WO2016116524A2 - Molécules organiques à utiliser dans des composants optoélectroniques - Google Patents

Molécules organiques à utiliser dans des composants optoélectroniques Download PDF

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WO2016116524A2
WO2016116524A2 PCT/EP2016/051166 EP2016051166W WO2016116524A2 WO 2016116524 A2 WO2016116524 A2 WO 2016116524A2 EP 2016051166 W EP2016051166 W EP 2016051166W WO 2016116524 A2 WO2016116524 A2 WO 2016116524A2
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substituted
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formula
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WO2016116524A3 (fr
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David Ambrosek
Michael Danz
Harald FLÜGGE
Jana Friedrichs
Tobias Grab
Andreas Jacob
Stefan Seifermann
Daniel Volz
Liaptsis GEORGIOS
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Cynora Gmbh
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Definitions

  • the invention relates to purely organic, biphenyl-type molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic components.
  • OLED organic light-emitting diodes
  • OLEDs are usually realized in layer structures, which consist predominantly of organic materials.
  • layer structures consist predominantly of organic materials.
  • FIG. 1 The heart of such components is the emitter layer, in which usually emitting molecules are embedded in a matrix.
  • the energy contained in the excitons can be emitted by the corresponding emitters in the form of light, in this case speaking of electroluminescence.
  • An overview of the function of OLEDs can be found, for example, in H. Yersin, Top. Curr. Chem., 2004, 241, 1 and H. Yersin, "Highly Efficient OLEDs with Phosphorescent Materials”; Wiley-VCH, Weinheim, Germany, 2008.
  • a new generation of OLEDs is based on the utilization of delayed fluorescence (TADF: thermally activated delayed fluorescence or singlet harvesting).
  • TADF thermally activated delayed fluorescence or singlet harvesting
  • Cu (I) complexes can be used which, due to a small energy gap between the lowest triplet state ⁇ and the overlying singlet state Si (AE (Si-Ti)), can thermally recombine triplet exitones into a singlet state.
  • AE overlying singlet state Si
  • transition metal complexes purely organic molecules (without metal ion) can exploit this effect.
  • the invention relates to purely organic molecules which can be used in optoelectronic components.
  • Such organic molecules have a structure of the formula 1 or have a structure of the formula 1:
  • A, B, ⁇ ', B' monocyclic aromatic ring systems.
  • the nuclei (atoms) of the ring systems consist of carbon atoms.
  • B and A or B 'and A' form with each other linear, maximum of two single cycles, condensed systems which are connected only via a single single bond between A and A '.
  • a radical R' is bound to each carbon atom of the cores of the ring systems A, B, A 'and B', which is not part of two ring systems or via which does not take place the binding of A and A '.
  • a radical R' is bound.
  • rings A, B, A 'and B' all of the carbon atoms of the cores which are not part of two ring systems or which are not involved in the bonding of A and A 'are bonded to one R' ,
  • R ' is either a radical R * or a radical AF, containing at least two different chemical entities AF1 and AF2, each attached to rings A, B and A', B ', and wherein the at least two different chemical moieties AF1 and AF2 are bound to different rings A and A 'and A and B' and B and A 'and B and B', respectively.
  • the at least two different chemical units AF1 and AF2 are located on the different rings A and B and A 'and B', respectively. That is, if the chemical unit AF1 is attached in single or multiple number to the ring A or B, the different chemical unit AF2 must be connected in single or multiple number to the ring A 'and B' and vice versa.
  • R 3 is independently selected for each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H Atoms may be replaced by F or CF 3 ; two or more substituents R 3 may also together form a mono- or polycyclic, aliphatic ring system.
  • R is independently selected in each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H Atoms can be replaced by F or CF 3 ; two or more substituents R 8 may also together form a mono- or polycyclic, aliphatic ring system.
  • An aryl group in the sense of this invention contains 6 to 60 aromatic ring atoms;
  • a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are in particular N, O, and S. If other definitions are given in the description of the present invention, for example with regard to the number of aromatic ring atoms or the heteroatoms contained therein, these apply.
  • An aryl group or heteroaryl group is understood to mean a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example naphthalene, phenanthrene, quinoline or carbazole.
  • a condensed (fused) aromatic or heteroaromatic polycycle consists in the context of the present application of two or more fused simple aromatic or heteroaromatic cycles.
  • An aryl or heteroaryl group which may be substituted in each case by the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic compounds is understood in particular to mean groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrenes, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; Pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, isoquinoline
  • 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 context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are in particular selected from, N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups by a non-aromatic moiety (in particular less than 10% of the various atoms), such as, for example, a sp3-hybridized C, Si or N atom, an sp 2 -hybridized C, N or O atom or a sp-hybridized carbon atom, may be connected.
  • systems such as 9, 10-T-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc.
  • aromatic ring systems are also to be considered as aromatic ring systems in the art
  • systems in which two or more aryl groups are connected for example by a linear or cyclic alkyl, alkenyl or alkynyl groups or by a silyl group are understood as aromatic or heteroaromatic ring systems in the context of this invention, such as systems such as biphenyl, terphenyl or diphenyltriazine.
  • aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case with radicals as defined above and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, naphthalene , Anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenyls, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydro-pyrene, cis- or trans- indenofluorene, truxene, isotruxene, spirotruxene, spiroiso
  • AF Organic chemical entity (remainder). There are at least two different chemical entities AF1 and AF2 included. Provided that two different AFs always occur in one molecule, there can be at least two identical AFs in the molecule.
  • AF1 a first chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system);
  • AF2 a second chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system);
  • AF2 always has a lower (mathematical) HOMO value compared to AF1 (and correspondingly a lower LUMO number than AF1).
  • the possible chemical entities AF are limited to the structures listed in Table 1.
  • the chemical entities AF1 and AF2 are linked to one another such that the electronic communication between them is interrupted. This disruption is characterized by localization of the HOMO and LUMO frontier orbits on separate parts of the molecule, allowing for a charge-transfer transition.
  • the chemical units AF1 and AF2 are connected to one another via a separator such that the electronic communication between them is interrupted, which is characterized by the localization of the frontier orbitals HOMO and LUMO on separate parts of the molecule.
  • the separator may have any structure as long as an interruption of the electronic communication is ensured.
  • the energy values HOMO (AF1), HOMO (AF2), LUMO (AF1), LUMO (AF2) are calculated using the density functional theory (DFT), whereby the attachment positions of the chemical entities AF and the separators are saturated with a hydrogen atom corresponding to their chemical valences .
  • DFT density functional theory
  • the limits given refer to orbital energies in unit eV, which are calculated using the BP86 functional (Becke, AD Phys.Rev.A1988, 38, 3098-3100 and Perdew, JP Phys Rev. B1986, 33, 8822-8827).
  • the electronic communication between the two chemical entities AF1 and AF2 via conjugated bonds with an optional separator is disrupted when the frontier orbitals HOMO and LUMO are located on separate parts of the molecule, allowing for a charge-transfer transition.
  • the localization of the frontier orbitals HOMO or LUMO is determined using the density functional theory (DFT) with the BP86 functional (Becke, AD Phys.Rev.A1988, 38, 3098-3100, Perdew, JP Phys. Rev. B1986, 33, 8822-8827 ):
  • the single electron wave function calculates the single electron density by squaring and integrates it over the space occupied by the part of the molecule.
  • This space can be determined from the atomic coordinates and van der Waals radii of the atoms.
  • the resulting number corresponds to the proportion of orbital on the moiety.
  • a majority separation of the frontier orbitals corresponds to an overlap parameter O in the range of 0.1-20% to allow a charge-transfer transition.
  • ) b results from the integral over the entire space over the respective smaller value of the squared wave function:
  • the organic molecules have a structure of formula 2 or have a structure of formula 2, wherein the definitions given in formula 1 apply and the organic molecule has at least two different chemical units AF1 and AF2. Provided that two different AFs always occur in one molecule, additional AFs may be identical to the former.
  • n and m can each assume the values 0 and 1.
  • Molecules according to the invention result from substitution of the backbones by means of the chemical units AF1 and AF2.
  • the possible substitution patterns with AF1 are shown on a phenyl ring of formula 2-1. These can easily be applied to the second (unsubstituted) ring. The substitution patterns also apply to the second chemical entity AF2.
  • substitution patterns can also be applied to fused ring systems.
  • the monosubstitution on a naphthyl system is shown by way of example.
  • Further substitution patterns can be prepared by the person skilled in the art based on formulas 2-1 1 to 2-28.
  • the wavy line indicates the point of attachment to another aromatic ring system.
  • Molecules according to the invention result from the basic body (formulas 2-1 to 2-3) and the substitution patterns shown in formulas 2-1 1 to 2-35.
  • the substitution pattern 2-12 taking into account that at least two chemical units AF1 and AF2, wherein AF2 is always attached to the other ring system, must be included, resulting molecules according to the invention 2-36 bis 2-54:
  • additional AFs may be identical to the former.
  • the part of the organic molecule according to formula 1 or formula 2 which is not a chemical entity AF is also called a separator S.
  • the unit AF1 has a structure of the formula 1b or has a structure of the formula 1b
  • VG3 bridging group at each occurrence is independently O, S, CR **, C, an element-element single bond between X and Y or between X and K, where not 2 units VG3 simultaneously an element-element single bond between X and Y and between X and K; BR **, NR **, GeR ** 2 , AsR ** 2 , SiR ** 2 , where not two units
  • Z is independent of each other CR **, N at each occurrence;
  • V a maximum of three of these units are included
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • R * is defined as in Formula 1.
  • the attachment of the unit AF1 to the separator can be carried out only via a ring formed from C atoms, the connection via a heterocyclic ring is excluded.
  • the unit AF1 has a structure of the sub-formulas 1 .1 to 1 .7 or has a structure of the sub-formulas 1.1 to 1.7
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • the unit AF1 has a structure of the sub-formulas 1 .8 to 1 .10 or has a structure of the sub-formulas 1.8 to 1.10
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formula 1 .1 1 or has a structure of the sub-formula 1.1 1
  • U is CR **, N, where a maximum of 3 units U are N at the same time, and no adjacent units U are N at the same time;
  • Alk is methyl, ethyl, propyl / so-propyl, butyl, tert-butyl, pentyl, hexyl, 2-ethylhexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl;
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1 .12 to 1 .19 or has a structure of the sub-formulas 1.12 to 1.19
  • M is H, deuterium, alkyl, phenyl, pyridyl, CN, with a maximum of 4 units M simultaneously being CN, or denotes a chemical bond to a separator S, where exactly one M is a chemical bond to a separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1.20 to 1.21 or has a structure of the sub-formulas 1.20 to 1.21
  • Het is NR **, O, S, S0 2 ;
  • D is N, CR **;
  • T is N, CR **, with a maximum of 2 units T equal to N, and no adjacent units T being N simultaneously;
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1.22 to 1.33 or has a structure of the sub-formulas 1.22 to 1.33
  • V is at each occurrence CR **, N, where at least one unit V is equal to N; and wherein a maximum of two units V are N at a time; and wherein two adjacent units V are not equal to N at a time.
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • R * is defined as in Formula 1.
  • the unit AF2 has a structure of the formula 3 or has a structure of the formula 3
  • n 0, 1;
  • VG1 bridging group, is selected from the group consisting of
  • VG2 bridging group at each occurrence is independently selected from the group consisting of CR ** 2 , NR **, O, S and a CC single bond, where two units VG2 are not simultaneously equal to one CC single bond;
  • R *** is R ** or is selected from the following units, wherein a maximum of two of the radicals R *** are simultaneously one of the following units:
  • R ** is independently at each occurrence either a radical R * or denotes a chemical bond to the separator S, where exactly one R ** is a chemical bond to the separator S.
  • R * is defined as in formula 1.
  • the unit AF2 has a structure of the formula 4 or has a structure of the formula 4
  • X is CR ** 2 , NR **, oxygen, sulfur, a direct bond, with a maximum of two placeholders X being simultaneously a direct bond, which are not part of the same ring; and, moreover, the definitions given for formula 3 apply.
  • at least one AF2 of the organic molecule has a structure of the formula 4A1-4A7 or has a structure of the formula 4A1 -4A7;
  • X is C (R **) 2 , NR **, oxygen, sulfur; and, moreover, the definitions given for formula 3 apply.
  • the organic molecule has a structure of the formula 5 or has a structure of the formula 5
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units: and, moreover, the definitions given for formula 4 apply.
  • the organic molecule has a structure of the formula 6 or has a structure of the formula 6
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of the formula 7 or has a structure of the formula 7
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • Table 1 List of chemical entities AF.
  • a given chemical entity may represent one chemical entity AF1 in one organic molecule and one chemical entity AF2 in another molecule. Provided that two different AFs always occur in one molecule, additional AFs may be identical to the former. Possible connecting points of the chemical unit AF to a separator S are denoted by lowercase letters.
  • Table 2 Examples of organic molecules according to the invention ((AF1) 0 -S- (AF2) P ).
  • the naming of the molecules on the left contains the first chemical group AF1 from Table 1, which is bound via a separator S (molecular unit without AFs) to a second chemical group AF2 (from Table 1), which is mentioned on the right, where o and p are the number of the respective chemical units AF1 and AF2.
  • the separator S functionally distinguishes the organic molecules from prior art molecules, since the type of separation of AFs (donors and acceptors) shown here is not yet known.
  • AFs donors and acceptors
  • Known organic emitters usually consist of directly linked chemical units. Separation of the conjugated aromatic systems has not taken place so far, especially in connection with the localization of HOMO and LUMO on separate parts of the molecule. Separators serve to interrupt the electronic communication between the chemical units AF1 and AF2 by linking the units such that the frontier orbitals HOMO and LUMO lie on mostly separate parts of the molecule, which need not necessarily be the case without the separator.
  • separators do not significantly alter the position of the HOMO or LUMO of the AFs shown in Table 1. Not significant in the context of this invention is a change of not more than +/- 0.4 eV. The calculation of such energies is known and works according to the manner described above by DFT calculation.
  • spectroscopic selection rules symmetric molecules
  • UV / VIS spectroscopy UV / VIS spectroscopy
  • quantum chemical calculation of the oscillator strength it can be predicted whether a quantum mechanical transition is allowed.
  • the goal is a decay time of ⁇ 50 ps. With a long decay time of the (organic) emitter, saturation effects quickly occur at high current intensities, which adversely affects the component lifetime and prevents the achievement of high brightness levels.
  • a measure of the decay time is the quantum mechanical overlap integral, which is approximately represented by the overlap parameter O defined above.
  • the smaller the overlap integral the more separated the frontier orbitals HOMO and LUMO, and the more likely the charge-transfer transition.
  • the probability of TADF emission decreases due to decreasing oscillator strengths.
  • the overlap integral In order to achieve efficient TADF emission with short decay times, the overlap integral must be controlled in a targeted manner.
  • the desired overlap is achieved by the suitable choice of a separator S according to the invention.
  • a measure of the decay time is the AE (Si-Ti) distance. This is influenced by the overlap of HOMO and LUMO.
  • the size of the quantum mechanical overlap integral which can be calculated by the above-mentioned DFT method, can be controlled in a targeted manner by selecting the separator. If it comes to the complete separation of HOMO and LUMO this has a value of 0.
  • the probability of an efficient emission of the organic molecule decreases drastically. At a value of 1 there is no longer delayed fluorescence (TADF) but spontaneous emission.
  • the desired overlap is achieved by the suitable choice of a separator S according to the invention.
  • the separators S shown here fulfill in particular two essential functional features (see FIG.
  • the HOMO energy is lower than the HOMO energy of the donor chemical unit AF and
  • the LUMO energy is higher than the LUMO energy of the acceptor chemical entity AF.
  • organic molecules according to the invention are shown in Table 3, which result from combining the above-defined pairs of chemical entities AF1 and AF2, the separator S and the definition of the linkage. Further organic molecules can be obtained by combining said molecular units, wherein at least two different AF are contained in the molecule.
  • the naming of the molecules is carried out according to the scheme AF-S-AF, with reference to Table 1 for the naming of the chemical entity AF, since the numbers used in Table 1 are also used in Table 3. If there are more than two AFs in the molecule, the two AFs will interact with each other, with their respective HOMO and LUMO positions most likely to follow the above conditions.
  • Table 3 Organic molecules according to the invention according to the scheme AF-S-AF. In a molecule at least two different AFs are contained, whereby these can be identical starting from values 3 and larger. S stands for a separator S. In brackets the values for AHOMO, ALUMO and Gap are indicated.
  • 35 - s - 37 (0.92 2.09 0.96)
  • 35 - s - 43 (.34 1.64 1.41)
  • 35 - s - 46 (.93 1.16 1.89)

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des molécules organiques à utiliser en particulier dans des composants optoélectroniques tels que des diodes électroluminescentes organiques (OLED). Selon l'invention, la molécule organique désigne une structure de formule 1 (Formule 1), formule 1 dans laquelle A, B et A', B' désignent des systèmes cycliques aromatiques monocycliques, les cycles annelés B ou B' annelés à A ou A' sont facultatifs et les noyaux des systèmes cycliques sont constitués d'atomes de carbone ; B et A ou B' et A' formant entre eux des systèmes linéaires condensés constitués de deux cycles simples maximum. Les deux systèmes condensés sont reliés par une liaison simple unique entre A et A' ; un R' est lié dans les cycles A, B, A' et B' sur tous les atomes de C des noyaux, qui ne font pas partie des deux systèmes cycliques ou qui ne forment pas la liaison de A à A', R' étant soit un radical R*, soit AF.
PCT/EP2016/051166 2015-01-20 2016-01-20 Molécules organiques à utiliser dans des composants optoélectroniques WO2016116524A2 (fr)

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CN111333681A (zh) * 2018-12-19 2020-06-26 烟台显华光电材料研究院有限公司 一类用作磷光材料的过渡金属配合物及其应用
CN111349013A (zh) * 2018-12-21 2020-06-30 陕西师范大学 一类手性深蓝色荧光材料及其制备方法
CN112262127A (zh) * 2018-06-15 2021-01-22 三星显示有限公司 杂环化合物和包括该杂环化合物的有机发光器件
US12122749B2 (en) 2018-06-15 2024-10-22 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device comprising same

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JP4590825B2 (ja) * 2003-02-21 2010-12-01 コニカミノルタホールディングス株式会社 白色発光有機エレクトロルミネッセンス素子
US8080658B2 (en) * 2007-07-10 2011-12-20 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent element and organic electroluminescent element employing the same
JP5194596B2 (ja) * 2007-07-11 2013-05-08 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR102011228B1 (ko) * 2009-07-31 2019-08-14 유디씨 아일랜드 리미티드 유기 전계 발광 소자
US9209411B2 (en) * 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
JP6644673B2 (ja) * 2013-03-22 2020-02-12 メルク パテント ゲーエムベーハー 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック

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* Cited by examiner, † Cited by third party
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CN112262127A (zh) * 2018-06-15 2021-01-22 三星显示有限公司 杂环化合物和包括该杂环化合物的有机发光器件
US12122749B2 (en) 2018-06-15 2024-10-22 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device comprising same
CN111333681A (zh) * 2018-12-19 2020-06-26 烟台显华光电材料研究院有限公司 一类用作磷光材料的过渡金属配合物及其应用
CN111333681B (zh) * 2018-12-19 2023-04-07 烟台显华光电材料研究院有限公司 一类用作磷光材料的过渡金属配合物及其应用
CN111349013A (zh) * 2018-12-21 2020-06-30 陕西师范大学 一类手性深蓝色荧光材料及其制备方法
CN111349013B (zh) * 2018-12-21 2023-04-07 陕西师范大学 一类手性深蓝色荧光材料及其制备方法

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