Organic molecules for use in optoelectronic devices
The invention relates to an organic molecule, especially for use in optoelectronic components. The organic molecule contains a first chemical unit having or consisting of a structure of formula I and two second chemical units D each having or consisting of, identically or differently at each instance, a structure of formula II where the first chemical unit is joined to each of the two second chemical units D via a single bond; where T, V is independently an attachment point of the single bond between the chemical unit of formula I and a chemical unit D or H; W, X, Y is independently an attachment point of the single bond between the chemical unit of formula I and a chemical unit D or selected from the group consisting of H, CN and CF 3 ; where exactly one radical selected from W, X and Y is CN or CF 3 and exactly two radicals selected from the group consisting of T, V, W, X and Y are an attachment point of the single bond between the chemical unit according to formula I and a chemical unit D.
1. A composition comprising:
(a) at least one light emitting organic molecule in the form of an emitter;
(b) one or more host materials other than the at least one light emitting organic molecule of component (a); and
(c) optionally one or more dyes and/or one or more solvents;
wherein the at least one light emitting organic molecule of component (a) comprises a structure of formula VI:
where
R 1 and R 2 are the same or different at each instance and are selected from the group consisting of:
H, deuterium;
a linear alkyl group having 1 to 5 carbon atoms, a linear alkenyl or alkynyl group having 2 to 8 carbon atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium; and
an aromatic or heteroaromatic ring system which has 5 to 15 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals;
R a is the same or different at each instance and is selected from the group consisting of:
H, deuterium, N(R 5 ) 2 , OH, Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 7 R 5 CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group which has 1 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group which has 2 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group which has 3 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals;
an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals;
R 5 is the same or different at each instance and is selected from the group consisting of:
H, deuterium, N(R 6 ) 2 , OH, Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 7 R 6 CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group which has 1 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group which has 2 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group which has 3 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals;
an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals; and
R 6 is the same or different at each instance and is selected from the group consisting of:
H, deuterium, OH, CF 3 CN, F;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms;
where each of the R a , R 3 , R 4 or R 5 radicals together with one or more further R a , R 3 , R 4 or R 5 radicals may form a mono- or polycyclic, aliphatic, aromatic and/or benzofused ring system.
2. The composition according to claim 1 , wherein R 1 and R 2 of the at least one light emitting organic molecule are the same or different at each instance and are H, methyl or phenyl.
3. An optoelectronic device comprising a composition comprising:
(a) at least one light emitting organic molecule in the form of an emitter;
(b) one or more host materials other than the at least one light emitting organic molecule of component (a); and
(c) optionally one or more dyes and/or one or more solvents;
wherein the at least one light emitting organic molecule of component (a) comprises a structure of formula VI:
where
R 1 and R 2 are the same or different at each instance and are selected from the group consisting of:
H, deuterium;
a linear alkyl group having 1 to 5 carbon atoms, a linear alkenyl or alkynyl group having 2 to 8 carbon atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium; and
an aromatic or heteroaromatic ring system which has 5 to 15 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals;
R a is the same or different at each instance and is selected from the group consisting of:
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 which has 1 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group which has 2 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group which has 3 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals;
an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals;
R 5 is the same or different at each instance and is selected from the group consisting of:
H, deuterium, N(R 6 ) 2 , OH, Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 7 R 6 CF 3 , CN, F, Br, I;
a linear alkyl, alkoxy or thioalkoxy group which has 1 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group which has 2 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group which has 3 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals;
an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals; and
R 6 is the same or different at each instance and is selected from the group consisting of:
H, deuterium, OH, CF 3 CN, F;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms;
where each of the R a , R 3 , R 4 or R 5 radicals together with one or more further R a , R 3 , R 4 or R 5 radicals may form a mono- or polycyclic, aliphatic, aromatic and/or benzofused ring system.
4. The optoelectronic device according to claim 3 , comprising:
a substrate;
an anode;
a cathode, where the anode or the cathode has been applied to the substrate; and
at least one light-emitting layer which is arranged between the anode and the cathode and comprises the composition according to claim 1 .
5. The optoelectronic device according to claim 3 , wherein the optoelectronic device is an organic light-emitting diode (OLEDs), a light-emitting electrochemical cell, an OLED sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser and a down-conversion element.
6. The optoelectronic device according to claim 3 , wherein R 1 and R 2 of the at least one light emitting organic molecule are the same or different at each instance and are H, methyl or phenyl.
7. An optoelectronic device, comprising:
a substrate;
an anode;
a cathode, where the anode or the cathode has been applied to the substrate; and
at least one light-emitting layer which is arranged between the anode and the cathode and comprises a light emitting organic molecule and a host material; wherein the light emitting organic molecule comprises a structure of formula VI:
where
R 1 and R 2 are the same or different at each instance and are selected from the group consisting of:
H, deuterium;
a linear alkyl group having 1 to 5 carbon atoms, a linear alkenyl or alkynyl group having 2 to 8 carbon atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium; and
an aromatic or heteroaromatic ring system which has 5 to 15 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals;
R a is the same or different at each instance and is selected from the group consisting of:
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 which has 1 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group which has 2 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group which has 3 to 40 carbon atoms and may be substituted in each case by one or more R 5 radicals, where one or more nonadjacent CH 2 groups may be 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 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals;
an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted in each case by one or more R 5 radicals;
R 5 is the same or different at each instance and is selected from the group consisting of:
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 which has 1 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group which has 2 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group which has 3 to 40 carbon atoms and may be substituted in each case by one or more R 6 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 and where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals;
an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted in each case by one or more R 6 radicals; and
R 6 is the same or different at each instance and is selected from the group consisting of:
H, deuterium, OH, CF 3 , CN, F;
a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a linear alkenyl or alkynyl group having 2 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 carbon atoms, where one or more hydrogen atoms may be replaced by deuterium, CN, CF 3 or NO 2 ;
an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms;
an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and
a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms;
where each of the R a , R 3 , R 4 or R 5 radicals together with one or more further R a , R 3 , R 4 or R 5 radicals may form a mono- or polycyclic, aliphatic, aromatic and/or benzofused ring system.
8. The optoelectronic device according to claim 7 , wherein R 1 and R 2 of the light emitting organic molecule are the same or different at each instance and are H, methyl or phenyl.