Organic metal complexes
View Patent ↗The present invention relates inter alia to novel organic metal complexes comprising, e.g., platinum and specific side groups, their preparation and their use in electronic devices.
1. A compound according to Formula (9),
wherein
Z is phenyl,
M is a transition metal or metal ion;
z4 is 1,
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of two or more of these groups; two or more radicals R 1 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of two or more of these groups; two or more adjacent radicals R 2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F; two or more substituents R 3 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
W is, identically or differently on each occurrence, selected from a compound of the following Formula (2)
where the rings B′ and F′ can be substituted with one or more R1 selected from substituted or unsubstituted aliphatic, aromatic or heteroaromatic ring having 5 to 60 atoms or a substituted or unsubstituted polycyclic ring system, which is optionally condensed with the adjacent rings,
X is CR 1 ;
T is selected identically or differently on each occurrence and is —C(R 1 ) 2 , —Si(R 1 ) 2 , —N, —NR 1 , —O, —S, —C(═O), —S(═O), —SO 2 , —CF 2 , —SF 4 , —P, —P(═O)R 1 , —PF 2 , —P(═S)R 1 , —As, —As(═O), —As(═S), —Sb, —Sb(═O) or —Sb(═S);
U is —N—;
V is selected independently on each occurrence and is C(R 1 ) 2 , NR 1 , O or S;
K is R 1 ;
M′ is a phenyl which is either unsubstituted or substituted by one or more R 1 ;
N is R 1 ;
k is 0 thus M′ and ring C′ are not bonded via K to each other;
m is 0;
n is 0;
r is 1 or 2;
s is 0 or 1;
t is 1; and
v is 0 and ring D′ is a 5 membered ring.
2. The compound according to claim 1 , wherein M is Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, or Pt.
3. The compound according to claim 1 , wherein W is, identically or differently on each occurrence, selected from a compound of the following Formulae (72) to (77)
wherein R 1 is defined as in claim 1 and ## denotes the position of binding between W and Z or the metal M-bearing core.
4. The compound according to claim 1 , wherein R 1 is, identically or differently on each occurrence, selected from the following Formulae (84) to (242)
wherein the R 1 having the Formulae (84) to (242) can be, identically or differently on each occurrence, substituted with one or more R 2 and wherein the lines indicate the position of binding.
5. A composition comprising at least one compound according to claim 1 and at least one organic functional material selected from hole transport material (HTM), hole injection material (HIM), electron transport material (ETM), electron injection material (EIM), hole blocking material (HBM), exciton blocking material (ExBM), host or matrix material, fluorescent emitter, and phosphorescent emitter.
6. The composition according to claim 5 , wherein the at least one organic functional material is a matrix material selected from ketones, phosphinoxides, sulfoxides, sulfones, triarylamines, carbazoles, indolocarbazoles, indenocarbazoles, aza-carbazoles, bipolar matrix materials, silanes, azaborolenes, boronesters, triazines, zinc complexes, diaza- or tetraazasiloles or diazaphospholes or mixtures thereof.
7. An electronic device which comprises the composition according to claim 6 wherein the device is an organic electroluminescent device, an organic light emitting diode, polymer light emitting diode, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell, or an organic laser diode and the composition is in one or more light emitting layers.
8. A formulation comprising at least one compound according to claim 1 and at least one solvent.
9. An electronic device which comprises the compound according to claim 1 .
10. The electronic device according to claim 9 , wherein the device is an organic electroluminescent device, an organic light emitting diode, polymer light emitting diode, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell, or an organic laser diode.
11. An electroluminescent device comprising at least one compound according to claim 1 .
12. A process for phototherapy in medicine which comprises irradiating or treating humans or animals with the electroluminescent device according to claim 11 .
13. A cosmetic which comprises the electroluminescent device according to claim 11 .
14. A method for the treatment of the skin with phototherapy which comprises treating the skin by employing a light emitting device comprising a compound according to claim 1 .
15. A compound according to Formula (9),
wherein
Z is phenyl,
M is a transition metal or metal ion;
z4 is 0,
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of two or more of these groups; two or more radicals R 1 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of two or more of these groups; two or more adjacent radicals R 2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F; two or more substituents R 3 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
W is, identically or differently on each occurrence, selected from a compound of the following Formula (2)
where the rings B′ and F′ can be substituted with one or more R1 selected from substituted or unsubstituted aliphatic, aromatic or heteroaromatic ring having 5 to 60 atoms or a substituted or unsubstituted polycyclic ring system, which is optionally condensed with the adjacent rings,
X is CR 1 ;
T is selected identically or differently on each occurrence and is —C(R 1 ) 2 , —Si(R 1 ) 2 , —N, —NR 1 , —O, —S, —C(═O), —S(═O), —SO 2 , —CF 2 , —SF 4 , —P, —P(═O)R 1 , —PF 2 , —P(═S)R 1 , —As, —As(═O), —As(═S), —Sb, —Sb(═O) or —Sb(═S);
U is —N—;
V is selected independently on each occurrence and is C(R 1 ) 2 , NR 1 , O or S;
K is, if m =1, C(R 1 ) 2 or a single bond between M′ and ring C′;
M′ is a phenyl which is either unsubstituted or substituted by one or more R 1 ;
N is, if m =1, C(R 1 ) 2 or a single bond between M′ and ring E′;
k is 0 thus M′ and ring C′ are not bonded via K to each other;
m is 1;
n is 0 and M′ and ring E′ are not bonded via N to each other;
r is 1 or 2;
s is 0 or 1;
t is 1; and
v is 0 and ring D′ is a 5 membered ring.
16. The compound according to claim 15 , wherein M is Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, or Pt.
17. The compound according to claim 15 , wherein W is, identically or differently on each occurrence, selected from a compound of the following Formulae (72) to (77)
wherein R 1 is defined as in claim 15 and ## denotes the position of binding between W and Z or the metal M-bearing core.
18. The compound according to claim 15 , wherein R 1 is, identically or differently on each occurrence, selected from the following Formulae (84) to (242)
wherein the R 1 having the Formulae (84) to (242) can be, identically or differently on each occurrence, substituted with one or more R 2 and wherein the lines indicate the position of binding.
19. A composition comprising at least one compound according to claim 15 and at least one organic functional material selected from the group consisting of hole transport material (HTM), hole injection material (HIM), electron transport material (ETM), electron injection material (EIIVI), hole blocking material (HBM), exciton blocking material (ExBM), host or matrix material, fluorescent emitter and phosphorescent emitter.
20. The composition according to claim 19 , wherein the at least one organic functional material is a matrix material selected from ketones, phosphinoxides, sulfoxides, sulfones, triarylamines, carbazoles, indolocarbazoles, indenocarbazoles, azacarbazoles, bipolar matrix materials, silanes, azaborolenes, boronesters, triazines, zinc complexes, diaza- or tetraaza-siloles or diazaphospholes or mixtures thereof.
21. An electronic device which comprises the composition according to claim 19 wherein the device is an organic electroluminescent device , an organic light emitting diode, polymer light emitting diode, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell, or an organic laser diode and the composition is in one or more light emitting layers.
22. A formulation comprising at least one compound according to claim 15 and at least one solvent.
23. An electronic device which comprises the compound according to claim 15 .
24. The electronic device according to claim 23 , wherein the device is an organic electroluminescent device , an organic light emitting diode, polymer light emitting diode, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell, or an organic laser diode.
25. An electroluminescent device comprising at least one compound according to claim 15 .
26. A process for phototherapy in medicine which comprises irradiating or treating humans or animals with the electroluminescent device according to claim 25 .
27. A cosmetic which comprises the electroluminescent device according to claim 25 .
28. A method for the treatment of the skin with phototherapy which comprises treating the skin by employing a light emitting device comprising a compound according to claim 15 .