DE102016121562B4 - Organic molecules, in particular for use in organic optoelectronic devices - Google Patents

Abstract

und
- eine zweite chemische Einheit aufweisend eine oder bestehend aus einer Struktur gemäß

wobei die erste chemische Einheit über eine Einfachbindung mit der zweiten chemischen Einheit verknüpft ist;
und wobei L^B ausgewählt ist aus einer der Strukturen gemäß Unterformeln Ia bis Ic:

wobei gilt:
§ ist der Anknüpfungspunkt der Einfachbindung zwischen der zentralen Phenylgruppe der ersten chemischen Einheit und L^B;
$ ist der Anknüpfungspunkt der Einfachbindung zwischen der zentralen Triazinylgruppe der ersten chemischen Einheit und L^B;
T ist der Anknüpfungspunkt der Einfachbindung zwischen der ersten chemischen Einheit und der chemischen Einheit oder ist ausgewählt aus der Gruppe bestehend aus R² und CN;
V ist H oder der Anknüpfungspunkt der Einfachbindung zwischen der ersten chemischen Einheit und der zweiten chemischen Einheit;
W ist Anknüpfungspunkt der Einfachbindung zwischen der ersten chemischen Einheit und
der zweiten chemischen Einheit oder ist ausgewählt aus der Gruppe bestehend aus R² und CN;
X ist ausgewählt aus der Gruppe bestehend aus R² und CN;
Y ist ausgewählt aus der Gruppe bestehend aus R² und CN;
# kennzeichnet den Anknüpfungspunkt der Einfachbindung zwischen der zweiten chemischen Einheit und der ersten chemischen Einheit;
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;
R¹ ist bei jedem Auftreten gleich oder verschieden H, Deuterium, eine lineare Alkylgruppe mit 1 bis 5 C-Atomen, eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 8 C-Atomen, eine verzweigte oder cyclische Alkyl-, Alkenyl- oder Alkinylgruppe mit 3 bis 10 C-Atomen, wobei ein oder mehrere H-Atome durch Deuterium ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 15 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste R⁶ substituiert sein kann;
R² ist bei jedem Auftreten gleich oder verschieden H, Deuterium, eine lineare Alkylgruppe mit 1 bis 5 C-Atomen, eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 8 C-Atomen, eine verzweigte oder cyclische Alkyl-, Alkenyl- oder Alkinylgruppe mit 3 bis 10 C-Atomen, wobei ein oder mehrere H-Atome durch Deuterium ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 15 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste R⁶ substituiert sein kann;
R^1a, R^1b und R^1c ist bei jedem Auftreten gleich oder verschieden H, Deuterium, eine lineare Alkylgruppe mit 1 bis 5 C-Atomen, eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 8 C-Atomen, eine verzweigte oder cyclische Alkyl-, Alkenyl- oder Alkinylgruppe mit 3 bis 10 C-Atomen, wobei ein oder mehrere H-Atome durch Deuterium ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 15 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste 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 oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen 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)(R^S), 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 durch einen oder mehrere Reste R⁵ substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die durch einen oder mehrere Reste R⁵ substituiert sein kann, oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche durch einen oder mehrere Reste 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 oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen 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 durch einen oder mehrere Reste R⁶ substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die durch einen oder mehrere Reste R⁶ substituiert sein kann, oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche durch einen oder mehrere 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 oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 5 C-Atomen oder eine verzweigte oder cyclische Alkyl-, Alkenyl-, Alkinyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 5 C-Atomen, 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 oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen;
wobei 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 kann;
wobei genau ein Rest ausgewählt aus der Gruppe bestehend aus W, X und Y gleich CN ist und genau ein Rest ausgewählt aus der Gruppe bestehend aus T, V und W gleich dem Anknüpfungspunkt der Einfachbindung zwischen der ersten chemischen Einheit gemäß Formel I und der zweiten chemischen Einheit ist und
weiterhin die Maßgabe gilt, dass T gleich H ist, wenn V gleich dem Anknüpfungspunkt der Einfachbindung zwischen der ersten chemischen Einheit gemäß Formel I und der zweiten chemischen Einheit und W gleich CN ist;
und dass W gleich H ist, wenn T gleich CN und V gleich dem Anknüpfungspunkt der Einfachbindung zwischen der ersten chemischen Einheit und der zweiten chemischen Einheit ist.

Having organic molecule
- A first chemical unit having or consisting of a structure according to

and
- A second chemical unit having or consisting of a structure according to

wherein the first chemical entity is linked to the second chemical entity via a single bond;
and where L ^{B is} selected from one of the structures according to sub-formulas Ia to Ic:

where:
§ is the point of attachment of the single bond between the central phenyl group of the first chemical unit and L ^B ;
$ is the point of attachment of the single bond between the central triazinyl group of the first chemical unit and L ^B ;
T is the point of attachment of the single bond between the first chemical unit and the chemical unit or is selected from the group consisting of R ² and CN;
V is H or the point of attachment of the single bond between the first chemical unit and the second chemical unit;
W is the point of attachment of the single bond between the first chemical unit and
the second chemical unit or is selected from the group consisting of R ² and CN;
X is selected from the group consisting of R ² and CN;
Y is selected from the group consisting of R ² and CN;
# identifies the point of attachment of the single bond between the second chemical unit and the first chemical unit;
Z is on each occurrence, identically or differently, a direct bond or is 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 ;
R ¹ is on each occurrence, identically or differently, H, deuterium, a linear alkyl group with 1 to 5 carbon atoms, a linear alkenyl or alkynyl group with 2 to 8 carbon atoms, a branched or cyclic alkyl, alkenyl or alkynyl group 3 to 10 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which can be substituted by one or more radicals R ⁶ ;
On each occurrence, R ² , identically or differently, is H, deuterium, a linear alkyl group with 1 to 5 C atoms, a linear alkenyl or alkynyl group with 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group 3 to 10 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which can be substituted by one or more radicals R ⁶ ;
R ^1a , R ^1b and R ^1c are on each occurrence, identically or differently, H, deuterium, a linear alkyl group with 1 to 5 C atoms, a linear alkenyl or alkynyl group with 2 to 8 C atoms, a branched or cyclic alkyl , Alkenyl or alkynyl group with 3 to 10 carbon atoms, where one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which is substituted by one or more radicals R ⁶ can;
R ^a , R ³ and R ⁴ are on each occurrence, identically or differently, 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 with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or Thioalkoxy group with 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R ⁵ , one or more non-adjacent CH ₂ groups being 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 ^S ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ can be replaced and one or more H atoms can 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 can each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ ;
R ⁵ is on each occurrence, identically or differently, H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or
Thioalkoxy group with 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R ⁶ , 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 can be replaced and where one or more H atoms can be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which can be substituted by one or more R ⁶ radicals, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more R ⁶ radicals , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁶ ;
R ⁶ is on each occurrence, identically or differently, H, deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group with 1 to 5 carbon atoms or a linear alkenyl or alkynyl group with 2 to 5 carbon atoms Atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 5 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms;
where each of the radicals R ^a , R ³ , R ⁴ or R ^{5 can} also form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system with one or more further radicals R ^a , R ³ , R ⁴ or R ⁵ ;
where exactly one radical selected from the group consisting of W, X and Y is CN and exactly one radical selected from the group consisting of T, V and W is the point of attachment of the single bond between the first chemical unit according to formula I and the second chemical Unity is and
the proviso also applies that T is H when V is the point of attachment of the single bond between the first chemical unit according to formula I and the second chemical unit and W is CN;
and that W is H when T is CN and V is the point of attachment of the single bond between the first chemical unit and the second chemical unit.

Description

The invention relates to purely organic molecules and their use in organic light-emitting diodes (OLEDs) and in other organic optoelectronic devices.
From the WO 2017/011531 A2 organic light emitting diode materials are known. The JP 2009-246097 A and the JP 2003-282270 A describe organic electroluminescent devices.

description

The present invention was based on the object of providing molecules which are suitable for use in optoelectronic devices.

This problem is solved by the new class of organic molecules described here.

The organic molecules according to the invention are purely organic molecules, that is to say have no metal ions and are thus differentiated 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% and more. In particular, the molecules according to the invention show 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 a comparable color.

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

und

• - eine zweite chemische Einheit D aufweisend eine oder bestehend aus einer Struktur gemäß Formel II,

The organic molecules contain a first chemical unit having or consisting of a structure according to formula I:

and

• - A second chemical unit D having or consisting of a structure according to formula II,

The first chemical unit is linked to the second chemical unit D via a single bond.

L ^B is an (optionally substituted) para-, meta- or ortho-phenylene group selected from one of the structures according to sub-formulas Ia to Ic:

§ is the point of attachment of the single bond between the central phenyl group of the first chemical unit and L ^B.

$ is the point of attachment of the single bond between the central triazinyl group of the first chemical unit and L ^B.

T is the point of attachment of the single bond between the first chemical unit and the second chemical unit D or selected from the group consisting of R ² and CN.

V is H or the point of attachment of the single bond between the first chemical unit and the second chemical unit D.

W is the point of attachment of the single bond between the first chemical unit and the second chemical unit D or selected from the group consisting of R ² and CN.

X is selected from the group consisting of R ² and CN.

Y is selected from the group consisting of R ² and CN.

# is the point of attachment of the single bond between the second chemical unit D and the first chemical unit.

Z is on each occurrence, identically or differently, a direct bond or is 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 .

R ¹ is on each occurrence, identically or differently, H, deuterium, a linear alkyl group with 1 to 5 carbon atoms, a linear alkenyl or alkynyl group with 2 to 8 carbon atoms, a branched or cyclic alkyl, alkenyl or alkynyl group 3 to 10 carbon atoms, where one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which can be substituted by one or more radicals R ⁶ .

On each occurrence, R ² , identically or differently, is H, deuterium, a linear alkyl group with 1 to 5 C atoms, a linear alkenyl or alkynyl group with 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group 3 to 10 carbon atoms, where one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which can be substituted by one or more radicals R ⁶ .

R ^1a , R ^1b and R ^1c are on each occurrence, identically or differently, H, deuterium, a linear alkyl group with 1 to 5 C atoms, a linear alkenyl or alkynyl group with 2 to 8 C atoms, a branched or cyclic alkyl , Alkenyl or alkynyl group with 3 to 10 carbon atoms, where one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which is substituted by one or more radicals R ⁶ can.

R ^a , R ³ and R ⁴ are on each occurrence, identically or differently, 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 with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, each of which is substituted by one or more radicals R ⁵ can be, where one or more non-adjacent CH ₂ groups are 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 ^S ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ can be replaced and one or more H atoms can be replaced by deuterium , CN, CF ₃ or NO ₂ can be replaced; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ .

R ⁵ is on each occurrence, identically or differently, H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R ⁶ , 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 can be replaced and it is possible for one or more H atoms to be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which can be substituted by one or more R ⁶ radicals, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more R ⁶ radicals , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁶ .

R ⁶ is on each occurrence, identically or differently, H, deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group with 1 to 5 carbon atoms or a linear alkenyl or alkynyl group with 2 to 5 carbon atoms Atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 5 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms.

Each of the radicals R ^a , R ³ , R ⁴ or R ⁵ can also form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system with one or more further radicals R ^a , R ³ , R ⁴ or R ⁵ .

Exactly one radical selected from the group consisting of W, X and Y is equal to CN and exactly one radical selected from the group consisting of T, V and W is equal to the point of attachment of the single bond between the first chemical unit according to formula I and the second chemical unit Unit D.

Furthermore, the proviso applies that T is H if V is the point of attachment of the single bond between the first chemical unit and the second chemical unit D and W is CN; and that W is H if T is CN and V is the point of attachment of the single bond between the first chemical unit and the second chemical unit D.

In one embodiment, R ^{1 is,} identically or differently, methyl or phenyl on each occurrence.

In one embodiment, R ^{2 is} on each occurrence, identically or differently, H, methyl or phenyl.

In one embodiment, R ² is H on each occurrence.

In one embodiment, exactly one radical is selected from the group consisting of W, X and Y equal to CN.

In one embodiment, R ^1a , R ^1b and R ^{1c are} each on each occurrence, identically or differently, H, methyl or phenyl.

In one embodiment, R ^1a , R ^1b, and R ^1c are H.

In one embodiment, L ^{B has} a structure according to sub-formulas la.

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

where for # and R ^a the definitions given for formula I and II apply.

wobei
R^b bei jedem Auftreten gleich oder verschieden ist 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 oder eine lineare Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen 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 durch einen oder mehrere Reste R⁵ substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die durch einen oder mehrere Reste R⁵ substituiert sein kann, oder eine Diarylaminogruppe, Diheteroarylaminogruppe oder Arylheteroarylaminogruppe mit 10 bis 40 aromatischen Ringatomen, welche durch einen oder mehrere Reste R⁵ substituiert sein kann. Ansonsten gelten die oben genannten Definitionen.In a further embodiment of the organic molecules according to the invention, the second chemical unit D has a structure of the formula IIb, the formula IIb-2, the formula IIb-3 or the formula IIb-4 or consists of:

in which
R ^{b is} identical or different on each occurrence and is 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 one Alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C atoms, each of which can be substituted by one or more radicals R ⁵ , where one or more non-adjacent CH ₂ groups are 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 can be replaced and wherein one or more H atoms can 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 can each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ . Otherwise, the above definitions apply.

wobei die oben genannten Definitionen gelten.In a further embodiment of the organic molecules according to the invention, the second chemical unit D has a structure of the formula IIc, the formula IIc-2, the formula IIc-3 or the formula IIc-4 or consists of:

where the above definitions apply.

In a further embodiment of the organic molecules according to the invention, R ^{b is} independently selected at each occurrence from the group consisting of Me, ⁱ Pr, ^t Bu, CN, CF ₃ , Ph, each of which is represented by one or more radicals selected from Me, ⁱ Pr , ^t Bu, CN, CF ₃ or Ph can be substituted, pyridinyl which is substituted in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph can be, pyrimidinyl, which in each case can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, carbazolyl, which in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu , CN, CF ₃ or Ph can be substituted, triazinyl, which can be substituted in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, and N (Ph) ₂ .

In a further embodiment of the organic molecules according to the invention, R ^{b is} independently selected at each occurrence from the group consisting of Me, ⁱ Pr, ^t Bu, CN, CF ₃ , Ph, each of which is represented by one or more radicals selected from Me, ⁱ Pr , ^t Bu, CN, CF ₃ or Ph can be substituted, pyridinyl which can be substituted in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, pyrimidinyl which in each case by one or several radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph can be substituted and triazinyl, which in each case can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph .

In a further embodiment, R ^{b is} independently selected at each occurrence from the group consisting of Me, ^t Bu, CN, CF ₃ and Ph, each of which is selected by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph may be substituted.

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).Examples of the second chemical group D are shown below:

where the above definitions apply to #, Z, R ^a , R ³ , R ⁴ and R ⁵ . In one embodiment, the radical R ^{5 is} selected identically or differently on each occurrence from the group consisting of H, methyl, ethyl, phenyl and mesityl.
In one embodiment, R ^{a is} selected identically or differently on each occurrence 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 one of the formulas IIIa, IIIb or IIIc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula IIIa.

wobei R^c bei jedem Auftreten unabhängig voneinander ausgewählt ist aus der Gruppe bestehend aus Me, ⁱPr, ^tBu, CN, CF₃, Ph, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Pyridinyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Pyrimidinyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Carbazolyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, Triazinyl, das jeweils durch einen oder mehrere Reste ausgewählt aus Me, ⁱPr, ^tBu, CN, CF₃ oder Ph substituiert sein kann, und N(Ph)₂
und ansonsten die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IIIa-I, IIIb-I or IIIc-I or consist of:

where R ^{c is} independently selected on each occurrence from the group consisting of Me, ⁱ Pr, ^t Bu, CN, CF ₃ , Ph, each of which is selected by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, pyridinyl, which in each case can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, pyrimidinyl, which in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph can be substituted, carbazolyl, each of which can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, triazinyl, each of which can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph can be substituted, and N (Ph) ₂
and otherwise the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IIIa-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IIIa-II, IIIb-II or IIIc-II or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IIIa-II or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IIIa-III, IIIb-III or IIIc-III or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula IIla-III.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Illa-IV, IIIb-IV or IIIc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula IIla-IV.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IVa, IVb or IVc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IVa or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IVa-I, IVb-I or IVc-I or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IVa-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IVa-II, IVb-II or IVc-II or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IVa-III, IVb-III or IVc-III or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IVa-IV, IVb-IV or IVc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IVa-IV or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Va, Vb or Vc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula Va.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Va-I, Vb-I or Vc-I or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula Va-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Va-II, Vb-II or Vc-II or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Va-III, Vb-III or Vc-III or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Va-IV, Vb-IV or Vc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula Va-IV or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Via, Vlb or Vlc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula VIa.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Vla-I, Vlb-I or Vlc-I or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula Vla-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIa-II, VIb-II or VIc-II or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIa-III, VIb-III or VIc-III or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIa-IV, VIb-IV or VIc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula Vla-IV or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Vlla, Vllb or Vllc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula VIIa or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIa-I, VIIb-I or VIIc-I or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula VIIa-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIa-II, VIIb-II or VIIc-II or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIa-III, VIIb-III or VIIc-III or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIa-IV, VIIb-IV or VIIc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula VIIa-IV.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Villa, Vlllb or Vlllc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula Villa.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIIa-I, VIIIb-I or VIIIc-I or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula VIIa-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIIa-II, VIIIb-II or VIIIc-II or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIIa-III, VIIIb-III or VIIIc-III or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas VIIla-IV, VIIlb-IV or VIIlc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula VIIa-IV or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IXa, IXb or IXc or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have or consist of a structure of the formula IXa.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IXa-I, IXb-I or IXc-I or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IXa-I or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IXa-II, IXb-II or IXc-II or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IXa-III, IXb-III or IXc-III or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas IXa-IV, IXb-IV or IXc-IV or consist of:

where the above definitions apply.

In one embodiment, the organic molecules according to the invention have a structure of the formula IXa-IV or consist thereof.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Xa, Xb or Xc or consist of:

where the above definitions apply.

wobei die oben genannten Definitionen gelten.In one embodiment, the organic molecules according to the invention have a structure of one of the formulas Xla, Xlb or Xlc or consist of:

where the above definitions apply.

In a further embodiment of the organic molecules according to the invention, R ^{c is} independently selected at each occurrence from the group consisting of Me, ⁱ Pr, ^t Bu, CN, CF ₃ , Ph, each of which is represented by one or more radicals selected from Me, ⁱ Pr , ^t Bu, CN, CF ₃ or Ph can be substituted, pyridinyl which can be substituted in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, pyrimidinyl which in each case by one or several radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph can be substituted and triazinyl, which in each case can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph .

In a further embodiment, R ^{c is} independently selected on each occurrence from the group consisting of Me, ^t Bu, CN, CF ₃ and Ph, each of which is selected by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph may be substituted.

For the purposes of this invention, an aryl group contains 6 to 60 aromatic ring atoms; a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. The Heteroatoms are in particular N, O and / or S. If in the description of certain embodiments of the invention other definitions that deviate from the definition mentioned are given, for example with regard to the number of aromatic ring atoms or the heteroatoms contained, these apply.

An aryl group or heteroaryl group is understood to mean a simple aromatic cycle, that is benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example phenanthrene, quinoline or carbazole. For the purposes of the present application, a condensed (fused) aromatic or heteroaromatic polycycle consists of two or more simple aromatic or heteroaromatic rings condensed with one another.

An aryl or heteroaryl group, which can be substituted by the above-mentioned radicals and which can be linked via any positions on the aromatic or heteroaromatic, is understood to mean in particular groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzopyrene, 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, pyrazineimidazole, quinoxalineimidazole, oxazole, benzoxazole, napthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, benzyne, 1,3-pyramidine, benzine, benzo-thiazole, 1,3,5-triazine, 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, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or combinations of the groups mentioned.

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 can also be substituted by the groups mentioned above, 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, neoPentyl, 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, trifluoro-methyl, 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) -cyclohex-1-yl- understood. An alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. An alkynyl group is understood to mean, 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 triplet (T ₁ ) below 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 microseconds, in particular at most 100 microseconds, at most 50 microseconds, or at most 10 microseconds and / or have a main emission band with 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 have an emission maximum at between 420 and 500 nm, between 430 and 480 nm, or between 450 and 470 nm.

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

In a further aspect, the invention relates to a method for producing an organic molecule according to the invention of the type described here (with a possible subsequent reaction), wherein (1,3,5-triazinyl) phenylboronic acid pinacol ester, a corresponding (1,3,5-triazinyl) phenylboronic acid or a corresponding (1,3,5-triazinyl) phenylboronic acid ester is used as starting material. Exemplary (1,3,5-triazinyl) phenylboronic acid pinacol esters according to the invention are 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol esters, 4- (4,6-dimethyl-1,3,5-triazinyl) phenylboronic acid pinacol esters , 4- (1,3,5-triazinyl) phenylboronic acid pinacol ester, 3- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester, 3- (4,6-dimethyl-1,3,5-triazinyl) phenylboronic acid pinacol ester, 3- (1,3,5-triazinyl) -phenylboronic acid pinacol ester, 2- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester, 2- (4,6-dimethyl-1,3, 5-triazinyl) phenylboronic acid pinacol ester or 2- (1,3,5-triazinyl) phenylboronic acid pinacol ester. According to the invention, exemplary corresponding (1,3,5-triazinyl) phenylboronic acids 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid, 4- (4,6-dimethyl-1,3,5-triazinyl) phenylboronic acid, 4- (1,3,5-triazinyl) phenylboronic acid, 3- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid, 3- (4,6-dimethyl-1,3,5-triazinyl ) phenylboronic acid, 3- (1,3,5-triazinyl) phenylboronic acid, 2- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid, 2- (4,6-dimethyl-1,3,5- triazinyl) phenylboronic acid or 2- (1,3,5-triazinyl) phenylboronic acid.

In the above scheme, the chemical group CN has been replaced by CF ₃ in one embodiment.

In one embodiment, a (1,3,5-triazinyl) phenylboronic acid pinacol ester, a corresponding (1,3,5-triazinyl) phenylboronic acid or a corresponding (1,3,5-triazinyl) phenylboronic acid ester is used as starting material with a bromo-fluoro-benzonitrile , Chloro-fluoro-benzonitrile or iodo-fluoro-benzonitrile implemented in a palladium-catalyzed cross-coupling reaction. According to the invention, for example, 4-bromo-3-fluoro-benzonitrile, 4-chloro-3-fluoro-benzonitrile, 4-iodo-3-fluoro-benzonitrile, 4-bromo-2-fluoro-benzonitrile, 4-chloro-2- fluoro-benzonitrile, 4-iodo-2-fluoro-benzonitrile, 3-bromo-5-fluoro-benzonitrile, 3-chloro-5-fluoro-benzonitrile, 3-iodo-5-fluoro-benzonitrile, 2-bromo-5- fluoro-benzonitrile, 2-chloro-5-fluoro-benzonitrile, 2-iodo-5-fluoro-benzonitrile, 2-bromo-4-fluoro-benzonitrile, 2-chloro-4-fluoro-benzonitrile, 2-iodo-4- fluoro-benzonitrile, 3-bromo-4-fluoro-benzonitrile, 3-chloro-4-fluoro-benzonitrile, 3-iodo-4-fluoro-benzonitrile, 2-bromo-3-fluoro-benzonitrile, 2-chloro-3- fluoro-benzonitrile or 2-iodo-3-fluoro-benzonitrile can be used. The product is obtained by deprotonation of the corresponding amine and subsequent nucleophilic substitution of the fluorine group. Here, a nitrogen heterocycle in the sense of a nucleophilic aromatic substitution is implemented with an educt 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 host material in an organic optoelectronic device, in particular where the organic optoelectronic device is selected from the group consisting of:

• • organic light emitting diodes (OLEDs),
• • light-emitting electrochemical cells,
• • OLED sensors, especially in gas and steam sensors that are not hermetically shielded from the outside,
• • 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 that are different from the organic molecule according to the invention and
3. (c) optionally one or more dyes and / or one or more organic solvents.

In one embodiment, the composition according to the invention consists of an organic molecule according to the invention and one or more host materials. The host material or materials have, in particular, triplet (T ₁ ) and singlet (S ₁ ) energy levels which are higher in energy than the triplet (T ₁ ) and singlet (S ₁ ) energy levels of the organic molecule according to the invention. In one embodiment, in addition to the organic molecule according to the invention, the composition has an electron-dominant and a hole-dominant host material. The highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of the hole-dominant host material are in particular higher in energy than that of the electron-dominant host material. The HOMO of the hole-dominant host material is energetically below the HOMO of the organic molecule according to the invention, while the LUMO of the electron-dominant host material is energetically above the LUMO of the organic molecule according to the invention. In order to avoid exciplex formation between emitter and host material or host materials, the materials should be selected so that the energy distances between the respective orbitals are small. The distance between the LUMO of the electron-dominant host material and the LUMO of the organic molecule according to the invention is in particular less than 0.5 eV, preferably less than 0.3 eV, even more preferably less than 0.2 eV. The distance 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, even more preferably less than 0.2 eV.

In a further aspect, the invention relates to an organic optoelectronic device which has an organic molecule according to the invention or a composition according to the invention. The organic optoelectronic device is in particular formed as a device selected from the group consisting of organic light-emitting diode (OLED); light emitting electrochemical cell; OLED sensors, in particular gas and vapor sensors that are not hermetically shielded from the outside; 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.

Having an organic optoelectronic device

• - a substrate,
• - an anode and
• a cathode, the anode or the cathode being applied to the substrate, and
• - At least one light-emitting layer, which is arranged between the anode and cathode and which has an organic molecule according to the invention, 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 the following layer structure, for example:

1. 1. 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.

Individual layers are only available in an optional manner. Furthermore, several of these layers can coincide. And there can be multiple individual layers in the component.

According to one embodiment, at least one electrode of the organic component is designed to be translucent. Here, “translucent” refers to a layer that is permeable to visible light. The translucent layer can be clearly translucent, that is to say transparent, or at least partially absorbing light and / or partially scattering light, so that the translucent layer can also be diffuse or translucent milky, for example. In particular, a layer designated here as translucent is made 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 by the fact that the cathode is on the substrate and the other layers are applied in a correspondingly inverted manner:

1. 1. Substrate (carrier material)
2. 2. 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

Individual layers are only available in an optional manner. Furthermore, several of these layers can coincide. And there can be multiple individual layers in the component.

In one embodiment, the inverted OLED uses the anode layer of typical construction, e.g. an ITO layer (indium tin oxide) connected as a cathode.

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

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

An encapsulation can also be arranged over the electrodes and the organic layers. The encapsulation can be implemented, for example, in the form of a glass cover or in the form of a thin-layer encapsulation.

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

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 can be used as the anode of the optoelectronic device ₄ , GaInO ₃ , Zn ₂ In ₂ O ₅ or In ₄ Sn ₃ O ₁₂ or mixtures of different transparent conductive oxides are used.

For example, PEDOT: PSS (poly-3,4-ethylenedioxythiophene: polystyrene sulfonic 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'-bisphenyl- (1, 1'-biphenyl) -4,4'-diamine), NPNPB (N, N'-diphenyl-N, N'-di- [4- (N, N-diphenylamino) 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). The layer thickness is 10-80 nm as an example. Furthermore, small molecules can be used (e.g. copper phthalocyanine (CuPc, e.g. 10 nm thick)) or metal oxides such as MoO ₃ , V ₂ O ₅ .

Tertiary amines, carbazole derivatives, polyethylenedioxythiophene doped with polystyrene sulfonic acid, polyaniline doped with camphorsulfonic acid poly-TPD (poly (4-butylphenyl-diphenyl-amine)), [alpha] -NPD (poly (4-butylphenyl-diphenyl-amine) can be used as materials for an HTL )), 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). An example of a layer thickness is 10 nm to 100 nm.

The HTL can have a p-doped layer which has an inorganic or organic dopant in an organic hole-conducting matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide, for example, can be used as inorganic dopants. For example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper pentafluorobenzoate (Cu (I) pFBz) or transition metal complexes can be used as organic dopants. The layer thickness is exemplary from 10 nm to 100 nm.

As materials of an electron blocking layer, 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). The layer thickness is 10 nm to 50 nm as an example.

The emitter layer EML or emission layer consists of or contains emitter material or a mixture comprising at least two emitter materials and optionally one or more host materials. Suitable host materials are for example 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 emitter material emitting in the green or in the red 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 e.g. ME Thompson et al., Chem. Mater. 2004, 16, 4743 ) or other so-called wide-gap matrix materials can be used. The layer thickness is exemplary from 10 nm to 250 nm.

The hole blocking layer HBL can, for example, be BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), bis- (2-methyl-8-hydroxychinolinato) - (4-phenylphenolato) aluminum (III) (BAIq), Nbphen (2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline), Alq3 (aluminum-tris (8-hydroxyquinoline)), TSPO1 (diphenyl-4- triphenylsilylphenylphosphine oxide) or TCB / TCP (1,3,5-tris (N-carbazolyl) benzene / 1,3,5-tris (carbazol) -9-yl) benzene). The layer thickness is exemplary from 10 nm to 50 nm.

The electron transport layer ETL can, for example, contain materials based on AIQ ₃ , TSPO1, BPyTP2 (2,7-di (2,2'-bipyridin-5-yl) triphenyl), Sif87, Sif88, 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. The layer thickness is exemplary from 10 nm to 200 nm.

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

Metals or alloys can serve as materials for the cathode layer, for example Al, Al> AlF, Ag, Pt, Au, Mg, Ag: Mg. Typical layer thicknesses are 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 through the formation of a thin protective oxide layer.

Examples of suitable materials for encapsulation are aluminum oxide, vanadium oxide, zinc oxide, zirconium oxide, titanium oxide, hafnium oxide, lanthanum oxide, tantalum oxide.

In one embodiment of the organic optoelectronic device according to the invention, the organic molecule according to the invention is used as emission material in a light-emitting layer EML, it being 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 more than 30 hours, in particular of more than 70 hours, or of more than 100 hours, or of more than 150 hours and in particular of more than 200 hours.

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

In one embodiment, the light-emitting layer can exclusively have an organic molecule according to the invention in 100% concentration, the anode and the cathode being applied to the substrate and the light-emitting layer being applied between the anode and the cathode.

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

In a further embodiment of the invention, the organic optoelectronic device has: 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 ) and singlet (S ₁ ) energy levels are higher in energy than the triplet (T ₁ ) and singlet (S ₁ ) energy levels of the organic molecule, the anode and the cathode is applied to the substrate and the hole- and electron-injecting layer is applied between the anode and cathode, and the hole- and electron-transporting layer is applied between the hole- and electron-injecting layer, and the light-emitting layer is applied between the hole- and electron-transporting layer .

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

In one embodiment, the production method comprises the processing of the organic molecule according to the invention by means of 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.

According to the invention is also 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) process,
• - Is coated with a carrier gas sublimation, and / or
• - is made from solution or with a printing process.

Known methods are used in the production of the optoelectronic device according to the invention. In general, the layers are applied individually to a suitable substrate in successive deposition process steps. The usual methods such as thermal evaporation, chemical vapor deposition (CVD) and physical vapor deposition (PVD) can be used for gas phase deposition. For active matrix OLED (AMOLED) displays, the deposition takes place on an AMOLED backplane as a substrate.

Alternatively, layers of solutions or dispersions in suitable solvents can be applied. Examples of suitable coating processes are spin coating, dip coating and jet printing methods. According to the invention, the individual layers can be produced using the same or different coating methods.

Examples

General synthesis scheme I:

General synthesis instructions AAV1:

4-(4,6-diphenyl-1,3,5-triazinyl)phenylboronsäurepinakolester (1,20 Äquivalente), 4-Brom-3-fluor-benzonitril (1,00 Äquivalente), Pd₂(dba)₃ (dba = Dibenzylideneaceton) (0,02 Äquivalente), 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl, (SPhos) (0,04 Äquivalente) und tribasisches Kaliumphosphat (2,00 Äquivalente) werden unter Stickstoff in einem Toluol/Wasser-Gemisch (Verhältnis 10:1) bei 100 °C für 12 bis 15 h gerührt. Anschließend wird die Reaktionsmischung in 200 mL gesättigte Natriumchlorid-Lösung gegeben der ausfallende Feststoff abfiltriert, mit Wasser gewaschen und getrocknet. Das erhaltene Rohprodukt wird durch Umkristallisation gereinigt und das Produkt als Feststoff erhalten. Erfindungsgemäß kann statt Boronsäurepinakolester auch eine entsprechende Boronsäure oder ein entsprechender Boronsäureester verwendet werden.

4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester (1.20 equivalents), 4-bromo-3-fluoro-benzonitrile (1.00 equivalents), Pd ₂ (dba) ₃ (dba = Dibenzylideneacetone) (0.02 equivalents), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, (SPhos) (0.04 equivalents) and tribasic potassium phosphate (2.00 equivalents) are mixed under nitrogen in a toluene / water mixture ( Ratio 10: 1) stirred at 100 ° C. for 12 to 15 h. The reaction mixture is then poured into 200 ml of saturated sodium chloride solution and the precipitated solid is filtered off, washed with water and dried. The crude product obtained is purified by recrystallization and the product is obtained as a solid. According to the invention, a corresponding boronic acid or a corresponding boronic acid ester can also be used instead of boronic acid pinacol ester.

General synthesis instructions AAV2:

Z2 is synthesized analogously to AAV1, with 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester being reacted with 4-bromo-2-fluoro-benzonitrile.

General synthesis instructions AAV3:

Z3 is synthesized analogously to AAV1, with 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester being reacted with 3-bromo-6-fluoro-benzonitrile.

General synthesis instructions AAV4:

Z4 is synthesized analogously to AAV1, with 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester being reacted with 2-bromo-5-fluoro-benzonitrile.

General synthesis instructions AAV5:

Z5 is synthesized analogously to AAV1, with 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester being reacted with 2-bromo-4-fluoro-benzonitrile.

General synthesis instructions AAV6:

Z6 is synthesized analogously to AAV1, with 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester being reacted with 3-bromo-4-fluoro-benzonitrile.

General synthesis instructions AAV7:

Z7 is synthesized analogously to AAV1, with 4- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester being reacted with 2-bromo-3-fluoro-benzonitrile.

General synthesis instructions AAV8:

Z1, Z2, Z3, Z4, Z5, Z6 or Z7 (1.00 equivalent each), the corresponding donor molecule DH (1.00 equivalent) and tribasic potassium phosphate (2.00 equivalent) are suspended in DMSO under nitrogen and Stirred at 110 ° C. (16 h). The reaction mixture is then poured into saturated sodium chloride solution and extracted three times with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent is then removed. The crude product is finally purified by recrystallization from toluene or by flash chromatography. The product is obtained as a solid.

In order to obtain the corresponding R ¹ substituted compounds, instead of 3- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester, the corresponding triazine substituted in the corresponding derivative with 4- and 6-position R ¹ , 3- (2,6-R ¹ -1,3,5-triazinyl) phenylboronic acid pinacol ester, for example 3- (4,6-dimethyl-1,3,5-triazinyl) phenylboronic acid pinacol ester.

If the corresponding 3- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester is used, the corresponding meta-bridged derivative from Z1 to Z7 is obtained, which contains a bridge L ^B according to sub-formula Ib. If the corresponding 2- (4,6-diphenyl-1,3,5-triazinyl) phenylboronic acid pinacol ester is used, the corresponding ortho-bridged derivative from Z1 to Z7 is obtained, which contains a bridge L ^B according to sub-formula Ic. The rest of the implementation is analogous to AAV8.

In particular, 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).

Photophysical measurements

Pretreatment of optical glasses

All glasses (cuvettes and substrates made of quartz glass, diameter: 1 cm) were cleaned after each use: rinsing three times each with dichloromethane, acetone, ethanol, demineralized water, soaking in 5% Hellmanex solution for 24 hours, rinsing thoroughly with demineralized water. The optical glasses were blown off with nitrogen for drying.

Sample preparation, film: spin coating

Device: Spin150, SPS euro.

The sample concentration corresponded to 10 mg / ml, made up in toluene or chlorobenzene. 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. After coating, the films were dried in air for 1 min at 70 ° C. on a precision heating plate from LHG.

Photoluminescence Spectroscopy and TCSPC

Steady-state emission spectroscopy was carried out with a fluorescence spectrometer from Horiba Scientific, model FluoroMax-4, equipped with a 150 W xenon arc lamp, excitation and emission monochromators and a Hamamatsu R928 photomultiplier tube, as well as a "time-correlated one-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).

The 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. Sources of excitation:

• 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).

mit e_i: Durch den Fit vorhergesagte Größe und o_i: gemessenen Größe.The evaluation (exponential fitting) was carried out with the DataStation software package and the DAS 6 evaluation software. The fit was given using the chi-square method $$c^2={\displaystyle {\sum }_{k=1}^i\frac{{\left(e_i-O_i\right)}^2}{e_i}}$$

with e _i : size predicted by the fit and o _i : measured size.

Quantum efficiency determination

The photoluminescence quantum yield (PLQY) was measured using an Absolute PL Quantum Yield Measurement C9920-03G system from Hamamatsu Photonics. This consists of a 150 W xenon gas discharge lamp, automatically adjustable Czerny-Turner monochromators (250 - 950 nm) and an integrating sphere with a highly reflective Spectralon coating (a Teflon derivative), which is connected to a PMA-12 multi-channel detector via a fiber optic cable BT (back thinned) CCD chip with 1024 x 122 pixels (size 24 x 24 µm) is connected. The evaluation of the quantum efficiency and the CIE coordinates was carried out 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 Absorbtionsmaximum 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) Carrying out quality assurance: Anthracene in ethanol with a known concentration is used as the reference material.
2. 2) Determination of the excitation wavelength: First the absorption maximum of the organic molecule was determined and excited with it.
3. 3) Performing the sample measurement:
   • The absolute quantum yield of degassed solutions and films under a nitrogen atmosphere was determined.

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

with the number of photons n _photon and the intensity Int.

Manufacture and characterization of organic electroluminescent devices from the gas phase

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

These not yet optimized OLEDs can be characterized as standard; 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 service life of the OLEDs can be determined from the time course of the electroluminescence spectra. The LT50 value corresponds to the time at which the luminance has dropped to 50% of the starting value. Similarly, the LT70 value corresponds to the time during which the luminance has dropped to 70% of the starting value.

The values result from the average of the various pixels in an OLED.

HPLC-MS:

HPLC-MS spectroscopy was measured with an HPLC system from Agilent (1100 series) with a connected MS detector (Thermo LTQ XL). An Eclipse Plus C18 column from Agilent with a particle size of 3.5 µm, a length of 150 mm and an internal diameter of 4.6 mm was used for the HPLC. The solvents acetonitrile, water and tetrahydrofuran were used in these concentrations without a pre-column and at room temperature: Solvent A: H ₂ O (90%) MeCN (10%) Solvent B: H ₂ O (10%) MeCN (90%) Solvent C: THF (100%)

This gradient was used with an injection volume of 15 µL and a concentration of 10 µg / mL: Flow [ml / min] Time [min] A [%] B [%] C [%] Pressure [bar] 0.3 0 80 20th - 115 0.3 5 80 20th - 115 0.3 14th 0 90 10 65 0.3 25th 0 90 10 65 0.3 26th 80 20th - 115 0.3 33 80 20th - 115

The sample is ionized by APCI (atmospheric pressure chemical ionization).

example 1

Beispiel 1 wurde nach AAV1 (Ausbeute 63%) und AAV8 hergestellt (Ausbeute 60%). ¹H-NMR (500 MHz, CDCl₃): d = 8.69-8.70 (m, 3 H), 8.55 (d, 2 H), 8.34 (s, 2 H), 7.94-8.00 (m, 3 H), 7.70 (d, 3 H), 7.59-7.63 (m, 3 H), 7.53-7.56 (m, 3 H), 7.45-7.49 (m, 4 H), 7.33-7.38 (m, 3 H), 7.17 (d, 1 H) ppm.

Example 1 was prepared according to AAV1 (yield 63%) and AAV8 (yield 60%). ¹ H-NMR (500 MHz, CDCl ₃ ): d = 8.69-8.70 (m, 3 H), 8.55 (d, 2 H), 8.34 (s, 2 H), 7.94-8.00 (m, 3 H), 7.70 (d, 3 H), 7.59-7.63 (m, 3 H), 7.53-7.56 (m, 3 H), 7.45-7.49 (m, 4 H), 7.33-7.38 (m, 3 H), 7.17 ( d, 1 H) ppm.

MS (HPLC-MS), m / z: 728.

1 shows the emission spectrum of Example 1 (10% in PMMA). The emission maximum is at 476 nm. The photoluminescence quantum yield (PLQY) is 64% and the half width is 0.45 eV.

Further examples of molecules according to the invention:

Figure list

• 1 ein Emissionsspektrum von Beispiel 1 in 10 % PMMA.

It shows:

• 1 an emission spectrum of Example 1 in 10% PMMA.

Claims (18)

Having organic molecule - having a first chemical unit having or consisting of a structure according to

and - a second chemical unit having or consisting of a structure according to

wherein the first chemical entity is linked to the second chemical entity via a single bond; and where L ^{B is} selected from one of the structures according to sub-formulas Ia to Ic:

where: § is the point of attachment of the single bond between the central phenyl group of the first chemical unit and L ^B ; $ is the point of attachment of the single bond between the central triazinyl group of the first chemical unit and L ^B ; T is the point of attachment of the single bond between the first chemical unit and the chemical unit or is selected from the group consisting of R ² and CN; V is H or the point of attachment of the single bond between the first chemical unit and the second chemical unit; W is the point of attachment of the single bond between the first chemical unit and the second chemical unit or is selected from the group consisting of R ² and CN; X is selected from the group consisting of R ² and CN; Y is selected from the group consisting of R ² and CN; # identifies the point of attachment of the single bond between the second chemical unit and the first chemical unit; Z is on each occurrence, identically or differently, a direct bond or is 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 ; R ¹ is on each occurrence, identically or differently, H, deuterium, a linear alkyl group with 1 to 5 carbon atoms, a linear alkenyl or alkynyl group with 2 to 8 carbon atoms, a branched or cyclic alkyl, alkenyl or alkynyl group 3 to 10 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which can be substituted by one or more radicals R ⁶ ; On each occurrence, R ² , identically or differently, is H, deuterium, a linear alkyl group with 1 to 5 C atoms, a linear alkenyl or alkynyl group with 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group 3 to 10 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which can be substituted by one or more radicals R ⁶ ; R ^1a , R ^1b and R ^1c are on each occurrence, identically or differently, H, deuterium, a linear alkyl group with 1 to 5 C atoms, a linear alkenyl or alkynyl group with 2 to 8 C atoms, a branched or cyclic alkyl , Alkenyl or alkynyl group with 3 to 10 carbon atoms, where one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system with 5 to 15 aromatic ring atoms, each of which is substituted by one or more radicals R ⁶ can; R ^a , R ³ and R ⁴ are on each occurrence, identically or differently, 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 with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl -, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R ⁵ , one or more non-adjacent CH ₂ groups 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 ^S ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ can be replaced and one or more H atoms can 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 can each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ ; R ⁵ is on each occurrence, identically or differently, H, deuterium, N (R ⁶ ) ₂ , OH, Si (R ⁶ ) ₃ , B (OR ⁶ ) ₂ , OSO ₂ R ⁶ , CF ₃ , CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R ⁶ , 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 can be replaced and it is possible for one or more H atoms to be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which can be substituted by one or more R ⁶ radicals, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more R ⁶ radicals , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁶ ; R ⁶ is on each occurrence, identically or differently, H, deuterium, OH, CF ₃ , CN, F, a linear alkyl, alkoxy or thioalkoxy group with 1 to 5 carbon atoms or a linear alkenyl or alkynyl group with 2 to 5 carbon atoms Atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 5 carbon atoms, it being possible for one or more H atoms to be replaced by deuterium, CN, CF ₃ or NO ₂ ; or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms; where each of the radicals R ^a , R ³ , R ⁴ or R ^{5 can} also form a mono- or polycyclic, aliphatic, aromatic and / or benzo-fused ring system with one or more further radicals R ^a , R ³ , R ⁴ or R ⁵ ; where exactly one radical selected from the group consisting of W, X and Y is CN and exactly one radical selected from the group consisting of T, V and W is the point of attachment of the single bond between the first chemical unit according to formula I and the second chemical Unit and the proviso that T is H if V is the point of attachment of the single bond between the first chemical unit according to formula I and the second chemical unit and W is CN; and that W is H when T is CN and V is the point of attachment of the single bond between the first chemical unit and the second chemical unit. Organic molecule after Claim 1 where R ^{1 is,} identically or differently, methyl or phenyl on each occurrence. Organic molecule after Claim 1 , where R ^{2 is} on each occurrence, identically or differently, H, methyl or phenyl. Organic molecule after Claim 1 to 3 , where R ^1a , R ^1b and R ^{1c are} on each occurrence, identically or differently, H, methyl or phenyl. Organic molecule after Claim 1 to 4th , wherein the second chemical unit has a structure of the formula IIa:

where for # and R ^a the in Claim 1 the definitions mentioned apply. Organic molecule after Claim 1 to 5 , wherein the second chemical unit has a structure of the formula IIb:

where R ^b on each occurrence identically or differently 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 one Alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C atoms, each of which can be substituted by one or more radicals R ⁵ , where one or more non-adjacent CH ₂ groups are 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 ^S ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ can be replaced and wherein one or more H atoms can 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 can each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ ; and for # and R ⁵ the in Claim 1 the definitions mentioned apply. Organic molecule after Claim 1 to 5 , wherein the second chemical unit has a structure of the formula llc:

where R ^b on each occurrence identically or differently 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 one Alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a linear alkenyl or alkynyl group with 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group with 3 to 40 C atoms, each of which can be substituted by one or more radicals R ⁵ , where one or more non-adjacent CH ₂ groups are 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 ^S ), SO, SO ₂ , NR ⁵ , O, S or CONR ⁵ can be replaced and wherein one or more H atoms can 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 can each be substituted by one or more radicals R ⁵ , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group with 10 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ⁵ ; and the in Claim 1 the definitions mentioned apply. Organic molecule after Claim 6 or 7th , where R ^b on each occurrence, identically or differently, is Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, each of which is substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph pyridinyl, which can be substituted in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph, pyrimidinyl, which in each case by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph can be substituted, triazinyl, which in each case can be substituted by one or more radicals selected from Me, ⁱ Pr, ^t Bu, CN, CF ₃ or Ph. Process for the production of an organic molecule according to Claim 1 to 8th , wherein a (1,3,5-triazinyl) phenylboronic acid pinacol ester, a corresponding (1,3,5-triazinyl) phenylboronic acid or a corresponding (1,3,5-triazinyl) phenylboronic acid ester is used as starting material. Using an organic molecule after Claim 1 to 8th as a luminescent emitter and / or as host material and / or as electron transport material and / or as hole injection material and / or as hole blocking material in an organic optoelectronic device. Use after Claim 10 , the organic optoelectronic device being selected from the group consisting of: • organic light-emitting diodes (OLEDs), • light-emitting electrochemical cells, • OLED sensors, • organic diodes, • organic solar cells, • organic transistors, • organic field effect transistors, • organic Lasers and • down-conversion elements. Composition comprising or consisting of: (a) at least one organic molecule according to one of Claims 1 to 8th and (b) one or more emitter and / or host materials derived from the molecule Claim 1 to 8th are different and (c) optionally one or more dyes and / or one or more solvents. Composition according to Claim 12 , wherein the at least one organic molecule according to one of Claims 1 to 8th is in the form of an emitter and / or host. Organic optoelectronic device comprising an organic molecule Claim 1 to 8th or a composition according to Claim 12 or 13 . Organic optoelectronic device according to Claim 14 , shaped as a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, organic diode, organic solar cell, organic transistor, organic field effect transistor, organic laser and down-conversion element. Organic optoelectronic device according to Claim 14 or 15th , 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 anode and cathode and which an organic molecule after Claim 1 to 8th or a composition according to Claim 12 or 13 having. Method for producing an optoelectronic component, wherein an organic molecule according to Claim 1 to 8th is used. Procedure according to Claim 17 comprising processing the organic molecule using a vacuum evaporation method or from solution.

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