EP4590653A1 - Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques - Google Patents

Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques

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Publication number
EP4590653A1
EP4590653A1 EP23772882.9A EP23772882A EP4590653A1 EP 4590653 A1 EP4590653 A1 EP 4590653A1 EP 23772882 A EP23772882 A EP 23772882A EP 4590653 A1 EP4590653 A1 EP 4590653A1
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EP
European Patent Office
Prior art keywords
formula
group
radicals
aromatic
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23772882.9A
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German (de)
English (en)
Inventor
Philipp Stoessel
Rouven LINGE
Stefan Schramm
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
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Merck Patent GmbH
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Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP4590653A1 publication Critical patent/EP4590653A1/fr
Pending legal-status Critical Current

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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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    • C07D241/40—Benzopyrazines
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    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Definitions

  • the present invention relates to nitrogen-containing heterocycles for use in electronic devices, in particular in organic electroluminescent devices, as well as electronic devices, in particular organic electroluminescent devices, containing these materials.
  • phosphorescent organometallic complexes are often used as emitting materials. For quantum mechanical reasons, using organometallic compounds as phosphorescence emitters can result in up to four times the energy and power efficiency. In general, there is still room for improvement in electroluminescent devices, particularly in electroluminescent devices that exhibit triplet emission (phosphorescence).
  • the properties of phosphorescent electroluminescent devices are not only determined by the triplet emitters used.
  • the other materials used, such as matrix materials, are also of particular importance here. Improvements to these materials can therefore also lead to significant improvements in the properties of the electroluminescent devices.
  • electroluminescent devices comprise additional layers in addition to an emission layer, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and/or charge generation layers. These layers have a significant influence on the performance of electroluminescent devices.
  • the object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which lead to good device properties when used in this device, as well as to provide the corresponding electronic device .
  • Electron injection materials, electron transport materials and hole blocking materials in particular contribute to these properties.
  • the properties of the matrix materials, also referred to herein as host materials also have a significant influence on the service life and efficiency of the organic electroluminescent device.
  • a further object of the present invention can be seen in providing compounds which are suitable for use in phosphorescent or fluorescent electroluminescence devices, in particular as matrix material.
  • the compounds, particularly when used as host material, electron injection material, electron transport material or hole blocking material in organic electroluminescent devices, should lead to devices that have excellent color purity.
  • the electronic devices should be able to be used or adapted for many purposes.
  • the performance of the electronic devices should be maintained over a wide temperature range.
  • the subject of the present invention is a compound comprising at least one structure of the formula (I), preferably a compound according to the formula (I), where the following applies to the symbols:
  • Z a stands, identically or differently, for Ar, R c , L 1 -Q, or L 1 -N(Ar)2, preferably for R c , L 1 -Q or L 1 -N(Ar)2;
  • Q represents, identically or differently at each occurrence, an electron transport group, preferably a nitrogen-containing heteroaryl group having 5 to 12 ring atoms, particularly preferably having 6 to 12 ring atoms, which may be substituted by one or more radicals R d ;
  • L 1 represents, identically or differently at each occurrence, a bond or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R;
  • R a is, identically or differently, a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 10 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 10 carbon atoms, each with one or several radicals R 2 can be substituted, or an aromatic or heteroaromatic ring system with 5 to 20 aromatic ring atoms, which can each be substituted by one or more radicals R 2 , preferably a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, which can each be substituted with one or more R 2 radicals, or a phenyl group, which can each be substituted with one or more R 2 radicals, two or more, preferably adjacent substituents R a form a ring system with one another;
  • R b is identical or different in each occurrence: H, D, straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 10 carbon atoms or a branched or cyclic alkyl, alkoxy or Thioalkoxy group with 3 to 10 carbon atoms, each of which can be substituted with one or more R 2 radicals, or an aromatic or heteroaromatic ring system with 5 to 20 aromatic ring atoms, each of which can be substituted by one or more R 2 radicals can, preferably H, D, a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms or a phenyl group, each of which can be substituted with one or more R 2 radicals, in this case two , preferably adjacent substituents R b form a ring system with one another, particularly preferably H or D;
  • R 2 is selected identically or differently from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more H atoms can be replaced by D, F, CI, Br, I or CN and can be substituted by one or more alkyl groups, each with 1 to 4 carbon atoms can, in which case two or more, preferably adjacent, substituents R 2 can form a ring system with one another.
  • An aryl group in the sense of this invention contains 6 to 40 carbon atoms;
  • a heteroaryl group contains 3 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aryl group or heteroaryl group is either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc.
  • aryl or heteroaryl group for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
  • aromatics linked to each other by a single bond such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
  • An electron-deficient heteroaryl group in the sense of the present invention is a heteroaryl group that has at least one heteroaromatic six-membered ring with at least one nitrogen atom. Further aromatic or heteroaromatic five-membered rings or six-membered rings can be fused to this six-membered ring. Examples of electron-poor heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline or quinoxaline.
  • An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system in the sense of this invention contains 3 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • an aromatic or heteroaromatic ring system is to be understood as meaning a system which does not necessarily only contain aryl or heteroaryl groups, but rather which also includes several aryl or heteroaryl groups replaced by a non-aromatic unit, such as B. a C, N or O atom can be connected.
  • aromatic ring systems for example such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.
  • aromatic ring systems in the sense of this invention, and also systems in which two or more aryl groups, for example a short alkyl group is connected.
  • the aromatic ring system is preferably selected from fluorene, 9,9'-spirobifluorene, 9,9-diarylamine or groups in which two or more aryl and/or heteroaryl groups are linked to one another by single bonds.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 20 carbon atoms and in which individual H atoms or CH2 groups are also substituted by the above-mentioned groups
  • An alkoxy group with 1 to 40 carbon atoms is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s- Pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclo-octyloxy, 2-ethylhexyloxy, pentafluorethoxy and 2,2,2-trifluorethoxy.
  • a thioalkyl group with 1 to 40 carbon atoms includes, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio,
  • 2-Ethylhexylthio trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynyl thio, butynylthio, pentinylthio, Hexynylthio, heptynylthio or octynylthio understood.
  • alkyl, alkoxy or thioalkyl groups according to the present invention can be straight chain, branched or cyclic, where one or several non-adjacent CH2 groups can be replaced by the above-mentioned groups;
  • one or more H atoms can also be replaced by D, F, CI, Br, I, CN or NO2, preferably F, CI or CN, more preferably F or CN, particularly preferably CN.
  • aromatic or heteroaromatic ring system with 5 - 60 or 5 to 40 aromatic ring atoms which can also be substituted with the above-mentioned radicals and which can be linked via any position on the aromatic or heteroaromatic, is understood to mean in particular groups, which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-lndeno-fluorene, cis- or trans-lndenocarbazole, cis- or trans-lndolocarbazole, trux
  • the formulation that two or more radicals can form a ring together is intended to mean, among other things, that the two radicals are linked to one another by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following diagram.
  • the compounds according to the invention can preferably comprise at least one structure of the formulas (1-1) to (I-4), and are particularly preferably selected from the compounds of the formulas (1-1) to (I-4),
  • the group Q stands, identically or differently, for an electron transport group, the electron transport group preferably representing a nitrogen-containing heteroaryl group with 5 to 12 ring atoms, particularly preferably with 6 to 12 ring atoms, which can be substituted with one or more radicals R d .
  • the group Q preferably represents an electron-poor heteroaryl group, which particularly preferably further has the properties set out above and below.
  • the group Q represents a nitrogen-containing heteroaryl group with 6 to 12 ring atoms with at least two nitrogen atoms in a ring, which can be substituted with one or more radicals R d , which are in the vicinity of at least two of the Carbon atoms in a ring of nitrogen atoms are not connected to a hydrogen atom.
  • Electron transport groups are well known in the art and promote the ability of compounds to transport and/or conduct electrons. These include, in particular, nitrogen-containing substances Heteroaryl group with 5 to 12 ring atoms, particularly preferably with 6 to 12 ring atoms, these generally representing electron-poor heteroaryl groups.
  • the group Q represents a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and/or benzimidazole group, preferably a Pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and/or benzimidazole group stands, particularly preferably a pyrimidine, triazine, quinazoline and/or quinoxaline group, particularly preferably a pyrimidine and/or Triazine group, very particularly preferred for a triazine group which can be substituted with one or more radicals R d .
  • the group Q stands for a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and/or benzimidazole group, particularly preferably for a pyrimidine, triazine, quinazoline and/or quinoxaline group, particularly especially preferably for a pyrimidine and/or triazine group, very particularly preferably for a triazine group, which can be substituted by one or more radicals R d , where the carbon atoms located in the vicinity of at least two of the nitrogen atoms in a ring are not connected to a hydrogen atom.
  • the group Q can be a pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, imidazole and/or benzimidazole group, preferably a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and/or benzimidazole group, which can be substituted by one or more radicals R d , where the carbon atoms adjacent to at least two of the nitrogen atoms are connected to an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 .
  • the particular advantages that can be achieved by this embodiment include, in particular, a longer service life of the electronic devices.
  • the group Q represents a pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, imidazole and/or benzimidazole group, preferably a pyrimidine, pyrazine group.
  • the group Q represents a pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, imidazole and/or benzimidazole group, preferably a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and/or benzimidazole group, which can be substituted with one or more radicals R d , the carbon atoms adjacent to at least two of the nitrogen atoms having a straight-chain alkyl -, alkoxy or thioalkoxy group with 1 to 40
  • the group Q is selected identically or differently for each occurrence from structures of the formulas (Q-1) to (Q-16), where R d has the one mentioned above, in particular for formula (I), the dashed bonds mark the binding positions and the other symbols have the following meaning:
  • Y 1 represents 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2; n is independently 0, 1, 2 or 3 on each occurrence, preferably 0, 1 or 2; and m is independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, on each occurrence.
  • structures (Q-1) to (Q-14) are preferred, structures (Q-1) to (Q-8) are particularly preferred and the structures (Q-1), (Q-4), (Q -7) and (Q-12) are particularly preferred and the structure (Q-1) is very particularly preferred.
  • the group Q is selected identically or differently for each occurrence from structures of the formulas (Q-1 ') to (Q-15'),
  • R d has the one mentioned above, in particular for formula (I), the dashed bonds mark the binding positions and the other symbols have the following meaning:
  • R e is, identically or differently, a group N(Ar')2 or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can each be substituted by one or more radicals R 1 ; two radicals R e can also be with each other or a radical R e with another group, in particular a radical R e, form a ring system;
  • Y 1 is 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2; n is independently 0, 1, 2 or 3 in each occurrence, and n is in each Occurrence independently 0, 1, 2 or 3, preferably 0, 1 or 2, and m on each occurrence is independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2.
  • the group Q is selected identically or differently for each occurrence from structures of the formulas (Q-1a), (Q-1b), (Q-1c), (Q-1d), (Q-1e), (Q-1f), (Q-1g), (Q-1h), (Q-1 i), (Q-1j), (Q-1 k), (Q-11), (Q-1m) and/or (Q-1 n),
  • R 1 has the one mentioned above, in particular for formula (I), the dashed bond marks the binding position and the following applies to the indices used: j is independently 0, 1, 2 or 3, preferably 0, 1 or 2, for each occurrence; h is independently 0, 1, 2, 3 or 4 on each occurrence, preferably 0, 1 or 2;
  • I is independently 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2.
  • the group Ar is selected identically or differently for each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, Pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which can be substituted with one or more radicals R, preferably phenyl, biphenyl, fluorene, dibenzofuran, triphenylene, indolocarbazole.
  • the group L 1 represents a bond, identically or differently, or is selected from structures of the formulas (L 1 -1) to (L 1 -22),
  • R has the meaning mentioned above, in particular for formula (I), and the dashed bond marks the binding position.
  • the sum of the indices i, j and h in structures of the formulas (L 1 -1) to (L 1 - 22) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2.
  • the group Q does not comprise any carbazole group, preferably no carbazole group and/or no substituents of the formula N(Ar')2, N(R 1 )2 and particularly preferably no hole transport group.
  • the group L 1 does not comprise any carbazole group, preferably no carbazole group and/or no substituents of the formula N(Ar')2, N(R 1 )2 and particularly preferably no hole transport group.
  • Compounds in which the groups L 1 and/or Q do not include a hole transport group are particularly suitable as electron injection materials, electron transport materials or Hole blocking material used in a corresponding layer, which layer generally does not contain any emitting compound.
  • the group L 1 comprises a hole transport group, preferably a carbazole group and/or a substituent of the formula N(Ar')2, and particularly preferably a carbazole group.
  • the group Q comprises a hole transport group, preferably a carbazole group and/or a substituent of the formula N(Ar')2, and particularly preferably a carbazole group.
  • Compounds in which the groups L 1 and/or Q comprise a hole transport group are particularly suitable as host materials that are used in combination with an emitting compound.
  • Hole transport groups are well known in the art. These include, in particular, di- or triarylamine groups, carbazole groups and groups with similar properties.
  • the compounds according to the invention comprise a structure of the formulas (II-1) to (II-44), whereby the compounds according to the invention can be particularly preferably selected from the compounds of the formulas (II-1) to (II-44),
  • X represents N, CR, or C, either identically or differently, in the event that a group binds to the structure
  • X I stands, identically or differently, for N or CR d , preferably for N;
  • X 2 represents N or CR d , preferably CR d ;
  • Y represents 0, S, NR or C(R)2, preferably 0, NR or C(R)2; and Y 1 represents 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2.
  • structures A/compounds of the formulas (11-1), (II-2), (II-3), (II-6), (II-7), (11-12), (11-17), ( 11-18), (II-23), (II-28), (II-29), (II-34), (II-39) and (II-40) preferred and structures A/compounds of the formulas (11- 1), (II-6), (II-7), (II-12) and (II-34) are particularly preferred.
  • the compounds according to the invention comprise a structure of the formulas (111-1) to (III-48), whereby the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (111-1) to (III-48),
  • Y is 0, S, NR or C(R)2, preferably 0, NR or C(R)2;
  • Y 1 is 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2; n is independently 0, 1, 2 or 3 on each occurrence, preferably 0, 1 or 2; m is independently 0, 1, 2, 3 or 4 on each occurrence, preferably 0, 1 or 2.
  • the sum of the indices m and n can be at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.
  • the radical R, Ra , Rc , Rd does not comprise an aromatic or heteroaromatic ring system which has three linearly fused aromatic 6 rings, preferably none of the radicals R, Ra , Rc , R d comprises an aromatic or heteroaromatic ring system which has three linearly fused aromatic 6-rings.
  • the radical R, Ra , Rc , Rd does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings fused together, preferably none of the radicals R, Ra , Rc , Rd comprises an aromatic or heteroaromatic ring system which has three aromatic 6-rings fused together. Furthermore, it can particularly preferably be provided that the group L1 does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings fused together.
  • the group Q does not comprise an aromatic or heteroaromatic ring system which has three aromatic rings fused together.
  • the group Ar does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings fused together.
  • the compound does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings fused together.
  • At least two, preferably adjacent, radicals R, R d form a fused ring with the further groups to which the two radicals R, R d bind, the two radicals R, R d form at least one structure of the formulas (RA-1) to (RA-12).
  • Formula RA-10 Formula RA-11 Formula RA-12 where R 1 has the meaning set out above, the dashed bonds represent the attachment points to the atoms of the groups to which the two radicals R, R d are bound, and the other symbols have the following meaning:
  • Structures of the formulas RA-1, RA-3, RA-4 and RA-5 are preferred and structures of the formulas RA-4 and RA-5 are particularly preferred.
  • Formula RA-4a Formula RA-4c wherein the dashed bonds represent the attachment points to the atoms of the groups to which the two radicals R, R d bind, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the symbols R 1 , R 2 , R f and the indices s and t have the meaning set out above, in particular for formula (I) and/or formulas (RA-1) to (RA-12).
  • At least two, preferably adjacent, radicals R, R d preferably form a fused ring with the further groups to which the two radicals R, R d bind, the two radicals R, R d having structures of the formula (RB ) to form
  • Formula RB where R 1 has the meaning given above, in particular for formula (I), the dashed bonds represent the connection points via which the two radicals R, R d bind, the index m 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 4 is C(R 1 )2, NR 1 , NAr', BR 1 , BAr', O or S, preferably C(R 1 )2, NAr' or O, particularly preferably C (R 1 )2 or 0, where Ar' has the meaning given above, in particular for formula (I).
  • the at least two radicals R, R d form the structures of the formula (RB) and form a fused ring, represent radicals R, R d from neighboring groups X, X 2 or represent radicals R, R d , which each bind to neighboring carbon atoms, these carbon atoms preferably being connected via a bond.
  • the sum of the indices r, s, t, v, m and n is preferably 0, 1, 2 or 3, particularly preferably 1 or 2.
  • the compounds particularly preferably comprise at least one structure of the formulas (IV-1) to (IV-4); particularly preferred are the
  • Formula (IV-3) Formula (IV-4) where the symbols R, R a , R b , R c and R d have the meanings mentioned above, in particular for formula (I), the symbol o for the condensation sites of the at least one fused ring and the following applies to the other indices used: i is independently 0, 1 or 2, preferably 0 or 1, for each occurrence.
  • the fused ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to ( RA-4f) and/or (RB) is formed, as shown above, preferably formed by structures of the formulas (RA-1) to (RA-12) and/or (RA-1a) to (RA-4f). is. It can preferably be provided that the compounds have at least two fused rings, with at least one fused ring formed by structures of the formulas (RA-1) to (RA-12) and/or (RA-1a) to (RA-4f). and another ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB).
  • the substituents R, R c , R d , R e and R 1 according to the above formulas are not connected to the ring atoms of the ring system to which the substituents R, R c , R d , R e and R 1 bond form a fused aromatic or heteroaromatic ring system.
  • radicals R a , R b , R c preferably do not form a ring system with other groups. If substituents R a form a ring system with one another, this ring is preferably formed from exactly two radicals R a which are bonded to a carbon atom.
  • the compound according to the invention is substituted with aromatic or heteroaromatic groups R, R c , R d , Re , R 1 or R 2 , it is preferred if these do not contain any aryl or heteroaryl groups with more than two aromatic groups condensed directly to one another Have six-membered rings.
  • the substituents particularly preferably have no aryl or heteroaryl groups with six-membered rings fused directly to one another. This preference is due to the low triplet energy of such structures.
  • Fused aryl groups with more than two aromatic six-membered rings fused directly to one another which are nevertheless also suitable according to the invention, are phenanthrene and triphenylene, since these also have a high triplet level.
  • radical R, R c , R d , Re , R 1 or R 2 does not comprise an aromatic or heteroaromatic ring system which has three linearly fused aromatic 6 rings, preferably none of the radicals R being an aromatic one or heteroaromatic ring system which has three linearly fused aromatic 6-rings.
  • the group Z a , L 1 -Q, L 1 -N(Ar)2 can form a continuous conjugation with the group to which the group Z a , L 1 -Q, L 1 -N(Ar)2 is bonded according to formula (I) or the preferred embodiments of this formula.
  • a continuous conjugation of the aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings.
  • a further link between the aforementioned conjugated groups, which occurs for example via an S, N or O atom or a carbonyl group, does not harm a conjugation.
  • the substituents R, R c , R d , R e and R 1 according to the above formulas do not form a fused aromatic or heteroaromatic ring system, preferably not a fused ring system, with the ring atoms of the ring system.
  • two radicals which can in particular be selected from R, R c , R d , Re , R 1 and/or R 2 , form a ring system together, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic .
  • the residues that form a ring system with one another can be adjacent, that is, these residues are bonded to the same carbon atom or to carbon atoms that are directly bonded to one another, or they can be further apart from one another.
  • the ring systems provided with the substituents R, R d , Re , R 1 and/or R 2 can also be connected to one another via a bond, so that ring closure can be brought about in this way.
  • At least one radical R, R d is the same or different on each occurrence and is selected from the group consisting of a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-76, preferably the substituents R, R d either form a condensed ring, preferably according to the structures of the formulas (RA-1) to (RA-12) or (RB) or the substituent R, R d , R e is selected identically or differently on each occurrence from the group consisting of an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-76, and/or the group Ar' is selected identically or differently on each occurrence from the groups of the following formulas Ar-1 to Ar-76,
  • Ar 1 is, identically or differently at each occurrence, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which may each be substituted by one or more radicals R 1 ;
  • the substituent R 1 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 .
  • this substituent R 1 is the same or different distinguished each occurrence for an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 18 aromatic ring atoms, which has no fused aryl groups and which has no fused heteroaryl groups in which two or more aromatic or heteroaromatic 6 -Ring groups are fused directly to one another, and which can also be substituted by one or more radicals R 2 .
  • Phenyl, biphenyl, terphenyl and quaterphenyl are preferred.
  • Triazine, pyrimidine and quinazoline, as listed above for Ar-47 to Ar-50, Ar-57 and Ar-58, are also preferred, although these structures can be substituted by one or more radicals R 2 instead of R 1 .
  • the substituents R 1 which are bonded to this carbon atom are preferably identical or different on each occurrence and represent a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2 .
  • R 1 is very particularly preferably a methyl group or a phenyl group.
  • the radicals R 1 can also form a ring system with one another, resulting in a spiro system.
  • R, R d is selected from the group consisting of H, D, F, CN, NO2, Si(R 1 )s, B(OR 1 )2, a straight chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, where the alkyl group can in each case be substituted with one or more radicals R 1 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms , preferably with 5 to 40 aromatic ring atoms, which can each be substituted by one or more radicals R 1 .
  • substituent RR d is the same or different each time it occurs, selected from the group consisting of H, D, F, a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C -Atoms, where the alkyl group can each be substituted with one or more radicals R 1 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each represented by one or more radicals R 1 can be substituted.
  • At least one radical R, R d preferably a substituent R, R d, which is the same or different in each occurrence, is selected from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted with one or more radicals R 1 , or a group N(Ar')2, particularly preferably at least one substituent R, R d is the same or different in each occurrence and is selected from the group consisting of an aromatic or heteroaromatic ring system 6 to 30 aromatic ring atoms, which can be substituted with one or more radicals R 1 , or a group N(Ar')2.
  • At least one substituent R, R d is selected from the group consisting of an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted with one or more radicals R 1 .
  • the substituents R, R d either form a ring according to the structures of the formulas (RA-1) to (RA-12), (RA-1 a) to (RA-4f) or (RB) or the substituent R, R d is the same or different at each occurrence selected from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more radicals R 1 , or one Group N(Ar')2.
  • the radical R, R d is preferably the substituent R, R d, identical or different in each occurrence, selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic Ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, which can each be substituted with one or more radicals R 1 .
  • At least one radical R, R d , R e represents an aromatic or heteroaromatic ring system with 5 to 13 aromatic ring atoms, which can be substituted with one or more radicals R 1 .
  • At least one radical, preferably a substituent R, R d , R e is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which each have one or more R 1 radicals.
  • the term substituent means in particular that R is not H.
  • the substituents R can be the same or different if two or more substituents are present which are selected from the aromatic or heteroaromatic group mentioned.
  • the groups R a bonded to a carbon atom are selected from straight-chain alkyl groups with 1 to 10 carbon atoms or branched or cyclic alkyl groups with 3 to 10 carbon atoms, each with one or more radicals R 2 can be substituted, preferably deuterated, in which case two or more, preferably adjacent substituents R a can form a ring system with one another. If adjacent substituents R a form a ring system with one another, this ring is preferably formed from exactly two radicals R a .
  • the groups R a bonded to a carbon atom are selected from aromatic or heteroaromatic ring systems with 5 to 20 aromatic ring atoms, which can each be substituted by one or more radicals R 2 , preferably represent phenyl groups, each of which can be substituted by one or more radicals R 2 , preferably deuterated, in which case two or more, preferably adjacent substituents R a can form a ring system with one another. If adjacent substituents R a form a ring system with one another, this ring is preferably formed from exactly two radicals R a .
  • the group R a stands for methyl, ethyl, propyl, phenyl or two groups R a that bind to the same C atom form a cycloalkyl radical with 5 or 6, preferably 5 carbon atoms, the group R a preferably represents methyl, whereby these groups can be deuterated
  • the group R b stands for methyl, ethyl, propyl or two groups R b which are bonded to the same C atom form a cycloalkyl radical having 5 or 6, preferably 5 carbon atoms, where the group R b preferably stands for H, D, methyl, ethyl, propyl, where these groups can be deuterated, where the group R b particularly preferably stands for H or D.
  • the group R c can be H, D, methyl, ethyl, propyl, where these groups can be deuterated, where the group R c can preferably be H or D.
  • R f is the same or different for each occurrence and is selected from the group consisting of a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, where the alkyl group each can be substituted with one or more R 1 radicals, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which can each be substituted by one or more R 2 radicals.
  • R f is the same or different each time it occurs, selected from the group consisting of a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, where the alkyl group in each case can be substituted with one or more radicals R 2 , an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted with one or more radicals R 2 .
  • R f is selected from the same or different for each occurrence Group consisting of a straight-chain alkyl group with 1 to 5 carbon atoms or a branched or cyclic alkyl group with 3 to 5 carbon atoms, where the alkyl group can in each case be substituted with one or more radicals R 2 or with an aromatic or heteroaromatic ring system 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, which can each be substituted with one or more R 2 radicals.
  • R f is selected the same or differently for each occurrence from the group consisting of a straight-chain alkyl group with 1 to 6 carbon atoms or a cyclic alkyl group with 3 to 6 carbon atoms, where the alkyl group in each case may be substituted by one or more R 2 radicals, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals; Two radicals R f can also form a ring system together.
  • R f is selected the same or differently for each occurrence from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, where the alkyl group can each be substituted with one or more R 2 radicals, but is preferably unsubstituted, or an aromatic ring system with 6 to 12 aromatic ring atoms, in particular with 6 aromatic ring atoms, each of which is replaced by one or more, preferably non-aromatic, radicals R 2 may be substituted, but is preferably unsubstituted; Two radicals R f can form a ring system together.
  • R f is selected identically or differently for each occurrence from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms, or a branched alkyl group with 3 to 6 carbon atoms.
  • R f represents a methyl group or a phenyl group, where two phenyl groups together can form a ring system, with a methyl group being preferred over a phenyl group.
  • Preferred aromatic or heteroaromatic ring systems for which the substituents R, R c , R d , Re, R f or Ar or Ar' stand, are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl , in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position can, spirobifluorene, which can be linked via the 1 -, 2-, 3- or 4-position, naphthalene, in particular 1 - or - linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which can be linked via the 1 -, 2-, 3 or 4 position, dibenzofuran, which can be linked via the 1, 2, 3 or 4 position, dibenz
  • the structures Ar-1 to Ar-76 listed above are particularly preferred, with structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), ( Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-76) preferred and structures of the formulas (Ar-1), (Ar-2) , (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred.
  • R 1 substituents
  • these substituents R 1 are to be replaced by R and in the case of R f , these substituents R 1 are to be replaced by R 2 .
  • R, R d , R e are groups of the formula -Ar 4 -N(Ar 2 )(Ar 3 ), where Ar 2 , Ar 3 and Ar 4 are the same or different in each occurrence for an aromatic or heteroaromatic ring system 5 to 24 aromatic ring atoms, which can each be substituted with one or more radicals R 1 .
  • the total number of aromatic ring atoms of Ar 2 , Ar 3 and Ar 4 is a maximum of 60 and preferably a maximum of 40.
  • Ar 4 and Ar 2 can be connected to one another and/or Ar 2 and Ar 3 to one another also by a group selected from C(R 1 )2, NR 1 , O or S.
  • Ar 4 and Ar 2 are preferably linked to one another or of Ar 2 and Ar 3 with each other ortho to the position of the connection with the nitrogen atom.
  • none of the groups Ar 2 , Ar 3 or Ar 4 are connected to one another.
  • Ar 4 is preferably an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, which can each be substituted with one or more R 1 radicals.
  • Ar 4 is particularly preferably selected from the group consisting of ortho-, meta- or para-phenylene or ortho-, meta- or para-biphenyl, which can each be substituted by one or more radicals R 1 but are preferably unsubstituted.
  • Ar 4 is very particularly preferably an unsubstituted phenylene group.
  • Ar 2 and Ar 3 are preferably the same or different in each occurrence as an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which can each be substituted with one or more R 1 radicals.
  • Particularly preferred groups Ar 2 and Ar 3 are identical or different in each occurrence, selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta -, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene , 1 -, 2-
  • Ar 2 and Ar 3 are identical or different in each occurrence, selected from the group consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched ter - phenyl, quaterphenyl, especially ortho-, meta-, para- or branched quaterphenyl, fluorene, especially 1-, 2-, 3- or 4-fluorene, or spirobifluorene, especially 1-, 2-, 3- or 4 -Spirobifluorene.
  • R 1 is the same or different each time it occurs, selected from the group consisting of H, D, F, CN, a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, where the alkyl group can each be substituted with one or more radicals R 2 , or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which can each be substituted by one or more R 2 radicals.
  • R 1 is the same or different each time it occurs, selected from the group consisting of H, a straight-chain alkyl group with 1 to 6 carbon atoms, in particular with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, where the alkyl group can be substituted with one or more R 2 radicals, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which is replaced by one or several radicals R 5 can be substituted, but is preferably unsubstituted.
  • R 2 is H, an alkyl group with 1 to 4 carbon atoms or an aryl group with 6 to 10 carbon atoms, which is substituted with an alkyl group with 1 to 4 carbon atoms can be, but is preferably unsubstituted.
  • the alkyl groups preferably have not more than five carbon atoms, particularly preferably not more than 4 carbon atoms, very particularly preferably not more than 1 carbon atom.
  • the compounds of formula (I) or the preferred embodiments are used as a matrix material for a phosphorescent emitter or in a layer that is directly adjacent to a phosphorescent layer, it is further preferred if the compounds dung does not contain any fused aryl or heteroaryl groups in which more than two six-membered rings are fused directly to one another.
  • An exception to this are phenanthrene and triphenylene, which can be preferred due to their high triplet energy despite the presence of fused aromatic six-membered rings.
  • the compound comprises exactly two or exactly three structures according to formula (I).
  • the compounds are selected from compounds of the formula (D-1),
  • L 2 represents a bond or an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which is represented by one or more radicals R can be substituted, but is preferably unsubstituted, where R can have the meaning mentioned above, in particular for formula (I).
  • L 2 particularly preferably represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, which can in each case be substituted by one or more R 1 radicals, but is preferably unsubstituted, where R 1 is the can have the meaning mentioned above, in particular for formula (I).
  • the symbol L 2 set out, among other things, in formula (D1) stands, identically or differently, in each occurrence for a bond or an aryl or heteroaryl radical with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so on that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.
  • the group L 2 set out in formula (D1) comprises an aromatic ring system with at most four, preferably at most three, particularly preferably at most two fused aromatic and / or heteroaromatic 6-rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and/or dibenzothienyl structures are preferred over naphthyl structures.
  • Suitable aromatic or heteroaromatic ring systems L 2 are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, which can each be substituted by one or more radicals R 1 but are preferably unsubstituted.
  • a compound according to the invention is represented by at least one of the structures according to formulas (I), (1-1) to (I-4), (11-1) to (II-44), (111-1) to (III -48) and/or (IV-1) to (IV-4) can be displayed.
  • compounds according to the invention preferably comprising structures according to formulas (I), (1-1) to (I-4), (11-1) to (II-44), (111-1) to (III-48) and/or or (IV-1) to (IV-4) a molecular weight of less than or equal to 5000 g/mol, preferably less than or equal to 4000 g/mol, particularly preferably less than or equal to 3000 g/mol, particularly preferably less than or equal to 2000 g/mol mol, more particularly preferably less than or equal to 1200 g/mol and most preferably less than or equal to 900 g/mol.
  • preferred compounds according to the invention are characterized by the fact that they can be sublimated. These compounds generally have a molecular weight of less than approximately 1200 g/mol.
  • the compound does not contain any alkoxy, thioalkoxy or hydroxy groups.
  • the compound does not comprise a cyclobutyl radical with two oxygen atoms bonded to this cyclobutyl radical.
  • the compound does not contain any thiadiazyl group.
  • the ratio of electron transport groups, preferably pyrimidine, triazine, quinazoline and/or quinoxaline groups, to phenyl groups to which two cyclopentyl radicals are condensed is at least 0.6, preferably at least 0.8, particularly preferably at least 0.9. Furthermore, it can be provided that the ratio of electron transport groups, preferably pyrimidine, triazine, quinazoline and/or quinoxaline groups, to phenyl groups to which two cyclopentyl radicals are condensed, is at most 10, preferably at most 4, particularly preferably at most 1.5.
  • the compound comprising structures according to formula (I), preferably the compound according to formula (I) or a preferred embodiment of this structure/compound is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.
  • the basic structure of the compounds according to the invention can be represented in the ways outlined in the following schemes.
  • the individual synthesis steps such as coupling reactions that lead to C-C bonds and/or C-N bonds, are in principle known to those skilled in the art. These include, among others, reactions according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA.
  • the compounds according to the invention with electron transport groups in particular compounds comprising structures according to formula (I) can be obtained starting from phenyl compounds (1) to which a cyclopentyl group, preferably two cyclopentyl groups, is/are fused, by the following synthetic routes:
  • Heterocycle X-HetAr Heterocycle X-HetAr
  • R alkyl, aryl
  • X H, D, alkyl, aryl, Br can be represented.
  • the reaction sequence 1) or 2) can be repeated consecutively, so that compounds according to the invention which are symmetrically or asymmetrically di-substituted with -NAr2 or -Ar-NAr2 groups are obtained.
  • the scheme (1) is to be understood as an example, so that other groups X are also suitable, as set out in the examples.
  • a further subject of the present invention is therefore a process for producing a compound according to the invention, wherein a phenyl compound to which a cyclopentyl group, preferably two cyclopentyl groups, is/are fused is synthesized and at least one aromatic or heteroaromatic radical is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.
  • the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1 H-NMR and/or HPLC).
  • the compounds according to the invention can also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is possible in particular with compounds which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization preferably takes place via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups.
  • the compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.
  • the invention therefore also provides oligomers, polymers or dendrimers containing one or more of the structures of the formula (I) listed above and preferred embodiments of this formula or compounds according to the invention, where one or more bonds of the compounds according to the invention or the structures of the formula (I) and preferred embodiments of this formula for the polymer, oligomer or dendrimer are present. Depending on the linkage of the structures of formula (I) and preferred embodiments of this formula or the compounds, these therefore form a side chain of the Oligomers or polymers or are linked in the main chain.
  • the polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic. The same preferences as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units according to formula (I) or the preferred embodiments set out above and below are present in 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%.
  • Suitable and preferred comonomers which form the polymer skeleton are selected from fluorenes (e.g. according to EP 842208 or WO 2000/022026), spirobifluorenes (e.g. according to EP 707020, EP 894107 or WO 2006/061181), para- phenylenes (e.g.
  • WO 92/18552 carbazoles (e.g. according to WO 2004/070772 or WO 2004/113468), thiophenes (e.g. according to EP 1028136), dihydrophenanthrenes (e.g. according to WO 2005/014689), cis- and trans-indenofluorenes (e.g. according to WO 2004/041901 or WO 2004/113412), ketones (e.g. according to WO 2005/040302), phenanthrenes (e.g. according to WO 2005 /104264 or WO 2007/017066) or several of these units.
  • the polymers, oligomers and dendrimers can contain further units, for example hole transport units, in particular those based on triaryl amines, and/or electron transport units.
  • compounds according to the invention which are characterized by a high glass transition temperature are also of particular interest.
  • compounds according to the invention are particularly preferred, comprising structures according to the formula (I) or the preferred embodiments set out above and below, which have a glass transition temperature of at least 70 ° C, particularly preferably of at least 110 ° C, very particularly preferably of at least 125 ° C and particularly preferably at least 150 ° C, determined according to DIN 51005 (version 2005-08).
  • Formulations of the compounds according to the invention are required for processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene , (-)-Fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methyl-naphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4 -Methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene
  • a further subject of the present invention is therefore a formulation or a composition containing at least one compound according to the invention and at least one further compound.
  • the further compound can be, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation.
  • the further compound can also be at least one further organic or be an inorganic compound that is also used in the electronic device, for example an emitting compound and / or another matrix material.
  • At least one further compound is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters showing TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials and hole blocking materials, preferably host materials.
  • a further subject of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • the compounds according to the invention are used in an electronic device as host material, electron transport material, electron injection material or hole blocking material.
  • An electronic device containing at least one compound according to the invention.
  • An electronic device in the sense of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or layers that are made entirely of inorganic materials.
  • Particularly preferred electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, sOLED, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting Diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field effect Transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices ( O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLED
  • the organic electroluminescent device includes cathode, anode and at least one emitting layer. In addition to these layers, it can also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. Likewise, interlayers can be introduced between two emitting layers, which, for example, have an exciton-blocking function. However, it should be noted that not every one of these layers necessarily has to be present.
  • the organic electroluminescence device can contain an emitting layer, or it can contain several emitting layers.
  • emission layers they preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie different emitting compounds that can fluoresce or phosphorescent are used in the emitting layers. Systems with three emitting layers are particularly preferred, with the three layers showing blue, green and orange or red emission.
  • the organic electroluminescence device according to the invention can also be a tandem electroluminescence device, in particular for white-emitting OLEDs.
  • the compound according to the invention can be used in different layers, depending on the exact structure.
  • an organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments set out above in an emitting layer as a matrix material for phosphorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters.
  • the compound according to the invention can also be used in an electron transport layer and/or in a hole blocking layer.
  • the compound according to the invention is particularly preferably used as a matrix material for phosphorescent emitters, in particular for red, orange, blue, green or yellow, preferably for blue or green phosphorescent emitters, in an emitting layer, as a host material, electron transport material, electron injection material or hole blocking material.
  • the organic electroluminescence device comprises at least one emission layer and at least one electron transport layer and the electron transport layer contains the compound according to the present invention.
  • the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
  • phosphorescence is understood to mean luminescence from an excited state with a higher spin multiplicity, i.e. a spin state > 1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes should be viewed as phosphorescent compounds.
  • the mixture of the compound according to the invention and the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60 % by volume, in particular between 95 and 80% by volume, of the compound according to the invention based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter, based on the total mixture Emitter and matrix material.
  • the compound according to the invention is used as the only matrix material (“single host”) for the phosphorescent emitter.
  • a further embodiment of the present invention is the use of the compound according to the invention as a matrix material for a phosphorescent emitter in combination with another matrix material.
  • Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g. B.
  • CBP N,N-biscarbazolylbiphenyl
  • CBP CBP (N,N-biscarbazolylbiphenyl) or those in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, e.g. B. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, e.g. B.
  • bipolar matrix materials e.g. B. according to WO 2007/137725
  • silanes e.g. B. according to WO 2005/111172
  • azaboroles or boron esters e.g. B. according to WO 2006/117052
  • triazine derivatives e.g. B. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877
  • zinc complexes e.g. B.
  • diazasilol or tetra-azasilol derivatives e.g. B. according to WO 2010/054729
  • diazaphosphole derivatives e.g. B. according to WO 2010/054730
  • bridged carbazole derivatives e.g. B. according to WO 2011/042107, WO 2011/060867, WO 2011/088877 and WO 2012/143080
  • triphenylene derivatives e.g. B. according to WO 2012/048781
  • dibenzofuran derivatives e.g. B. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565 or biscarbazoles, e.g. B. according to JP 3139321 B2.
  • another phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present as a co-host in the mixture. Particularly good results are achieved if a red phosphorescent emitter is used as the emitter and a yellow phosphorescent emitter is used as the cohost in combination with the compound according to the invention.
  • a compound can be used as co-host that does not participate or does not participate to a significant extent in charge transport, as described, for example, in WO 2010/108579.
  • compounds which have a large band gap and do not themselves participate in the charge transport of the emitting layer, or at least not to a significant extent are suitable as co-matrix material.
  • Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680.
  • compounds according to the invention without special functional groups, for example hole transport groups and/or electron transport groups have advantageous properties.
  • Particularly suitable phosphorescent compounds are compounds which, when stimulated appropriately, emit light, preferably in the visible range, and also at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 contain, especially a metal with this atomic number.
  • Compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used as phosphorescence emitters, in particular compounds which contain iridium or platinum.
  • Examples of the emitters described above can be found in the applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 20 05/ 0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/1 02709, WO 2011/032626, WO 2011/ 066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/10 4045, WO 2015/117718, WO 2016/ 015815, WO 2016/124304, WO 2017/03
  • Examples of phosphorescent dopants are listed in the following table.
  • the compounds according to the invention are particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, such as those used, for example.
  • B. in WO 98/24271, US 2011/0248247 and US 2012/0223633 are described.
  • an additional blue emission layer is vapor-deposited over the entire surface of all pixels, even those with a color other than blue.
  • the organic electroluminescence device does not contain a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, ie the emitting layer is directly adjacent to the hole injection layer or the anode, and/or the emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described for example in WO 2005/053051.
  • a metal complex that is the same or similar to the metal complex in the emitting layer directly adjacent to the emitting layer as a hole transport or hole injection material, such as. B. described in WO 2009/030981.
  • an organic electroluminescence device characterized in that one or more layers are coated using a sublimation process.
  • the materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10'7 mbar.
  • An organic electroluminescence device is also preferred, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation.
  • the materials are applied at a pressure between 10' 5 mbar and 1 bar.
  • OVPD Organic Vapor Phase Deposition
  • OVJP Organic Vapor Jet Printing
  • an organic electroluminescence device characterized in that one or more layers of solution, such as. B. by spin coating, or with any printing process, such as. B. Screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • any printing process such as. B. Screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • Formulations for applying a compound according to formula (I) or its preferred embodiments set out above are new.
  • a further subject of the present invention is therefore a formulation containing at least one solvent and a compound according to formula (I) or its preferred embodiments set out above.
  • hybrid processes are possible in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.
  • the compounds according to the invention and the organic electroluminescence devices according to the invention are distinguished from the prior art in particular by a low refractive index (Refractive Index RI). Furthermore, these compounds and the organic electroluminescent devices obtainable from them have an improved service life. The other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least equally good. In another variant The compounds according to the invention and the organic electroluminescent devices according to the invention are characterized in particular by improved efficiency and/or operating voltage and a longer service life compared to the prior art.
  • the electronic devices according to the invention are characterized by one or more of the following surprising advantages over the prior art:
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials, have excellent efficiency.
  • compounds according to the invention according to formula (I) or the preferred embodiments set out above and below bring about a low operating voltage when used in electronic devices.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials, have a very good service life. In particular, these connections cause a low roll-off, i.e. a small drop in the power efficiency of the device at high luminances.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to Formula (I) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials, have very low refractive indices.
  • optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by a high PL and therefore high EL efficiency of emitters and an excellent energy transfer from the matrices to dopants.
  • the following syntheses are carried out under an inert gas atmosphere in dried solvents.
  • the metal complexes are also handled in the absence of light or under yellow light.
  • the solvents and reagents can, for. B. can be obtained from Sigma-ALDRICH or ABCR.
  • the respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have multiple enantiomeric, diastereomeric or tautomeric forms, one form is shown as a representative.
  • the yields depend on the steric demands of the LS1 to LS8, whereby the following descending series is typically observed: LS1 ⁇ LS2 ⁇ LS3 > LS4 > LS5 ⁇ LS6 ⁇ LS7 ⁇ LS8.
  • the heteroaryl-halogen coupling partners below, they are typically in the range of 25-50% for chlorides, in the range of 40-60% for bromides and in the range of 50-70% for iodides.
  • N ( Br— ⁇ ,N N ⁇
  • OLEDs according to the invention and OLEDs that serve as a reference is carried out according to a general process according to WO 2004/058911, which is adapted to the circumstances described here (layer thickness variation, materials used).
  • the compounds according to the invention can be used in the hole injection layer (HIL), hole transport layer (HTL) and in the electron blocking layer (EBL). All materials are thermally vapor deposited in a vacuum chamber.
  • the emission layer (EML) always consists of at least one matrix material (host material, host material) SMB (see Table 1) and an emitting dopant (dopant, emitter) D, which is added to the matrix material or materials by co-evaporation in a certain volume fraction is mixed in.
  • SMB:D 97:3%
  • the electron transport layer can also consist of a mixture of two materials, see Table 1.
  • the materials used to produce the OLEDs are shown in Table 5 or refer to the synthesis examples presented above.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) are calculated as a function of the luminance from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic and the service life are determined.
  • the EQE is specified in (%) and the voltage in (V) at a luminance of 1000 cd/m 2
  • the service life is determined at a starting luminance of 10,000 cd/m 2 .
  • the measured time in which the brightness of the reference fell to 80% of the initial brightness is set to 100%.
  • the service life of the OLED components containing the compounds according to the invention is given in percent for reference.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • Electron blocking layer see Table 1
  • Emission layer see Table 1
  • HBL Hole blocking layer
  • ETL Electron transport layer
  • Electron injection layer made of ETM2, 1 nm
  • the compounds A according to the invention can be in the hole injection layer (HIL); the hole transport layer (HTL), the electron blocking layer (EBL) and in the emission layer (EML) as matrix material (host material, host material) M (see Table 5) or A (see materials according to the invention).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EML emission layer
  • all materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer always consists of at least one or more Matrix materials M and a phosphorescent dopant Ir, which is added to the matrix material or materials by co-evaporation in a certain volume fraction.
  • a specification like M1 :M2:lr 55%:35%:10%) means that the material M1 is in a volume fraction of 55%, M2 in a volume fraction of 35% and Ir in a volume fraction of 10% in the layer is present.
  • the electron transport layer can also consist of a mixture of two materials.
  • the exact structure of the OLEDs can be found in Table 3. The materials used to produce the OLEDs are shown in Table 5 or refer to the synthesis examples presented previously.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic, as well as the service life.
  • the EQE in (%) and the voltage in (V) are given at a luminance of 1000 cd/m 2.
  • the service life is determined at an initial luminance of 1000 cd/m 2 for blue and red and 10000 cd/m 2 for green and yellow.
  • the measured time in which the brightness of the reference has dropped to 80% of the initial brightness is set to 100%.
  • the lifetime of the OLED components containing the compounds according to the invention is given in percent to the respective analogously constructed reference or, when using the compounds according to the invention as matrix material, to the component containing Ref-ETM2 in the ETL and HBM2 in the HBL.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer made of HTM1, 180 nm for blue, 50 nm for green, yellow and red
  • Electron blocking layer see Table 3
  • Emission layer see Table 3
  • HBL Hole blocking layer
  • Electron transport layer see Table 3
  • Electron injection layer made of ETM2, 1 nm
  • Aluminium cathode 100 nm
  • BP11 50%:50% 0 nm (30%: 6 ) 2 5%: 5%) 5 nm 25 nm 30 nm

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des hétérocycles contenant de l'azote qui sont appropriés pour être utilisés dans des dispositifs électroniques, et adaptés pour des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant ces hétérocycles.
EP23772882.9A 2022-09-22 2023-09-20 Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques Pending EP4590653A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22197219 2022-09-22
PCT/EP2023/075882 WO2024061948A1 (fr) 2022-09-22 2023-09-20 Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques

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EP4590653A1 true EP4590653A1 (fr) 2025-07-30

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KR (1) KR20250075641A (fr)
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KR20250075641A (ko) 2025-05-28

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