field effect transistor (OFET), and an organic organic device.
- OLED Organic Light-Emitting Diode
- OLED Organic Photovoltaic
- OEEC Organic Light Emitting Battery
- OFET organic field effect transistor
- Luminescent field effect transistor organic laser, organic spintronic device, organic sensor or organic plasmon emitting diode (Organic Plasmon Emitting Diode).
- the organic electronic device is an electroluminescent device such as an OLED, an OLEEC, and an organic light-emitting field effect transistor. Further, the organic mixture is used for a light-emitting layer for an OLED device.
- the ink of another embodiment includes an organic solvent and the above polymer.
- the polymer is as described above and will not be described herein.
- the above inks can be used in the preparation of organic electronic devices.
- the organic electronic device of an embodiment comprises the above boron-containing organic compound. Thereby the organic electronic device has a higher lifetime and a higher luminous efficiency.
- the organic electronic device includes an anode, a cathode, and a functional layer between the anode and the cathode; and the functional layer includes the boron-containing organic compound described above.
- Organic electronic devices may be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEEC), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic Spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diode), etc., particularly preferred are organic electroluminescent devices such as OLED, OLEEC, organic light-emitting field effect transistors.
- the light emitting layer of the electroluminescent device comprises one of the above boron-containing organic compounds, or comprises one of the above boron-containing organic compounds and one phosphorescent emitter, or comprises one of the above boron-containing organic compounds and one A host material or a boron-containing organic compound, a phosphorescent emitter, and a host material.
- an electroluminescent device particularly an OLED, comprises a substrate, an anode, a luminescent layer, and a cathode, which are sequentially stacked.
- the light emitting layer includes the above boron-containing organic compound.
- the substrate can be opaque or transparent.
- a transparent substrate can be used to make a transparent luminescent component, see Bulovic et al. Nature 1996, 380, p29, and Gu et al, Appl. Phys. Lett. 1996, 68, p2606.
- Substrate It is rigid or elastic.
- the substrate can also be plastic, metal, semiconductor wafer or glass.
- the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice.
- the substrate is flexible, optionally in a polymeric film or plastic, having a glass transition temperature Tg of 150 ° C or higher, preferably more than 200 ° C, more preferably more than 250 ° C, and most preferably more than 300 ° C. .
- the flexible substrate can be poly(ethylene terephthalate) (PET) or polyethylene glycol (2,6-naphthalene) (PEN).
- the anode can include a conductive metal or metal oxide, or a conductive polymer.
- the anode can easily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or a light-emitting layer.
- HIL hole injection layer
- HTL hole transport layer
- the absolute value of the difference between the work function of the anode and the HOMO level or the valence band level of the illuminant in the luminescent layer or the p-type semiconductor material as the HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV.
- anode material examples include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, and aluminum-doped zinc oxide (AZO).
- the anode material can also be other materials.
- the anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
- the anode is patterned.
- a patterned ITO conductive substrate is commercially available and can be used to prepare an organic electronic device according to the present embodiment.
- the cathode can include a conductive metal or metal oxide.
- the cathode can easily inject electrons into the EIL or ETL or directly into the luminescent layer.
- the work function of the cathode and the LUMO level or conductance of the illuminant in the luminescent layer or the n-type semiconductor material as an electron injection layer (EIL) or an electron transport layer (ETL) or a hole blocking layer (HBL)
- EIL electron injection layer
- ETL electron transport layer
- HBL hole blocking layer
- the absolute value of the difference in the band level is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. All materials which can be used as the cathode of the OLED are possible as the cathode material of the organic electronic device of the present embodiment.
- cathode material examples include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF 2 /Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like.
- the cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, and electron beam (e-beam).
- the OLED may further comprise other functional layers such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), and electron transport. Layer (ETL) or hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire disclosure of which is hereby incorporated by reference.
- an electron transport layer (ETL) or a hole blocking layer (HBL) in the electroluminescent device comprises the above boron-containing organic compound and is prepared by a solution processing method.
- the organic electroluminescent device light-emitting device has an emission wavelength of between 300 and 1000 nm, preferably between 350 and 900 nm, more preferably between 400 and 800 nm.
- the above-described organic electronic device is used in an electronic device.
- the electronic device is selected from a display device, a lighting device, a light source or a sensor.
- the organic electronic device may be an organic electroluminescent device.
- An electronic device of an embodiment includes the above-described organic electronic device, which has a higher lifetime and luminous efficiency.
- the organic electronic device of another embodiment includes the above polymer, which has a high service life and stability, and luminous efficiency.
- the organic electronic device is as described in the above embodiment, and details are not described herein again.
- the use of the above organic electronic device in an electronic device is selected from a display device, a lighting device, a light source or a sensor.
- the organic electronic device may be an organic electroluminescent device.
- An electronic device of another embodiment includes the above-described organic electronic device, which has a higher lifetime and luminous efficiency.
- the final product (2) is similar to the synthesis step of the product (1) in Example 1, except that the intermediate is composed of 9,9'-(2-bromo-1,3-phenyl).
- the bis(9H-carbazole) is replaced with 7,7'-(2-bromo-1,3-phenyl)bis(7H-benzo[c]carbazole), and the reaction temperature and reaction time used in the reaction are the same. .
- MS (ASAP) 516.5.
- the final product (3) is similar to the product (1) in Example 1, except that the intermediate is 9,9'-(2-bromo-1,3-phenyl).
- the intermediate is 9,9'-(2-bromo-1,3-phenyl).
- Replacement of bis(9H-carbazole) with 5,5'-(2-bromo-1,3-phenyl)bis(7,7-dimethyl-5,7-dihydroanthracene [2,1-b] Oxazole) the reaction temperature and reaction time used in the reaction process are the same.
- MS (ASAP) 648.4.
- the final product (4) is similar to the synthesis step of the product (1) in Example 1, except that the intermediate is composed of 9,9'-(2-bromo-1,3-phenyl).
- the intermediate is composed of 9,9'-(2-bromo-1,3-phenyl).
- the reaction temperature and reaction time used in the reaction process are the same.
- MS (ASAP) 746.6.
- the energy level of the organic compound material can be obtained by quantum calculation, for example, by TD-DFT (time-dependent density functional theory) by Gaussian 09W (Gaussian Inc.), and the specific simulation method can be found in WO2011141110.
- TD-DFT time-dependent density functional theory
- Gaussian 09W Gaussian Inc.
- the semi-empirical method “Ground State/Semi-empirical/Default Spin/AM1" (Charge 0/Spin Singlet) is used to optimize the molecular geometry, and then the energy structure of the organic molecule is determined by TD-DFT (time-dependent density functional theory) method.
- TD-SCF/DFT/Default Spin/B3PW91 and the base group "6-31G(d)” (Charge 0/Spin Singlet).
- the HOMO and LUMO levels are calculated according to the following calibration formula, and S 1 , T 1 and the resonance factor f(S 1 ) are used directly.
- HOMO(eV) ((HOMO(G) ⁇ 27.212)-0.9899)/1.1206
- HOMO (G) and LUMO (G) are direct calculation results of Gaussian 09W, the unit is Hartree. The results are shown in Table 1.
- the resonance factor f(S 1 ) is between 0.1986 and 0.7225, which can improve the fluorescence quantum luminescence efficiency of the material, which is much larger than the TADF material of the general DA architecture. Further, the value of ⁇ E(S 1 -T 1 ) is not more than 0.10 eV, and the delayed fluorescent luminescence condition of less than 0.30 eV is satisfied.
- the delayed fluorescent luminescent material of the D-A architecture is labeled with Ref 1 :
- a, cleaning of the conductive glass substrate when used for the first time, can be washed with a variety of solvents, such as chloroform, ketone, isopropyl alcohol, and then UV ozone plasma treatment;
- cathode LiF / Al (1nm / 150nm) in a high vacuum (1 ⁇ 10 -6 mbar) in the thermal evaporation;
- the device is encapsulated in a nitrogen glove box with an ultraviolet curable resin.
- the current-voltage (J-V) characteristics of each OLED device are characterized by characterization equipment while recording important parameters such as efficiency, lifetime and external quantum efficiency. It has been found that the luminous efficiency and lifetime of OLED1 (corresponding to the embodiment (1)) are both more than twice that of the OLED Ref1 (corresponding to the raw material (Ref1)), and the luminous efficiency of the OLED 3 (corresponding to the embodiment (3)) is three times that of the OLED Ref1. And the lifetime is more than 4 times, especially the maximum external quantum efficiency of OLED3 is more than 10%.
- the OLED 5 (corresponding to the embodiment (5)) is red light, and the rest are green light-emitting devices. It can be seen that the OLED device prepared by using the organic mixture of the invention has greatly improved luminous efficiency and lifetime, and the external quantum efficiency is also significantly improved.
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Abstract
一种含硼有机化合物及应用、有机混合物、有机电子器件,该含硼有机化合物的结构如通式(1)所示,该通式(1)中的取代基的定义与说明书中的相同。
Description
本申请要求于2016年11月23日提交中国专利局、申请号为201611047049.1、发明名称为“一种含硼热激发延迟荧光材料及其用途”的中国专利申请的优先权,其全部内容通过引用结合在本申请中。
本发明涉及有机光电材料技术领域,特别是涉及一种含硼有机化合物及其应用、有机混合物、有机电子器件。
有机半导体材料在合成上具有多样性,这对于制造成本相对较低以及其优良的光学与电学性能的有机发光二极管(Organic Light-Emitting Diode,OLED)具有较大的优势,从而使得其在光电器件(例如平板显示器和照明)的应用方面具有很大的潜力。
为了提高有机发光二极管的发光效率,各种基于荧光和磷光的发光材料体系已被开发出来,使用荧光材料的有机发光二极管具有可靠性高的特点,但其在电气激发下其内部电致发光量子效率被限制为25%,这是因为激子的单重激发态和三重激发态的分支比为1:3。与此相反,使用磷光材料的有机发光二极管已经取得了几乎100%的内部电致发光量子效率。但磷光OLED有一显著的问题,就是Roll-off效应,即发光效率随电流或亮度的增加而迅速降低,这对高亮度的应用尤为不利。
目前,有实际使用价值的磷光材料是铱和铂配合物,这种原材料稀有而昂贵,配合物的合成很复杂,因此成本也相当高。为了克服铱和铂配合物的原材料稀有和昂贵,及其合成复杂的问题,Adachi提出反向内部转换(reverse intersystem crossing)的概念,这样可以利用有机化合物,即不利用金属配合物,实现了可与磷光OLED相比的高效率。此概念已经通过各种材料组合得以实现,如:1)利用复合受激态(exciplex),参见Adachi等,Nature Photonics,Vol 6,p253(2012);2)利用热激发延迟荧光(TADF)材料,参见Adachi et al.,Nature,Vol 492,234,(2012)。但通常的具有TADF的有机化合物大多采用供电子(Donor)与缺电子或吸电子(Acceptor)基团相连的方式,从而引起最高占有轨道(HOMO)与最低未占有轨道(LUMO)电子云分布完全分离,缩小有机化合物单重态(S1)与三重态(T1)的差别(△EST),但与磷光发光材料相比,无论从效率还是寿命上相比,其性能仍有一定的差距。
发明内容
根据本申请的各种实施例,提供一种含硼有机化合物及其应用、有机混合物、有机电子器件,解决了背景技术中所涉及的一个或多个问题。
一种含硼有机化合物,所述有机化合物的结构如通式(1)所示:
其中,
Ar1~Ar7相同或不同,Ar1~Ar7独立地选自具有2-20个碳原子的芳香族、杂芳香族或者非芳香族环系;Ar1~Ar7的环上具有基团R1,所述基团R1在每次出现时相同或不同;
L1~L6相同或不同,L1~L6独立地选自氢键、含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃、含1-15个碳原子的环烷烃、具有2-20个碳原子的芳香族、具有2-20个碳原子的杂芳香族或具有2-20个碳原子的非芳香族环系;且当Y1~Y6中有一个或多个是单键或二桥基时,与其对应的L为氢键;
Y1~Y6相同或不同,Y1~Y6独立地选自单键、二桥或三桥联基,Y1~Y6独立地与其相邻的三个基团以单键或者双键相连;
R1选自-H、-F、-Cl、Br、I、-D、-CN、-NO2、-CF3、B(OR2)2、Si(R2)3、直链烷烃、烷烃醚、含1~10个碳原子烷烃硫醚、支链烷烃、环烷烃或含有3~10个碳原子的烷烃醚基团;
R2选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基、具有3至20个C原子的硫代烷氧基基团、具有3至20个C原子的甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团,氨基甲酰基基团、卤甲酰基基团、甲酰基基团、异氰基基团、异氰酸酯基团、硫氰酸酯基团或、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、B、F、可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系、具有5至40个环原子的芳氧基或杂芳氧基基团中一种或多种;其中,至少一个R2与所述基团键合的环形成单环或多环的脂族或芳族环,或者多个R2相互之间形成单环或多环的脂族或芳族环;
n为0、1或2;m为0、1或2。
上述含硼有机化合物在有机电子器件中的应用。
一种聚合物,所述聚合物中至少一个重复单元包括上述含硼有机化合物。
一种用于有机电子器件的有机混合物,所述有机混合物包括至少一种有机功能材料以及上述含硼有机化合物或者上述聚合物;所述有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、有机主体材料或发光材料。
一种用于有机电子器件的油墨,所述油墨包括有机溶剂以及上述含硼有机化合物或者上述聚合物或者上述有机混合物。
一种有机电子器件,包括功能层,所述功能层包括上述含硼有机化合物或者上述聚合物或者上述有机混合物,或者所述功能层由上述油墨制备而成。
本发明的一个或多个实施例的细节在下面的附图和描述中提出。本发明的其它特征、目的和优点将从说明书、附图以及权利要求书变得明显。
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合附图及实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用于解释本发明,并不用于限定本发明。
在本文中,组合物、印刷油墨以及油墨具有相同的含义,它们之间可以互换。主体材料、基质材料、Host材料以及Matrix材料具有相同的含义,它们之间可以互换。金属有机络合物、金属有机配合物以及有机金属配合物具有相同的含义,它们之间可以互换。
一实施例的含硼有机化合物的结构如通式(1)所示:
其中,
Ar1~Ar7相同或不同,Ar1~Ar7独立地选自具有2-20个碳原子的芳香族、杂芳香族或者非芳香族环系;Ar1~Ar7的环上具有基团R1,所述基团R1在每次出现时相同或不同;
L1~L6相同或不同,L1~L6独立地选自氢键、含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃、含1-15个碳原子的环烷烃、具有2-20个碳原子的芳香族、具有2-20个碳原子的杂芳香族或具有2-20个碳原子的非芳香族环系;且当Y1~Y6中有一个或多个是单键或二桥基时,与其对应的L为氢键;
Y1~Y6相同或不同,Y1~Y6独立地选自单键、二桥或三桥联基,Y1~Y6独立地与其相邻的三个基团以单键或者双键相连;
R1选自-H、-F、-Cl、Br、I、-D、-CN、-NO2、-CF3、B(OR2)2、Si(R2)3、直链烷烃、烷烃醚、含1~10个碳原子烷烃硫醚、支链烷烃、环烷烃或含有3~10个碳原子的烷烃醚基团;
R2选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基、具有3至20个C原子的硫代烷氧基基团、具有3至20个C原子的甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团,氨基甲酰基基团、卤甲酰基基团、甲酰基基团、异氰基基团、异氰酸酯基团、硫氰酸酯基团或、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、B、F、可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系、具有5至40个环原子的芳氧基或杂芳氧基基团中一种或多种;其中,至少一个R2与所述基团键合的环形成单环或多环的脂族或芳族环,或者多个R2相互之间形成单环或多环的脂族或芳族
环;
n为0、1或2;m为0、1或2。
上述含硼有机化合物可用于有机电子器件中,特别是用作有机电子器件中的发光层材料。上述含硼有机化合物的D基团与A基团同时包含于同一个共轭环中,从而便于实现在非D-A结构,使得其具有热激发延迟荧光发光特性,该含硼有机化合物的第一三重激发态T1与其第一单重激发态S1之间的能级差较小。从而使得该含硼有机化合物可作为TADF发光材料,由于该含硼有机化合物的第一三重激发态T1与其第一单重激发态S1之间的能级差较小,从而使得其三线态激子可以通过反向内部转换到单线态激子,从而使得通过其与合适的主体材料配合,能提高其作为有机电子器件的发光效率及寿命,进而使得有机电子器件的制造成本低,且具有效率高、寿命长、低滚降等优点。
在其中一个实施例中,Ar1~Ar7独立地选自具有2-20个碳原子数的芳香族环或杂芳香族环。需要说明的是,Ar1~Ar7的环上的氢可被一个或多个基团R1取代或者未取代,基团R1在每次出现时可以相同或不同。进一步地,芳香族环和/或杂芳香族环中的芳基或杂芳香基可以选自苯、萘、蒽、菲、吡啶、嵌二萘或噻吩。
在其中一实施例中,通式(1)中所示的L1~L6可相同或不同,L1~L6独立地选自含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃、含1-15个碳原子的环烷烃、具有2-20个碳原子的芳香族、具有2-20个碳原子的杂芳香族或者具有2-20个碳原子的非芳香族环系。
在其中一个实施例中,通式(1)中所示的n和m均选自0或1。
在其中一个实施例中,Y1~Y6独立地选自单键或具有如下一种或多种结构基团的二桥或三桥基:
其中,
R3、R4和R5独立地选自-H、-F、-Cl、Br、I、-D、-CN、-NO2、-CF3、B(OR2)2、Si(R2)3、直链烷烃、烷烃醚、含1~10个碳原子烷烃硫醚、支链烷烃、环烷烃或含有3~10个碳原子的烷烃醚基团;
R2选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基、具有3至20个C原子的硫代烷氧基基团、具有3至20个C原子的甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团,氨基甲酰基基团、卤甲酰基基团(-C(=O)-X,其中X代表卤素原子)、甲酰基基团(-C(=O)-H)、异氰基基团、异氰酸酯基团、硫氰酸酯基团或、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、B、F、可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系、具有5至40个环原子的芳氧基或杂芳氧基基团中一种或多种;其中,至少一个R2与所述基团键合的环形成单环或多环的脂族或芳族环,或者多个R2相互之间形成单环或多环的脂族或芳族环;
虚线键表示所述结构基团与其相邻的结构单元键合的键。
进一步地,Y1~Y6独立地选自单键或如上任一二桥或三桥基。
需要说明的是,在其中一个实施例中,芳香环系在环系中包含5~10个碳原子。杂芳香环系在环系中包含1~10个碳原子和至少一个杂原子,其中,碳原子和杂原子的总数至少为4。杂原子选自Si、N、P、O、S以及Ge中的一种或多种,特别优选选自Si、N、P、O以及S中的一种或多种。进一步地,在本实施例中,芳香族或杂芳香族环系不仅包括芳香基或杂芳香基的体系,而且,其中多个芳基或杂芳基也可以被短的非芳族单元间断(<10%的非H原子,优选小于5%的非H原子,比如C、N或O原子)。因此,9,9′-螺二芴,9,9-二芳基芴,三芳胺,二芳基醚等体系,对于该发明目的同样认为是芳香族环系。
此外,非芳香族环系在环系中包含1-10碳原子,且不仅包括饱和而且包括部分不饱
和的环状体系。环上的氢可以未被取代或被基团R1单取代或多取代,基团R1在每一次出现中可以相同或者不同,并且还可以包含一个或多个杂原子。其中,杂原子可以Si、N、P、O、S和/或Ge,特别优选选自Si、N、P、O和/或S。这些例如可以是类环己基或类哌啶体系,也可以是类环辛二烯环状体系。该术语同样适用于稠合的非芳香环系。进一步地,非芳香族环系在环系中可以包含1-3碳原子。
在其中一个实施例中,含硼有机化合物中的NH上的H原子或桥联基CH2基团可以被R1基团取代,R1可选自具有1-10个碳原子的烷基、具有1-10个碳原子的烷氧基或者具有2-10个碳原子的芳基或杂芳基。其中,具有1-10个碳原子的烷基可以选自甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、2-甲基丁基、正戊基、正己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟甲基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。具有1-10个碳原子的烷氧基可以选自甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基或者2-甲基丁氧基。具有2-10个碳原子的芳基或杂芳基取决于用途其可以是一价或二价的,在每一情况下也可以被上述提及的基团R1取代并可以通过任何希望的位置与芳香族或杂芳香环连接。进一步地,具有2-10个碳原子的芳基或杂芳基可以选自苯、萘、蒽、嵌二萘、二氢芘、屈、茈、萤蒽、丁省、戊省、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、硫芴、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩恶嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、恶唑、苯并恶唑、萘并恶唑、蒽并恶唑、菲并恶唑、异恶唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、二氮蒽、1,5-二氮杂萘、氮咔唑、苯并咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-恶二唑、1,2,4-恶二唑、1,2,5-恶二唑、1,3,4-恶二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑。1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、中氮茚或苯并噻二唑。此外,芳香和杂芳族环系认为特别是除上述提及的芳基和杂芳基之外,还指亚联苯基、亚三联苯、芴、螺二芴、二氢菲、四氢芘和顺式或者反式茚并芴。
在其中一个实施例中,Ar1-A7独立地包含如下结构基团中的一种或多种:
其中,X3选自CR6或N;
Y7选自CR7R8、SiR9R10、NR11、C(=O)、S或O;
其中,R6,R7,R8,R9,R10,R11独立地选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基、具有3至20个C原子的硫代烷氧基基团、具有3至20个C原子的甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团(-CN),氨基甲酰基基团(-C(=O)NH2)、卤甲酰基基团(-C(=O)-X,其中X代表卤素原子)、甲酰基基团(-C(=O)-H)、异氰基基团、
异氰酸酯基团、硫氰酸酯基团或、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、B、F、可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系、具有5至40个环原子的芳氧基或杂芳氧基基团中一种或多种;其中,R6,R7,R8,R9,R10,R11中至少一个与所述结构基团键合的环形成单环或多环的脂族或芳族环,或者R6,R7,R8,R9,R10,R11中至少两个相互键合形成单环或多环的脂族或芳族环。
进一步地,Ar1-A7可独立地选自上述任一基团。
进一步地,在其中一个实施例中,Ar1-A7独立地选自苯基。
更进一步地,该含硼有机物选自如下通式(2)-(7)所示的结构的一种:
其中,L1~L6可相同或不同,L1~L6独立地选自氢键、含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃、含1-15个碳原子的环烷烃、具有2-20个碳原子的芳香族、具有2-20个碳原子的杂芳香族或具有2-20个碳原子的非芳香族环系;且当Y1~Y6中有一个或多个是单键或二桥基时,与其对应的L为氢键;
Y1~Y6可相同或不同,Y1~Y6独立地选自单键、二桥或三桥联基,Y1~Y6独立地与其相邻的三个基团以单键或者双键相连;
n选自0、1或2;m选自0、1或2。
在其中一个实施例中,通式(1)-(7)中的L1~L6可相同或不同,L1~L6独立地选自含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃或含1-15个碳原子的环烷烃。
进一步地,在另一实施例中,L1~L6可相同或不同,所述所述L1~L6独立地包含以下结构单元中的一种或多种:
其中,n选自1、2、3或4。
进一步地,L1~L6可相同或不同,L1~L6独立地选自如上表格中的任一基团。
按照本发明的化合物,便于得到热激发延迟荧光TADF特性。按照热激发延迟荧光TADF材料(参见Adachi et al.,Nature Vol 492,234,(2012))的原理,当有机化合物的ΔE(S1-T1)足够小时,该有机化合物的三线态激子可以通过反向内部转换到单线态激子,从而实现高效发光。一般来说,TADF材料通过供电子(Donor)与缺电子或吸电子(Acceptor)基团相连而得,即具有明显的D-A结构。
在其中一个实施例中,该含硼有机化合物的ΔE(S1-T1)≤0.30eV,较好是≤0.25eV,更好是≤0.20eV,最好是≤0.10eV。其中,ΔE(S1-T1)表示该含硼有机化合物的第一三重激发态T1与含硼有机化合物的第一单重激发态S1之间的能级差。
在其中一个实施例中,L1-L6中至少有一个包含供电子基。供电子基可选自如下基团:
在另一实施例中,L1-L6中至少有一个包含吸电子基。吸电子基可选自可选自F、氰基或包含有如下基团的结构。
其中,n选自1、2或3;X1-X8独立地选自CR12或N,且X1-X8中至少一个选自N;Z1-Z3独立地选自C(R12)2、O或S;其中,所述R12选自氢键、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基或杂芳基。
需要说明的是,吸电子基可选自可选自F、氰基或上述任一基团。
在其他实施例中,L1-L6中至少有一个包含供电子基,且L1-L6中至少有一个包含吸电子基。其中,供电子基如上述所述,吸电子基也如上述所述。
上述含硼有机化合物可以作为有机功能材料用于有机电子器件中,尤其是OLED。有机功能材料可分为空穴注入材料(HIM)、空穴传输材料(HTM)、电子传输材料(ETM)、电子注入材料(EIM)、电子阻挡材料(EBM)、空穴阻挡材料(HBM)、发光体(Emitter)、主体材料(Host)以及有机染料。该含硼有机化合物可作为主体材料、电子传输材料或空穴传输材料。进一步地,该含硼有机化合物可作为磷光主体材料或共主体材料。
当该含硼有机化合物作为磷光主体材料时,该含硼有机化合物必须有适当的三线态能级。在其中一个实施例中,含硼有机化合物的T1≥2.2eV;其中,T1表示该含硼有机化合物的第一三重激发态。进一步地,较好地T1≥2.4eV,更好地T1≥2.6eV,更更好地T1≥2.65eV,最好地T1≥2.7eV。
需要说明的是,含硼有机化合物的功能取决于取代型式,按照通式(1)~(7)的有机化合物可以具有各种各样的功能,包括但不限于空穴传输功能,电子传输功能,发光功能,激子阻挡功能等。特别是通过取代基L1~L6描述了哪些化合物特别适用于哪些功能。取代基L1~L6对通式(1)~(8)单元的电子特性产生影响。
在其中一个实施例中,含硼化合物的环上的氢中至少有一个被氘代。进一步地,含硼化合物的环上的被氘代的氢占所述含硼化合物的环上的所有氢的5%-50%,较好是10%的H被氘代,更好是20%的H被氘代,更更好是30%的H被氘代,最好是40%的H被氘代。
有机化合物的三线态能级T1取决于该有机化合物中具有最大共轭体系的分结构。一般地,T1随共轭体系的增大而递减。在其中一个实施例中,通式(1)中,如通式(1a)所示的分结构,具有最大的共轭体系。
在其中一个实施例中,通式(1a)在去除取代基的情况下,其环原子数不超过36个,较好为不超过30个,更好为不超过26个,最好为不超过20个。
进一步地,在一实施例中,具有通式(1a)的含硼有机化合物的T1≥2.3eV,较好是≥2.5eV,更好是≥2.7eV,更更好≥2.75eV,最好是≥2.8eV。
当该含硼有机化合物作为磷光主体材料时,需要其具有较高的热稳定性。在一实施例中,该含硼有机化合物的玻璃化温度Tg≥100℃。进一步地,Tg≥120℃。更进一步地,Tg≥140℃。再进一步地,Tg≥160℃。更进一步地,Tg≥180℃。
在一实施例中,该含硼有机化合物具有TADF特性,并作为共主体或辅助主体材料。该含硼有机化合物也可作为发光体。通式(2)~(7)优选的单元的例子是以下的结构。这些结构可以在所有的可能取代的点上被取代。
在其中一个实施例中,含硼有机化合物为小分子材料。从而使得该含硼有机化合物可用于蒸镀型OLED。其中,在一实施例中,含硼有机化合物的分子量小于等于1000克/摩尔。进一步地,含硼有机化合物的分子量小于等于900克/摩尔。更进一步地,含硼有机化合物的分子量小于等于850克/摩尔。再进一步地,含硼有机化合物的分子量小于等于
800克/摩尔。再进一步地,含硼有机化合物的分子量小于等于700克/摩尔。
需要说明的是,本文中所定义的术语“小分子”是指不是聚合物,低聚物,树枝状聚合物,或共混物的分子。特别是,小分子中没有重复结构。小分子的分子量≤3000克/摩尔,较好是≤2000克/摩尔,最好是≤1500克/摩尔。
高聚物,即Polymer,包括均聚物(homopolymer),共聚物(copolymer),镶嵌共聚物(block copolymer)。另外在本发明中,高聚物也包括树状物(dendrimer),有关树状物的合成及应用请参见【Dendrimers and Dendrons,Wiley-VCH Verlag GmbH&Co.KGaA,2002,Ed.George R.Newkome,Charles N.Moorefield,Fritz Vogtle.】。
共轭高聚物(conjugated polymer)是一高聚物,它的主链backbone主要是由C原子的sp2杂化轨道构成,著名的例子有:聚乙炔polyacetylene和poly(phenylene vinylene),其主链上的C原子的也可以被其他非C原子取代,而且当主链上的sp2杂化被一些自然的缺陷打断时,仍然被认为是共轭高聚物。另外在本发明中共轭高聚物也包括主链上包含有芳基胺(aryl amine)、芳基磷化氢(aryl phosphine)及其他杂环芳烃(heteroarmotics)、有机金属络合物(organometallic complexes)等。
在一实施例中,含硼有机化合物的分子量大于等于700克/摩尔。从而使得该含硼有机化合物可用于印刷型OLED。进一步地,含硼有机化合物的分子量大于等于800克/摩尔。更进一步地,含硼有机化合物的分子量大于等于900克/摩尔。再进一步地,含硼有机化合物的分子量大于等于1000克/摩尔。再进一步地,含硼有机化合物的分子量大于等于1100克/摩尔
在一实施例中,该含硼有机化合物在25℃下在甲苯中的溶解度大于等于10mg/ml。进一步地,该含硼有机混合物在25℃下在甲苯中的溶解度大于等于15mg/ml。更进一步地,该含硼有机混合物在25℃下在甲苯中的溶解度大于等于20mg/ml。
上述含硼机化合物可以在有机功能材料中的应用。上述含硼有机化合物也可以在油墨中的应用。上述含硼有机化合物还可以在有机电子器件中的应用。
一实施例的聚合物,其中至少一个重复单元包括上述含硼有机化合物。聚合物可以为共轭高聚物或非共轭高聚物。当聚合物为非共轭高聚物时,上述含硼有机化合物在高聚物的侧链上。
上述聚合物在有机功能材料中的应用。上述聚合物也可以在油墨中的应用。上述聚合物还可以在有机电子器件中的应用。
一实施例的有机混合物包括至少一种有机功能材料以及上述含硼有机化合物。在其中一个实施例中,有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、有机主体材料或发光材料。例如在WO2010135519A1、US20090134784A1和WO 2011110277A1中对各种有机功能材料有详细的描述,特此将此三篇专利文件中的全部内容并入本文作为参考。有机功能材料可以是小分子和高聚物材料。
在其中一个实施例中,发光材料选自荧光发光体、磷光发光体、有机热激发延迟荧光材料或发光量子点材料。
在其一个实施例中,有机功能材料选自磷光发光体,含硼有机化合物作为主体材料;有机功能材料的重量百分比大于0小于等于30%。进一步地,有机功能材料的重量百分比大于0小于等于25%。更进一步地,有机功能材料的重量百分比大于0小于等于20%。
在其中一个实施例中,有机功能材料选自有机主体材料。含硼有机化合物作为发光材料。含硼有机化合物的重量百分比大于0小于等于30%。进一步地,含硼有机化合物的重量百分比大于0小于等于25%。更进一步地,含硼有机化合物的重量百分比大于0小于等于20%。更进一步地,含硼有机化合物的重量百分比大于0小于等于15%。
在其中一个实施例中,有机功能材料选自磷光发光体和有机主体材料,含硼有机化合
物为辅助发光材料或辅助主体材料;含硼有机化合物与磷光发光体的重量比为(1:2)-(2:1)。进一步地,含硼有机化合物的第一三重激发态可以高于磷光发光体的第一三重激发态。
在其中一个实施例中,有机功能材料选自TADF材料。
下面对单重态发光体,三重态发光体以及TADF材料作进一步较详细的描述(但不限于此)。
1、三重态发光体(Triplet Emitter)
三重态主体材料的例子并不受特别的限制,任何金属络合物或有机化合物都可能被用作为主体,只要其三重态能量比发光体,特别是三重态发光体或磷光发光体更高。可用作三重态主体(Host)的金属络合物的例子包括(但不限于)如下的一般结构:
M为金属;(Y3-Y4)是一两齿配体,Y3和Y4独立地选自C、N、O、P或S;;L为辅助配体;m为整数,其值从1到此金属的最大配位数;m+n为该金属的最大配位数。
在一个实施例中,可用作三重态主体的金属络合物有如下形式:
其中,(O-N)为两齿配体;金属与O和N原子配位。
在一实施例中,M可选自Ir或Pt。
可作为三重态主体的有机化合物的例子选自包含有环芳香烃基的化合物,例如苯、联苯、三苯基、苯并、芴;包含有芳香杂环基的化合物,如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚咔唑、吡啶吲哚、吡咯二吡啶、吡唑、咪唑、***类、恶唑、噻唑、恶二唑、恶***、二恶唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪类、恶嗪、恶噻嗪、恶二嗪、吲哚、苯并咪唑、吲唑、恶唑、二苯并恶唑、苯异恶唑、苯并噻唑、喹啉、异喹啉、邻二氮杂萘、喹唑啉、喹喔啉、萘、酞、蝶啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩恶嗪、苯并呋喃吡啶、呋喃并吡啶、苯并噻吩吡啶、噻吩吡啶、苯并硒吩吡啶和硒吩苯并二吡啶或包含有2至10环结构的基团。其中,基团可以是相同或不同类型的环芳香烃基团或芳香杂环基团,并彼此直接或通过至少一个以下的基团连结在一起,如氧原子、氮原子、硫原子、硅原子、磷原子、硼原子、链结构单元和脂肪环基团。其中,每个Ar可以进一步被取代,取代基可选为氢、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基和杂芳基。
在一个优选的实施方案中,三重态主体材料可选于包含至少一个以下基团的化合物:
其中,R1-R7独立地选自氢、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基或杂芳基;当它们是芳基或杂芳基时,它们与上述的Ar1和Ar2意义相同;n选自0-20中
整数;X1-X8独立地选自CH或N;X9选自CR1R2或NR1。
在下面的表中列出合适的三重态主体材料的例子。
2、磷光发光材料
磷光发光材料也称三重态发光体。三重态发光体是金属络合物,其通式为M(L)n;其中,M是金属原子;L为有机配体,其每次出现时可以是相同或不同,它通过一个或多个位置键接或配位连接到金属原子M上。n为大于1的整数。优选地,n选自1,2,3,4,5或6。在一实施例中,这些金属络合物通过一个或多个位置联接到一个聚合物上,最好是通过有机配体。
在一实施例中,金属原子M选自过渡金属元素、镧系元素或锕系元素。进一步地,金属原子M选自Ir,Pt,Pd,Au,Rh,Ru,Os,Sm,Eu,Gd,Tb,Dy,Re,Cu或Ag。更进一步地,金属原子M选自Os,Ir,Ru,Rh,Re,Pd或Pt。
在一实施例中,,三重态发光体包含有螯合配体,即配体,通过至少两个结合点与金属配位,特别优选考虑的是三重态发光体包含有两个或三个相同或不同的双齿或多齿配体。螯合配体有利于提高金属络合物的稳定性。
有机配体可选自苯基吡啶衍生物,7,8-苯并喹啉衍生物,2(2-噻吩基)吡啶衍生物,2(1-萘基)吡啶衍生物,或2苯基喹啉衍生物。所有这些有机配体都可能被取代,例如被含氟或三氟甲基取代。辅助配体可选自乙酸丙酮或苦味酸。
在一实施例中,用作三重态发光体的金属络合物的通式如下:
其中,M是金属,M选自过渡金属元素或镧系元素或锕系元素;
Ar1为环状基团,其每次出现时可以是相同或不同,且Ar1至少包含有一个施主原子,即有一孤对电子的原子,如氮或磷,通过它环状基团与金属配位连接;Ar2为环状基团,其每次出现时可以是相同或不同,Ar2至少包含有一个C原子,通过它环状基团与金属连接;Ar1和Ar2由共价键联接在一起,可各自携带一个或多个取代基团,它们也可再通过取代基团联接在一起;L每次出现时可以是相同或不同,L为辅助配体,优选于双齿螯合配体,最好是单阴离子双齿螯合配体;m选自1,2或3,优选地是2或3,特别优选地是3;n选自0,1,或2,优选地是0或1,特别优选地是0。
一些三重态发光体的材料极其应用的例子可在下述专利文件和文献中找到:WO 200070655,WO 200141512,WO 200202714,WO 200215645,EP 1191613,EP 1191612,EP 1191614,WO 2005033244,WO 2005019373,US 2005/0258742,WO 2009146770,WO 2010015307,WO 2010031485,WO 2010054731,WO 2010054728,WO 2010086089,WO 2010099852,WO 2010102709,US 20070087219 A1,US 20090061681 A1,US 20010053462 A1,Baldo,Thompson et al.Nature 403,(2000),750-753,US 20090061681 A1,US 20090061681 A1,Adachi et al.Appl.Phys.Lett.78(2001),1622-1624,J.Kido et al.Appl.Phys.Lett.65(1994),2124,Kido et al.Chem.Lett.657,1990,US 2007/0252517 A1,Johnson et al.,JACS 105,1983,1795,Wrighton,JACS 96,1974,998,Ma et al.,Synth.Metals 94,1998,245,US 6824895,US 7029766,US 6835469,US 6830828,US 20010053462 A1,WO 2007095118 A1,US 2012004407A1,WO 2012007088A1,WO2012007087A1,WO 2012007086A1,US 2008027220A1,WO 2011157339A1,CN 102282150A,WO 2009118087A1。特此将上述列出的专利文件和文献中的全部内容并入本文作为参考。
3、热激活延迟荧光发光材料(TADF):
传统有机荧光材料只能利用电激发形成的25%单线态激子发光,器件的内量子效率较低(最高为25%)。尽管磷光材料由于重原子中心强的自旋-轨道耦合增强了系间穿越,
可以有效利用电激发形成的单线态激子和三线态激子发光,使器件的内量子效率达到100%。但磷光材料昂贵,材料稳定性差,器件效率滚降严重等问题限制了其在OLED中的应用。热激活延迟荧光发光材料是继有机荧光材料和有机磷光材料之后发展的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(ΔEst),三线态激子可以通过反系间穿越转变成单线态激子发光。这可以充分利用电激发下形成的单线态激子和三线态激子。器件内量子效率可达到100%。
TADF材料需要具有较小的单线态-三线态能级差,一般是ΔEst<0.3eV,较好是ΔEst<0.2eV,更好是ΔEst<0.1eV,最好是ΔEst<0.05eV。在一实施例中,TADF有较好的荧光量子效率。一些TADF发光的材料可在下述专利文件中找到:CN103483332(A),TW201309696(A),TW201309778(A),TW201343874(A),TW201350558(A),US20120217869(A1),WO2013133359(A1),WO2013154064(A1),Adachi,et.al.Adv.Mater.,21,2009,4802,Adachi,et.al.Appl.Phys.Lett.,98,2011,083302,Adachi,et.al.Appl.Phys.Lett.,101,2012,093306,Adachi,et.al.Chem.Commun.,48,2012,11392,Adachi,et.al.Nature Photonics,6,2012,253,Adachi,et.al.Nature,492,2012,234,Adachi,et.al.J.Am.Chem.Soc,134,2012,14706,Adachi,et.al.Angew.Chem.Int.Ed,51,2012,11311,Adachi,et.al.Chem.Commun.,48,2012,9580,Adachi,et.al.Chem.Commun.,48,2013,10385,Adachi,et.al.Adv.Mater.,25,2013,3319,Adachi,et.al.Adv.Mater.,25,2013,3707,Adachi,et.al.Chem.Mater.,25,2013,3038,Adachi,et.al.Chem.Mater.,25,2013,3766,Adachi,et.al.J.Mater.Chem.C.,1,2013,4599,Adachi,et.al.J.Phys.Chem.A.,117,2013,5607,特此将上述列出的专利或文章文件中的全部内容并入本文作为参考。
在下面的表中列出一些合适的TADF发光材料的例子。
上述有机混合物在油墨中的应用。
上述有机混合物在有机电子器件中的应用。从而使得该有机电子器件的发光效率和寿命都更高。
一实施例的有机混合物包括包括至少一种有机功能材料以及上述聚合物。关于该有机功能材料的性能和选择等如上一实施例所述,在此不再赘述。
一实施例的油墨,包括有机溶剂和上述含硼有机化合物。油墨即为组合物。从而该组合物用于印刷工艺时,油墨的粘度,表面张力是重要的参数。合适的油墨的表面张力参数适合于特定的基板和特定的印刷方法。
在一实施例中油墨在工作温度或在25℃下的表面张力约在19dyne/cm到50dyne/cm范围内;更好是在22dyne/cm到35dyne/cm范围内;最好是在25dyne/cm到33dyne/cm范围内。
在一实施例中,油墨在工作温度或25℃下的粘度约在1cps到100cps范围内;较好是在1cps到50cps范围内;更好是在1.5cps到20cps范围内;最好是在4.0cps到20cps范围内。从而使得该组合物更便于喷墨印刷。
粘度可以通过不同的方法调节,如通过合适的溶剂选取和油墨中功能材料的浓度。包含有金属有机配合物或高聚物的油墨可方便人们将印刷油墨按照所用的印刷方法在适当的范围调节。一般地,组合物中包含的有机功能材料的重量比为0.3%~30wt%,较好的为0.5%~20wt%,更好的为0.5%~15wt%,更更好的为0.5%~10wt%,最好的为1%~5wt%。
在一实施例中,有机溶剂包括第一溶剂,该第一溶剂选自基于芳族和/或杂芳族的溶剂。进一步地,该第一溶剂可以为脂肪族链/环取代的芳族溶剂、或芳族酮溶剂,或芳族醚溶剂。
第一溶剂的例子有,但不限于:基于芳族或杂芳族的溶剂:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二甲苯、间二甲苯、对二甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、1-甲氧基萘、环己基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、1,3-二丙氧基苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、α,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、二苄醚等;基于酮的溶剂:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮,异佛尔酮、2,6,8-三甲基-4-壬酮、葑酮、2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、佛尔酮、二正戊基酮;芳族醚溶剂:3-苯氧基甲苯、丁氧基苯、苄基丁基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本***、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚、戊醚c己醚、二辛醚、乙二醇二丁醚、二乙二醇二***、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚;酯溶剂:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。
进一步地,该第一溶剂还可以选自脂肪族酮,例如,2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、佛尔酮、二正戊基酮等;或脂肪族醚,例如,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二***、二乙二醇丁基甲醚、二乙二醇二丁醚、
三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚以及四乙二醇二甲醚中的一种或多种。
在一实施例中,该有机溶剂还包括第二溶剂,该第二溶剂选自甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷以及茚中的一种或多种。
在一实施例中,该油墨可以是溶液或悬浮液。这根据含硼有机化合物和有机溶剂之间的相容性来确定。
在一实施例中,该组合物中含硼有机化合物的重量百分比为0.01至20wt%,较好的是0.1至15wt%,更好的是0.2至10wt%,最好的是0.25至5wt%的有机化合物。
一实施例中,上述组合物在制备有机电子器件中的应用。尤其地,其作为涂料或印刷油墨在制备有机电子器件时的用途,特别优选的是通过打印或涂布的制备方法。
其中,适合的打印或涂布技术包括(但不限于)喷墨打印,喷印(Nozzle Printing),活版印刷,丝网印刷,浸涂,旋转涂布,刮刀涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印或狭缝型挤压式涂布等。优选的是凹版印刷,喷印及喷墨印刷。该组合物还可以包括组份例,盖组份例选自表面活性化合物、润滑剂、润湿剂、分散剂、疏水剂以及粘接剂中的一种或多种,从而可以用于调节粘度,成膜性能,提高附着性等。有关打印技术,及其对有关溶液的相关要求,如溶剂及浓度,粘度等,的详细信息请参见Helmut Kipphan主编的《印刷媒体手册:技术和生产方法》(Handbook of Print Media:Technologies and Production Methods),ISBN 3-540-67326-1。
一实施例中,上述含硼有机化合物在有机电子器件中的应用。该有机电子器件可选自有机发光二极管(Organic Light-Emitting Diode,OLED)、有机光伏电池(Organic Photovoltage,OPV)、有机发光电池(OLEEC)、有机场效应管(organic field2effect transistor,OFET)、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器或有机等离激元发射二极管(Organic Plasmon Emitting Diode)。在一实施例中,该有机电子器件为电致发光器件,如OLED、OLEEC及有机发光场效应管。进一步地,该有机混合物用于用于OLED器件的发光层。
另一实施例的油墨包括有机溶剂和上述聚合物。该聚合物如上述所述,在此不再赘述。
上述油墨可以在制备有机电子器件中应用。
一实施例的有机电子器件包括上述含硼有机化合物。从而该有机电子器件具有较高的寿命和较高的发光效率。
在其中一个实施例中,有机电子器件包括阳极、阴极以及位于阳极和阴极之间的功能层;功能层包括上述含硼有机化合物。有机电子器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode)等,特别优选的是有机电致发光器件,如OLED,OLEEC,有机发光场效应管。
在其中一个实施例中,电致发光器件的发光层包含一种上述含硼有机化合物,或包含一种上述含硼有机化合物和一种磷光发光体,或包含一种上述含硼有机化合物和一种主体材料,或包含一种上述含硼有机化合物、一种磷光发光体以及一种主体材料。
在其中一个实施例中,电致发光器件,尤其是OLED,包括依次层叠的基片、阳极、发光层以及阴极。发光层包括上述含硼有机化合物。
基片可以是不透明或透明的。透明的基板可以用来制造一个透明的发光元器件,请参见Bulovic等Nature 1996,380,p29,和Gu等,Appl.Phys.Lett.1996,68,p2606。基片可
以是刚性的或弹性的。基片也可以是塑料,金属,半导体晶片或玻璃。优选地,基片具有平滑的表面。无表面缺陷的基板是特别理想的选择。在一实施例,基片是柔性的,可选于聚合物薄膜或塑料,其玻璃化温度Tg为150℃以上,较好是超过200℃,更好是超过250℃,最好是超过300℃。柔性基板可以为聚(对苯二甲酸乙二醇酯)(PET)或聚乙二醇(2,6-萘)(PEN)。
阳极可包括导电金属或金属氧化物、或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个的实施例中,阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包括但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO以及铝掺杂氧化锌(AZO)等。阳极材料也可以其他材料。阳极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。在其他实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本实施例的有机电子器件。
阴极可包括导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。所有可用作OLED的阴极的材料都可能作为本实施例的有机电子器件的阴极材料。阴极材料的例子包括但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发以及电子束(e-beam)等。
当电致发光器件为OLED时,OLED还可以包含其他功能层,如空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)或空穴阻挡层(HBL)。适合用于这些功能层中的材料在上面及在WO2010135519A1、US20090134784A1和WO2011110277A1中有详细的描述,特此将此三篇篇专利文件中的全部内容并入本文作为参考。
在其中一个实施例中,该电致发光器件中的电子传输层(ETL)或空穴阻挡层(HBL)包含上述含硼有机化合物,并且通过溶液加工的方法制备而成。
在一实施例中,该有机电致发光器件发光器件的发光波长在300到1000nm之间,较好的是在350到900nm之间,更好的是在400到800nm之间。
在一实施例中,上述有机电子器件在电子设备中的应用。电子设备选自显示设备、照明设备、光源或传感器。其中,有机电子器件可以为有机电致发光器件。
一实施例的电子设备,包括上述有机电子器件,其具有更高的寿命和发光效率。
另一实施例的有机电子器件包括上述聚合物,其具有较高的使用寿命和稳定性、以及发光效率。有机电子器件如上一实施例所述,在此不再赘述。
上述有机电子器件在电子设备中的应用。电子设备选自显示设备、照明设备、光源或传感器。其中,有机电子器件可以为有机电致发光器件。
另一实施例的电子设备,包括上述有机电子器件,其具有更高的寿命和发光效率。
实施例1
250ml的三口烧瓶中加入4.86g,10mmol 9,9'-(2-溴-1,3-苯基)二(9H-咔唑)以及100ml干燥甲苯,在N2气氛中,冷却至-30摄氏度,逐滴加入(6.0ml,1.7M,10.2mmol)n-BuLi正已烷溶液。升高温度至60摄氏度反应2小时,减压蒸除其中的正已烷溶剂。将反应液再次冷却至-30摄氏度,加入10.5mol三溴化硼溶液,升至室温下搅拌0.5小时,然后将反应液冷却至0摄氏度,加入21mmol N,N-二异丙基乙基胺,待滴加完毕,升温至室温搅拌,再继续升温至120摄氏度搅拌3小时,将反应液冷却至室温。加入碳酸钠水溶液与乙酸乙酯淬灭反应。水相用乙酸乙酯萃取并合并有机相,旋蒸掉其中的溶剂,得到粗品,用快速硅胶柱纯化得到纯品。用甲苯与乙酸乙酯重结晶,得产品白色固体粉末。MS(ASAP)=416.1。
实施例2
在本实施例中,最终产物(2)与实施例1中的产物(1)的合成步骤类似,所不同的是中间体由9,9'-(2-溴-1,3-苯基)二(9H-咔唑)更换成7,7'-(2-溴-1,3-苯基)二(7H-苯并[c]咔唑),反应过程所用到的反应温度以及反应时间相同。MS(ASAP)=516.5。
实施例3
在本实施例中,最终产物(3)与实施例1中的产物(1)的合成步骤类似,所不同的是中间体由9,9'-(2-溴-1,3-苯基)二(9H-咔唑)更换成5,5'-(2-溴-1,3-苯基)二(7,7-二甲基-5,7-二氢茚[2,1-b]咔唑),反应过程所用到的反应温度以及反应时间相同。MS(ASAP)=648.4。
实施例4
在本实施例中,最终产物(4)与实施例1中的产物(1)的合成步骤类似,所不同的是中间体由9,9'-(2-溴-1,3-苯基)二(9H-咔唑)更换成11,11'-(2-溴-1,3-苯基)二(5-苯基-5,11-二氢吲哚
[3,2-b]咔唑),反应过程所用到的反应温度以及反应时间相同。MS(ASAP)=746.6。
实施例5
在本实施例中,最终产物(5)与实施例1中的产物(1)的合成步骤类似,所不同的是中间体由9,9'-(2-溴-1,3-苯基)二(9H-咔唑)更换成7,7'-(2-溴-1,3-苯基)二(7H-萤蒽并[1,9-bc]咔唑),反应过程所用到的反应温度以及反应时间相同。MS(ASAP)=664.4。
有机化合物材料的能级可通过量子计算得到,比如利用TD-DFT(含时密度泛函理论)通过Gaussian09W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。首先用半经验方法“Ground State/Semi-empirical/Default Spin/AM1”(Charge 0/Spin Singlet)来优化分子几何结构,然后有机分子的能量结构由TD-DFT(含时密度泛函理论)方法算得“TD-SCF/DFT/Default Spin/B3PW91”与基组“6-31G(d)”(Charge 0/Spin Singlet)。HOMO和LUMO能级按照下面的校准公式计算,S1,T1和谐振因子f(S1)直接使用。
HOMO(eV)=((HOMO(G)×27.212)-0.9899)/1.1206
LUMO(eV)=((LUMO(G)×27.212)-2.0041)/1.385
其中HOMO(G)和LUMO(G)是Gaussian 09W的直接计算结果,单位为Hartree。结果如表一所示。
表一
材料 | HOMO[eV] | LUMO[eV] | f(S1) | T1[eV] | S1[eV] | ΔST |
(1) | -5.67 | -2.85 | 0.3457 | 2.51 | 2.58 | 0.07 |
(2) | -5.69 | -2.96 | 0.4036 | 2.23 | 2.33 | 0.10 |
(3) | -5.55 | -2.85 | 0.5076 | 2.41 | 2.50 | 0.09 |
(4) | -5.34 | -2.78 | 0.1986 | 2.36 | 2.40 | 0.04 |
(5) | -5.59 | -3.01 | 0.7225 | 1.92 | 2.00 | 0.08 |
其中,谐振因子f(S1)均处于0.1986到0.7225之间,可很好地提高材料的荧光量子发光效率,比起一般的D-A体系结构的TADF材料大很多。而且ΔE(S1–T1)的值不大于0.10eV,满足小于0.30eV的延迟荧光发光条件。
与上述延荧光发光材料进行比较的是D-A体系结构的延迟荧光发光材料以Ref 1标记:
OLED器件的制备:
具有ITO/NPD(35nm)/5%(1)~(5):DPEPO(15nm)/TPBi(65nm)/LiF(1nm)/Al(150nm)/阴极的OLED器件的制备步骤如下:
a、导电玻璃基片的清洗:首次使用时,可用多种溶剂进行清洗,例如氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、HTL(35nm),EML(15nm),ETL(65nm):在高真空(1×10-6毫巴,mbar)中热蒸镀而成;
c、阴极:LiF/Al(1nm/150nm)在高真空(1×10-6毫巴)中热蒸镀而成;
d、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及外部量子效率。经检测,OLED1(对应实施例(1))的发光效率和寿命都是OLEDRef1(对应原材料(Ref1))的2倍以上,OLED3(对应实施例(3))的发光效率是OLED Ref1的3倍,而寿命是4倍以上,特别是OLED3的最大外部量子效率达到10%以上。OLED5(对应实施例(5))为红光,其余的均为绿光发光器件。可见,采用本发明的有机混合物制备的OLED器件,其发光效率和寿命均得到大大提高,且外部量子效率也得到明显提高。
Claims (19)
- 一种含硼有机化合物,其特征在于,所述含硼有机化合物的结构如通式(1)所示:其中,Ar1~Ar7相同或不同,Ar1~Ar7独立地选自具有2-20个碳原子的芳香族、杂芳香族或者非芳香族环系;Ar1~Ar7的环上具有基团R1,所述基团R1在每次出现时相同或不同;L1~L6相同或不同,L1~L6独立地选自氢键、含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃、含1-15个碳原子的环烷烃、具有2-20个碳原子的芳香族、具有2-20个碳原子的杂芳香族或具有2-20个碳原子的非芳香族环系;且当Y1~Y6中有一个或多个是单键或二桥基时,与其对应的L为氢键;Y1~Y6相同或不同,Y1~Y6独立地选自单键、二桥或三桥联基,Y1~Y6独立地与其相邻的三个基团以单键或者双键相连;R1选自-H、-F、-Cl、Br、I、-D、-CN、-NO2、-CF3、B(OR2)2、Si(R2)3、直链烷烃、烷烃醚、含1~10个碳原子烷烃硫醚、支链烷烃、环烷烃或含有3~10个碳原子的烷烃醚基团;R2选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基、具有3至20个C原子的硫代烷氧基基团、具有3至20个C原子的甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团,氨基甲酰基基团、卤甲酰基基团、甲酰基基团、异氰基基团、异氰酸酯基团、硫氰酸酯基团或、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、B、F、可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系、具有5至40个环原子的芳氧基或杂芳氧基基团中一种或多种;其中,至少一个R2与所述基团键合的环形成单环或多环的脂族或芳族环,或者多个R2相互之间形成单环或多环的脂族或芳族环;n为0、1或2;m为0、1或2。
- 根据权利要求1所述的含硼有机化合物,其特征在于,所述Ar1~Ar7独立地选自具有2-20个碳原子数的芳香族环或杂芳香族环。
- 根据权利要求1所述的含硼有机化合物,其特征在于,所述L1~L6相同或不同, 所述L1~L6独立地选自含1-15个碳原子的直链烷烃、含1-15个碳原子的支链烷烃、含1-15个碳原子的环烷烃、具有2-20个碳原子的芳香族、具有2-20个碳原子的杂芳香族或者具有2-20个碳原子的非芳香族环系。
- 根据权利要求1所述的含硼有机化合物,其特征在于,所述Ar1-A7独立地选自如下任一基团;其中,X3选自CR6或N;Y7选自CR7R8、SiR9R10、NR11、C(=O)、S或O;其中,R6,R7,R8,R9,R10,R11独立地选自H、D、具有1至20个C原子的直链烷基、具有1至20个C原子的烷氧基、具有1至20个C原子的硫代烷氧基基团、具有3至20个C原子的支链、具有3至20个C原子的环状的烷基、具有3至20个C原子的烷氧基、具有3至20个C原子的硫代烷氧基基团、具有3至20个C原子的甲硅烷基基团、具有1至20个C原子的取代的酮基基团、具有2至20个C原子的烷氧基羰基基团、具有7至20个C原子的芳氧基羰基基团、氰基基团,氨基甲酰基基团、卤甲酰基基团、甲酰基基团、异氰基基团、异氰酸酯基团、硫氰酸酯基团或、异硫氰酸酯基团、羟基基团、硝基基团、CF3基团、Cl、B、F、可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系、具有5至40个环原子的芳氧基或杂芳氧基基团中一种或多种;其中,R6,R7,R8,R9,R10,R11中至少一个与所述结构基团键合的环形成单环或多环的脂族或芳族环,或者R6,R7,R8,R9,R10,R11中至少两个相互键合形成单环或多环的脂族或芳族环。
- 根据权利要求5所述的含硼有机化合物,其特征在于,所述Ar1-A7独立地选自苯基。
- 根据权利要求1所述的含硼有机化合物,其特征在于,至少一个L包括供电子基和/或至少一个L包括吸电子基;其中,L为L1、L2、L3、L4、L5或L6。
- 根据权利要求1所述的含硼有机化合物,其特征在于,所述含硼化合物的环上的氢中至少有一个被氘代。
- 根据权利要求1所述的含硼有机化合物,其特征在于,所述含硼有机化合物的T1≥2.2eV;其中,所述T1表示所述含硼有机化合物的第一三重激发态。
- 根据权利要求1-13中任一项所述的含硼有机化合物在有机电子器件中的应用。
- 一种聚合物,其特征在于,所述聚合物中至少一个重复单元包括如权利要求1-13中任一项所述的含硼有机化合物。
- 一种用于有机电子器件的有机混合物,其特征在于,所述有机混合物包括至少一种有机功能材料以及如权利要求1-13中任一项所述的含硼有机化合物或者如权利要求15所述的聚合物;所述有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、有机主体材料或发光材料。
- 一种用于有机电子器件的油墨,其特征在于,所述油墨包括有机溶剂以及如权利要求1-13中任一项所述的的含硼有机化合物或者如权利要求15所述的聚合物或者如权利要求16所述的有机混合物。
- 一种有机电子器件,其特征在于,包括功能层,所述功能层包括如权利要求1-13中任一项所述的含硼有机化合物或者如权利要求15所述的聚合物或者如权利要求16所述的有机混合物,或者所述功能层由如权利要求17所述的油墨制备而成。
- 根据权利要求18所述的有机电子器件,其特征在于,所述有机电子器件选自电致发光器件;所述电致发光器件包括依次层叠的基片、阳极、发光层以及阴极;所述发光 层包括所述含硼有机化合物。
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US20200066997A1 (en) | 2020-02-27 |
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