DE102017102662A1 - Organic molecules, in particular for use in organic optoelectronic devices - Google Patents

Abstract

The invention relates to an organic molecule, in particular for use in optoelectronic components. According to the invention, the organic molecule contains a first chemical entity comprising one or consisting of a structure according to formula I and two second chemical entities each identical or different in each occurrence having one or consisting of a structure according to formula II, wherein the first chemical entity in each case a single bond is linked to the two second chemical moieties; T, V is independently a point of attachment of the single bond between the chemical entity of Formula I and a second chemical moiety or H; W, X, Y is independently a point of attachment of the single bond between the chemical moiety according to formula I and a second chemical moiety or selected from the group consisting of H, CN and CF, wherein one of the two Q is CR and the other Q is N; and exactly one radical selected from W, X and Y is CN or CF and exactly two radicals selected from the group consisting of T, V, W, X and Y are the point of attachment of the single bond between the first chemical moiety and a second chemical moiety. and - two second chemical units D each identical or different in each occurrence having one or consisting of a structure according to formula II, Here, the first chemical unit is linked via a single bond with the two second chemical units D.T is the point of attachment of the single bond between is the point of attachment of the single bond between the chemical entity of formula I and a chemical entity D or HW is the point of attachment of the single bond between the chemical entity of formula I and a chemical entity D or is selected from the group from H, CN and CF.X is the point of attachment of the single bond between the chemical entity of Formula I and a chemical entity D or is selected from the group consisting of H, CN and CF.Y is the point of attachment of the single bond between the chemical entity of Formula I. and a chemical entity D or is selected from the group consisting of H, CN and CF;

Description

The invention relates to purely organic molecules and their use in organic light emitting diodes (OLEDs) and in other organic optoelectronic devices.

description

The object of the present invention was to provide molecules which are suitable for use in optoelectronic devices.

This object is achieved by the invention, which provides a new class of organic molecules.

The organic molecules according to the invention are purely organic molecules, ie have no metal ions and are thus different from the metal complex compounds known for use in organic optoelectronic devices.

The organic molecules according to the invention are distinguished by emissions in the blue, sky-blue or green spectral range. The photoluminescence quantum yields of the organic molecules according to the invention are in particular 20% or more. In particular, the molecules according to the invention exhibit thermally activated delayed fluorescence (TADF). The use of the molecules according to the invention in an optoelectronic device, for example an organic light emitting diode (OLED), leads to higher efficiencies of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.

The blue spectral range here means the visible range of less than 470 nm. The sky-blue spectral range is understood to mean the range from 470 nm to 499 nm. The green spectral range is understood to mean the range from 500 nm to 599 nm. The emission maximum lies within the respective range.

und

• - zwei zweite chemische Einheiten D jeweils bei jedem Auftreten gleich oder verschieden aufweisend eine oder bestehend aus einer Struktur gemäß Formel II,
  
  • Hierbei ist die erste chemische Einheit jeweils über eine Einfachbindung mit den zwei zweiten chemischen Einheiten D verknüpft.
  • T ist Anknüpfungspunkt der Einfachbindung zwischen der chemischen Einheit gemäß Formel I und einer chemischen Einheit D oder ist H.
  • V ist Anknüpfungspunkt der Einfachbindung zwischen der chemischen Einheit gemäß Formel I und einer chemischen Einheit D oder ist H.
  • W ist Anknüpfungspunkt der Einfachbindung zwischen der chemischen Einheit gemäß Formel I und einer chemischen Einheit D oder ist ausgewählt aus der Gruppe bestehend aus H, CN und CF₃.
  • X ist Anknüpfungspunkt der Einfachbindung zwischen der chemischen Einheit gemäß Formel I und einer chemischen Einheit D oder ist ausgewählt aus der Gruppe bestehend aus H, CN und CF₃.
  • Y ist Anknüpfungspunkt der Einfachbindung zwischen der chemischen Einheit gemäß Formel I und einer chemischen Einheit D oder ist ausgewählt aus der Gruppe bestehend aus H, CN und CF₃;
  • # ist Anknüpfungspunkt der Einfachbindung zwischen der jeweiligen chemischen Einheit D und der chemischen Einheit gemäß Formel I.
  • Z ist bei jedem Auftreten gleich oder verschieden eine direkte Bindung oder ausgewählt aus der Gruppe bestehend aus CR³R⁴, C=CR³R⁴, C=O, C=NR³, NR³, O, SiR³R⁴, S, S(O) und S(O)₂.
  • Q ist bei jedem Auftreten CR^Q oder N.
  • R^Q ist bei jedem Auftreten gleich oder verschieden R¹ oder R*.
  • R* ist gleich CN oder CF₃.
  • R¹ ist bei jedem Auftreten gleich oder verschieden H, Deuterium, eine lineare Alkylgruppe mit 1 bis 5 C-Atomen, wobei jeweils ein oder mehrere H-Atome durch Deuterium ersetzt sein können; eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 8 C-Atomen, wobei jeweils ein oder mehrere H-Atome durch Deuterium ersetzt sein können; eine verzweigte oder cyclische Alkyl-, Alkenyl- oder Alkinylgruppe mit 3 bis 10 C-Atomen, wobei jeweils ein oder mehrere H-Atome durch Deuterium ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 15 aromatischen Ringatomen, das jeweils mit einem oder mehreren Resten R⁶ substituiert sein kann.
  • R^a, R³ und R⁴ ist bei jedem Auftreten gleich oder verschieden H, Deuterium, N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F, Br, I, eine lineare Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂, NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂, NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder eine verzweigte oder cyclische Alkyl-, Alkenyl-, Alkinyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂, NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 60 aromatischen Ringatomen, das jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann; oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die mit einem oder mehreren Resten R⁵ substituiert sein kann; oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche mit einem oder mehreren Resten R⁵ substituiert sein kann.
  • R⁵ ist bei jedem Auftreten gleich oder verschieden H, Deuterium, N(R⁶)₂, OH, Si(R⁶)₃, B(OR⁶)₂, OSO₂R⁶, CF₃, CN, F, Br, I, eine lineare Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁶ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁶C=CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C=O, C=S, C=Se, C=NR⁶, P(=O)(R⁶), SO, SO₂,NR⁶, O, S oder CONR⁶ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁶ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁶C=CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C=O, C=S, C=Se, C=NR⁶, P(=O)(R⁶), SO, SO₂,NR⁶, O, S oder CONR⁶ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder eine verzweigte oder cyclische Alkyl-, Alkenyl-, Alkinyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁶ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁶C=CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C=O, C=S, C=Se, C=NR⁶, P(=O)(R⁶), SO, SO₂, NR⁶, O, S oder CONR⁶ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 60 aromatischen Ringatomen, das jeweils mit einem oder mehreren Resten R⁶ substituiert sein kann; oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die mit einem oder mehreren Resten R⁶ substituiert sein kann; oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche mit einem oder mehreren Reste R⁶ substituiert sein kann.
  • R⁶ ist bei jedem Auftreten gleich oder verschieden H, Deuterium, OH, CF₃, CN, F, eine lineare Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 5 C-Atomen, wobei jeweils ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 5 C-Atomen, wobei jeweils ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder eine verzweigte oder cyclische Alkyl-, Alkenyl-, Alkinyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 5 C-Atomen, wobei jeweils ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können; oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 60 aromatischen Ringatomen; oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen; oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen.
  • Erfindungsgemäß kann jeder der Reste R^a, R³, R⁴ oder R⁵ auch mit einem oder mehreren weiteren Resten R^a, R³, R⁴ oder R⁵ ein mono- oder polycyclisches, aliphatisches, aromatisches und/oder benzoanelliertes Ringsystem bilden.
  • Erfindungsgemäß ist eines der beiden Q gleich N und das andere Q gleich CR^Q, wobei eines der beiden R^Q gleich R* ist und das andere R^Q gleich R¹ ist, wobei R*gleich CF₃ oder CN ist.
  • Erfindungsgemäß ist genau ein Rest ausgewählt aus W, X und Y gleich CN oder CF₃ und genau zwei Reste ausgewählt aus der Gruppe bestehend aus T, V, W, X und Y sind gleich einem Anknüpfungspunkt einer Einfachbindung zwischen der chemischen Einheit gemäß Formel I und einer chemischen Einheit D.

The organic molecules contain a first chemical entity, which have a structure according to formula I or consist of a structure according to formula I,

and

• - two second chemical units D each having, identically or differently, on each occurrence one or consisting of a structure according to formula II,
  
  • Here, the first chemical unit is linked to the two second chemical units D via a single bond.
  • T is the point of attachment of the single bond between the chemical entity of formula I and a chemical entity D or is H.
  • V is the point of attachment of the single bond between the chemical entity of formula I and a chemical entity D or is H.
  • W is the point of attachment of the single bond between the chemical entity according to formula I and a chemical entity D or is selected from the group consisting of H, CN and CF ₃ .
  • X is a point of attachment of the single bond between the chemical entity of formula I and a chemical entity D or is selected from the group consisting of H, CN and CF ₃ .
  • Y is a point of attachment of the single bond between the chemical entity of formula I and a chemical entity D or is selected from the group consisting of H, CN and CF ₃ ;
  • # is the point of attachment of the single bond between the respective chemical unit D and the chemical unit according to formula I.
  • Z is each time the same or different a direct bond or selected from the group consisting of CR ³ R ⁴ , C = CR ³ R ⁴ , C = O, C = NR ³ , NR ³ , O, SiR ³ R ⁴ , S , S (O) and S (O) ₂ .
  • Q is CR ^Q or N at each occurrence.
  • R ^Q is the same or different at each occurrence as R ¹ or R *.
  • R * is equal to CN or CF ₃ .
  • R ¹ is the same or different H, deuterium, a linear alkyl group having 1 to 5 carbon atoms at each occurrence, each one or more H atoms may be replaced by deuterium; a linear alkenyl or alkynyl group having 2 to 8 C atoms, wherein in each case one or more H atoms may be replaced by deuterium; a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein in each case one or more H atoms may be replaced by deuterium, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, each with a or a plurality of R ⁶ may be substituted.
  • R ^a , R ³ and R ⁴ are each the same or different at each occurrence H, deuterium, N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted with one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups is replaced by R ⁵ C =CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C =O, C =S, C =Se, C =NR ⁵ , P ( = O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and where one or more H atoms are replaced by deuterium, CN, CF ₃ or NO ₂ may be replaced; or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted with one or more R ⁵ radicals; or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms which may be substituted by one or more R ⁵ radicals; or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms which may be substituted by one or more R ⁵ groups.
  • R ⁵ is the same or different H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br at each occurrence. I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted by one or more R ⁶ radicals, one or more non-adjacent CH ₂ groups being replaced by R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O, S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ and wherein one or more H atoms are represented by deuterium , CN, CF ₃ or NO ₂ may be replaced; or a linear alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more R ⁶ radicals, one or more non-adjacent CH ₂ groups being replaced by R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O, S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ and wherein one or more H atoms are represented by deuterium, CN, CF. ₃ or NO ₂ can be replaced; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted with one or more R ⁶ radicals, wherein one or more non-adjacent CH ₂ groups R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O, S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted with one or more R ⁶ radicals; or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more R ⁶ radicals; or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more R ⁶ radicals.
  • R ⁶ is the same or different H, deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, each containing one or more H atoms by deuterium, CN, CF ₃ or NO ₂ may be replaced; or a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein in each case one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein in each case one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms; or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms.
  • According to the invention, each of the radicals R ^a , R ³ , R ⁴ or R ^{5 can} also form, with one or more further radicals R ^a , R ³ , R ⁴ or R ^5, a monocyclic or polycyclic, aliphatic, aromatic and / or benzoanellated ring system.
  • According to the invention one of the two Q is equal to N and the other Q is CR ^Q , wherein one of the two R ^Q is R * and the other R ^Q is R ¹ , wherein R * is CF ₃ or CN.
  • According to the invention, exactly one radical selected from W, X and Y is CN or CF ₃ and exactly two radicals selected from the group consisting of T, V, W, X and Y are equal to a point of attachment of a single bond between the chemical moiety according to formula I and a chemical entity D.

wobei für R¹, T, V, W, X, und Y für Formel I und II genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Ia or consist of a structure of the formula Ia:

where R ¹ , T, V, W, X, and Y for formula I and II definitions apply.

In one embodiment, R ^{1 is the} same or different at each occurrence as H, methyl or phenyl.

In one embodiment, W is CN.

wobei für # und R^a die für Formel I und II genannten Definitionen gelten. In a further embodiment of the organic molecules, the chemical group D at each occurrence identically or differently has a structure of the formula IIa or consists of a structure of the formula IIa:

where # and R ^{a are} the definitions given for formulas I and II.

wobei gilt

• R^b ist bei jedem Auftreten gleich oder verschieden N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F, Br, I, eine lineare Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂,NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können;
• oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂, NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können;
• oder eine verzweigte oder cyclische Alkyl-, Alkenyl-, Alkinyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch R⁵C=CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C=O, C=S, C=Se, C=NR⁵, P(=O)(R⁵), SO, SO₂, NR⁵, O, S oder CONR⁵ ersetzt sein können und wobei ein oder mehrere H-Atome durch Deuterium, CN, CF₃ oder NO₂ ersetzt sein können;
• oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 60 aromatischen Ringatomen, das jeweils mit einem oder mehreren Resten R⁵ substituiert sein kann;
• oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die mit einem oder mehreren Resten R⁵ substituiert sein kann;
• oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche mit einem oder mehreren Resten R⁵ substituiert sein kann. Ansonsten gelten die oben genannten Definitionen.

In a further embodiment of the organic molecules according to the invention, the chemical entity D at each occurrence identically or differently has a structure of the formula IIb, of the formula IIb-2, of the formula IIb-3 or of the formula IIb-4 or consists thereof:

where is true

• R ^b is the same or different at each occurrence N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear Alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ;
• or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ;
• or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ;
• or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted with one or more R ⁵ radicals;
• or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms which may be substituted by one or more R ⁵ radicals;
• or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms which may be substituted by one or more R ⁵ groups. Otherwise, the above definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment of the organic molecules according to the invention, the chemical entity D at each occurrence identically or differently has a structure of the formula IIc, of the formula IIc-2, of the formula IIc-3 or of the formula IIc-4 or consists thereof:

where the definitions above apply.

• Me,
• ⁱPr,
• ^tBu,
• CN,
• CF₃,
• Ph, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Pyridinyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Pyrimidinyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Carbazolyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Triazinyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• und N(Ph)₂.

In a further embodiment of the organic molecules according to the invention, R ^{b is} independently selected from the group consisting of each occurrence

• me,
• ⁱ Pr,
• ^t Bu,
• CN,
• CF ₃ ,
• Ph, which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Pyridinyl by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Pyrimidinyl which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Carbazolyl, each of which having one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Triazinyl, each of which having one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• and N (Ph) ₂ .

wobei für #, Z, R^a, R³, R⁴ und R⁵ die oben genannten Definitionen gelten. In einer Ausführungsform ist der Rest R⁵ bei jedem Auftreten gleich oder verschieden ausgewählt aus der Gruppe bestehend aus H, Methyl, Ethyl, Phenyl und Mesityl. In einer Ausführungsform ist R^a bei jedem Auftreten gleich oder verschieden ausgewählt aus der Gruppe bestehend aus H, Methyl (Me), i-Propyl (CH(CH₃)₂) (ⁱPr), t-Butyl (^tBu), Phenyl (Ph), CN, CF₃ und Diphenylamin (NPh₂).Exemplary embodiments of the chemical group D are shown below:

where #, Z, R ^a , R ³ , R ⁴ and R ^{5 are} the abovementioned definitions. In one embodiment, the radical R ⁵ on each occurrence is identically or differently selected from the group consisting of H, methyl, ethyl, phenyl and mesityl. In one embodiment, R ^a in each occurrence is the same or different selected from the group consisting of H, methyl (Me), i-propyl (CH (CH ₃ ) ₂ ) ( ⁱ Pr), t -butyl ( ^t Bu), phenyl (Ph), CN, CF ₃ and diphenylamine (NPh ₂ ).

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of the formula III-1, formula III-2 or formula III-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula III-1, wherein the definitions given for the formulas III-1 to III-3 apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula III-1, formula III-2 or formula III-3, where the abovementioned definitions apply and R * is CN.

wobei

• R^c bei jedem Auftreten unabhängig voneinander ausgewählt aus der Gruppe bestehend aus
• Me,
• ⁱPr,
• ^tBu,
• CN,
• CF₃,
• Ph, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Pyridinyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Pyrimidinyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Carbazolyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• Triazinyl, das jeweils mit einem oder mehreren Resten ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann,
• und N(Ph)₂ ist.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIa-1, formula IIIa-2 or formula IIIa-3:

in which

• R ^c at each occurrence independently selected from the group consisting of
• me,
• ⁱ Pr,
• ^t Bu,
• CN,
• CF ₃ ,
• Ph, which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Pyridinyl by one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Pyrimidinyl which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Carbazolyl, each of which having one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• Triazinyl, each of which having one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted,
• and N (Ph) ₂ is.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIa-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIb-1, formula IIIb-2 or formula IIIb-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIb-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIc-1, formula IIIc-2 or formula IIIc-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIc-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIId-1, formula IIId-2 or formula IIId-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIId-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIe-1, formula IIIe-2 or formula IIIe-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIe-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten. In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIf-1, formula IIIf-2 or formula IIIf-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIf-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIg-1, formula IIIg-2 or formula IIIg-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIg-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIh-1, formula IIIh-2 or formula IIIh-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IIIh-1, where the definitions above apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of the formula IV-1, formula IV-2 or formula IV-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IV-1, where the abovementioned definitions apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IV-1, formula IV-2 or formula IV-3, where the abovementioned definitions apply and R * is CN.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVa-1, formula IVa-2 or formula IVa-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVa-1, the definitions given above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVb-1, formula IVb-2 or formula IVb-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVb-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVc-1, formula IVc-2 or formula IVc-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVc-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVd-1, formula IVd-2 or formula IVd-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVd-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten. In a further embodiment, the organic molecules according to the invention have a structure of the formula IVe-1, formula IVe-2 or formula IVe-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVe-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVf-1, formula IVf-2 or formula IVf-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVf-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVg-1, formula IVg-2 or formula IVg-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVg-1, where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula IVh-1, formula IVh-2 or formula IVh-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula IVh-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula V-1, formula V-2 or formula V-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula V-1, where the abovementioned definitions apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula V-1, formula V-2 or formula V-3, where the abovementioned definitions apply and R * is CN.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Va-1, formula Va-2 or formula Va-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Va-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Vb-1, formula Vb-2 or formula Vb-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Vb-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Vc-1, formula Vc-2 or formula Vc-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Vc-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Vd-1, formula Vd-2 or formula Vd-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Vd-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Ve-1, formula Ve-2 or formula Ve-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Ve-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Vf-1, formula Vf-2 or formula Vf-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Vf-1, the definitions given above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Vg-1, formula Vg-2 or formula Vg-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Vg-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula Vh-1, formula Vh-2 or formula Vh-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula Vh-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of the formula VI-1, formula VI-2 or formula VI-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VI-1, where the abovementioned definitions apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VI-1, formula VI-2 or formula VI-3, where the abovementioned definitions apply and R * is CN.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIa-1, formula VIa-2 or formula VIa-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIa-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIb-1, formula VIb-2 or formula VIb-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIb-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIc-1, formula VIc-2 or formula VIc-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIc-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VId-1, formula VId-2 or formula VId-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VId-1, where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIe-1, formula VIe-2 or formula VIe-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIe-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIf-1, formula VIf-2 or formula VIf-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIf-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIg-1, formula VIg-2 or formula VIg-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIg-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIh-1, formula VIh-2 or formula VIh-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIh-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of the formula VII-1, formula VII-2 or formula VII-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VII-1, where the abovementioned definitions apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VII-1, formula VII-2 or formula VII-3, where the abovementioned definitions apply and R * is CN.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIa-1, formula VIIa-2 or formula VIIa-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIa-1, the definitions given above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIb-1, formula VIIb-2 or formula VIIb-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIb-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIc-1, formula VIIc-2 or formula VIIc-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIc-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIId-1, formula VIId-2 or formula VIId-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIId-1, the definitions given above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIe-1, formula VIIe-2 or formula VIIe-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIe-1, the definitions given above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIf-1, formula VIIf-2 or formula VIIf-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIf-1, where the definitions above apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIg-1, formula VIIg-2 or formula VIIg-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIg-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIh-1, formula VIIh-2 or formula VIIh-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIIh-1, where the abovementioned definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment, the organic molecules according to the invention have a structure of the formula VIII-1, formula VIII-2 or formula VIII-3:

where the definitions above apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIII-1, where the abovementioned definitions apply.

In a further embodiment, the organic molecules according to the invention have a structure of the formula VIII-1, formula VIII-2 or formula VIII-3, where the abovementioned definitions apply and R * is CN.

In one embodiment, R ^c is independently at each occurrence selected from the group consisting of Me, ⁱ Pr, ^Bu, Ph, which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, and carbazolyl, each of which having one or more groups selected from Me, ⁱ Pr, ^Bu, or Ph may be substituted, triazinyl which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN , CF ₃ or Ph, and N is (Ph) ₂ .

For the purposes of this invention, an aryl group contains from 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 / or S. If in the description of certain embodiments of the invention other definitions deviating from the abovementioned definition are given, 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 as meaning a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example 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, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, Indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazine imidazole, quinoxaline imidazole, oxazole, benzoxazole, napthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, Quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1, 2,5-oxadiazole, 1,3,5-triazine, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or combinations of said groups.

A cyclic alkyl, alkoxy or thioalkoxy group is understood here to mean a monocyclic, a bicyclic or a polycyclic group.

In the context of the present invention, a C ₁ - to C ₄₀ -alkyl group in which individual H atoms or CH ₂ groups may also be substituted by the abovementioned groups or by the abovementioned groups, for example the radicals methyl, ethyl , n-propyl, i -propyl, cyclopropyl, n -butyl, i -butyl, s -butyl, t -butyl, cyclobutyl, 2-methylbutyl, n -pentyl, s -pentyl, t -pentyl, 2-pentyl, neo -Pentyl, cyclopentyl, n-hexyl, s -hexyl, t -hexyl, 2-hexyl, 3-hexyl, neo -hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl , 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo [2,2,2] octyl, 2-bicyclo [2,2,2] octyl, 2- (2 , 6-dimethyl) octyl, 3- (3,7-dimethyl) octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1 , 1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-dimethyl n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1- Dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct 1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl , 1,1-diethyln-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1- (n-propyl) -cyclohex-1-yl, 1- (n Butyl) -cyclohex-1-yl, 1- (n-hexyl) -cyclohex-1-yl, 1- (n-octyl) -cyclohex-1-yl and 1- (n-decyl) cyclohexene -1-yl-understood. An alkenyl group is understood as meaning, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. By an alkynyl group is meant, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. A C ₁ - to C ₄₀ -alkoxy group is understood as meaning, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

One embodiment of the invention relates to organic molecules which have a ΔE (S ₁ -T ₁ ) value between the lowest excited singlet (S ₁ ) and the underlying triplet (T ₁ ) state of not higher than 5000 cm ^-1 , in particular not higher than 3000 cm ^-1 , or not higher than 1500 cm ^-1 or 1000 cm ^-1 and / or have an emission lifetime of at most 150 μs, in particular of at most 100 μs, of the highest 50 μs, or of at most 10 μs and / or a main emission band with a Having a half-width of less than 0.55 eV, in particular less than 0.50 eV, less than 0.48 eV, or less than 0.45 eV.

In particular, the organic molecules exhibit an emission maximum between 420 and 500 nm, between 430 and 480 nm, in particular between 450 and 470 nm.

In particular, the molecules have a blue material index (BMI), the quotients of the PLQY (in%) and their ClE _y color coordinate of the light emitted by the molecule according to the invention, greater than 150, in particular greater than 200, greater than 250 or from greater than 300 on.

In a further aspect, the invention relates to a process for the preparation of an organic molecule of the type described herein (with a possible subsequent reaction), wherein a 5-bromo-2-cyanobenzonitrile substituted in 3,4,6-position R ¹ used as starting material becomes:

In the above scheme, in one embodiment, the chemical group CN of the cyano-difluorophenylboronic acid and / or the 5-bromo-2-cyanobenzonitrile substituted in 3,4,6-position R ^{1 is} replaced by CF ₃ .

According to the invention, it is also possible to use a boronic acid ester instead of a boronic acid.

In one embodiment, a 5-bromo-2-cyanobenzonitrile substituted in 3,4,6-position R ^{1 is} reacted as reactant with a cyano-difluorophenylboronic acid or a corresponding cyano-difluorophenylboronic acid ester in a palladium-catalyzed cross-coupling reaction. According to the invention, 4-cyano-2,6-difluorophenylboronic acid, 4-cyano-2,5-difluorophenylboronic acid, 4-cyano-3,5-difluorophenylboronic acid, 3-cyano-2,4-difluorophenylboronic acid, 3-cyano-4, 5-difluorophenylboronic acid and 2-cyano-4,5-difluorophenylboronic acid or 4-cyano-2,6-difluorophenylboronic acid ester, 4-cyano-2,5-difluorophenylboronic acid ester, 4-cyano-3,5-difluorophenylboronic acid ester, 3-cyano-2, 4-difluorophenylboronic acid esters, 3-cyano-4,5-difluorophenylboronic acid esters and 2-cyano-4,5-difluorophenylboronic acid esters are used. The product is obtained by deprotonation of the corresponding amine and subsequent nucleophilic substitution of the two fluoro groups. Here, a nitrogen heterocycle is implemented in the sense of a nucleophilic aromatic substitution with a starting material E1. Typical conditions include the use of a base such as tribasic potassium phosphate or sodium hydride in an aprotic polar solvent such as dimethyl sulfoxide (DMSO) or N, N-dimethylformamide (DMF).

• • organischen lichtemittierenden Dioden (OLEDs),
• • lichtemittierenden elektrochemischen Zellen,
• • OLED-Sensoren, insbesondere in nicht hermetisch nach außen abgeschirmten Gas- und Dampf-Sensoren,
• • organischen Dioden,
• • organischen Solarzellen,
• • organischen Transistoren,
• • organischen Feldeffekttransistoren,
• • organischen Lasern und
• • Down-Konversions-Elementen.

In a further aspect, the invention relates to the use of the organic molecules as a luminescent emitter or as a host material in an organic optoelectronic device, in particular wherein the organic optoelectronic device is selected from the group consisting of:

• Organic light-emitting diodes (OLEDs),
• Light-emitting electrochemical cells,
• OLED sensors, especially in non-hermetically shielded gas and vapor sensors,
• Organic diodes,
• • organic solar cells,
• Organic transistors,
• Organic field effect transistors,
• • organic lasers and
• • Down conversion elements.

1. (a) mindestens einem erfindungsgemäßen organischen Molekül, insbesondere als Emitter und/oder Host, und
2. (b) mindestens ein, d. h. ein oder mehrere Emitter- und/oder Hostmaterialien, die von dem erfindungsgemäßen organischen Molekül verschiedenen ist bzw. sind und
3. (c) optional eine oder mehreren Farbstoffen und/ oder einem oder mehreren organischen Lösungsmitteln.

In a further aspect, the invention relates to a composition comprising or consisting of:

1. (a) at least one organic molecule according to the invention, in particular as emitter and / or host, and
2. (b) at least one, ie, one or more emitter and / or host materials other than the organic molecule of the invention, and
3. (c) optionally one or more dyes and / or one or more organic solvents.

In one embodiment, the composition of the invention consists of an organic molecule of the invention and one or more host materials. In particular, the host material (s) has first excited triplet (T ₁ ) energy levels that are higher in energy than the first excited triplet (T ₁ ) energy levels of the organic molecule of the invention and have first excited singlet (S ₁ ) energy levels are higher in energy than the singlet (S ₁ ) energy levels of the organic molecule of the invention.

The orbital energies and the energies of the excited states can be determined either by experimental methods or by the application of quantum chemical methods, in particular calculations of the density-functional theory. The energy of the highly occupied orbital E ^HOMO is, as known in the art, determined via cyclic voltammetry with an accuracy of 0.1 eV. The energy of the lowest unoccupied orbital E ^LUMO is calculated from the sum of E ^HOMO and E ^gap , where E ^gap is determined as follows: For a host molecule, for E ^gap , unless otherwise stated, the energy at which the emission of a 10% host (mass%) film in polymethyl methacrylate (PMMA). For an emitter molecule, E ^{gap is determined} as the energy at which the excitation and emission spectra of a 10% emitter (mass percent) film intersect in PMMA.

The energy of the first excited triplet state T ₁ is determined by the energy at which the emission starts at low temperature, typically 77 K. For a host molecule for which the energy difference between the first excited singlet state and the first excited triplet state differs by more than 0.4 eV, the phosphorescence is typically visible in the steady state spectrum in 2-Me-THF. The triplet energy can therefore be determined as the energy at which the phosphorescence spectrum starts. For TADF emitter molecules, the energy of the first triplet excited state T _{1 is determined} by the energy at which the delayed emission spectrum at 77 K starts, which is measured in PMMA in a 10% emitter molecule (mass percent) film, unless otherwise stated , For host and emitter molecules, the energy of the first excited singlet state S _{1 is determined} with the energy at which the emission spectrum begins, which, unless otherwise stated, is measured in a film with 10% host molecule or emitter molecule (mass percent) in PMMA.

In one embodiment, in addition to the organic molecule of the invention, the composition comprises an electron-dominant and a hole-dominant host material. The highest occupied orbital (HOMO) of the hole - dominant host material is in particular higher in energy than the HOMO of the Electron-dominant host material and the lowest unoccupied orbital (LUMO) of the hole-dominant host material are in particular higher in energy than the LUMO of the electron-dominant host material. In another embodiment, the HOMO of the hole-dominant host material is higher in energy than the HOMO of the organic molecule of the present invention, while the LUMO of the electron-dominant host material is energetically lower than the LUMO of the organic molecule of the present invention. In order to avoid exciplex formation between emitter and host material or host materials, the materials should be chosen such that the energy gaps between the LUMO of the electron-dominant host material and the LUMO of the organic molecule of the invention are in particular less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV. The energy gap between the HOMO of the hole dominating host material and the HOMO of the organic molecule according to the invention is in particular less than 0.5 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV.

In another embodiment, in addition to the organic molecule of the invention, the composition comprises an electron-dendritic host material. The energy difference between the highest occupied orbital (HOMO) of the organic molecule of the invention and the HOMO of the electron-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between - 0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV.

In another embodiment, in addition to the organic molecule of the invention, the composition comprises an electron-dendritic host material. The energy difference between the lowest unoccupied orbital (LUMO) of the organic molecule of the invention and the LUMO of the electron-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between - 0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV.

In another embodiment, in addition to the organic molecule of the invention, the composition has a hole-dominant host material. The energy difference between the highest occupied orbital (HOMO) of the organic molecule of the invention and the HOMO of the hole-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between - 0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV.

In another embodiment, in addition to the organic molecule of the invention, the composition has a hole-dominant host material. The energy difference between the lowest unoccupied orbital (LUMO) of the organic molecule of the invention and the LUMO of the hole-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between - 0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV.

In one embodiment, in addition to the organic molecule of the invention, the composition comprises an electron-dominant and a hole-dominant host material. The energy difference between the highest occupied orbital (HOMO) of the organic molecule of the invention and the HOMO of the electron-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between - 0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV, and the energy difference between the lowest unoccupied orbital (LUMO) of the organic molecule of the present invention and the LUMO of the electron-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV. Accordingly, the energy difference between the highest occupied orbital (HOMO) of the organic molecule of the invention and the HOMO of the hole-dominant host material is between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV, and the energy difference between the lowest unoccupied orbital (LUMO) of the organic molecule of the invention and the LUMO of the hole-dominant host material between -0.5 eV and 0.5 eV, preferably between -0.3 eV and 0.3 eV, more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV.

In a further aspect, the invention relates to an organic optoelectronic device comprising an organic molecule or a composition according to the invention. In particular, the organic optoelectronic device is formed as a device selected from the group consisting of organic light emitting diode (OLED); light-emitting electrochemical cell; OLED sensor, in particular non-hermetically shielded gas and vapor sensors; organic diode; organic solar cell; organic transistor; organic field effect transistor; organic laser and down-conversion element.

• - ein Substrat,
• - eine Anode und
• - eine Kathode, wobei die Anode oder die Kathode auf das Substrat aufgebracht sind, und
• - mindestens eine lichtemittierende Schicht, die zwischen Anode und Kathode angeordnet ist und die ein erfindungsgemäßes organisches Molekül aufweist, stellt einen weitere Ausführungsform der Erfindung dar.

An organic optoelectronic device comprising

• a substrate,
• an anode and
• a cathode, wherein the anode or the cathode are applied to the substrate, and
• - At least one light-emitting layer, which is arranged between the anode and cathode and having an inventive organic molecule, represents a further embodiment of the invention.

1. 1. Substrat (Trägermaterial)
2. 2. Anode
3. 3. Lochinjektionsschicht (hole injection layer, HIL)
4. 4. Lochtransportschicht (hole transport layer, HTL)
5. 5. Elektronenblockierschicht (electron blocking layer, EBL)
6. 6. Emitterschicht (emitting layer, EML)
7. 7. Lochblockierschicht (hole blocking layer, HBL)
8. 8. Elektronenleitschicht (electron transport layer, ETL)
9. 9. Elektroneninjektionsschicht (electron injection layer, EIL)
10. 10. Kathode.

In one embodiment, the optoelectronic device is an OLED. A typical OLED has, for example, the following layer structure:

1. 1st substrate (carrier material)
2. 2. anode
3. 3. hole injection layer (HIL)
4. 4. hole transport layer (HTL)
5. 5. Electron blocking layer (EBL)
6. 6. emitter layer (EML)
7. 7. hole blocking layer (HBL)
8. 8. electron transport layer (ETL)
9. 9. Electron Injection Layer (EIL)
10. 10. Cathode.

In this case, individual layers are only available in an optional manner. Furthermore, several of these layers can coincide. And there may be multiple layers in the component multiple times.

According to one embodiment, at least one electrode of the organic component is made translucent. Here, "translucent" refers to a layer that is transparent to visible light. In this case, the translucent layer can be clear translucent, that is transparent, or at least partially light-absorbing and / or partially light-scattering, so that the translucent layer can also be translucent, for example, diffuse or milky. In particular, a layer designated here as translucent is formed as transparent as possible, so that in particular the absorption of light is as low as possible.

1. 1. Substrat (Trägermaterial)
2. 2. Kathode
3. 3. Elektroneninjektionsschicht (electron injection layer, EIL)
4. 4. Elektronenleitschicht (electron transport layer, ETL)
5. 5. Lochblockierschicht (hole blocking layer, HBL)
6. 6. Emissionsschicht bzw. Emitterschicht (emitting layer, EML)
7. 7. Elektronenblockierschicht (electron blocking layer, EBL)
8. 8. Lochtransportschicht (hole transport layer, HTL)
9. 9. Lochinjektionsschicht (hole injection layer, HIL)
10. 10. Anode

According to a further embodiment, the organic component, in particular an OLED, has an inverted structure. The inverted structure is characterized in that the cathode is located on the substrate and the other layers are applied correspondingly inverted:

1. 1st substrate (carrier material)
2. 2nd cathode
3. 3. electron injection layer (EIL)
4. 4. electron transport layer (ETL)
5. 5. hole blocking layer (HBL)
6. 6. Emission layer or emitter layer (EML)
7. 7. Electron blocking layer (EBL)
8. 8. hole transport layer (HTL)
9. 9. Hole injection layer (HIL)
10. 10. anode

In this case, individual layers are only available in an optional manner. Furthermore, several of these layers can coincide. And there may be multiple layers in the component multiple times.

In one embodiment, in the inverted OLED, the anode layer of the typical structure, for example an ITO layer (indium tin oxide), is connected as the cathode.

According to a further embodiment, the organic component, in particular an OLED, has a stacked construction. In this case, the individual OLEDs are arranged one above the other and not next to each other as usual. By a stacked structure, the generation of mixed light can be made possible. For example, this design can be used in the generation of white light, the entire visible spectrum of which is typically imaged by the combination of the emitted light from blue, green and red emitters. Furthermore, significantly longer lifetimes compared to conventional OLEDs can be achieved with virtually the same efficiency and identical luminance. For the stacked construction, a so-called charge generation layer (CGL) is optionally inserted between two OLEDs. This consists of an n-doped and a p-doped layer, wherein the n-doped layer is typically applied closer to the anode.

In one embodiment - a so-called tandem OLED - occur two or more emission layers between the anode and cathode. In one embodiment, three emission layers are arranged one above the other, wherein an emission layer emits red light, an emission layer emits green light, and an emission layer emits blue light, and optionally further charge generation, blocking or transport layers are applied between the individual emission layers. In a further embodiment, the respective emission layers are applied directly adjacent. In a further embodiment, a charge generation layer is in each case located between the emission layers. Furthermore, emission layers directly adjacent and separated by charge generation layers can be combined in an OLED.

Furthermore, an encapsulation may be arranged above the electrodes and the organic layers. The encapsulation can be embodied, for example, in the form of a glass cover or in the form of a thin-layer encapsulation.

The carrier material of the optoelectronic device may be, for example, glass, quartz, plastic, metal, a silicon wafer or any other suitable solid or flexible, optionally transparent material. The carrier material may comprise, for example, one or more materials in the form of a layer, a film, a plate or a laminate.

As the anode of the optoelectronic device, for example, transparent conductive metal oxides such as ITO (indium tin oxide), zinc oxide, tin oxide, cadmium oxide, titanium oxide, indium oxide or aluminum zinc oxide (AZO), Zn ₂ SnO ₄ , CdSnO ₃ , ZnSnO ₃ , MgIn ₂ O ₄ , GaInO ₃ , Zn ₂ In ₂ O ₅ or In ₄ Sn ₃ O ₁₂ or mixtures of different transparent conductive oxides.

As materials of a HIL, for example, PEDOT: PSS (poly-3,4-ethylenedioxythiophene: polystyrenesulfonic acid), PEDOT (poly-3,4-ethylenedioxythiophene), m-MTDATA (4,4 ', 4 "-tris [phenyl (m) tolyl) amino] triphenylamine), spiro-TAD (2,2 ', 7,7'-tetrakis (N, N-diphenylamino) -9,9-spirobifluorene), DNTPD (4,4'-bis [N- [4 - {N, N-bis (3-methylphenyl) amino} phenyl] -N-phenylamino] biphenyl), NPB (N, N'-bis (1-naphthalenyl) -N, N'-bis-phenyl- (1 , 1'-biphenyl) -4,4'-diamine), NPNPB (N, N'-diphenyl-N, N'-di- [4- (N, N-diphenyl-amino) -phenyl] -benzene), MeO- TPD (N, N, N ', N'-tetrakis (4-methoxyphenyl) benzene), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile) or spiro-NPD (N, N') diphenyl-N, N'-bis (1-naphthyl) -9,9'-spirobifluorene-2,7-diamine), for example, the layer thickness is 10-80 nm. Further, small molecules may be used (e.g. Copper phthalocyanine (CuPc eg 10 nm thick)) or metal oxides such as, for example, MoO ₃ , V ₂ O ₅ .

As materials of an HTL, tertiary amines, carbazole derivatives, polystyrenesulfonic acid-doped polyethylenedioxythiophene, camphorsulfonic acid-doped polyaniline poly-TPD (poly (4-butylphenyl-diphenyl-amine)), [alpha] -NPD (poly (4-butylphenyl-diphenyl-amine) )), TAPC (4,4'-cyclohexylidene bis [N, N-bis (4-methylphenyl) benzenamine]), TCTA (tris (4-carbazoyl-9-ylphenyl) amine), 2-TNATA (4.4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN or TrisPcz (9,9'-diphenyl-6- (9- phenyl-9H-carbazol-3-yl) -9H, 9'H-3,3'-bicarbazole.) By way of example, the layer thickness is 10 nm to 100 nm.

The HTL may comprise a p-doped layer comprising an inorganic or organic dopant in an organic hole-conducting matrix. As inorganic dopant, for example, transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide can be used. Examples of suitable organic dopants are tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper Pentafluorobenzoate (Cu (I) pFBz) or transition metal complexes can be used. By way of example, the layer thickness is 10 nm to 100 nm.

As materials of an electron-blocking layer it is possible to use, for example, mCP (1,3-bis (carbazol-9-yl) benzene), TCTA, 2-TNATA, mCBP (3,3-di (9H-carbazol-9-yl) biphenyl), tris Pcz (9,9'-diphenyl-6- (9-phenyl-9H-carbazol-3-yl) -9H, 9'H-3,3'-bicarbazole), CzSi (9- (4-tert-butylphenyl) 3,6-bis (triphenylsilyl) -9H-carbazole) or DCB (N, N'-dicarbazolyl-1,4-dimethylbenzene). By way of example, the layer thickness is 10 nm to 50 nm.

The emitter layer EML or emission layer consists of or comprises emitter material or a mixture comprising at least two emitter materials and optionally one or more host materials. Suitable host materials include mCP, TCTA, 2-TNATA, mCBP, CBP (4,4'-bis- (N-carbazolyl) -biphenyl), Sif87 (dibenzo [b, d] thiophen-2-yltriphenylsilane), Sif88 (Dibenzo [b, d] thiophen-2-yl) diphenylsilane) or DPEPO (bis [2 - ((oxo) diphenylphosphino) phenyl] ether). For green or red-emitting emitter material or a mixture comprising at least two emitter materials, the common matrix materials such as CBP are suitable. For emitter material emitting in the blue or a mixture comprising at least two emitter materials, UHG matrix materials (ultra-high energy gap materials) (see, for example, US Pat. ME Thompson et al., Chem. Mater. 2004, 16, 4743 ) or other so-called wide-gap matrix materials. By way of example, the layer thickness is 10 nm to 250 nm.

The hole blocking layer HBL may be, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), bis (2-methyl-8-hydroxyquinolinato) - (4-phenylphenolato) aluminum (III) (BAlq), Nbphen (2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum tris (8-hydroxyquinoline)), TSPO1 (diphenyl-4-) triphenylsilylphenyl-phosphine oxide) or TCB / TCP (1,3,5-tris (N-carbazolyl) benzene / 1,3,5-tris (carbazol) -9-yl) benzene). By way of example, the layer thickness is 10 nm to 50 nm.

The electron transport layer ETL can be, for example, materials based on AlQ ₃ , TSPO 1, BPyTP 2 (2,7-di (2,2'-bipyridin-5-yl) triphenyl), Sif 87, Sif 88, BmPyPhB (1,3-bis [3, 5-di (pyridin-3-yl) phenyl] benzene) or BTB (4,4'-bis- [2- (4,6-diphenyl-1,3,5-triazinyl)] - 1,1'-biphenyl ) exhibit. By way of example, the layer thickness is 10 nm to 200 nm.

As materials of a thin electron injection layer EIL, for example, CsF, LiF, 8-hydroxyquinolinolatolithium (Liq), Li ₂ O, BaF ₂ , MgO or NaF can be used.

As materials of the cathode layer metals or alloys may serve, for example Al, Al> AIF, Ag, Pt, Au, Mg, Ag: Mg. Typical layer thicknesses are from 100 nm to 200 nm. In particular, one or more metals are used which are stable in air and / or which are self-passivating, for example by forming a thin protective oxide layer.

As materials for encapsulation, for example, alumina, vanadium oxide, zinc oxide, zirconium oxide, titanium oxide, hafnium oxide, lanthanum oxide, tantalum oxide are suitable.

In one embodiment of the organic optoelectronic device according to the invention, the organic molecule according to the invention is used as the emission material in a light-emitting layer EML, wherein it is used either as a pure layer or in combination with one or more host materials.

One embodiment of the invention relates to organic optoelectronic devices which have an external quantum efficiency (EQE) at 1000 cd / m ² of greater than 5%, in particular greater than 8%, in particular greater than 10%, or greater than 13%, or greater than 16%. and in particular of greater than 20% and / or an emission maximum at a wavelength between 420 nm and 500 nm, in particular between 430 nm and 490 nm, or between 440 nm and 480 nm and in particular between 450 nm and 470 nm and / or an LT80 value at 500 cd / m ² of greater than 30 h, in particular greater than 70 h, or of greater than 100 h, or of greater than 150 h and in particular greater than 200 h.

The mass fraction of the organic molecule according to the invention at the emitter layer EML is in a further embodiment in a light-emitting layer in optical light-emitting devices, in particular in OLEDs, between 1% and 80%. In one embodiment of the organic optoelectronic device according to the invention, the light-emitting layer is applied to a substrate, wherein preferably an anode and a cathode are applied to the substrate and the light-emitting layer is applied between anode and cathode.

In one embodiment, the light-emitting layer may comprise only an organic molecule according to the invention in 100% concentration, wherein the anode and the cathode are applied to the substrate, and the light-emitting layer is applied between the anode and cathode.

In one embodiment of the organic optoelectronic device according to the invention, a hole and electron injecting layer between anode and cathode, and a hole and electron transporting layer between hole and electron injecting layer, and the light emitting layer between holes and electron transporting layer are applied.

The organic optoelectronic device comprises in a further embodiment of the invention: a substrate, an anode, a cathode and at least one hole- and electron-injecting layer, and at least one hole- and electron-transporting layer, and at least one light-emitting layer, the organic according to the invention Molecule and one or more host materials whose triplet (T ₁ ) energy levels are higher in energy than the triplet (T ₁ ) energy levels of the organic molecule and whose singlet (S ₁ ) energy levels are higher than the singlet energy (S ₁ ). Energy levels of the organic molecule, wherein the anode and the cathode is applied to the substrate, and the hole and electron injecting layer between the anode and cathode is applied, and the hole and electron transporting layer between holes and electron injecting layer is applied, and the light emitting S Is applied between holes and electron transporting layer.

In a further aspect, the invention relates to a method for producing an optoelectronic component. In this case, an organic molecule according to the invention is used.

In one embodiment, the manufacturing method comprises processing the organic molecule of the invention by a vacuum evaporation method or from a solution.

• - mit einem Sublimationsverfahren beschichtet wird,
• - mit einem OVPD (Organic Vapor Phase Deposition) Verfahren beschichtet wird,
• - mit einer Trägergassublimation beschichtet wird, und/oder
• - aus Lösung oder mit einem Druckverfahren hergestellt wird.

The invention also provides a method for producing an optoelectronic device according to the invention, in which at least one layer of the optoelectronic device

• is coated with a sublimation process,
• is coated with an OVPD (Organic Vapor Phase Deposition) method,
• is coated with a carrier gas sublimation, and / or
• - made from solution or with a printing process.

In the production of the optoelectronic device according to the invention known methods are used. Generally, the layers are individually applied to a suitable substrate in successive deposition steps. In the vapor deposition process, conventional methods such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) can be used. For active matrix OLED (AMOLED) displays, the deposition onto an AMOLED backplane takes place as a substrate.

Alternatively, layers of solutions or dispersions may be applied in suitable solvents. Exemplary suitable coating methods are spin-coating, dip-coating and jet-printing methods. According to the invention, the individual layers can be produced both via the same and via different coating methods.

Examples

General Synthetic Scheme I

In the above scheme, the chemical group CN of cyano-difluorophenylboronic acid and / or the substituted in 3,4,6-position R ¹ -substituted 5-bromo-2-cyanobenzonitrils may be replaced by CF ₃ .

5-Brom-2-cyanopyridin (1,00 Äquivalente), 4-Cyano-3,5-difluorphenylboronsäure (1,20 Äquivalente), Pd₂(dba)₃ (0,04 Äquivalente), 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (0,16 Äquivalente) und tribasisches Kaliumphosphat (2,50 Äquivalente) werden unter Stickstoff in einem Toluol/Wasser-Gemisch (Verhältnis 10:1) bei 100 °C für 17 h gerührt. Durch typische Aufreinigungsmethoden wie Extraktion oder Filtration und anschließendem Entfernen des jeweiligen Lösungsmittels wird das Produkt als Feststoff erhalten. Durch Umkristallisation und/oder Säulenchromatographie kann das Produkt bei Bedarf weiter aufgereinigt werden. Erfindungsgemäß kann statt einer Boronsäure auch ein entsprechender Boronsäureester verwendet werden. Statt Toluol können weitere geeignete Lösungsmittel wie z.B. Dioxan eingesetzt werden.General Synthesis AAV1:

5-Bromo-2-cyanopyridine (1.00 equivalents), 4-cyano-3,5-difluorophenylboronic acid (1.20 equivalents), Pd ₂ (dba) ₃ (0.04 equivalents), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (SPhos) (0.16 equiv.) And potassium phosphate tribasic (2.50 equiv.) Are stirred under nitrogen in a toluene / water mixture (10: 1 ratio) at 100 ° C for 17 h. Typical purification methods, such as extraction or filtration and subsequent removal of the particular solvent, give the product as a solid. By recrystallization and / or column chromatography, the product can be further purified if necessary. According to the invention, instead of a boronic acid, it is also possible to use a corresponding boronic acid ester. Instead of toluene, other suitable solvents such as dioxane can be used.

General Synthesis AA 2:

The synthesis of Z2 is analogous to AAV1, wherein 5-bromo-2-cyanopyridine is reacted with 3-cyano-2,4-difluorophenylboronic acid.

General Synthesis AAV3:

The synthesis of Z3 is analogous to AAV1, wherein 5-bromo-2-cyanopyridine is reacted with 4-cyano-2,6-difluorophenylboronic acid.

General Synthesis AAV4:

The synthesis of Z4 is analogous to AAV1, wherein 5-bromo-2-cyanopyridine is reacted with 4-cyano-2,5-difluorophenylboronic acid.

General Synthesis AAV5:

The synthesis of Z5 is analogous to AAV1, wherein 5-bromo-2-cyanopyridine is reacted with 2-cyano-4,5-difluorophenylboronic acid.

General Synthesis AAV6:

The synthesis of Z6 takes place analogously to AAV1, with 5-bromo-2-cyanopyridine being reacted with 3-cyano-4,5-difluorophenylboronic acid.

General Synthesis AAV7:

Z1, Z2, Z3, Z4, Z5 or Z6 (each 1.00 equivalents), the corresponding donor molecule DH (2.00 equivalents) and tribasic potassium phosphate (4.00 equivalents) are suspended under nitrogen in DMSO and at 120 ° C stirred (16 h). Subsequently, the reaction mixture is poured into water. The precipitated solid is filtered and washed with water. The precipitated solid is dissolved in dichloromethane, dried over sodium sulfate, filtered and the solvent is then removed. The crude product is finally purified by recrystallization from ethanol or flash chromatography. The product is obtained as a solid.

Specifically, DH corresponds to a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g. 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1, 8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2- Phenylcarbazole, 2-tert-butylcarbazole) or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

General experimental procedures

Cyclic voltammetry

Cyclic voltammograms of 10 ^-3 molar solutions of the organic molecules in dichloromethane and tetrabutylammonium hexafluorophosphate (0.1 mol / l) as the supporting electrolyte were recorded using a Model 600D Series Electrochemical Analyzer with Workstation (CH Instruments) at a scan rate of 100 mV s ^-1 . The measurements were carried out at room temperature, under protective gas atmosphere with a three-electrode arrangement (working and counter electrode: Pt-Wire, reference electrode: Pt-Wire) and calibrated against FeCp ₂ / FeCp ₂ ⁺ as an internal standard. HOMO and LUMO data were corrected by means of ferrocene as an internal standard against SCE and calculated according to the following formulas: E _CV-HOMO = - (1.4 * 0.978 * (Ox / V - ferrocene / V) + 4.6) eV.

Bills according to the density functional theory

For the optimization of molecular structures, the BP86 functional was used, using the resolution of identity approximation (RI). Excitation energies were calculated for the BP86-optimized structures using the time-dependent DFT method (TD-DFT) using the B3LYP function. In all calculations, def2-SV (P) basis sets and an m4 grid were used for numerical integration. All DFT calculations were performed with the Turbomole program package (version 6.5) (TURBOMOLE V6.4 2012, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; available from http: // www. turbomole.com).

Photophysical measurements

Sample preparation, film: spin-coating

Device: Spin150, SPS euro.

The sample concentration corresponded to 10 mg / ml, prepared in a suitable solvent. Program: 1) 3 s at 400 rpm; 2) 20 s at 1000 rpm at 1000 rpm / s. 3) 10 s at 4000 rpm at 1000 rpm / s. The films were dried after coating for one minute at 70 ° C in air on a precision hot plate of LHG.

Photoluminescence spectroscopy and TCSPC

Steady-state emission spectroscopy was performed on a Horiba Scientific FluoroMax-4 fluorescence spectrometer equipped with a 150 W xenon-arc lamp, excitation and emission monochromators and a Hamamatsu R928 photomultiplier tube, and a time-correlated single photon count (Time -correlated single-photon counting, TCSPC) option. Emission and excitation spectra were corrected by standard correction curves.

• NanoLED 370 (Wellenlänge: 371 nm, Pulsdauer: 1,1 ns)
• NanoLED 290 (Wellenlänge: 294 nm, Pulsdauer: <1 ns)
• SpectraLED 310 (Wellenlänge: 314 nm)
• SpectraLED 355 (Wellenlänge: 355 nm).

Emission decay times were also measured on this system using the TCSPC method with the FM-2013 accessory and a TCSPC hub from Horiba Yvon Jobin. Excitation sources:

• NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns)
• NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns)
• SpectraLED 310 (wavelength: 314 nm)
• SpectraLED 355 (wavelength: 355 nm).

The evaluation (exponential fitting) was carried out with the software package DataStation and the DAS 6 evaluation software. The fit was given by the chi-square method.

Quantum efficiency determination

The photoluminescence quantum yield (PLQY) was measured by Hamamatsu Photonics Absolute PL Quantum Yield Measurement C9920-03G system. This consists of a 150 W xenon gas discharge lamp, automatically adjustable Czerny-Turner monochromators (250 - 950 nm) and an Ulbricht sphere with highly reflecting Spektralon coating (a Teflon derivative), which is connected via a fiber optic cable with a PMA-12 multichannel detector BT (back thinned) CCD chip with 1024 x 122 pixels (size 24 x 24 microns) is connected. The evaluation of the quantum efficiency and the CIE coordinates took place with the help of the software U6039-05 version 3.6.0.

The emission maximum is given in nm, the quantum yield Φ in% and the CIE color coordinates as x, y values.

1. 1) Durchführung der Qualitätssicherung: Als Referenzmaterial dient Anthracene in Ethanol mit bekannter Konzentration.
2. 2) Ermitteln der Anregungswellenlänge: Es wurde zuerst das Absorptionsmaximum des organischen Moleküls bestimmt und mit diesem angeregt.
3. 3) Durchführung der Probenmessung:
   • Es wurde von entgasten Lösungen und Filmen unter Stickstoff-Atmosphäre die absolute Quantenausbeute bestimmt.

The photoluminescence quantum yield was determined according to the following protocol:

1. 1) Implementation of quality assurance: The reference material is anthracenes in ethanol of known concentration.
2. 2) Determining the Excitation Wavelength: First, the absorption maximum of the organic molecule was determined and excited with it.
3. 3) Execution of the sample measurement:
   • The absolute quantum yield was determined for degassed solutions and films under a nitrogen atmosphere.

mit der Photonenzahl n_photon und der Intensität Int.The calculation was carried out system-internally according to the following equation: $${\mathrm{\Phi }}_{PL}=\frac{n_{pHOtOn}.emittiert}{n_{pHOtOn}.absOrbiert}=\frac{{\displaystyle \int \frac{\lambda }{Hc}}\left[In{t}_{emittiert}^{PrObe}\left(\lambda \right)-In{t}_{absOrbiert}^{PrObe}\left(\lambda \right)\right]d\lambda }{{\displaystyle \int \frac{\lambda }{Hc}\left[In{t}_{emittiert}^{Referenz}\left(\lambda \right)-In{t}_{absOrbiert}^{Referenz}\left(\lambda \right)\right]d\lambda }}$$

with the photon number n _photon and the intensity int.

All photophysical measurements were determined in the medium given in each case and at room temperature.

Preparation and characterization of organic electroluminescent devices from the gas phase

With the organic molecules according to the invention, OLED devices can be created by means of vacuum sublimation technology. If a layer contains several components, the ratio of these is given in percentage by mass.

These not yet optimized OLEDs can be characterized by default; For this purpose, the electroluminescence spectra, the external quantum efficiency (measured in%) as a function of the brightness, calculated from the light detected by the photodiode, and the current are recorded. The lifetime of the OLEDs can be determined from the time course of the electroluminescence spectra. The specified LT50 value corresponds to the time at which the luminance has fallen to 50% of the starting value. Analogously, the LT70 value corresponds to the time at which the luminance has fallen to 70% of the starting value.

The values given result from the average of the different pixels of an OLED. The spectra shown each show a measurement series of a pixel.

HPLC-MS:

HPLC-MS spectroscopy was measured on an Agilent HPLC system (1100 series) with a connected MS detector (Thermo LTQ XL). For HPLC, a RP column 4.6mm x 150mm, 5.0μm particle size from Waters was used. It was worked without precolumn and at room temperature with the solvents acetonitrile, water and tetrahydrofuran in these concentrations: Solvent A: H ₂ O (90%) MeCN (10%) Solvent B: H ₂ O (10%) MeCN (90%) Solvent C: THF (100%)

It was operated with an injection volume of 15 μL and a concentration of 0.5 mg / ml. Flow [ml / min] Time [min] A [%] B [%] D [%] 3 0 40 50 10 3 10 10 15 75 3 16 10 15 75 3 16,01 40 50 10 3 20 40 50 10

The ionization of the sample is carried out by APCI (atmospheric pressure chemical ionization).

example 1

Example 1 was prepared according to AAV1-1 (yield 68%) and AAV7 (yield 72%). MS (HPLC-MS), m / z (retention time): 535, (4.33 min)
1 shows the emission spectrum of Example 1 (10% in PMMA). The emission maximum is 483 nm. The photoluminescence quantum yield (PLQY) is 75% and the half-width is 0.43 eV.

Example 2

Example 2 was prepared according to AAV1-1 (yield 68%) and AAV7 (yield 58%). MS (HPLC-MS), m / z (retention time): 759, (9.05 min)
2 shows the emission spectrum of Example 2 (10% in PMMA). The emission maximum is 500 nm. The photoluminescence quantum yield (PLQY) is 68% and the half-width is 0.43 eV.

Example 3

Example 3 was prepared according to AAV1 (yield 68%) and AAV7 (yield 51%).
3 shows the emission spectrum of Example 3 (10% in PMMA). The emission maximum is 537 nm. The photoluminescence quantum yield (PLQY) is 30% and the half width is 0.44 eV.

Further examples of organic molecules according to the invention:

list of figures

• 1 Emissionsspektrum von Beispiel 1 in 10 % PMMA.
• 2 Emissionsspektrum von Beispiel 2 in 10 % PMMA.
• 3 Emissionsspektrum von Beispiel 3 in 10 % PMMA.

Show it:

• 1 Emission spectrum of Example 1 in 10% PMMA.
• 2 Emission spectrum of Example 2 in 10% PMMA.
• 3 Emission spectrum of Example 3 in 10% PMMA.

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited non-patent literature

• M. E. Thompson et al., Chem. Mater. 2004, 16, 4743 [0155]

Claims (15)

An organic molecule comprising - a first chemical entity comprising or consisting of a structure according to formula I.

and - two second chemical units, each identical or different on each occurrence, comprising or consisting of a structure according to formula II,

wherein the first chemical moiety is linked to the two second chemical moieties via a single bond; T is the point of attachment of the single bond between the first chemical entity and a second chemical entity, or is H; V is the point of attachment of the single bond between the first chemical entity and a second chemical entity, or is H; W is the point of attachment of the single bond between the chemical entity of formula I and a second chemical entity or is selected from the group consisting of H, CN and CF ₃ ; X is a point of attachment of the single bond between the first chemical moiety and a second chemical moiety or is selected from the group consisting of H, CN and CF ₃ ; Y is the point of attachment of the single bond between the first chemical entity of formula I and a second chemical entity, or is selected from the group consisting of H, CN and CF ₃ ; # denotes the point of attachment of the single bond between a second chemical entity and the first chemical entity; Z is each time the same or different a direct bond or selected from the group consisting of CR ³ R ⁴ , C = CR ³ R ⁴ , C = O, C = NR ³ , NR ³ , O, SiR ³ R ⁴ , S , S (O) and S (O) ₂ ; Q is CR ^Q or N at each occurrence; R ^Q is the same or different at each instance, R ¹ or R *; R * is equal to CN or CF ₃ ; R ¹ is the same or different H, deuterium, a linear alkyl group having 1 to 5 carbon atoms at each occurrence, each one or more H atoms may be replaced by deuterium; a linear alkenyl or alkynyl group having 2 to 8 C atoms, wherein in each case one or more H atoms may be replaced by deuterium; a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein in each case one or more H atoms may be replaced by deuterium; or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, the each may be substituted with one or more R ⁶ ; R ^a , R ³ and R ⁴ are each the same or different at each occurrence H, deuterium, N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted with one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups is replaced by R ⁵ C =CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C =O, C =S, C =Se, C =NR ⁵ , P ( = O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, each of which may be substituted with one or more R ⁵ groups, or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms each substituted with one or more R ⁵ groups may, or a Diarylaminogruppe, Diheteroarylaminogruppe or Arylheteroarylaminogruppe having 10 to 40 aromatic ring atoms, which may be substituted in each case with one or more radicals R ⁵ ; R ⁵ is the same or different H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br at each occurrence. I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted by one or more R ⁶ radicals, one or more non-adjacent CH ₂ groups being replaced by R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O, S or CONR ⁶ , and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a linear alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more R ⁶ radicals, one or more non-adjacent CH ₂ groups being replaced by R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O, S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted with one or more R ⁶ radicals, wherein one or more non-adjacent CH ₂ groups R ⁶ C = CR ⁶ , C≡C, Si (R ⁶ ) ₂ , Ge (R ⁶ ) ₂ , Sn (R ⁶ ) ₂ , C = O, C = S, C = Se, C = NR ⁶ , P (= O) (R ⁶ ), SO, SO ₂ , NR ⁶ , O, S or CONR ⁶ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, each of which may be substituted with one or more R ⁶ groups, or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms each substituted with one or more R ⁶ groups may, or a Diarylaminogruppe, Diheteroarylaminogruppe or Arylheteroarylaminogruppe having 10 to 40 aromatic ring atoms, which may be substituted in each case with one or more radicals R ⁶ ; R ⁶ is the same or different H, deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, each containing one or more H atoms by deuterium, CN, CF ₃ or NO ₂ may be replaced; or a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein in each case one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein in each case one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having from 10 to 40 aromatic ring atoms; where each of the radicals R ^a , R ³ , R ⁴ or R ^{5 can} also form with one or more further radicals R ^a , R ³ , R ⁴ or R ⁵ a mono- or polycyclic, aliphatic, aromatic and / or benzoanelliertes ring system; one Q is equal to N and the other Q is CR ^Q ; wherein one R ^Q is R * and the other R ^Q is R ¹ ; wherein exactly one radical selected from the group consisting of W, X and Y is CN or CF ₃ and exactly two radicals selected from the group consisting of T, V, W, X and Y is a point of attachment of the single bond between the first chemical Unit and a second chemical entity. Organic molecule after Claim 1 in which the first chemical entity has a structure of the formula Ia or consists of such a structure:

wherein for R ¹ , T, V, W, X, and Y, the in Claim 1 These definitions apply. Organic molecule after Claim 1 or 2 where R ^{1 is,} identically or differently, H, methyl or phenyl on each occurrence. Organic molecule after Claim 1 to 3 where W is CN. Organic molecule after Claim 1 to 4 in which the second chemical entity identically or differently has, on each occurrence, a structure of the formula IIa or consists of such a structure:

where # and R ^{a are} the in Claim 1 These definitions apply. Organic molecule after Claim 1 to 5 in which the second chemical unit has in each case a structure of the formula IIb or consists of such a structure:

where R ^{b is} identical or different for each occurrence N (R ⁵ ) ₂ , OH, Si (R ^s ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear Alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R ⁵ , or a diarylamino group, Diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms each of which may be substituted with one or more R ⁵ groups; and for # and R ⁵ the in Claim 1 These definitions apply. Organic molecule after Claim 1 to 5 in which the second chemical unit has in each case a structure of the formula IIc or consists of such a structure:

wherein R ^b in each occurrence is identical or different N (R ⁵ ) ₂ , OH, Si (R ⁵ ) ₃ , B (OR ⁵ ) ₂ , OSO ₂ R ⁵ , CF ₃ , CN, F, Br, I, a linear Alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, one or more non-adjacent CH ₂ groups denoted by R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R ⁵ radicals, wherein one or more non-adjacent CH ₂ groups R ⁵ C = CR ⁵ , C≡C, Si (R ⁵ ) ₂ , Ge (R ⁵ ) ₂ , Sn (R ⁵ ) ₂ , C = O, C = S, C = Se, C = NR ⁵ , P (= O) (R ⁵ ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ may be replaced and wherein one or more H atoms may be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, each of which may be substituted with one or more R ⁵ groups, or an aryloxy or heteroaryloxy group having from 5 to 60 aromatic ring atoms each substituted with one or more R ⁵ groups or a diarylamino group, diheteroarylamino group or arylheteroarylamino group may be substituted with 10 to 40 aromatic ring atoms, each with one or more radicals R ⁵ ; and by the way the in Claim 1 These definitions apply. Organic molecule after Claim 6 or 7 Wherein R ^b at each occurrence, identically or differently, Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph, which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph be substituted can pyridinyl, each of which may be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, pyrimidinyl, each having one or more radicals selected from Me, ⁱ Pr, ^t Bu , CN, CF ₃ or Ph may be substituted, triazinyl which in each case with one or more groups selected from Me, ⁱ Pr, ^Bu, CN, CF ₃ or Ph may be substituted, or carbazolyl, which by one or more radicals may be selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph. Process for the preparation of an organic molecule according to Claim 1 to 8th in which a 3,4-position R ¹ -substituted, in the 2-position R * -substituted and in the 5-position halogen-substituted pyridine or in 3,5,6-position R ¹ -substituted, in 2 Position R * -substituted and 4-position halogen-substituted pyridine or a 2,4,6-position R ¹ -substituted, 3-position R * -substituted and 5-position halogen-substituted pyridine in starting material is used. Use of an organic molecule according to Claim 1 to 8th as a luminescent emitter and / or as a host material and / or as an electron transport material and / or as a hole injection material and / or as a hole blocking material in an organic optoelectronic device. Use after Claim 10 wherein the organic optoelectronic device is selected from the group consisting of: • organic light-emitting diodes (OLEDs), • light-emitting electrochemical cells, • OLED sensors, especially in non-hermetically shielded gas and vapor sensors, • organic diodes, • organic solar cells, • organic transistors, • organic field-effect transistors, • organic Lasers and down-conversion elements. A composition comprising or consisting of: (a) at least one organic molecule according to any one of Claims 1 to 8th in particular in the form of an emitter and / or host, and (b) one or more emitter and / or host materials derived from the molecule Claim 1 to 8th different and (c) optionally one or more dyes and / or one or more solvents. An organic optoelectronic device comprising an organic molecule Claim 1 to 8th or a composition according to Claim 12 , in particular formed as a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, in particular non-hermetically outwardly shielded gas and vapor sensors, organic diode, organic solar cell, organic transistor, organic field effect transistor , organic laser and down-conversion element. Organic optoelectronic device according to Claim 13 , comprising - a substrate, - an anode and - a cathode, wherein the anode or the cathode are applied to the substrate, and - at least one light-emitting layer which is arranged between the anode and cathode and which detects an organic molecule Claim 1 to 8th or a composition according to Claim 12 having. A method for producing an optoelectronic component, wherein an organic molecule according to Claim 1 to 8th in particular comprising processing the organic molecule by means of a vacuum evaporation process or from a solution.

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