ORGANIC MOLECULES FOR USE IN OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic molecule, in particular for use in optoelectronic components. According to the invention, the organic molecule has a structure of Formula I

##STR00001##

with XCN or CF3, D=

##STR00002##

wherein # is the point of attachment of unit D to one of the phenyl rings shown in Formula I; Z is a direct bond or is selected from the group consisting of CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2;

In each occurrence R.sup.1 and R.sup.2 is the same or different, is H, deuterium, a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.6; and wherein at least one R.sup.a is not H, and wherein at least one R.sup.2 is H.

Claims

1. An organic molecule, comprising a structure of Formula I ##STR00074## with XCN or CF3, and D= ##STR00075## wherein # is the point of attachment of unit D to one of the phenyl rings shown in Formula I; Z is a direct bond or is selected from the group consisting of CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2; in each occurrence R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of: H, deuterium; a linear alkyl group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium; a linear alkenyl or alkynyl group having 2 to 8 C atoms, wherein one or more H atoms can be replaced by deuterium; a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium; and an aromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.6; in each occurrence R.sup.a, R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of: H, deuterium, N(R.sup.5).sub.2, OH, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case can be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.5; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; in each occurrence R.sup.5 is the same or different and is selected from the group consisting of: H, deuterium, N(R.sup.6).sub.2, OH, Si(R.sup.6).sub.3, B(OR.sup.6).sub.2, OSO.sub.2R.sup.6, CF.sub.3, CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.6, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.6, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.6, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.6; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.6; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.6; in each occurrence R.sup.6 is the same or different and is selected from the group consisting of: H, deuterium, OH, CF.sub.3, CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.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; wherein each of the radicals R.sup.a, R.sup.3, R.sup.4 or R.sup.5 can also form a mono- or polycyclic, aliphatic, aromatic and/or benzoannelated ring system with one or more further radicals R.sup.a, R.sup.3, R.sup.4 or R.sup.5; and wherein at least one R.sup.a is not H, and wherein at least one R.sup.2 is H.

2. The organic molecule according to claim 1, wherein R.sup.1 is H or methyl and R.sup.2 is H.

3. The organic molecule according to claim 1, wherein both X are CN.

4. The organic molecule according to claim 1, wherein D comprises a structure of Formula IIa: ##STR00076## wherein # and R.sup.a have the aforestated meanings.

5. The organic molecule according to claim 1, wherein D comprises a structure of Formula IIb: ##STR00077## wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: N(R.sup.5).sub.2, OH, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.5; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and # and R.sup.5 have the aforestated meanings.

6. The organic molecule according to claim 1, wherein D comprises a structure of Formula IIc: ##STR00078## wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: N(R.sup.5).sub.2, OH, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R5)2, .sup.Ge(R5)2, Sn(R5)2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.5; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and # and R.sup.5 have the aforestated meanings.

7. The organic molecule according to claim 5, wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: Me, .sup.iPr, .sup.tBu, CN, CF.sub.3; Ph, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyridinyl, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyrimidinyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; carbazolyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; and N(Ph).sub.2.

8. A method for producing an organic molecule according to claim 1, wherein a in 6 position R.sup.1-substituted and in 3 and 5 position R.sup.2-substituted 2-bromo-4-fluorobenzonitrile or a in 6 position R.sup.1-substituted and in 3 and 5 position R.sup.2-substituted 2-bromo-4-fluorobenzotrifluoride is used as the educt.

9. An optoelectronic device comprising an organic molecule according to claim 1.

10. The optoelectronic device according to claim 9, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

11. A composition comprising: (a) at least one organic molecule according to claim 1, as an emitter and/or host, and (b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 1, and (c) optionally one or more dyes and/or one or more solvents.

12. An optoelectronic device comprising the composition according to claim 11.

13. The optoelectronic device according to claim 12, comprising: a substrate, an anode and a cathode, wherein the anode or the cathode are disposed on the substrate, and at least one light-emitting layer, which is disposed between the anode and the cathode and which comprises the composition according to claim 11.

14. (canceled)

15. (canceled)

16. The optoelectronic device according to claim 9, wherein the organic molecule is one of an emitter and an absorber in the optoelectronic component.

17. The optoelectronic device according to claim 10, wherein the organic molecule is one of an emitter and an absorber in the optoelectronic component.

18. The optoelectronic device according to claim 16, wherein the proportion of the organic molecule in the emitter or absorber is in the range of 1% to 80%.

19. The optoelectronic device according to claim 9, comprising a substrate, an anode and a cathode, wherein the anode or the cathode is applied to the substrate, and at least one light-emitting layer is disposed between anode and cathode and which comprises the organic molecule.

20. The organic molecule according to claim 2, wherein both X are CN.

21. The organic molecule according to claim 6, wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: Me, .sup.iPr, .sup.tBu, CN, CF.sub.3; Ph, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyridinyl, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyrimidinyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; carbazolyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; and N(Ph).sub.2.

22. A process for producing an optoelectronic component, comprising processing of the organic molecule according to claim 1 by a vacuum vaporization process or from a solution.

Description

FIGURES

[0168] The figures show:

[0169] FIG. 1 Emission spectrum of Example 1 in 10% PMMA.

[0170] FIG. 2 Emission spectrum of Example 2 in 10% PMMA.

[0171] FIG. 3 Emission spectrum of Example 3 in 10% PMMA.

[0172] FIG. 4 Emission spectrum of Example 4 in 10% PMMA.

[0173] FIG. 5 Emission spectrum of Example 5 in 10% PMMA.

[0174] FIG. 6 Emission spectrum of Example 6 in 10% PMMA.